This reflection on leadership in a hyper-growth startup argues that self-management is the most crucial skill. Management in such a chaotic environment is inherently reactive and emotionally draining, not strategic and proactive. The key to effectiveness is to abandon "ruinous empathy"—the futile attempt to please everyone—and instead fiercely conserve personal energy for high-impact moments. This is achieved by accepting failure and tradeoffs as constant, communicating them transparently, and focusing on maximizing success in key areas rather than fighting every fire.
I was the first engineer and 3rd employee at a company that grew from a problem statement to a team of over 550 people with a $1.3B valuation in 3 years. Over that time, I moved from being the only engineer to managing managers and leading a team of ~22. What did I learn?
It surprised me how challenging it was to maintain my identity amid the pressures of hyper-growth. Today, I'm "battle-hardened" and want to share some lessons in striving to be my best self in that chaotic environment. I learned about the power of strong relationships with teammates and how to ask effective questions to diagnose problems across teams. But first and critically, I learned about managing yourself.
These insights are difficult to deliver in a narrative format, so I've divided this post into several sections:
Few individual tasks as a manager are difficult on their own. However, there are numerous areas requiring focus, and you need to conserve your energy for tasks that carry a heavy burden.
Managers are humans placed in positions of power, and they often struggle with how to use that power [ref]. Teammates, also human, become frustrated by organizational issues affecting their happiness, such as career growth and compensation. They are uncertain how to address these frustrations and consequently direct them toward their manager. Resolving structural issues takes quarters or even years—time that direct reports don't feel they have. As a result, managers end up expending much of their energy setting expectations and managing frustrations. This leaves little capacity for addressing systemic issues or leading major initiatives.
For me, the dissonance between what I wanted to accomplish and what I was actually doing made it difficult to fully focus on the task at hand. The emotional and personal challenges were substantial. I recall a low point where I hadn't slept for days and resorted to drinking half a bottle of NyQuil. Still sleepless, I went to the gym for an hour and then continued working a full day. Regular exercise and peer networks like Orbital NYC were invaluable during recovery.
I envisioned management as a series of deliberate actions toward accomplishing significant objectives. In reality, the opposite often occurs. Management is frequently reactive, and major decisions carry substantial emotional weight. At a high-growth company like Cityblock Health (where in year two, staff increased from ~20 to ~140), management constantly lags behind, and emotions run high.
Several critical practices helped me maintain the manager mindset:
Align your expectations with reality. Expect change [ref].
Confront failure and performance issues directly.
Manage your energy. Do not work if you lack the necessary focus. You cannot easily reverse management mistakes.
Prioritize sleep. The challenges will remain tomorrow, but you'll be better equipped to address them.
💣 Confront Failure
Clearly communicate what you can or cannot accomplish and help others do the same.
Discussing failure is emotionally challenging for achievement-driven individuals (and for most people). It becomes easier once you recognize that everyone experiences failure. Failure is the environment we all navigate. We make tradeoffs, and every tradeoff disappoints someone somewhere—identify where and plan accordingly or communicate about it openly.
I attempted to minimize the number of people I disappointed, but this approach took a significant toll ('ruinous empathy'). I often arrived at compromise solutions that left everyone somewhat dissatisfied.
Now, rather than treating tradeoffs as harm mitigation problems, I concentrate resources in areas that are working well to maximize success. Success isn't about trying to win every battle but setting early expectations about which battles you expect to win and communicating those priorities clearly. I like to say that "we are always experiencing failures but never a failure."
Later in this post, I discuss goals. Helping your direct reports become comfortable discussing their near-term objectives and supporting them when they fall short is essential. When you model the practice of discussing your goals and failures in team settings, those same conversations with your direct reports become more natural.
🍃 Energy Conservation
I initially thought that when people encounter difficult problems, they would read, research, and thoroughly discuss potential solutions. However, the reality is that you often have just three minutes in a meeting before needing to move on.
