I had a former VP of engineering that built a habit of writing a weekly update during his first 90 days on the role. I think there were two main reasons for him to do this:

• Synthesising and communicating learnings.
• Demonstrating activity.

Both are practices of learning & doing in public, rather than behind closed doors. The assumption here is that people in the community you’re serving are invested in your collective success and will help you course-correct to become a better steward.

Personally, I’ve found a written weekly update really helpful when a lot is happening in your environment, in your projects, or for yourself. With a lot of motion, I’ve found it easy to get lost in local swirls and eddies of action and thought and even the power of day-over-day inertia. I’ve also found it a great practical example of mindfulness in the workplace, where it has become a session in gratitude or a moment to reflect and practice awareness.

This is a potent activity for an (onboarding?) leader when a trusting community receives your updates and acts to support you. Your updates need to provide a rudder for course correction: explicit and implicit openings in your updates seeking feedback to correct perspectives, proposed actions, what-have-you. Learning in the open like this also benefits in building stronger communal ties. This approach is beneficial even without sending learnings to the broader world. I strongly recommend pushing for a community to learn with, yet I’ve found much value with myself as the sole audience.

As an individual, the practice is not much different – write your update as before; later, you need to review this as a critical reader to see what can be done differently. It is essential to sequence these items and partitions them as independent activities. I literally have different times to write and read the updates, not for logistical reasons, but to let me entirely adopt the right mindset. When writing, I need to synthesise, demonstrate, and ask for help. When reading, I need to internalise, understand and offer assistance. These are different operating modes for me that need separation in time. Occasionally, I’ll go back and read several updates in a row to understand how my thinking has evolved and what has been implicitly lost to time. I don’t keep a strict schedule for the latter. Still, I have found that this winds up happening 2-3 times a quarter (usually when writing an update and wondering aloud why or how I got here).

When (re-)reading my update, I likely won’t have the answers to my previous self’s calls for help. In a distributed update, there’s an implicit push for feedback. In solo mode, I need to pull in resources. The “reader” headspace helps me put some distance between the person-with-the-problem and think more holistically about how to help. Whom can I tag? Are there resources already? Is there a related domain? When distributing your update, make sure that your recipients can frame and answer the same questions.

I've found the golden rule is to omit status information in writing an update. Updates build upon previous updates, incrementally adding new learnings and areas of uncertainty; a status blurb rarely captures either of these critical facets. The update also needs to make it easy for readers to take action. I try to synthesise my learnings down into a principle and adjoin the requisite facts to support. Ensuring that it speaks very clearly to the strengths of the community I’m addressing also improves callback rates.

I prefer to have my updates as full-fledged written text, not bulleted sentences, phrases or fragments. I write a half-page at most, capturing the critical aspects of what I’ve learnt, implications (to myself, others, projects, org), and where I’m unconfident or uncertain. I don’t layer in links to docs, resources, graphs, or anything else. This structure is low friction for me. I can review my week, jump into a blank page, and start typing productively. You will need to tailor this for the style that works best for you. Just ensure to keep the principles above inviolate.

Even when I have a lot of varied or different projects in flight, I’ve never really had to vary this format. These days, I serve a few distinct communities and am toying with the idea of having a slightly longer, all-encompassing update that I would judiciously edit/synthesise for each community to meet my preferred form. But I haven’t actually done this yet.

I do these updates weekly. Depending on how quickly your environment changes, you may need to vary this. I can’t imagine doing this less frequently than fortnightly, TBH, since in my context, so much can change in that time. Similarly, more often than weekly, it becomes a chore, defeating the point.

“Leader” or not, the practice has been helpful for me. I haven’t been the best at keeping this habit, dropping because of changing priorities or just poor time management. Changing the minimum acceptance criteria when I’m pressed in these situations is really helpful. It can be a permanent change or a temporary one: you pick your adventure. Even with a spotty application, I’ve found it beneficial. It embodies aspects of mindfulness (reflection, gratitude and awareness) and active learning (synthesis, framing and call-for-help). When shared with a community, it helps bring them together through honest, shared, and inherently vulnerable communication focused on a shared experience and outcome. There are so many ways to implement this, but those key aspects really draw me to this practice.

I set up an SPV with AngelList a couple of months ago to bring friends into an investment opportunity. I’ve never used AngelList (AL) to form an SPV, but after looking at Carta (contact us for pricing? ew.) and Assure (wound up being more expensive than AL), I took the leap.

The Good

Formation and collection of funds was a breeze with AL. I found their online help valuable for a first-timer such as myself. Creation was turnkey, and the most time-consuming part was creating the deal memo and risk disclosures (a feature, not a bug IMO). From the LP side, things were easy too: quick to go from deal acceptance to accreditation to money transfers with a support e-mail for questions. AL made this entire process seamless.

The Bad

Things started floundering at closing, though. Except for the initial formation, where a helpful rep double checks key deal details, the entire process to closing is seemingly automated, but not after closing. Once I closed the deal, nothing happened. For days. I eventually reached out to the leads support channel; perhaps I needed to get the ball rolling?

They responded a day or two later and got things started, confirming the raise specifics, carry schedule and signature block. I connected AL to my investment’s CEO, and everything was running well again! Papers shuffled to-and-fro, confirmations were sent, and AL proclaimed the deal complete.

The Ugly

But they forgot the pro-rata side letter! I responded to the AL leads support immediately after noticing this; the wire was scheduled to be sent the following day! The CEO for my investment picked up on this too and quickly put together the side letter and sent it off to AL for signature. AL executed the letter, and the rest closed as planned. Everything worked out at the end, so no harm, no foul?

The Takeaway

Online help documentation pre-closing was quite clear; however, there’s a shortage of information available for closing and beyond, leaving me guessing around what is supposed to happen. It would be helpful if AL puts out a “what to expect while closing” article detailing what leads and AL need to do.

However, missing out on the pro-rata side letter as part of the deal closing made me lose trust in AL. From my perspective, there are two key documents here: the SAFE agreement and the pro-rata side letter. If startup investment is AL’s bread-and-butter, how could they lose track of one of the two critical documents here!

No harm, no foul, right? Sure. The onus is always on me as an investor or GP to ensure that everything is in order. I followed through on that responsibility here, and there wasn’t an issue, but a miss so seemingly basic by AL has dinged my trust in them. It’s not so large that I’d consider leaving the platform for future deals, but I’m warier of the brand, whatever that brings with it.

Update: Cloudflare's recent article on egress pricing, talking about how egress pricing hasn't kept pace with technological advances and is a lock-in mechanism acts to compound the frictions described below.

a16z's article on cloud costs calls out how adopting the cloud comes at the expense of operating margins. For several businesses (as the Twitter thread shows), this isn't an issue; top-line growth is more critical. Inevitably, a company shifts into a bottom-line or margin focus. This is where Sarah and Martin call out that the cloud taketh. A hybrid cloud strategy manages this dichotomy using standard OSS offerings to move compute, memory and storage (CMS) workloads flexibly from the cloud to corporate DCs. The problem is that data and ML workloads, critical drivers of value generation in current tech companies, can't operate in this hybrid cloud model. They are locked to cloud vendors because of the substantial network effect their managed ecosystem provides and the unparalleled price-to-performance ratio from deep vertical integration. Business centrality, combined with the considerable CAGR of Data+ML, makes this far more concerning to me than the portability of CMS workloads.

Before digging in, a point to clarify: Sarah and Martin are talking about bringing workloads from a Cloud provider to a company owned & operated data centre (O&O DC) in a one-time exodus (repatriation). General hybrid cloud approaches offer flexibility in the location (e.g. Azure, AWS, O&O DCs) and the movement of workloads (e.g. multihoming services "continually" based on price). When it comes to Data+ML, for the assertions above, the distinction isn't highly relevant. Where it matters is when there's a lot more flexibility in moving workloads that I'll cover towards the end (hint: egress fees).

