I recently dug into a powerful conversation with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week, and it’s a timely playbook for anyone navigating the shift from founder to CEO.
What resonated most with me is how central self-awareness is to startup leadership—and how hard it is for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa highlights both the right questions to ask and how to get at the root of what people are actually saying in their feedback. In my own practice leading product management, I’ve learned that a multi-source feedback loop is non-negotiable if you want to grow faster than your company’s complexity.
To invite real candor, I set clear expectations up front, guarantee anonymity when appropriate, and ask for specific examples. Prompts I rely on include: What should I start, stop, and continue? When have I been most and least effective? What’s one behavior that would most improve my impact? I also ask for a confidence rating and context (e.g., cross-functional vs. team settings), which surfaces patterns that one-off comments miss. This simple structure keeps feedback actionable for product management leadership and founder-led GTM environments where speed can mask weak signals.
Of course, the hardest part is what to do with what you hear. Not every piece of feedback is useful, and Alisa’s guidance aligns with my own rubric: look for themes across sources, weigh input by proximity to the work and blast radius, separate facts from feelings, and test changes through small, time-boxed experiments. I operationalize changes in my day-to-day routine with calendar nudges, pre-commitments (e.g., publish decision criteria before important calls), and a trusted peer who can observe and nudge me in real time. Small, consistent behavior changes compound faster than sporadic big swings.
We also surface the most common opportunities for growth that show up again and again: communication and decision-making. I’ve seen how a CEO’s personality is unconsciously reflected in the company culture—pace, rigor, appetite for risk, how we treat “no,” and whether we bias toward outcomes vs output. To counter the “shadow of the leader,” I make these drivers explicit: write down decision guardrails, publish decision logs, and define what “good” looks like for communication quality and speed across functions.
Another area we dig into is how to have effective conversations about layering and letting people go. Layering—bringing in experienced leaders above early high performers—works when expectations are clear, roles are well-scoped, and dignity is preserved throughout. My playbook: share the business rationale, define success metrics and timelines, offer a growth path where possible, and avoid ambiguity that erodes trust. When exits are necessary, clarity, compassion, and speed protect both people and culture.
Finally, I’ve adopted a brief reflection ritual that Alisa recommends every founder incorporate into their daily routine. Mine takes ten minutes at day’s end: What mattered most today? What did I learn? What will I do differently tomorrow? This lightweight cadence keeps me honest about progress, especially in the messy middle of the IC to manager transition and the broader journey from scrappy founder to established CEO. It’s also a lifesaver for leaders who struggle to give away their Legos.
You can follow Alisa on Twitter at @AlisaCohn.
Inspired by this post on First Round.
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