Wingman
The bigger the decision, the fewer people you can talk to about it.
I'm that person.
You already know something isn't right
You've been sitting with it for a while now.
Not a crisis. Something quieter.
A low-grade weight that's there when you wake up and there when you lie down.
You're functioning fine on the surface. But something underneath won't resolve, and you can't name it precisely enough to act on it.
You can't tell your boss. You can't tell your team. You probably can't fully explain it to your partner without it turning into a bigger conversation than you're ready for.
So you sit with it.
And the longer you sit, the heavier it gets.
Most leaders think they have one big problem. They usually have three or four.
A restructure colliding with a career decision colliding with a leadership team that isn't functioning colliding with power dynamics nobody will name out loud.
That's why it's stuck. Not because it's hard. Because it's several hard things pretending to be one.
I pull the strands apart. I diagnose what's actually in the way on each one.
And I build a strategy to move through it. In weeks, not months.
Different stories.
Same three moves.
Stuck on a career move - Mark
Mark had a job offer in a different country. Big change. Everything uncertain. He'd been stuck for weeks.
One question broke it open: what does good actually look like for you and your family?
Turns out he already knew. Long-term in Dubai wasn't it. He just hadn't said it out loud.
Then we named the worst case. The risk he'd been staring at for weeks was far smaller than the fear around it.
Mark took the job. Five years later, he's still there.
Stuck on positioning - David
David led a specialist team at a global firm. Strategic, high-impact work.
But the leadership team only measured deal size.
He was invisible in the room that mattered.
We started with one question: is this a battle you can win, or one you need to walk away from?
We built the case. Repositioned his division around the firm's own strategy. Found two senior allies. Gave him a ring-fenced proof of concept.
Six months later, his division was the example the firm pointed to when clients asked what made them different.
Stuck on a transformation - Nadia
Nadia was 6 months into a transformation across 4 countries.
Behind schedule. Two regional GMs blocking progress. The board wanted results by year-end.
The GMs weren't resisting the system. They were resisting a loss of control nobody had addressed.
We rebuilt the rollout order. Started with the GM who was already aligned. Gave him a visible win. Used that as proof for the others.
The board got their results. Three months late, which was 9 months earlier than it was heading.
Built in the cockpit.
Proven in business.
16 years flying fast jets in the Royal Air Force.
That's where I learned that hesitation is the most expensive habit in leadership.
After the RAF, 12 years running large-scale operations in the UAE. 10,000+ staff. $250M budgets. 17 countries. COO, Divisional VP, Transformation Lead.
The decisions looked different after the cockpit. The mechanics were the same.
Incomplete information. Real consequences. No perfect answer.
With real results:
16
Years RAF fast-jet operations
10,000
Staff under operational leadership
17
Countries of operations
$250M
Budgets accountable for
Two ways to work with me.
The Diagnostic
90 minutes. One session.
You arrive with the visible problem. You leave with the real one named, a clear next move, and the downside mapped so you can actually act.
Most people need this, not months of engagement.
The Strategic Sprint
Four weeks. Full diagnostic and roadmap.
For when the situation is bigger than one session can hold.
Multiple strands, real organisational complexity, and you need a strategy, not just a next move.
If I think you need the Sprint, I'll tell you on the Diagnostic call. If you just needed 90 minutes, I'll tell you that too.
If this sounds like your situation, tell me.
If I think I can help, I'll suggest a 20-minute call.
If I can't, I'll tell you that too.
Got Questions? Good.
Smart people ask before they say yes.
What is this, exactly?
Strategic advisory. You bring a situation that's stuck - a career decision, a positioning problem, a transformation that isn't moving. I diagnose what's actually in the way, build a strategy to move through it, and deliver a concrete plan. It's not coaching. There's no ongoing check-in schedule and I'm not holding you accountable to habits. It's a defined engagement with a deliverable at the end.
How much does it cost?
$7,500 for the full Sprint. If you've already done a diagnostic session first, that comes off the total. You're not paying for two things - you're making a decision in two stages.
What happens first?
A 20-minute call. You tell me what's going on. I'll tell you honestly whether I think I can help. If I can, I'll outline what the engagement looks like. If I can't, I'll say so. No pitch, no pressure.
How long does it take?
Four weeks, plus a 30-day check-in. Week one is deep diagnostic. Weeks two and three build and pressure-test the strategy. Week four is delivery and implementation plan.
Why so fast?
Because I've done this hundreds of times. I don't need three months to understand your situation. Most clients have clarity within the first session that they haven't had in months. Speed is the feature, not a shortcut.
What if my problem isn't a decision?
It rarely arrives that way. Most people come in thinking they have one big problem. They usually have three or four tangled together. The first job is separating them. Once that happens, the path forward becomes obvious.
Is this for people who are struggling?
No. Most clients are performing well by any external measure. The issue is something underneath — a situation that won't resolve, a move they can't quite commit to, a dynamic nobody will name out loud. High-functioning people with real problems they can't talk about internally.
Who do you typically work with?
Senior leaders, founders, capable professionals. People who are carrying something they can't resolve alone. People who've got the experience to know when something's wrong and the self-awareness to want to do something about it.
Do you work outside the UAE?
Yes. Most of the work happens over video. Location doesn't matter. The problem does.
What's the Decision Workshop?
A recorded 60-minute session called The Wingman Decision Workshop. It's the framework behind every engagement I run - built in the cockpit, tested across 12 years of operational leadership. If you're sitting with something you can't resolve and want to understand how I think before committing to anything, start there. $97 and you can watch it today.
Why should I trust a fighter pilot with my situation?
16 years flying fast jets. 12 years running large-scale operations - 10,000 staff, $250M budgets, 17 countries. I've been in the room when things actually went wrong, not just advised from outside it. The instincts are the same whether the stakes are airborne, corporate or personal. Incomplete information, real consequences, no perfect answer.
What if you can't help me?
I'll tell you on the first call. Not after four weeks. If I don't think I'm the right person for your situation, I'll say so directly. That's not a sales tactic. It's how I work.
Wingman
WINGMAN
/ˈwɪŋmən/ noun
A pilot who flies alongside and protects the lead aircraft. The person who has your back when it matters most.
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