Network Effects in Data & ML Offerings

Building a single ML model requires several services: data ingestion, streaming/batch processing, warehousing, training to name just a few. End users, such as data scientists and machine learning engineers, repeatedly traverse this entire graph of services to get their work done. As a result, weak links become significant bottlenecks; results suffer since useful tools are effectively walled off or wall times exceed users' fatigue thresholds. By building managed services that optimise this chain-link system, cloud providers unlock a tremendous amount of value. Beyond optimising a golden path, cloud providers work hard to have these services interconnect exceedingly well. This factorial interconnectivity is essential to users navigating amorphous ML and DS problems by effortlessly switching between tools, services and approaches as the problems dictate. This network effect and the corresponding value that the organisation is reaping needs to be overcome when repatriating. Choices here can have substantial impacts on user and organisational productivity.

Compounding Value with Vertical Integration

TPUs from GCP are the best example of this hurdle to workload portability: a custom-designed ASIC accelerator that has an outstanding price-to-performance ratio for select ML inference workloads. Unless you're willing to spin up an ASIC design division and have a substantive scale to amortise significant hardware design expenses, it's hard to beat this one. It isn't just about the hardware; the entire stack from software to hardware is jointly optimised. At Twitter, we noticed that system calls like memcpy are optimised as part of training on GKE (Google's Kubernetes offering) using NVidia GPUs. This deep vertical integration compounds the raw performance gains of cloud providers' strategic assets (e.g. TPUs). The rapid technological evolution in the ML space, both hardware and software, isn't helping ease portability. Replicating this degree of optimisation requires a skills-diverse talent pool and strategic partnerships with hardware vendors, further raising the bar for workload repatriation.

Other Frictions: Operations & Egress

Behind the success of cloud providers are substantial operations teams. Deep operational knowledge helps drive costs down, and building this from scratch in a vertically integrated ecosystem takes a lot of patience and commitment. The number of services required in Data+ML use cases magnifies operational needs too.

Colocating data consumers and producers is the status quo best practice, but this doubles requirements when repatriating. The problem is that there isn't an alternative: separating these two workloads gets pinched by egress costs. If GCP has the best Data+ML ecosystem and AWS has the best CMS solutions, what's to be done? Lay fibre to peering points? Expensive; however, cloud providers offer a direct connection product with near-zero unit economics, which makes this a viable margin improvement tactic. It does sound an awful lot like a telecoms business when you start plumbing many distinct cloud vendors across several geographies, though, bringing along a comparable bar for return-on-capital^equinix.

What is to be done?

Optimising for margins by repatriating cloud workloads is a reasonable solution depending on the focus of your company. Unfortunately, it isn't an option for Data+ML. OSS solutions, like Kubeflow, are single-point solutions with no end-to-end ecosystem emerging (yet). While pathways to portability on the software stack are emerging, there's little on the hardware side, leave alone competitive vertically integrated offerings. The ongoing and rapid evolution of the ML domain is both a feature and a bug: on the one hand there are opportunities to redress this barrier,  on the other, technical investments become obsolete much sooner.

I'm not sure if a general product that competes with the cloud can exist. Still, for established and well-understood use cases and an appetite to lose on performance but save on price, a repatriation option is definitely viable. Moving ML workloads between clouds is a much more feasible proposition as competition between providers fuels a technology arms race; Kubernetes is arguably an example of this. Perhaps such an arms race would yield vendor-independent solutions. Today, a well-heeled Cloud customer with clearly defined use cases and workflows, a deep appetite to build, maintain and advance a sticky Data+ML platform^choice, can take a crack at finding a globally optimal price-performant solution. This becomes easier if they're willing to sacrifice on performance.

Underpinning all of this optimisation is fundamental visibility of your costs! Billing consoles have done a solid job exposing usage, but you often need to extract data for a deeper analysis. GCP, for example, lets you export to BigQuery for detailed analysis. Getting cost details across cloud providers and on-prem is more challenging, especially in a standardised form. I'm hoping this is where tools like Vantage^founder can provide an edge: aggregating and standardising multi-cloud billing. Taking it a step further and seeing product-line level PnL with ease, gauging how Cloud spend (or the lack of it) is affecting product outcomes, is the dream.

At Twitter, we're still in the early days of operating in a hybrid cloud environment. We've identified that it makes sense to rely on the Cloud for our present needs: focus and velocity. Consequently, in the Data+ML space, we are focused on our partnership with GCP. We have a more balanced perspective for CMS workloads and are thinking about how the cloud and our O&O DCs interact with capacity, technology, and costs. We're working with AWS and GCP here to figure out what makes sense as a company. There's so much more to be done, and over the coming years, I think the industry at large will start figuring out how portability comes together for both Data+ML and CMS workloads.

Epilogue: Spot Pricing

I've also observed a key difference in pricing strategy between CMS and Data+ML products from cloud providers: the lack of spot pricing. CMS products such as EC2 offer a discounted price for surplus capacity, but Data+ML managed products generally don't have this option. Sustained usage or minimum commitment discounts certainly exist, but spot (preemptible on GCP) pricing offers substantially better price points, a pricing feature that never made it to the Data+ML product space. If you're rolling solutions atop managed Cloud infrastructure, spot pricing is still viable, but not for managed services. Unfortunately, high-value Cloud products such as data warehouses come only as a managed service.

Thanks

Spades of thanks to a bunch of folks like Alex Esber and Ben Schaechter for providing feedback on drafts.

1. I believe Equinix operates in this space and would be a potential partner. I have to call out that I'm not very knowledgeable about optionality and cost trade-offs here.
2. This is really hard to verify, in a counterfactual sense, given the implicit bias towards convergence when focusing on cost optimisation. The only counterpoint that I've found, and we've seen at Twitter, is to mandate choice: teams have the choice to use the best solution for their needs. This creates more diversity in the solutions pool that customer-focused Platform teams can leverage to understand gaps and evolve offerings.
3. Founder Ben Shaechter is a good friend of a friend and how I discovered Vantage.

tl;dr? Keep track of surprises, they provide you with a measure of health, especially for rocky relationships. Treat the surprise as an intervention point to build deeper alignment to grow trust.

Surprises aren't good. While an unexpected birthday gift is pleasant, in the workplace, a surprise is a bad thing. Surprises befuddle planning. The more uncertain, positive or negative, future outcomes are, the harder it is to plan, creating frustration.

This problem occurs even at an interpersonal level. When working with another person, strong partnerships need to build a mutual understanding: partners need to trust each other's motives and predict each other's actions. Surprises disrupt this, making the partnership inefficient, unsatisfying, and even contentious.

Predictability in partnerships is essential for decentralised execution. Aligned on a set of principles or other decisioning directives, strong partners execute independently with minimal coordination. The greater the number of surprises, the more often check-ins are needed, and the partnership becomes less efficient. The more shocking the surprise, the more intense each check-in becomes, and the more drained everyone gets. If this trust debit isn't replenished, the relationship falls into disarray.

I've found that the number of surprises is a (surprisingly) good metric for the health of a partnership. Relationships can buffet the smaller pleasant or unpleasant surprises, but the shocking ones are the focus. Shocking surprises as a metric of health has been effective at both reforming and strengthing relationships. I keep a counter that helps me track this over time, reviewing it regularly for rocky relationships.

Outside of tracking, surprises create a natural intervention point. Whenever I feel the visceral reaction coming from a surprise, I immediately take note to follow up with a mini-retro. Ignore the formalism implied in the word retro; this is solely an opportunity for me to have a conversation with my colleague around expectations and outcomes. Like a retro, this isn't about blame. The goal is for us to understand each other better, and I set aside other expectations. I'm looking to share my thinking, hear theirs, and hopefully internalise this to reduce future surprises.

This only works if everyone is genuinely leaned into becoming better partners. For struggling partnerships, this is hard as trust is compromised. Cerebrally, I know this is the right approach, yet it is emotionally hard to put myself in a situation that can cause heartburn. I've approached these situations by starting slowly:

1. Asking for permission to share my thinking.
2. (Re)stating my intentions to learn and understand explicitly.
3. Sharing my fears that what I say would be misconstrued as criticism.
4. Leveraging a framework like situation-behaviour-impact.

