If you've never worked with an executive coach, you might naturally ask yourself—what happens in coaching?
And even if you've worked with a coach before, there are some many flavors, styles, and approaches to how coaches operate. Some coaches never give advice and primarily ask questions. Some coaches share their direct experience often, others rarely do.
This is meant to be a non-exhaustive list of the topics and kinds of conversations I have with clients and the types of things we work through in session.
April 2025
Latin Am Male Founder
- Resolving tension between his cofounders (one more rigid and anxious, one more relaxed and avoidant)
- Identifying personal areas of growth ahead of Series A fundraise
- Emotionally processing in aftermath of a romantic breakup
South Asian Male Founder
- Decision to push back a product launch
- Ways to delegate more responsibility to the team
East Asian Male Founder
- Performance issues with leader on his team
- Being off track on financial projections for the year
- Carving out more time to spend with family
August 2024
White Female Founder
- Sales pipeline and planned upcoming outbound customer acquisition activity
- Response to recent investor questions / concerns
South Asian Female Leader
- Planning upcoming travel / possible sabbatical / family leave
- Strategized how to communicate better with the CEO
South Asian Male Founder
- Losing significant amounts of capital in the markets
- Dealing with a team member's parental leave
- Working through some problematic coping mechanisms
White Male Founder
- Review decision making process for picking strategic direction for business
- Brainstormed how to test assumptions
- Set up a plan for gathering more data from users
March 2024
Female Founder (Neurodivergent, Seed stage)
- Evaluated progress towards monthly growth targets
- Prioritized big rocks for the week
- Discussed new hire's first performance review
Male and Female Founders (Black, Hapa, Bootstrapped)
- Discussed learnings from interviewing customers of a competitive offering
- Brainstormed how to apply learnings into a quickly testable product hypothesis
Male Founder (South Asian, Seed stage, Pivot)
- Considered a major product / strategy decision that needed immediate action
- Examined which values founder wanted to prioritize when making the decision
- Brainstormed possible alternatives or backup plans if decision backfires
Male Executive (White, Series B)
- Discussed how to give feedback to senior manager currently on a performance improvement plan (PIP) and setting expectations on what "good looks like"
- Discussed how to create more space in schedule to prioritize strategic planning amidst a challenging and unexpected family emergency
Male and Female Founders (White, Seed, pivot)
- Completed retrospective on timeline, emotional journey, and lessons of adding and eventually firing a third cofounder while pivoting the business
- Typically working with the Female founder, was able to observe both founders in communication
Female Founder (woman, South Asian, in transition)
- Explored and reinforced significance of founder's identity shift over 2 years of entrepreneurial endeavors (sometimes a return to the same place on XY coordinates masks a shift in the Z dimension)
- Discussed how to act out of authentic desire rather than from place of scarcity as founder reenters the workforce in a new role (tough job market + possibility of moving for a role was creating stress)
Male Founder (East Asian, bootstrapped)
- Discussed how to navigate relationship tension / conflict with upcoming parental visit (last year's visit went Very Poorly).
- Analyzed a specific Slack message exchange / disagreement between client and another founder that seemed likely to spark conflict
- Offer suggestions on how client could better communicate concerns while leaving room for new information and ultimately resolving the conflict productively
Male Executive (East Asian, PE-funded)
- Explored client's values as a father and the struggle to balance the "chip on your shoulder" ambition with individual expression and personal satisfaction that he wants for his kids
- Discussed plans to reallocate scope of one of client's direct reports, and navigating the optics of the change both upwards and downwards
- Considered possibility of conducting a 360 leadership review