Founder Reps: The 90-Day Leadership Sprint
One quarter. One mission. One upgrade in how you lead.
You don’t need another book, podcast, or hour-long coaching call. You need a single sprint with focused reps; small, intentional actions that compound into better leadership habits.
Founder Reps turns insight into capability: clear decisions, calmer communication, and consistent action, one five-minute rep at a time.
Why Sprint?
You’ve tried the usual options. Most don’t fit the way founders actually work.
| The Old Way | The Sprint |
|---|---|
| Executive coaching — long conversations that fade once the call ends. | Micro-coaching — focused reps that stick because you practice. |
| Leadership programs — inspiring in the room, forgotten the next day. | Maniacal focus — a mission built from your 360, your sole focus for 90 days. |
| Habit apps — generic prompts that miss your context and lack focus. | Custom assignments — simple, relevant reps that match your challenges. |
| Peer Groups — great conversation, but slow progress between meetings. | Founder Circles — peer accountability, anchored by actionable feedback. |
The Leadership Sprint combines what actually works: honest feedback, deliberate practice, and accountability, delivered in a cadence that fits a founder’s life.
The 5 Step Sprint
1️⃣ Diagnostic → Find the One Thing That Matters Most
We start with clarity, not guesswork.
You choose 4–6 people who work closely with you. They complete a short confidential survey, and when helpful, a brief call. You complete a self-assessment.
I map the overlaps, contradictions, and patterns that show how you lead when things go well, and when they don’t. Then I build your AI leadership agent; trained on your 360, self-assessment, public information, written patterns, and (if you choose) recent emails and meeting notes.
This gives us a sharper picture, faster.
A System That Gets Smarter With Every Sprint
Your diagnostic is used only for your Sprint, but the patterns (not the data) contribute to a shared learning model that strengthens the system over time.
As more founders run Sprints, the framework, the reps, and the recommendations all get sharper.
You get the benefit of a private AI assistant and a system that improves with every cohort.
Outcome: a clear map of strengths, friction points, and the behavioral themes with the highest leverage.
Here’s what that looks like in practice.
Example directly from a real diagnostic.
Theme Identified: “Calm Under Pressure”
Self 4.5
Peers 3.2
Your self-perception is higher than the team’s experience. That gap is where we work.
“Great instincts, but gets intense when things break.”
“Speed increases when stress increases.”
“The team doesn’t always know how he’ll react.”
“Moves fast — sometimes too fast for others to follow.”
Coach Summary
Across peers, direct reports, and your own self-assessment, the signal was clear: strong operator, unpredictable tone under stress. A good supplement here is Stillness Is the Key (Ryan Holiday), especially on choosing your pace.
Sprint Mission
Show up with steady presence when intensity rises.
Reps
- Slow first responses by 5–10 seconds
- Ask one clarifying question before reacting
- Share reasoning before decisions
Improving behavior under pressure enhances everything: clarity, trust, speed, morale, and decision quality. This is how we translate raw feedback into a 90-day mission that actually changes behavior.
2️⃣ Mission → Choose the One Thing
From your diagnostic, we pinpoint the one behavior where change will have the greatest impact on your leadership in the next 90 days.
Not five things.
Not “everything you need to fix.”
One behavior with the highest upside.
This becomes your Sprint Mission, the one upgrade we attack with maniacal focus.
Outcome: your 90-day target: specific, behavioral, and measurable.
3️⃣ Reps → Build the New Behavior
Around your mission, you get short reps you can do between meetings.
A rep might be:
- a pause
- a choice
- a written decision
- a tone adjustment
- a question asked differently
- or a micro-experiment with your team
Each one makes the new behavior easier to access and harder to ignore.
Outcome: steady, visible, low-friction progress.
Example Reps
Each assignment is a short, specific action designed to reinforce your Sprint Mission. A few examples.