You should proactively deter surprises on your part as well. Whenever I think that something I'm doing may be surprising, a sync is warranted. The threshold varies with urgency and context, but I often err on the side of caution. Usually, this is just a quick Slack exchange and, if nothing else, builds confidence in my predictions.

Partnerships need more than reactive attention to flourish. Consequently, surprises are a guardrail metric, and the structure above helps me consistently invest in improving my relationships. Successful partnerships are built atop boring reliability—reserve excitement for the things you do and discover together.

Related Reads

Here are a few interesting articles and books that informed different aspects of my thinking above. Please know that I may collect Amazon affiliate credits for purchasing through some of these links. Any credits I earn are used to buy and read things I think are cool.

• Superpartnerships
• Use Situation-Behaviour-Impact to Understand Intent
• "Crucial Conversations," K. Patterson, J. Grenny, R. McMillan, A. Switzler
• "Talking to Strangers", Malcolm Gladwell
• "The Language of Life & Business Coaching," Chad Hall

tl;dr? Jump straight to the key takeaways.

Personal growth is a constant topic in the workplace. Any conversation about progress, levelling or advancement infringes on this abstract subject. I've both sought and asked for help with it often, yet, I've struggled in getting it right, so much so that I nearly gave up on it. Growth seemed to be an elusive lottery event: you somehow get it if you're at the right time and place.

I resorted to using a patchwork of requests to people I admired in an effort to continue growing. Some requests yielded successes whilst others languished or quietly faded away. Numerous requests, variations in their framing, mixed successes and incremental learnings finally formed a critical insight: personal growth, as I was referring to it, is three different things - coaching, sponsorship and mentorship^lara-hogan. This lets me get specific on important yet different internal development and external support needs and highlights differing requirements for a support network^terms. Whenever thinking about personal growth, I was conflating these three, asking for the wrong thing and omitting help for the right!

Coaching: Personal Learning

Coaching focuses on learning^pip. Successful coaching is a well-scoped personal development activity that has a clear output, timeline and success criteria. If you were being coached to run a 3-hour marathon, the coach would provide a concrete weekly mileage plan, with benchmarks and care routines until race day. Coaching focuses on how rather than why or even what, the latter two questions often being better suited to mentorship and sponsorship. Content and delivery are personalised in successful coaching: coaching to run a marathon is different for a trail runner than a cyclist.

A Coaching Example

Say I'm learning Scala so that I can use it for a smaller project next quarter. I ask my expert-friend Melissa how to get going. Sharing my specific experience, e.g. Python, Node, Java stack ranked in comfort; she suggests an online course, other online resources and a topical book. That's enough for me to self-learn. I circle back after a few weeks, as I've progressed, asking for practical examples of variance within Scala. I have a handle but need to internalise it better. Melissa shares a few pointers from our codebase with me and walks me through them. With a couple of examples in hand, I spend more time solo to get familiar and follow up with increasingly refined questions. To cement things, Melissa shares a few canonical examples of how variance is used in our codebase. She also proposes a couple of mini-projects, building off these examples, to get me more practice. Learning Scala was my coaching exercise with a finite timeline (quarter-ish) and an outcome (contribution to our codebase). My coach provided me with sufficient support to ensure that I could be successful and helped me learn when I was struggling.

Sponsorship: Proving Grounds

Sponsorship is an opportunity to demonstrate your talent. Skills built through coaching are integrated with others in meaningful projects that let you learn and grow. The value from these projects isn't purely internal: successful sponsorship opportunities generate extrinsic value to the team, product, or other audience. Rehearsing lines teach much, a stage performance teaches more.

I find that ideal sponsorship opportunities should either focus on integrating or scaling skills, but not both simultaneously. When integrating skills, I'm trying something I'm unfamiliar with and need a space where existing strengths can keep work standards high. Once comfortable with these skills, I need to understand where I can continue to grow and learn, and opportunities that scale my skills become essential. This duality doesn't translate perfectly to messier real-life opportunities, but I've found that if I'm thinking about what I'm scaling versus integrating, I'm better focused on learning through application.

A Sponsorship Example

I've been working on rebuilding our data systems, however, the effort seems to have plateaued. We made substantial progress within our existing division, but there are now dependencies against the larger organisation, and it's challenging to move ahead. The broader organisation is large and amorphous, and I wasn't sure how to get plugged in. I've worked with the data platform lead a few times and contacted him to see how I can help their division. Some ideas come forth: a few short term projects and access/introduction to a company-wide forum. The team and I can't do all the proposed projects, so we stack ranked a few opportunities looking at the effort, reward and counterfactual. We tackle these to build organisational rapport, better understand broader pain points, and help them with our expertise. I also start taking part in the company-wide forum with the support of the data platform lead. This allowed me to build new relationships with the platform and broad organisational leaders. For the next six months, this forum provided me with other opportunities to improve our data systems and highlighted gaps and pain points through the company in first-hand accounts. I was able to bring these back to the team to steer our efforts with focus, eventually building valuable inroads into the broader organisation.

Mentorship: The Glue

Mentorship connects sponsorship and coaching together. By understanding your abilities today, and your vision for tomorrow, effective mentorship is a strategic pursuit to achieve this vision. Successful mentorship works by repeatedly building a diagnosis, hypothesis and a set of ensuing coherent actions^good-bad taking inputs from tangible projects and personal experiences.

A diagnosis is an educated guess on the best way to get there from here. No matter how much time is spent in research and vetting, it is always a guess. This is where coaching and sponsorship help: in providing confidence signals. Coaching extracts my affinity for tangible skills (e.g. building design docs, gathering requirements, building mocks). Sponsorship tests and reveals my affinity for using these skills to create tangible value (e.g. shipping feature X, a root-cause-analysis of Y, growing DAUs by Z). Situations where working on the project is more enjoyable than leveraging the skills required, the opposite, and a spectrum of intermediates are common. This is where good mentors are invaluable: working together with you to resolve conflicting interests to build a hypothesis that frames the direction forward.

There can be many hypotheses, however, strong mentorship focuses on identifying the prime reason. This resultant hypothesis guides a set of coherent actions: next steps that work collectively to move the hypothesis forward. Some will be coaching exercises (e.g. focus on improving succinctness in presenting); others will be non-developmental (e.g. build a list of presentation opportunities).

A Mentorship Mini Example

As a tech lead, a past cross-functional experience has highlighted a few friction points: communicating direction effectively to the team, prioritising and getting buy-in, and being effective at debugging and responding effectively to urgent & on-call events. My struggles here have made it harder to get more of these high-visibility opportunities that I both seek and enjoy. My mentor has collected feedback from colleagues and myself, and we think getting better at triaging and solving urgent problems will build comfort with the systems and confidence with others. This needs some coaching on these systems and to find a lower-stakes opportunity where we can still apply our learnings in practice. We line up some coaching by pairing up with a couple of senior engineers. With no shortage of incidents, we have another opportunity, but to ensure that we're not jeopardising the product, we think pairing up with another tech lead to drive this incident successfully will sell our sponsor (the PM) on our participation. She's a lot more experienced than I and while I'll drive, she'll ensure that I'm successful and act as a backstop. My mentor has been very helpful in identifying and managing this risk, and driving some of the conversations on my behalf. Not a typical arrangement, but everyone is bought in thanks to the organisational trust extended to me by others, and I get another bite of the apple.

Building a Vision with Mentorship

Personal, and by extension career, vision is critical. Journeys presuppose a destination, even if that destination is in flux. Mentors that help navigate this vision are very hard to come by in my experience. Successful mentors require a deep understanding and relationship with the mentee that is very personal. This deep context means that starting a new mentorship relationship to clarify vision struggles. However, evolving one into this space has been successful and benefits from extra runway to improve trust and explore interpersonal working styles.

Using all Three

Coaching is a development activity that builds upon and adds to your aptitudes. Sponsorship provides a forum to produce meaningful value whilst solidying your aptitudes and learning about yourself. Mentorship is both the glue connecting these together, and the overarching guiding force.

