📋Notes: A real coaching session (vol. 5)
Hi!
Many of you ask for notes from real coaching sessions so you can understand what executive coaching looks like in practice.
A second time founder is struggling with the challenge of keeping his company alive - and his personal identity and relationship with failure
With his kind permission I'm sharing summary notes from our coaching session.
Feel free to leave any comments or questions on the post.
Thanks!
Parin
Context
The coachee, a second-time CEO, is leading a consumer tech startup that is struggling to achieve product-market fit.
With only six months of runway remaining, the immense pressure is leading to exhaustion and a profound sense of guilt from missing out on family time with young children.
A central internal conflict revolves around whether to continue pursuing the venture or to explore alternative paths.
This isn't just about the business; it is deeply tied to his identity as a founder and the daunting and understandable fear of failure.
Goal of Session
The Goal of the Coachee:
To make a definitive decision in the next few weeks about whether to pivot, push through, or shut down the current venture.
“I need clarity on what success or failure looks like and how to make a decision I won't regret, especially given what this means for my identity and reputation as a founder."
The focus for the Coach:
To help the coachee gain clarity on their options and create a structured decision-making process for the future of their company and their role as CEO.
This process must account for both business viability and personal well-being, directly addressing the deeply ingrained fear of failure and the impact on his identity as a founder.
Reality Today
Current Situation:
Product-Market Fit: Still elusive. Multiple product iterations have launched, but user acquisition and retention metrics remain stagnant. Key user feedback indicates confusion around the core value proposition and inconsistent feature usage.
Financial Runway: Six months of operating capital remaining and steps taken already to reduce costs
Team Morale: There is an underlying tension due to the prolonged struggle and financial pressure. The coachee senses a quiet desperation in some interactions with his team members.
Personal Toll:
Exhaustion: Significant. Averaging 15-16 hour days, seven days a week. Sleep quality is poor.
Family Impact: Missing significant milestones with young children. Partner has expressed concern about their absence and stress levels. Guilt is a major factor for the CEO.
Mental State: Feels a blend of determination and deep fatigue. Questioning his own judgment and ability. Pressure from investors and advisors. The weight of this being a second venture amplifies the feeling of having "been here before" and the desire to avoid past challenges.
Market Signals: Competitors are emerging with similar solutions and are well funded, some showing stronger early traction.
Founder Identity & Fear of Failure: The coachee explicitly articulated the difficulty of separating their personal worth from the venture success. He has a strong internal narrative about what it means to be a "successful founder," and the current struggle is directly challenging that identity. The thought of shutting down feels like a personal failure, not just a business one, impacting self-perception and future prospects. This fear of being seen as a failure by peers, investors, and even himself, is a significant barrier to clear decision-making.
Key Data Points/Observations:
Latest user interviews (3 conducted) revealed a desire for a solution to a slightly different problem than the product currently addresses. This is a potential pivot point, but would require significant development and a re-evaluation of the core vision.
Options to explore
Brainstormed Options (Coachee-generated, coached for breadth):
Pivot: Re-evaluate the core problem, build a new MVP based on recent user feedback, and seek bridge funding for the new direction. (Requires significant emotional and financial commitment; high risk, but aligns with his drive to solve problems).
Continue "as is" with one final push: Allocate remaining resources to marketing/sales efforts to see if product-market fit can be forced. (Low probability, high burn rate, likely shortens runway further. Acknowledged as potentially prolonging the inevitable, but appealing as "not giving up").
Explore acquisition/acquihire: Seek out potential buyers for the technology or team. (Unlikely given lack of PMF, but worth exploring. Could provide a softer landing and allow the coachee to transition without feeling like a complete "shutdown").
Shut down the company: Liquidate assets, assist the team with job placement, and move on. (The most emotionally charged option; directly confronts the fear of failure and the perception of ending a founders journey).
Step down as CEO: Bring in new leadership with a fresh perspective, potentially remain on the board. (An alternative to full shutdown, allows for continuation of the venture without the direct leadership burden).
Take a short break/recharge: Acknowledge exhaustion, step back for 1-2 weeks to gain perspective. (Risky given runway, but could improve decision quality by combating burnout and allowing emotional distance).
Considerations for Each Option:
Impact on Runway: How does each option impact the six-month timeline?
Emotional Cost: What is the personal toll of each option, particularly regarding the founder identity and fear of failure?
Probability of Success: Realistic assessment based on current data.
Impact on Team/Investors: How will each option be received and managed?
Personal Values Alignment: Which option aligns best with his long-term aspirations (family, career, mental health, and his evolving definition of success)?
What is next?
Chosen Next Steps:
Deep Dive into Pivot Feasibility (Next 1 week):
Validate the new problem area identified in recent user interviews.
Develop a lean MVP concept for the new direction.
Gauge engineering team capacity and enthusiasm for a significant pivot.
Draft a high-level budget for the pivot to understand extended runway needs. This is about gathering data to determine if a pivot is a viable path forward or just a delay of confronting the current reality.
Schedule Investor Check-ins (Next 1.5 weeks):
Brief investors on the current challenges and potential pivot.
Sound them out on willingness to provide bridge funding for a new direction. Be transparent about runway. This directly addresses the external perception aspect of their founder identity.
Evaluate Personal "Go/No-Go" Criteria (Ongoing):
He will define clear personal thresholds for continuing (e.g., "I will only continue if I see X traction within Y timeframe after a pivot," "I will only continue if I can commit to Z hours per week for family time").
He will specifically define what a "win" looks like personally if he continues, beyond just financial success. This is crucial for reframing his definition of success beyond solely the outcome of this specific venture, helping to decouple his identity from the startup's fate.
Prioritize Personal Recharge (Immediate):
Commit to a "hard stop" at 7 PM three nights this week to have dinner with family.
Schedule one full day off (Saturday) within the next two weeks to completely disconnect and spend time with children. This is a direct counter to the exhaustion and a step towards personal well-being.
Research Acquisition Landscape (Ongoing, low priority for now):
Spend minimal time exploring potential "acqui-hire" targets to understand the market. This offers an alternative outcome that might feel less like a "failure" and more like a strategic exit.
Accountability and Commitment:
Next session to review findings from pivot feasibility, investor discussions, and personal reflection.
He will come prepared with his personal "go/no-go" criteria explicitly written down, including reflections on what "failure" truly means to him right now.