Free resource

The Executive Transition Audit

Five questions every senior leader should ask before their next career move.

The higher you go, the more each career move costs, and the fewer people you can talk to honestly about it. A promotion, a new organisation or a change of direction can be the best decision you ever make. It can also be a move made for the wrong reasons, at the wrong time, without the support you need.

I've spent more than 20 years in senior HR, watching leaders make these decisions from the other side of the table. The ones who thrive have usually asked themselves a few hard questions first. This audit gives you those questions.

How to use it: set aside 30 minutes somewhere quiet. Answer each question honestly, in writing if you can. Then rate how ready you feel on that question from 1 (not at all) to 5 (completely). There are no right answers. What matters is what you notice.

01

Why this move, and why now?

Are you moving towards something you want, or away from something you don't? Both are valid, but a move driven only by frustration, boredom or a difficult boss often brings the same problems with it. Timing matters too: what is happening in your life, your organisation and the market right now?

  • If nothing about my current situation changed, would I still want this?
  • What am I hoping this move will give me that I don't have today?
  • What would I regret if I waited another year, or if I didn't wait?

My readiness: 1  ·  2  ·  3  ·  4  ·  5

02

What will success look like in 12 months, and who decides?

At senior level, success is rarely defined by the job description. It is judged by a small number of people, often against expectations nobody has written down. Leaders who stumble in new roles usually haven't misjudged the work. They've misjudged what was really expected of them.

  • What three outcomes would make this move clearly worthwhile a year from now?
  • Who will judge whether I've succeeded, and what do they care about most?
  • What unspoken expectations or history might come with this role?

My readiness: 1  ·  2  ·  3  ·  4  ·  5

03

Which strengths got me here, and which could hold me back?

The skills that earn a promotion are not always the ones that make you successful after it. Deep expertise, being the person who fixes things, or driving results personally can all become liabilities when the job is to set direction, delegate and lead through others.

  • What am I known for, and will the next role need more or less of it?
  • What will I need to stop doing, or let go of, to succeed at the next level?
  • Where have I had feedback I've been reluctant to act on?

My readiness: 1  ·  2  ·  3  ·  4  ·  5

04

Who do I need on my side, and where do I stand with them today?

Senior appointments and early success depend on relationships as much as ability. Decisions about who gets promoted, and who gets backed when things get difficult, are often shaped by sponsors and influencers you may never see in the room.

  • Who are the five people whose support matters most for this move?
  • Who is actively sponsoring me, and who might quietly oppose me?
  • Which relationship, if I invested in it now, would make the biggest difference?

My readiness: 1  ·  2  ·  3  ·  4  ·  5

05

What am I not willing to compromise?

Every senior role asks for something in return: time, energy, visibility, sometimes your values. Knowing your limits before you start makes it far easier to hold them under pressure, and to spot early if a role isn't right for you.

  • What matters most to me outside work, and how will this move affect it?
  • Which of my values would I find hardest to protect in this organisation?
  • What early warning signs would tell me the cost is getting too high?

My readiness: 1  ·  2  ·  3  ·  4  ·  5

What your scores tell you

Add up your five readiness scores.

  • 20–25: Ready to move. You have a clear rationale and a good grasp of what lies ahead. Focus on a strong start: your first 90 days will shape how you're seen for years.
  • 13–19: Nearly there. The direction feels right, but one or two areas need more thought. Look at your lowest score: that's where a move is most likely to come unstuck.
  • 5–12: Pause and get clear. This doesn't mean don't move. It means the decision deserves more space before you commit, ideally with someone who can challenge your thinking.

Whatever your score, look again at the question you found hardest to answer. It is usually the one most worth talking through.

Want to talk it through?

I offer a free, confidential 30-minute strategy call for leaders weighing up their next move. We'll look at your answers together, and you'll leave with a clearer view of your next step, whether or not we go on to work together.

Book a confidential strategy call

Book at jeannawenhamcoaching.com

Jeanna Wenham · Executive & Leadership Coach · ILM Level 7 · Chartered MCIPD · EMCC Professional Member