All three of these activities exist on a spectrum. Coaching can range from self-guided reading to instructor-led coursework. Sponsorship varies from staccato engagements (e.g. a C-suite presentation) to more regular opportunities (e.g. driving a feature team); scale (in time and resources) and scope of these also vary of course. A formal mentor or mentorship programme to a council of advisors or a superpartner, mentorship too exists on a spectrum. All combinations of these exist, creating a lot of diversity.

The complexity can be overwhelming, it certainly was for me, but this isn't a make-it-or-break-it scenario. Understanding what you need and where you want to go are critical to have but are easily adjustable. Perfect is the enemy of the good: start off with an educated guess and go from there. Writing down what I'm pursuing and why, reflecting regularly and then iterating as needed is good process hygiene that helps me stay organised and honest to myself. A good mentor helps to manage this too.

Requirements for Coaches, Mentors & Sponsors

Mentors, sponsors and coaches have different roles and requirements. This is why I struggled previously with "growth": the mismatch in what I needed and what was offered by my partner doomed us. By getting more precise, I can build the best support structure, which invariably means that one person doesn't do all three.

Requirements: Coaches

Successful coaching is action-focused with clearly defined outcomes and timelines. Coaching can be self-guided, yet good coaches can accelerate skills development by at least an order of magnitude. Good coaches:

• assess and understand your current capabilities and build an appropriate curriculum
• provide effective feedback that close understanding gaps and are tailored to your working style
• are dependable; can be called upon to help

For introductory or broadly known topics, the Internet makes an ideal coach for me. Learning to create an iOS app is an excellent example of this. Many resources exist, but as things get more complex, options dwindle, and human coaches excel. Building your Hello World app is one thing, but creating an app that would be featured in the App Store another. I search for human coaches when the domain has inherent complexity,  hard-to-acquire depth or nuance borne from experience. Strong coaches have built up a library of design patterns and are effective at sharing them with you.

Internet resources are great for introductory topics, but for hard-to-acquire or complex knowledge, human coaches excel by sharing their hard discovered design patterns.

Multiple simultaneous coaches have been helpful when the domain is subjective or challenging. Public speaking is a good example and an area where the wisdom of the masses is helpful. I seek out coaches that bring unique perspectives that are not at odds with each others' insights. However, with multiple coaches, one needs to take a more active role in winnowing and internalising feedback.

Multiple coaches are helpful for subjective or challenging areas; seek out coaches that bring unique perspectives.

Requirements: Sponsors

Sponsors create or connect opportunities to build incremental value from your personal development. Successful sponsorship requires sponsors to:

• understand what the sponsored needs in an opportunity
• have a reliable and consistent method to discover or create opportunities
• extend their organisational trust to the sponsored

A good sponsor needs to understand the need and then materialise a matching opportunity. Requests aren't cut-and-dry and often require discovery and iteration, both with the sponsored and any other organisational partners to finesse the right opportunity. A sponsor with a process, formalised or not, is more likely to yield a high-quality opportunity. As a sponsor, having a reliable and consistent process is critical to ensure that I maintain a practice of sponsorship. Without consistency, I can create implicit biases by unevenly supporting people which can easily snowball into a large negative.

A good sponsor must extend organisational trust. Whether scaling or integrating skills, the sponsored is going outside of their comfort zone. By extending organisational clout, a sponsor increases the runway for success while also signalling confidence. When I've been stretching my abilities, this has been immensely helpful in getting me a crack at the bat and space to swing.

Good sponsors extend organisational trust increasing the runway for success and signalling confidence in you.

Trust is also critical in searching for a sponsor. I look to find ones whose incentives and successes align with mine as this greases the wheel, especially when extending trust - a naturally risky affair. Aligning incentives often takes explicit work on my part: I'll look to see if there are specific problems that my potential sponsors are facing where I can work with them. This builds trust and context that translates to a stronger sponsorship relationship.

A direct manager is a natural prime candidate. However, as my organisational scope has increased, my manager's ability to create appropriate opportunities has often diminished. Work becomes much more cross-cutting and abstract, and creating opportunities requires being in the proper forums or having suitable access. Changing managers may make sense, but you can also maintain your existing relationship and seek additional sponsors. I've found it helpful to build a network of potential sponsors in each company slowly over time. I draw from collaborators on past successful projects, referrals from my manager or peers and the occasional cold call.

Build a network of sponsors slowly but consistently drawing from past collaborators, referrals and cold calls.

Requirements: Mentors

Good mentors are good strategists, helping their protégé navigate to their vision. Requirements for a "good strategist" are challenging to pin down, but there are a few heuristics that I've found helpful below. Building a personal relationship is essential of course. Here are what I find as baseline requirements for a mentor:

• Deeply invested in you and your outcomes
• Compatible working styles, especially in communicating and feedback
• Able and willing to build a safe space and be vulnerable
• Organised: keeps track and follows-up effectively; manages the meta-aspects of mentorship
• (useful) Has different perspectives and experiences than you
• (useful) Has specific expertise navigating others/themselves through similar problems

Mentorship requires strong rapport, premised on trust, yielding honest and vulnerable conversations. A mentor's intent must be beyond reproach, especially when uncomfortable or challenging discussions come up. I've found that the challenge-to-support ratio, a crude metric around how often I'm directly challenged on a perspective versus supported, is a strong signal for a successful partnership and consequently mentor. I think the ratio sits somewhere between 3:2 and 1:2 for me, depending on the topic. Good mentors have been able to navigate this variation, supporting when I falter and challenging when I'm surging. Experience both general and specifically applicable to you is helpful, but neither a deal maker nor breaker alone. These are nice-to-haves that can really help unstick you but IMO it is important to not trade-off the other requirements.

Rapport, trust, honesty and vulnerability are critical to having a long-standing & successful mentorship. Experience, both in general and specific to your situation, are very useful but you should not compromise on the others.

An overlooked requirement for a mentor is their ability to organise. Mentorship can be a formal engagement with specific times, actions and requirements, an informal gathering, and everything in the middle. Navigating that gamut is a relationship exercise, but, also an organisational one. Managing expectations (what to expect from each other), logistics (e.g. meeting times, turn around times, follow ups), and information (e.g. taking & reviewing notes) are table stakes. Attention to structure ensures that the work put into the mentorship is catalysed into value efficiently. This process hygiene isn't solely the responsibility of the mentor, and some affinity for it is important in both parties. Lacking this, mentorships over longer time spans can become circular, tactical and eventually ineffective.

An organised mentor helps coalesce, structure and refine thinking. They also help build structure to ensure the mentorship stays on track and remains fruitful over time.

As with sponsorship, I slowly build a pool of potential mentors over time. Unlike sponsorship, the pool I draw from is much larger and not limited to the workplace. As long as they resonate with me on the points above, they're a candidate. Of course, sourcing from the workplace comes with shared, often helpful, context. Coaching and sponsorship partners, respected colleagues, superpartners are all potential sources amongst many others. I take a semi-active approach: while not explicitly looking for a mentor, I am explicitly looking for people with the qualities of a mentor. These are people I would enjoy working with, so even if mentorship isn't in the cards, I still have a potential colleague or advisor.

A pool of advisors or counsellors is very beneficial and a pleasant consequence of the search for mentors. Getting a fresh perspective on a line of thinking or seeking the wisdom-of-the-crowds on occasion can yield invaluable insights. Fact checking and seeing around corners are other high value benefits. Unlike a mentor, advisors are leveraged for their insights in a more limited or ad hoc scope. The relationship isn't transactional, but exists on a spectrum alongside a bona fide mentor.

Build a pool of potential mentors over time drawing from sources far and wide. Candidates from the workplace provide a natural context edge, of course. This pool of potentials serves double duty by also being a great source for future partnerships and advisors, if not bona fide mentors.

I would not recommend multiple simultaneous mentors. I've never experienced this personally as mentorship is very time and effort consuming, and I've never had the bandwidth to have more than one at a time. I'm also concerned with peanut buttering, since mentorship requires concerted effort. In short, I don't recommend having more than one mentor at a time but YMMV.

