Being Unconditionally Helpful

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.