Leadership Advantage Mastermind

For senior product and technology leaders who are tired of carrying the full weight of leadership alone.

The only room where you don't have to explain the context before you speak.

You're surrounded by people who either report to you, compete with you, or don't understand what you're actually navigating.

I know because I've been there. The higher you go, the fewer people you can think out loud with.

Even the best coaching can't replace a table of peers who actually get it.

Leaders who understand impossible trade-offs, organizational politics, and the gap between what the frameworks say and what actually works inside complex, risk-averse environments.

Leaders grow fastest when they're surrounded by people who understand the seat they're in.

That's what this is.

The room I wish I'd had

Andrea Michalek

I've been in masterminds for years: with coaches, with creators, with founders.

They've been my sounding board, my mirror, and often the only place I could skip the backstory and get straight to the real question.

I kept wondering: why don't product leaders have this?

We often lead in isolation.
We make high-stakes calls without a peer gut-check.
We perform confidence in rooms where admitting uncertainty feels like weakness.

Without this kind of space, leaders don't fail loudly.
They just carry more.
They make high-stakes decisions in isolation.
They move fast but not always in the right direction.
And eventually, the weight shows up as exhaustion, second-guessing, or stalled momentum.

And I see what happens when leaders don't find it.
They keep succeeding on paper while quietly burning through themselves.

12 sessions that change how you lead

Every two weeks, 90 minutes, same room of people who know your story.

Leaders don't come here to learn more frameworks.
They come because what used to work no longer does.

Two hot seats per session

You stop carrying unresolved decisions for weeks.

You bring a real challenge: the reorg you're navigating, the exec you can't read, the strategy bet you're second-guessing.

The room works it with you, pressure-testing your assumptions, offering angles you can't see from inside it, helping you land on what to do next.

A guided Beyond Incremental topic

You start seeing leverage where you used to see noise.

Each session includes a framework or provocation from me on leading through ambiguity, escaping the Validation Trap, building authority without waiting for permission.

You'll leave with shared language and tools that compound over the six months.

What you walk away with:

  • Decisions you can stand behind when stakes are high and data is incomplete
  • Patterns you can interrupt in real time, not in hindsight
  • Language that earns trust with execs, boards, and teams
  • A personal operating system for leading without burnout

By month six, you'll have something most leaders don't: a peer group who's seen how you think, knows what you're navigating, and insight to work through what's next long after the cohort ends.

Only leaders. No audience.

Six to eight senior product and technology leaders.
No spectators.
No lurkers.

A room where you can say "I don't know what to do about this" without performing confidence you don't feel.

Peer-driven.
Transformation-focused.
Guided by someone who's been in your seat.

I've founded companies (one acquired twice), led both startup teams and global Fortune 500 teams, and now coach enterprise product leaders and serve as a fractional CTO/CPO.

I built this because I've seen what happens when leaders finally get a room where they can think out loud with people who get it.

This isn't about being understood.
It's about making better decisions faster, because you're pressure-testing them with peers who actually understand the terrain.

Also included

Beyond Incremental Framework

The backbone of how we work together.

A methodology for breakthrough leadership that gives the room shared language, not just shared problems.

Private Slack channel

Async support between sessions.

The conversation doesn't stop when the call ends.

60 min each

Two private coaching sessions with me

The group gives you peer perspective.

These give you direct access to work on what you can't bring to the room: politics, career moves, the stuff that needs a different kind of thinking partner.

Who this is for

Senior product and technology leaders: CPOs, VPs of Product, VPs of Engineering, Founders, CTOs, Directors. Leaders who are:

  • Driving innovation inside enterprise constraints
  • Navigating the tension between bold ideas and organizational realities
  • Looking for systematic approaches, not tactical hacks
  • Ready for accountability that actually sticks

This isn't networking. It's not content consumption.

It's a working group for leaders who want to transform how they operate, not just optimize around the edges.

This probably isn't for you if:

  • You're looking for a networking group or LinkedIn connections
  • You want to observe rather than participate
  • You're not willing to be honest about what's hard
  • You need permission from your calendar to prioritize yourself

The commitment

6 months together

A commitment to yourself, to the work, and to the other leaders counting on you to show up.

This is six months of high-caliber thinking, perspective, and accountability.
The kind leaders usually try to approximate through advisors, offsites, or years of trial and error.

Product Leaders Cohort Investment

$3,500

Apply Now

6 spots available. Founding cohort rate.

Applications close March 31, 2026 or when filled, whichever comes first.

Interested?

This isn't open enrollment.

I'm looking for six leaders who'll challenge each other and commit fully.

The application helps me understand if we're the right fit - for both of us.

Apply Now →