As Applied to Teams

As a leader on a team, a chief responsibility is growing team members. When it comes to coaching, sponsoring, and mentoring there are three core steps:

• understanding the needs of team members
• building networks of coaches, sponsors and mentors
• match-making & follow-up

Regular personal conversations should strive to understand what growth is needed and desired and look to diligently assess the specific needs for coaches, sponsors and mentors. Aggregating this information across the team provides a holistic view of how to help your team grow and helps shape the support structure you need to build for your team.

Finding coaches, mentors and sponsors at the team level is the same as for yourself, but with a larger, more diverse list of needs. Recruiting others to accelerate the search will help with the scale and peers within the team or on sister teams are strong candidates. In searching for coaches, sponsors and mentors, my personal experience shows that coaches and mentors within the team resonate most, while external partners are stronger sponsors. Not a rule, just an observation.

Connecting the team to support resources is the final activation step. Sometimes introductions are all that's needed. Other times a more guided 1:1:1 is helpful. In all cases, I've needed to spend time connecting, following up or otherwise incubating. Follow-ups over time are especially important as matches may fizzle out and need the occasional helping hand.

Process is critical to build scale and equitability. Approaching team growth in an ad hoc manner creates systemic biases of over- and under-served team members. Dedicate time to assess individuals' needs, aggregate those needs, build support networks and play matchmaker. Also important is to find others who can help manage this process. When running smoothly, it doesn't take much effort, but (say) 30% of the time more effort is needed and having a partner or two to spread the load makes this more sustainable and successful in the long run. A helpful side-effect of good process is that effective metrics can be built too. I'm still trying to understand what these look like but am starting with some simple counters of connections made and successful relationships. Once I have more meaningful data, I'll write more.

The Evolution of the Manager

Early in career, a manager normally fills all three roles. However, very quickly other coaches start stepping in, if not at the start. Onboarding or new hire orientation in most workplaces provide a natural framework for this sort of relationship, with a manager playing a pivotal role in introducing and shepherding people, with other team members supporting in part or whole.

With seniority, coaching is not something the manager is normally able to define. They can (and should) co-ordinate getting support but are normally unable to get specific as to what's needed. Since most managers have a strong sense of the day-to-day for their teams, a limited sense, if not complete, mentorship helps the two navigate to good solutions. As you grow in seniority, your manager isn't able to be your coach.

Sponsorship is a critical component of being a people manager. Regardless of seniority, my experience consistently calls out the importance of a manager being a sponsor. With large scopes, this can get much harder, and a larger sponsorship network than the manager alone is needed for success. Even with a limited ability to sponsor, managers should still facilitate constructing and expanding a sponsorship network.

As for mentorship, I haven't seen any consistent trends. Sometimes a manager is a strong mentor. Other times, they are an advisor. Since mentorships rely on a strong personal connection, this is somewhat expected. Good managers are consistently involved in personal growth though; an advisory role is the minimum IMO if not "full strength" mentorship.

When early in career, managers often perform all three roles: coach, sponsor and mentor. As your skills progress, supplemental coaches are needed and the manager as a coach takes a back seat. Managers are critical to sponsorship, either directly or by helping you build a sponsor network. As for mentorship, there's much more variety here, but a manager should at least be an advisor if not a mentor.

Key Takeaways

Thinking of personal growth in terms of coaching, sponsorship and mentorship, makes it more tangible, actionable and achievable. This framework helped me drive my own growth confidently. As I moved out of entry level roles, a lack of sponsorship made it difficult to understand what I needed. Mentorship meandered  taking me nowhere. Coaching became disconnected and apathy took over. As a mentor myself, I was often confused around what I needed to provide and how to explore their needs effectively, so that my help actually helps. This was magnified dramatically at a team level, especially when scaling teams aggressively. Luck is present more disproportionately in success than my ego would prefer, but by being clear and precise around what aspects of growth are important and essential for me, I've been able to work my way out of ruts and get better at pushing past plateaus.

• Thinking of personal growth as coaching, sponsorship, and mentorship clarifies your needs precisely and helps you seek support resources with greater success.
• Coaching is a well scoped development activity with clear outputs and timelines. Good coaches:
  • Assess and understand your current capabilities, and build an appropriate training plan.
  • Provide effective feedback that is easy to internalise and closes understanding gaps.
  • Are available and dependable to help.
• Sponsorship is an opportunity to demonstrate your talents generating value for yourself and others. It also lets you validate your strengths and discover areas for growth.
  • Build a network of sponsors slowly, drawing from peer & manager referrals, collaborators from past projects and cold calls.
  • Ensure your sponsors understand your needs, and can reliably create helpful opportunities for you.
  • Loans their organisational trust to you, giving you more runway and (organisational) confidence to be successful.
• Mentorship guides coaching and sponsorship to get you to your vision. Personal compatibility is needed; trust and a safe space that enables vulnerability is critical.
  • Mentors need to be deeply invested in you and your outcomes.
  • A mentor that can organise and structure this long-term engagement effectively is a key requirement as well.
  • Mentors with rich experiences, including similar concerns as yours, can be very helpful, but don't sacrifice on trust and vulnerability.
  • Building a pool of advisors, in complement to mentors, to fact check and vet thinking helps to bridge context and visibility gaps.
• For teams, get clear on what each member needs for each of coaching, mentorship & sponsorship. Build a support network for the team based on these needs and help matchmake relationships.
  • Build processes that you can share and iterate with others. This will help to ensure consistency and sustainability.

Related Reads

Here are a few interesting articles and books that informed different aspects of my thinking above. Please know that I may collect Amazon affiliate credits for purchasing through some of these links. Any credits I earn are used to buy and read things I think are cool.

• Good Strategy, Bad Strategy, Richard Rumelt.
• The Coaching Habit, Michael Bungay Stanier
• What Does Sponsorship Look Like, Lara Hogan
• What Great Mentorship Looks Like in a Hybrid Workplace, Harvard Business Review.

1. I first came across the term sponsorship when Lara Hogan talked about the challenges for advancing underrepresented groups in the workplace. Le mot juste, it ended my parade of clumsy alternative terms.
2. The terms I've used aren't universal and various books often conflate coaching with mentorship. Sponsorship is generally ignored unfortunately. A rose by any other name still smells as sweet: I would focus on smell rather than the name.
3. A PIP (performance improvement plan), a standard process in companies to improve "wayward" employee performance, is an example of a coaching-like process. Intent is important, and in this case, it isn't typically coaching, as it focuses on mitigating risk for the company rather than growth for the individual.
4. This split parallels strategic thinking closely. In this analogy, the vision is set by the desired sponsorship opportunity, execution capabilities defined by your current skills, and the strategy represented by mentorship connects the two. Everything about good strategy (and bad) applies here.
5. Chapter 4 of Good Strategy, Bad Strategy talks about this from the perspective of the structure of good strategy. It is an interesting read that I strongly recommend for how to think about challenging problems.

tl;dr? Jump straight to the key takeaways.

I’ve discovered that there are periods when I’m hyper-productive. My usual diligence gets me to my goal well: improved tools, approaches and skills pave this road. By contrast, hyper-productivity builds wormholes, moving me at seemingly infinite speed. Oddly, this has little to do with me and everything to do with my work partner. Not just a "typically good" partner, this specific person triggers a chain reaction in how I think and act, releasing an exponential amount of creativity in the process.

A superpartner is a specific person that triggers a chain reaction in how I think and act.

Engaging with a superpartner is tantamount to being part of a perpetual motion machine. The effort that I contribute to the partnership is amplified exponentially in both magnitude and precision. This positive feedback loop strikes deep at my core, encouraging me to lean in, contributing more for further amplification. The partnership is quick to identify and cull distractions, elevate standards, and inject psychological support, boosting my perseverance^{master-coaching}. My finite reserves of energy eventually leave me exhausted but energised by new insights and directions to pursue. Superpartnerships have challenged me to be the best version of myself without feeling challenging! Addicting.

I’ve experienced this thrice in my work career, and only now am I beginning to identify the symptoms and scratch away at the pathology. As I think about these superpartnerships, two aspects need care: frictions and accelerants. In keeping with our metaphor, frictions lose energy irrecoverably from our perpetual partnership machine. Accelerants are the opposite: they magnify or facilitate the transfer of effort into the partnership. Each of my superpartnerships require both, however, while I've never been able to overcome frictions (perhaps better considered blockers in this context), accelerants can be grown.