• Emotional Consistency → Rep:
“Before your next meeting, slow your first response by 5–10 seconds and ask one clarifying question. Afterward, note how the tone changed.”
• Intentional Decision-Making → Rep:
“Put one decision in writing today — no explanation, just clear direction. How did it change the way your team responded?”
• Collaboration & Delegation → Rep:
“End one message this week with appreciation instead of instruction. How did the other person react?”
Small reps.
Compounding returns.
Behavior you and your team can feel.
Each assignment takes just a few minutes and compounds into clearer communication, calmer decision-making, and teams that want to follow your lead.
4️⃣ Progress → The Founder Circle
Change sticks when you exercise with others.
You’re placed in a small circle of founders running their own sprints in parallel, each focused on one high-leverage behavior. Different missions, shared momentum.
We meet every 30 days for a tight, one-hour, founder-only session where we compare notes, review what’s working, and troubleshoot what’s not. It’s not group therapy and not a loose discussion. It’s fast, focused, and grounded in data from your Sprint Mission.
Inside each session we look at:
- Where the Sprint Mission showed up this month
- What rep made the biggest difference
- What friction point is still appearing
- What conversation or pattern needs attention next
Between sessions, the circle stays connected through a private channel; a quiet, signal-only place for quick updates, progress notes, and small asks.
Why it matters: learning beside peers makes patterns easier to see. Your insights sharpen, your habits stick, and your Sprint accelerates.
Your AI Agent Keeps You Moving Between Sessions
The Founder Circle gives you accountability from your peers, but the real day-to-day reinforcement comes from the combination of your agent and my coaching.
Your agent evolves alongside you, capturing patterns in your check-ins, your updates, and the work you’re doing. I use those signals to guide your next rep, sharpen the mission, and pull forward the moments where you’re getting better, or drifting.
The AI handles the memory and pattern-tracking. I handle the interpretation, direction, and precision.
Outcome:
No slippage. No backtracking. No “What were we working on again?” You get a human-guided system that stays alive between sessions and keeps you moving forward.
5️⃣ Results → See What Changed
At the 90 day mark, we check in with your original reviewers:
“What’s changed in how they lead? What’s easier? What feels different?”
You also keep your personalized AI assistant, now trained on your patterns, as a long-term decision, communication, and clarity tool.
Outcome: visible change in how people experience you, supported by a personal assistant that helps you maintain the momentum.
The Cadence
🗓 Monday → Quick assignment (2-minute read / 5-minute action)
💬 Wednesday → Check-in (“How’d it go?”)
🪞 Friday → Reflection (“Where did this show up again?”)
📅 Every 30 Days → 1-hour group session (“What rep made the biggest difference?”)
Why It Works
- Built for founders: focused, specific, schedule-proof.
- Behavioral reps, not theory: small exercises, compounding results.
- Feedback loops: shared progress in real time.
- Zero fluff: action → reflection → iteration.
What You’ll Gain
✅ Fewer bottlenecks so your team moves faster.
✅ Clearer communication and fewer errors.
✅ Leadership habits that last.
Why Me
I help founders and operators untangle complex problems, from capital to culture. After 25 years in startups, corporate leadership, and investing, I bring context and clarity to real-world leadership challenges.
I’ve facilitated Hampton founder groups for three years, coaching 30 + leaders running seven-nine figure companies. I’ve built and exited businesses in e-commerce, finance, and SaaS.
When we’re improving your leadership habits, we’re also tackling the real-world context that drives them; product launches, hiring crunches, incentive models, automation bottlenecks, and client fires. So this isn’t “executive coaching.” It’s founder-to-founder advisory built around data, feedback, and deliberate practice.
Recap
One Quarter. Lasting Change.
Ready to Run Your Sprint?
Join the Pilot Cohort
Limited to 6 founders. A focused 90-day sprint to build lasting leadership habits. Clearer decisions. Calmer communication. Stronger follow-through.
Start Your Sprint →