Leadership Insights From Growing 2X in 8 Months

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How does it feel when your team more than doubles in less than a year? Like your brain was put in a blender and someone kept pressing the button. I joined a 7-engineer, 40 employee, startup in August, by May we were 14 engineers, 100 people, and I was a manager. These are my lessons.

This talk has been presented at TechLead Conference 2025: AI in Orgs, check out the latest edition of this Tech Conference.

FAQ

Product-market fit is when the market demands more from you than you can keep up with, indicating that your product meets the needs of the market.

You know you have product-market fit when the market is pulling you forward, and you are struggling to meet demand and keep up with growth.

Working in a company with product-market fit feels chaotic, like being in a blender, as the company rapidly grows and demands constantly increase.

Communication is crucial when growing a team, as it ensures everyone is aligned and working towards the same goals, much like defusing a bomb in a cooperative game.

Leaders should focus on explaining their reasoning in decisions, provide targeted feedback based on team members' experience levels, and encourage growth through mentorship.

Leaders should focus on 'who not how' by delegating tasks to team members who are best suited for them, allowing leaders to handle higher-level strategic decisions.

User stories help focus on outcomes rather than just tasks, guiding the team to deliver work that truly benefits users and achieves desired results.

Writing down decisions and plans helps manage the chaos, allowing team members to keep track of progress and revisit ideas without overloading their memory.

Leaders should use the backlog to store non-critical ideas, allowing them to focus on current priorities while ensuring important ideas resurface when needed.

Flexibility in roadmap planning allows for adjustments as new information emerges, ensuring that long-term goals align with the evolving needs of the company.

Swizec Teller
Swizec Teller
15 min
18 Sep, 2025

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Video Summary and Transcription
Product-market fit is like being pushed by the market, needing more. A game analogy illustrates teamwork dynamics in handling tasks. Communication is key in team growth, allowing delegation for collective success. Experienced team members focus on clarity, delegation, and accountability. Prioritize assigning tasks to team members based on expertise. Embrace the role of a side quest specialist for long-term or short projects. Engage in mentorship and explain reasoning to foster team independence and growth. Mentorship occurs organically between tasks, influencing work approaches. Trust your team to make decisions by explaining your rationale. Mentor one skill at a time to ensure effective learning and application. Focus feedback, encourage newbies, address weak points of experts to enhance performance. Focus on feedback for beginners and experts, emphasize outcomes and timely feedback to enhance performance. Realize the importance of quick utility, user stories, and outcome-focused work. Utilize user stories, documentation, and flexible roadmaps for effective planning and decision-making. Embrace change, document ideas, focus on user stories, and leverage backlogs for effective planning and adaptation.
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