Frictions (a.k.a. Blockers)

Superpartners communicate and engage similarly to me. This style veers towards a lot of freeform discourse, is loosely structured and meandering yet directed. We have similar preferences in how and why we write, preferring to hash things out verbally at length and writing to clarify, introspect, strengthen and communicate. We also challenge each other using a similar approach and language that is never threatening. We’re not facsimiles of each other! Yet we are predictable in action - we reasonably know how (not what) the other will respond, and act appropriately^{understanding}. This deep alignment unlocks deep delegation, a state where we find our individual efforts are invisibly aligned.

The underlying cornerstone for superpartnership is psychological safety. My superpartner and I can bootstrap, grow and sustain a safe space where we can fluidly critique and compliment whilst being psychologically supportive. Conversations are unconditionally helpful. Trust is free-flowing.

These frictions are table stakes for me. I believe they are widely applicable, but if not, the essential theme of being frictionless must. Our perpetual motion machine cannot suffer losses stealing away energy. By communicating and acting in predictable ways, we inhibit these alignment and intent losses. Trust and safety eliminate barriers to share and explore. Lapsing on any of these is a death knell; the partnership is affected immediately and permanently.

Everyone will have unique requirements but the essential theme is to be frictionless in collaborating with your superpartner.

Accelerants

Superpartnerships collaboratively build and traverse a deeply connected knowledge graph. Shaping this graph is a dynamic generative and filtering activity, and superpartnerships have honed their skills here^divergent.

Communicating at the Shannon Limit

We’ve built our own pidgin language: my super partner and I communicate outwardly in a manner that seems to navigate syllogisms in large steps^darmok. We consistently share at our mutual Shannon limit: at the highest abstractions to maximise information density. As I dissect our conversations, I find them invariably littered with allegory, metaphor, parables, and other devices that efficiently compress and convey context and perspective. We each have built an arsenal of these tools to call upon built over time by our individual unique experiences.

Superforecasting

Superforecasters^book are individuals who are incredibly adept at prognostication. The linked book goes into great detail around their traits and habits, with the clear statement that this is a learnable skill. Until I read this book, I lacked the vocabulary to describe my other significant accelerant succinctly: superforecasting.

While we don’t manifest every habit or trait, the partnership can winnow ideas and think probabilistically. We don’t consistently frame our thinking about what comes next, yet our conversations naturally dig deeply into nth-degree implications. Exposing assumptions, revising estimates, thinking counterfactually and so on^book are consistent shared behaviours. Individually, I don’t think we’re necessarily strong or consistent in these areas, but together the whole is much greater than the parts.  

Odds & Ends

My categorisation above is Pareto efficient and necessarily incomplete. Several other pieces are vital but deftly managed with the foundation above. As I look around to other successful superpartnerships, I suspect that this offal is unique to me, but list them here given the uncertainty:

• Bias-to-action threshold: our boundary between talking and doing sets a shared conceptual finish line balancing discourse and action
• Perseverance and vulnerability: we reveal our soft underbelly, equip it with armour and build stamina for what comes ahead
• Passion and hard work: we invest deeply in what we do and what we don’t do

Communicating consistently with the highest information density and embodying characteristics of superforecasters are strong accelerants for superpartnerships.

Building a Superpartnership

I think of building a super partnership as analogous to hiring in tech^others. I’m “hiring” a partner for whom the must-have skills are the frictions above, and should-haves are the accelerants. Partially missing accelerants are acceptable but require partnership coaching & mentorship. It’s difficult to grow something from nothing or teach everything, so I veer towards those for whom things are partly clicking. Searching for a partner this way is a top-of-funnel hiring problem: how do I find a specialised candidate from a tiny pool of potentials?

I’m constantly looking for people who meet the minimum requirements above, searching at work, through friend groups, and any other network. I focus on finding a person and then thinking of opportunities to collaborate rather than the reverse. Occasionally I’m lucky, and this winds up being in my present focus area. But, if I look solely for people around a specific topic, I find the pool thins egregiously.

Once I’ve found someone, getting to know each other meaningfully through a small project where the outcome isn’t known or guaranteed is ideal. Uncertainty is essential for assessing our accelerants. The projects needn't be constrained to the context that you met your prospect in; I regularly have year-long personal projects that have become great proving grounds. The important thing is to get some material mileage with your partner-to-be.

In hiring, false positives are a source of great pain. They are less problematic here since the partnerships are opt-in and broken engagements can be wound up quickly, and civilly is my assumption. False negatives, however, are catastrophic. With a thin sourcing pool, I err towards being hopeful. The opportunity cost is ordinarily low, well-structured projects are strictly additive, and multiple swings at bat help you hit better. Like any self-learning process, a retro after an unsuccessful experience is hugely instructive.

Search wide-and-far; form short lists of people you want to work with; work on passion projects jointly; rinse & repeat until it sticks.

Other Observations

In dissecting and reviewing my and others' superpartnerships, there are a few additional items that come to mind around their sustainability and universality.

Symbiosis

While partnerships and symbiosis are synonymous, until now, I’ve focused a lot on the value to me, perhaps skewing the perception of a partnership. Superpartnerships only work and are sustainable if partners extract comparable benefits too. It may not always happen simultaneously, but over long runs, it must.

Two's Company, Three's a Crowd

Partnerships don't place restrictions on the number of partners, but I'm focusing only on partnerships of two people. It is challenging to find another simpatico individual; to find a third that is pair-wise compatible seems improbable, but not impossible; I just can't speak to it.

I do believe it possible to have multiple superpartnerships simultaneously. Right now, I haven't experienced multiples, but can see line of sight to get there. Ultimately, the amount of time and energy I have to invest limits how many can be maintained simultaneously. For me, this cap is at most two.

Portability

As these partnerships have aged, I’ve also noticed that they become both durable and transferable. Having built this perpetual motion machine in an initial area, I’ve found it portable to others. Reduced context and overlap do diminish its efficacy, but they are still valuable.

The Lindy Effect

The more meaningful time spent in a superpartnership, the longer it lasts and the better it is at value creation. "Meaningful time" is tricky. I've needed to ensure that not only is time spent on creativity but that our creative pursuits themselves are not static. Periodisation, as in sports, is important to maintain the partnership. In truth, I haven't had much difficulty with this. My superpartnerships have been naturally addicting, so spending time isn't a problem^rhythmic. The strong sense of psychological safety and all-encompassing curiosity also lends itself to variety.

Key Takeaways

1. Get a handle on the hard requirements in a partner. Safe spaces, compatible engagement styles are critical for me. Without these in play, the partnership can never form.
2. Accelerants are important to be able to build and mold the partnership. Communicating with high information density is a prerequisite. As is superforecasting ability.
3. Eyes and ears open! Search for potential superpartners everywhere. They need to meet the minimums above and also tick off some of your accelerators.
4. Create projects to collaborate on and try out the budding superpartnership. Results aren't immediate and some initial effort is needed. You should see things grow quickly though; if not you may need to continue your search.

Penn Jillette, of Penn & Teller, talks about how their superpartnership focuses on creating the absolute best performance while coming off lighthearted. They both have compatible characteristics that enable them to work together and bring out the best in each other. Sanjay & Jeff, Google's only Senior Distinguished Fellows, also form another superpartnership. They simultaneously dissect the same few hundred lines of code and pair to redefine data processing as we know it–all in the pursuit of excellence. The Book of Duos highlights others through time too. From the non-human world of machine learning, GANs also form a mathematical superpartnership^zero-sum in the pursuit of excellence too. When I spent time looking, I've found that history and the sciences are filled with examples.

Tomes of self-help texts, personal and other resources draw attention to a multitude of ways to grow solo. Personally, this has only taken me so far. To move past the plateau, searching and forming superpartnerships has been my lasting way to grow myself, and others.

