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Interactive Roundtable: The Technical Founder’s Leadership Playbook

November 24, 2025
November 24, 2025 1:00 PM
 Eastern US
Open in Zoom

If you’d rather be writing code than managing people, this session will feel familiar. It focuses on the practical shifts founders have to make as their company grows, especially when the job moves from doing the work to leading a team.

Tom Buchok walks through concrete questions that come up in this transition:

  • How to move from doing everything yourself to delegating in a way that holds up over time
  • What belongs in a clear go-to-market plan, and why each part matters
  • How to set OKRs people take seriously and run 1:1s that actually help teammates grow

The session is led by Tom Buchok, co-founder of MailCharts, who stepped into the CEO role unexpectedly. He shares how he used this approach to navigate a challenging period, steady the business, and ultimately exit on his own terms. Along the way, he reflects on how his view of management changed as the company grew.

Recoding Summary:

Tom's Three Steps:

Great leadership is a skill you can learn. Follow these three active steps to set direction, focus your team, and drive results.

Step 1: Clarify The Annual Goal

Give your team a clear, unified target. A well-defined annual plan ensures everyone sees the company's direction and understands their role in it.

  • Create a Single Source of Truth: Develop a clear, accessible document—like a Go-To-Market (GTM) strategy. This document should outline:
    • Our market and customers
    • Our key competitors
    • Our top annual goals
  • Answer the Big Questions: This "leadership platform" answers fundamental questions for your team: What do we stand for? Who do we serve? What does success look like this year?
  • Unlock Performance: When people understand how they can impact success, their performance and fulfillment skyrocket.

Step 2: Simplify Into Quarterly Goals

Break down the big annual vision into actionable, quarterly priorities. Your goal is to remove complexity so your team can execute effectively.

  • Break Down the Vision: Use a system like Objectives and Key Results (OKRs) to translate your annual strategy into clear, quarterly goals.
  • Do the Hard Work for Your Team: The leader's job is to distill the complex vision into simple, achievable targets. This creates focus and enables delegation.
  • Choose Your Framework: OKRs aren't the only solution. The key is to pick a measurement system that fits your company culture and stick with it.

Step 3: Communicate With A Weekly Rhythm

Build alignment and trust through consistent communication. A strong weekly rhythm ensures execution and lets you focus on the future.

  • Repeat Your Goals: Communicate priorities redundantly. Reiterate the quarterly and annual goals in every weekly team meeting.
  • Master the One-on-One: Treat weekly one-on-ones as your most important leadership tool.
    • The team member owns the agenda.
    • Focus on them, their growth, and their feedback—not just project updates.
  • Give Feedback Effectively:
    • Use a 7:1 ratio (7 positive comments for every 1 constructive one).
    • Deliver feedback immediately, preferably via video call.
    • Always link feedback back to company goals to show impact.

A Personal Leadership Story

Tom was thrust into the CEO role after his co-founder passed away, forcing him to learn leadership out of necessity. For him, the most fulfilling part of being a founder is building a strong, resilient company with a talented team you trust.

Key Insight: "Great companies are bought, not sold." Effective leadership is the ultimate driver of a company's value. To succeed, you must consciously shift from doing the work yourself to enabling others to do it successfully.

Q&A: Your Top Questions Answered

  • How do we make one-on-ones valuable?
    • For remote teams, they are essential for connection.
    • For in-person teams, focus on active listening and dedicated focus.
    • Adapt frequency as your company grows (e.g., weekly for new hires, bi-weekly for senior members).
  • What if I have too many direct reports?
    • Implement skip-level meetings (less frequent one-on-ones with non-direct reports).
    • Consider restructuring the organization to create a more manageable span of control.
  • How can I build better relationships with my team?
    • Invest in the personal side of one-on-ones. Ask about family, time off, and well-being. This builds a stronger team foundation.

Key Takeaways

  • Create your leadership platform. Draft a clear annual strategy to guide decisions.
  • Simplify every quarter. Define and communicate top priorities.
  • Communicate constantly. Use weekly one-on-ones and meetings to build trust.
  • Give feedback that lands. Make it timely, specific, and tied to goals.
  • Lead to enable others. Your role is to build and support a team that can execute.

Resources:

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