Get Unstuck — Wingman Executive
Get Unstuck · Multi-week engagement

When 90 minutes isn't enough.

Some situations don't resolve in a single session. Multiple decisions tangled together. A strategy that needs pressure-testing before you commit. A position you need to defend before it gets harder.

Engagement
From $2,995
Multi-week · Scoped to fit
Diagnose · Build · Deliver

Write to me. Tell me the situation. We'll scope it from there.

01 / Decisions Vs Situations

Some problems are decisions. Some are situations.

Get Clear is for one decision. You're stuck on a call. 90 minutes, the right questions, a clear next move. Done.

Get Unstuck is for the other thing.

A situation with multiple decisions inside it. Stakeholders pulling different ways. A strategy you suspect is wrong but can't yet prove. A position that isn't being recognised, where the cost of staying stuck is starting to compound.

You don't need more thinking. You need someone in the situation with you for a few weeks.

That's what this is.

02 / The Engagement

Three to four weeks. One situation, fully worked.

A scoped engagement with a clear shape. Not coaching. Professional work with defined outputs.

Week 1

Diagnose

A deep working session on what's actually going on. Stakeholders, dynamics, history, real constraints. By the end of week 1, the situation is fully visible. Often for the first time.

Weeks 2–3

Build

We construct the strategy. Stakeholder mapping. Positioning. Success criteria. Pressure-testing every assumption before it becomes a commitment. Multiple sessions, working iteratively.

Week 4

Deliver

Final session. Complete written strategy. 90-day roadmap with concrete actions. Decision points. Abort criteria you can refer back to when the situation moves.

03 / What You Walk Away With

Five outputs. Yours to keep.

No vague takeaways. Specific artefacts you can act on, share with people you trust, and refer back to as the situation moves.

01

The situation, fully mapped.

Presenting problem, underlying problem, moving parts, and how they interact. In writing.

02

A pressure-tested strategy.

Not a brainstorm. A strategy that's been challenged from multiple angles before you commit to it.

03

A 90-day roadmap.

Specific moves. Sequenced. With named decision points where you'll reassess.

04

Stakeholder and positioning work.

Who you need on side. How to position what you're doing. What success looks like in their eyes.

05

A written playbook.

One document. The situation, the strategy, the moves, the abort criteria. Yours to refer back to and update.

04 / Who It's For

If any of these sound familiar.

  • You're carrying a strategic decision with real stakes — a restructure, a market entry, a major hire, a pivot — and you need it pressure-tested before you commit.
  • You're navigating a stakeholder situation where the politics matter as much as the strategy, and getting it wrong has consequences.
  • You're at a career crossroads with multiple variables — role, sector, geography, family — and you need them worked through together, not separately.
  • You've done Get Clear and the situation is bigger than one session can resolve.

Not for

Therapy. Generic coaching. A regular sounding board. This is scoped work with defined outputs. Not an ongoing relationship.

05 / What This Looks Like In Practice

David led a high-impact team the leadership couldn't see.

Strategic Positioning · Multi-week engagement

Sometimes the work is finding out whether the position is winnable.

David ran a specialist team inside a global firm. Strategic engagements. Real outcomes. But the leadership measured one thing: deal size. His division did fewer, smaller, more strategic engagements. On their scorecard, he was a footnote.

He wasn't unsupported. He was unseen. And the cost of staying unseen was starting to compound.

The first question that mattered: is this a battle worth fighting, or one to walk away from?

We didn't try to answer it on day one. We built a process designed to find out. Four workstreams across the engagement.

Internal positioning.

We rewrote the narrative around David's work. Not the work. The story. Anchored to the firm's own stated strategy rather than its measurement system.

Appetite testing.

A structured way to find out whether the leadership had real appetite for change or were offering lip service. The answer would tell David whether the situation was recoverable.

Alliance building.

We mapped the stakeholders. Real influence vs. formal influence. Two senior figures emerged as the people who actually mattered. Not the obvious ones.

Proof of concept.

A bounded, low-risk initiative designed to test the new positioning in real conditions, with measurable signals.

The positioning landed with a few. The proof of concept produced the evidence we'd designed it to produce. But the appetite test came back honest. The leadership cohort that mattered most wasn't going to move off revenue as the primary measure.

That was the answer.

The strategy hadn't failed. The strategy had told him the truth. David made the call to leave with a written strategy, a stakeholder map, and clear decision criteria he could refer back to in the months after. He moved with conviction rather than regret.

Sometimes the work isn't to win the position. The work is to find out whether the position is winnable, fast enough to act on the answer.

06 / How The Engagement Runs

How it actually works.

  • Sessions Video calls. Usually 60–90 minutes. Frequency depends on the situation. Some weeks two, some weeks one.
  • Between sessions I'm working on the situation. Reading what you've sent. Drafting strategy options. Coming back with sharper questions.
  • Communication Email or message between sessions. Not 24/7. Responsive when it matters.
  • Your commitment Honesty about the situation. Time to think between sessions. Willingness to make decisions during the engagement, not after.
  • Mine Full attention on your situation while we're working together. Scoped work delivered to a defined timeline. Nothing left undone.

Already done Get Clear?

Your $495 is credited toward this. The 90 minutes already counts as the first diagnostic conversation.

Write to me.

Tell me the situation. Where you are. What's at stake. How urgent.

I'll come back with whether it fits, what scope makes sense, and what the engagement would cost.