Related Reads

Here are a few interesting articles and books that informed different aspects of my thinking above. Please know that I may collect Amazon affiliate credits for purchasing through some of these links. Any credits I earn are used to buy and read things I think are cool.

• "Life’s Work: An Interview with Penn Jillette", HBR.
• "The Friendship That Made Google Huge", The New Yorker.
• Superforecasting
• Deep Work
• Extreme Ownership
• Smarter, Faster, Better
• The Talent Code
• The Book of Duos

1. The Talent Code refers to this state as master coaching: an external system/individual that is able to foster deep practice and ignite motivation.
2. Extreme Ownership highlights this need from the perspective of delegation in a hierarchy: "...They do not need the full knowledge and insight of their senior leaders, nor do the senior leaders need the intricate understanding of the tactical level operators’ jobs. Still, it is critical that each have an understanding of the other’s role.".
3. A compatible perspective from Smarter, Faster, Better frames innovation as needing intellectual middlemen who straddle different domains as well as tensions that trigger divergent thinking.
4. Star Trek TNG afficionados should look to the episode Darmok for an example of stylised high bandwidth communication.
5. I strongly encourage folks read Superforecasting.
6. Dating, fantasy football, and other analogies work here, too.
7. Deep Work refers to this as a rhythmic practice. I don't know if other modalities (bimodal or journalistic) would work since I veer towards a rhythmic deep work practice myself.
8. The verbiage of zero-sum games isn't as well suited to a functional partnership, but the idea of two abstract entities in a system challenging each other to refine their output does align well.

tl;dr? Jump straight to the key takeaways.

I've unintentionally¹ fallen into the habit of being unconditionally helpful in working with others. It's not about offering assistance at every step, vocalising my thinking or a form of newspeak. It is a diligent, focused effort to ensure that the conversation and its participants move towards a positive outcome.

The moment I started to apply this, especially as it was sudden¹, I realised:

• how much of what I say isn't helpful for the context I was in, e.g. talking about past successes
• the things I say that are non-helpful can drag down openness even if they aren't hurtful, e.g. talking about a past success doesn't move the team closer to a solution
• I wasn't focused on driving everyone to the outcome as much as making myself and my team feel better, e.g. talking about a past success as a self-assurance ritual

Being unconditionally helpful had an immensely positive effect on my partners, even in a short period. It built situational trust, which grew into greater interpersonal trust over time. This has become my ultimate barometer of whether something is helpful: does it build trust²? Things that are unconditionally helpful never sow distrust. I hadn't recognised the friction created by being non-helpful until I inadvertently was forced only to be helpful.

Being unconditionally helpful is a diligent and proactive effort to ensure that all participants move towards a positive outcome. The barometer for helpfulness is if the conversation builds trust; unconditional helpfulness never sows distrust.

I began by following one of the principles recommended for mentoring: ask questions that encourage conversation and exploration as a priority. I don't avoid statements; instead, I'm emphasising genuine and thoughtful questions.

Emphasising Questions

When first internalising this approach, I focused on improving the quality of my questions. Articles, guides and books suggested a focus on conversation expanding (i.e. more value-added discussion) questions over ones that may bias towards conversation limiting (e.g. defensiveness). Despite a sustained effort, the practice of focusing first on questions in this manner did not come naturally to me, even in its native mentoring setting. I've spent a lot of time building a set of competencies: surely I need to share this with others? These competencies can be helpful, and to emphasise questions more than statements seemed to downplay the value I bring.

After struggling fruitlessly for some time, I reset my approach. Unconditional helpfulness is the core principle, and I circled back to how I can embody this best. The difficulty I was having centred around my preference to spend more time with statements than questions. This was the natural way for me to engage, and by focusing on questions first, I was optimising the smallest piece of the pie. Let's reverse that and then revisit questions.

Statements First

My method with statements is simple: only make a statement (henceforth an unconditionally helpful one) if it will unconditionally move the conversation forward. Motivation is essential here: it's about genuinely embodying a positive and helpful intent.

Only make a statement if it will unconditionally move the conversation forward.

I had assumed that my statements were helpful since I intended them to be helpful³! When I audited my statements⁴, I found a non-trivial number focused on advocating for my teams' and my successes or prior contributions⁵. In select situations, this is helpful and works to build trust. In most, I've experienced the opposite; at least, that's what it feels like when I'm on the receiving end. As I started constraining my statements, I realised how much of my typical conversation revolved, directly or indirectly, around this and other similar non-helpfulness.

Let me expand on the concept of unconditionally helpful statements with a few examples. I've found my statements fall into a few categories⁶:

• Declarative: I make assertions factual or otherwise, e.g. I have not seen the presentation yet.
• Synthesising: A part of active listening where we reflect on personal or collective statements, e.g. IIUC, the statement we're making is to focus on productionisation over freeform exploration.
• Explanatory: I'm clarifying actions or intent, e.g. To clarify, the team is genuinely looking for your input and insights.
• Pathos: statements that build an emotional connection, e.g. I feel that the last decision to migrate our stack pushed the team too hard.
• Signalling: used to convey social cues and status, e.g. We've been very successful as a team with adopting Cloud technologies.
• random: a catch-all for odds-and-ends, e.g. small talk, critical social glue such as thanks⁷

Intentional Practice

For each of these categories, I reflect on statements that strictly move the conversation forward, i.e. be helpful versus non-helpful. e.g. That is unconditionally false is a declarative statement that isn't helpful: it doesn't advance the conversation. Consider instead My understanding of Dataflow is that we would lower costs with the Shuffle Service. Statements can also cross categories, e.g. We are concerned with the uncertainty of chargebacks and their effect on our ability to adopt new Cloud technologies. A more nuanced example could be: Dataflow has reduced our costs 10-fold, but your team isn't leveraging this; depending on the context, this may be unconditionally helpful, but it may not, although partly beneficial.

I found this sort of reflection immensely helpful to both train and fine-tune my helpfulness engine. I've purposefully slowed down during conversations, focusing critically on the type of statement and its helpfulness before responding. For discussions that could be challenging⁸, talking through several options ahead of time has been very helpful. Since the categories above represent responses to a set of triggering situations, this conditioning improved my responses' quality and specificity. I wound up improving my situational playbook in effect.

I've purposefully slowed down in conversation, focusing critically on the helpfulness of my statements before responding. This conditioning improved my responses' quality and specificity, improving my situational playbook.

Thoughtful Questions

By focusing first on helpful statements, I naturally created space for thoughtful questions. My learnings around asking questions were now a high leverage area of investment. Following the guidance outlined in mentorship texts, the underpinning assumption in thoughtful questions is that others are best able to discover and solve problems, not yourself. Consequently, questions are primed to focus on exploring ideas and thoughtfulness, encouraging novel discourse over superficial and reductive responses. In a mentorship setting with limited agency and visibility, spending most of your time on these types of questions makes a lot of sense to me. Less so otherwise. By focusing on unconditional helpfulness, relaxing this requirement lets me mix statements and questions freely. It lets me bring my expertise to play.

By focusing on unconditional helpfulness, I can mix statements and questions freely, letting me bring my expertise to play.

The mechanics for asking questions follow the recommendations for mentorship that I've synthesised and repeated here:

• focus on how, what or when makes things happen: these are conversation expanding enquiries
  • How can we leverage Dataflow's Streaming Service to manage our costs better?
  • What would be the key advantages to rewriting this in Scalding versus Dataflow?
  • When would it make sense for Finance to migrate from Vertica to BigQuery?
• avoid why questions: these are conversation limiting inquiries
  • Why aren't we using Dataflow's Streaming Service to manage our costs better?
  • Why not just use Dataflow to rewrite this job?
  • Why can't Finance use BigQuery today?

The content of the questions matters substantially, of course! Lipstick on a pig and all. However, my observation is that the framing above magnifies the quality of the responses and the ensuing conversation. Just as with statements, intentional practice through reflection and planning was immensely beneficial for me; I applied the same tactics here too.