Small, quick wins accumulated day after day are how you build something great. Managing your energy so you can fully engage during those critical three-minute windows is essential.
An effective manager of managers can have a substantial impact with minimal energy expenditure. This requires quickly mapping prior experiences to new challenges. For me, writing this post (and others) helps ensure these lessons remain accessible, allowing me to retrieve them efficiently even during low-energy periods.
"I have yet to see any problem, however complicated, which, when you looked at it in the right way, did not become still more complicated." [ref]
Helping the Team
Long ago, I learned that my job as a manager is to help others accomplish "the right work." I've tried numerous approaches to bring the right people together, adjusted meeting cadences, and refined approval processes to provide teams with necessary information and business drivers. Yet I often wondered if anything was working.
A significant aspect of managing across multiple teams is the ability to quickly assess long-term projects and the personal dynamics within them. With accurate information, finding solutions is often straightforward. However, obtaining accurate information is simultaneously simple and extraordinarily difficult.
Understanding teams and active projects requires asking uncomfortably basic questions. Ideally, ask as someone who genuinely wants to help (building trust and psychological safety are key) rather than as a leadership figure conducting an interrogation that prompts defensive or inaccurate responses. It also requires persistence in ensuring work aligns with business objectives and that technological investments are strategic rather than "promotion-driven" [ref].
Regarding what questions to ask, I find these factors for effective collaboration from Camille Fournier valuable for evaluating teams and projects:
Are you communicating effectively with one another?
Do you know where you are going?
Do you know how you are getting there?
Do you know how to determine if you are making progress?
Have you done the work to ensure your team can actually accomplish their tasks?
⚽️ Goals
To gain a higher-level perspective on organizational activities, many companies establish formal goals. Until recently, I had never worked in an organization with a formal goal-setting process. Previous companies focused more on delivering specific deliverables by specific dates. Goals require more nuance.
The process I recommend is to spend a few minutes in 1:1 meetings writing 2-3 objectives you plan to accomplish in the next 30 days. Begin by "working backward" from the impact of the work. Ask, "What impact do you want this project to have, and how will you measure that impact?" Set the impact as the deliverable rather than the feature itself, and agree on a target date. After several impact-driven meetings, you can introduce the SMART framework to evaluate whether each goal is:
Specific – targeting a specific area for improvement.
Measurable – quantifying or at least suggesting an indicator of progress.
Achievable – possible to accomplish within the timeframe.
Realistic – stating what results can realistically be achieved given available resources.
Time-related – specifying when the result(s) can be achieved.
I prefer maintaining a somewhat informal approach, mentally referencing the SMART methodology while helping team members set ambitious but achievable goals.
Although my team members and I often fell short of our goals, this process enhanced our ability to anticipate obstacles and enabled us to prioritize projects that addressed those obstacles. Additionally, it provided quick performance feedback that we could promptly deliver to team members
References
🧘 My Personal Practices
Develop a hobby or personal practice completely disconnected from work.
Build a network of peers you can consult for advice (and whom you support in return). [ref]
Identify memorable principles to ground you.
Expect to encounter significant pressure. That is normal. Practice pushing back by listening and asking questions, not by being negative or defeatist.
Read management literature but recognize that reality is messier than theory. Consult peers at your company rather than relying solely on internet advice. This will help you better understand their leadership style.
Build psychological safety and allow space for venting, but then guide teammates toward constructive action [ref].
Identify aspects of your work that bring you satisfaction and fulfillment.
Leadership involves creating a compelling narrative that engages people. Validating team members' experiences, demonstrating vulnerability, and maintaining transparency are valuable but insufficient for leadership.
🗝 My Core Values
The two things that matter are people and performance—in that order. [ref]
Lead through positivity.
Be a source of unwavering consistency.
Relationships are long-term investments; projects are short-term endeavors.
Make myself redundant and create opportunities for others.
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