Adoption Pains

Forced helpfulness was uncomfortable. Dropping my "wasted" statements  required me to surrender credit personally. I've worked hard to push things forward for myself and my teams, and forgoing credit felt like a disservice. My thinking would likely differ in a more hostile work environment or one with a more transactional or zero-sum culture, but this is not my experienced norm. At first, I told myself that I was "letting the work speak for itself," but this didn't sit well with me. Pushing myself through the discomfort, eliminating non-helpfulness, I quickly recognised a dissonance between my service-oriented and recognition-seeking mindset. Soon enough, my mind found reward elsewhere: I began to appreciate the fruits of our labour directly - the impact on the customer and the value created by the team. This brought me so much closer to the team and the customer.

My mind found reward elsewhere: I began to directly appreciate the fruits of our labour: the impact on the customer and the value created by the team.

Rather than how our work reflected our success, I shifted to how it reflected our customer's success. By focusing on customer success repeatedly, I improved my understanding of my customer, their needs and success: I was conditioning my customer empathy muscle. Over just a few weeks of practice, my empathy for my customers grew substantially, letting me be even more effective in larger, cross-team forums, especially in challenging contexts. Being better situated, empathetically, naturally allowed me to frame my conversation, thinking, and language in a much more inclusive tone focused on solving for our customer.

A knock-on benefit of being unconditionally helpful is the cultural standard showcased for the team. By pushing to be genuinely beneficial while reducing non-helpfulness, in addition to growing empathy, everyone was also energised and leaned into each other. This materially improved progress, and in challenging situations, the perseverance of the team improved. This change subtly altered and magnified behaviour standards: the juxtaposition between non-helpfulness and helpfulness in conversations increased, helping further to identify and close the differential. I want to think that the new behaviour will stick and scale through the team - only time will tell.

Building Consistency

My mix of thoughtful questions and unconditionally helpful statements can improve. Staying on track is challenging because of the deep patterns that I've built over time, and I'm leveraging a few accountability mechanisms to help:

• personal reminders at the start of each meeting
  • My meeting minutes template in Notion has a callout at the top to remind me to remain unconditionally helpful.
• helpfulness prompts and survey responses from colleagues
  • I use 360 feedback surveys with specific questions on helpfulness, e.g. Am I helpful in uncertain times, clarifying what needs to happen?
• personal reviews
  • I have a weekly Stoic practice where I go through my various conversations and reflect on where they can improve.
• accountability buddy
  • I have publicised my approach to close colleagues so that they can call me out if I'm straying.

Success in habit formation and personal change only occurs for me if I'm intrinsically motivated. If I embark on an academic journey, for which the gains don't provide me with any meaningful growth, I've never stuck with it. At the other end of habit formation, I've also struggled the most when I'm closely tracking my growth! Even ignoring the finite precision possible in such measurements, this fixation biases me towards a quick and significant win rather than conditioning me for an extended series of smaller gains. My best habit structure focuses on aligning intrinsic motivators, building a good support structure, and then letting the system produce results, with checkpoints twice a year. This approach also tends to be well aligned with review cycles at many workplaces.

Key Takeaways

1. Form a helpfulness baseline: get feedback from colleagues and partners and review your past interactions.
   • Are you consistently moving conversations forward? Are you perceived as helpful? Do your relationships grow in trust?
   • What is your mix of statements to questions? Which of the two do you need to push on more?
2. Prepare and review intentionally; e.g. how can I frame that more helpfully?
   • Prepare for conversations, thinking about how you can be unconditionally helpful.
   • Review conversations, especially challenging ones, calling out how you could be more unconditionally helpful.
3. Make your statements unconditionally helpful: actively designed to move the conversation forward strictly.
   • Slow down your responses. Focusing on not responding helped me.
   • Actively frame and choose your statements to be unconditionally helpful.
4. Leverage how and what for your questions much more than why. Focus on expanding the conversation while driving it forward.
   • Just as before, slowing responses, actively choosing and framing questions was 90% of the battle.
5. Work incrementally and consistently. Build habits and accountability systems to keep you on target. Results take time, and a watched pot never boils.

This entire line of thinking is in its infancy. There are natural limits to its utility, such as environments that are openly hostile or partners that pre-dispose to operating zero-sum. One-on-ones follow the same rules, but familiarity, trust and context change the mix of questions-to-statements for me, especially in a long and close working relationship. Diligent and proactive application has helped me grow trust, situational understanding and readiness, customer & team empathy and grow cultural standards. It was uncomfortable at first and is sometimes challenging to navigate. I've valued the workplace rewards it has brought, but most of all the contentment in knowing that I'm working to be a better person.

My writing above used the example of an interpersonal live meeting. I have found this works well for me in asynchronous and real-time discussions. Varied platforms (e.g. Slack, e-mail) and different forums (e.g. one-on-ones, team meetings, design/product requirements doc reviews) too. Although the magnitude of the impact varies between these various media, I've found it to exist all the same.

Epilogue: Effects on Influence and Leadership

As I've grown in my career, I've migrated from directly working on a problem end-to-end to helping others be successful end-to-end. This has uniquely challenged my ability to solve problems: how can I deliver results when I have limited agency and visibility? The universal feedback that I've received is: lead the team to success.

There is a volume of material in business books, online articles and individual experiences on leadership. Still, the most salient lesson for me comes from the proverb:

You can lead a horse to water, but you can't make it drink.

Successful leadership isn't about control. The positive examples of leaders I've seen had never leveraged this to effect results, even when they were in a direct position of power to do so. They leverage the skills of influence: writing, speaking, synthesis, problem-solving, relationship building and much more. They focus on convincing the proverbial horse to drink. As I moved to lower agency and visibility, to be successful, I necessarily needed to scale my ability and effectiveness at influence. Being unconditionally helpful is my cornerstone here: it is critical to convey positive intent and lubricates influence building.

Being unconditionally helpful is my cornerstone here: it is critical to convey positive intent and lubricates influence building.

Influence has accelerators and hindrances, and unconditionally helpful and non-helpful conversations align neatly. Unconditionally helpful statements and questions accelerate my influence score with my partners by focusing my efforts solely on helping them pursue their outcomes. Influence also exhibits a network effect where a reputation of helpfulness opens doors and buys trust - another accelerator. This is essential when dealing with challenging situations in far-off organisational units (e.g. SEV-0 escalations).

A high ratio of unconditionally-helpful-to-not also boosts a different aspect of my influence: someone who can get things done effectively and noiselessly. Working on large initiatives with diverse teams, attitudes and cultures is bound to bring conflict into the picture. While this approach isn't a panacea, it reduces the opportunities for conflict and the time to resolution.

A high ratio of unconditionally-helpful-to-not reduces the opportunities for conflict and the time to resolution.

As I pick up more significant and abstract initiatives, managing my influence this way helps reduce the collaboration tax, improving my odds of success.

Thanks

Thanks so much to Esber, Jorunn, and Sushma for providing me feedback at multiple stages of writing this article; Greg for valuable QA and Erika for the encouragement.

1. I first discovered this by being in a position where I needed to support and advocate for another's advancement, despite them leveraging much of my work with no attributed credit.
2. Trust is built over a sequence of positive interactions. Charlatanism and other confidence tricks are examples of where trust is broken in the face of (apparent) helpfulness. My implicit assumption is the desire, and ability to be helpful is earnest.
3. A mismatch between action and intention is the critical component in fundamental attribution errors. Consequently, I think effort spent minimising this helps prevent a significant source of "intention misunderstanding."
4. I looked at my Slack messages and one-on-ones, keeping track of the mix and running informal surveys.
5. Generally, the mix of unconditionally helpful to not may not be what you expected; I'm describing the specific case of how the skew manifested for me.
6. I haven't mentioned silence. While it certainly can be used as a statement, it does so when juxtaposed with vocalised statements: a type of negative space statement. Very meta to think about the categorisation, but I found it fruitless.
7. Being thankful is also unconditionally helpful since it grows appreciation, trust and moves subsequent, if not the current, outcomes forward.
8. A conversation can be, and sometimes must be difficult, challenging or otherwise "hard", in order to be helpful. Providing specific coaching feedback is one such example, e.g. In that last meeting, I noticed that after your statement to takeover the agenda, the other participants stopped contributing.