A Career Review for Senior Leaders: 8 Questions to Check You're Heading the Right Way

A few years ago I was driving home after a long trip, tired and following the satnav without thinking. An hour in, my friends noticed it had rerouted us towards a charging station miles off course. All that careful driving had taken us further from where we wanted to be.

Senior careers drift in exactly the same way. You're busy, you're delivering, the diary is full, and nobody stops to check whether the destination is still the right one. Being too busy to review your direction is like being too busy to stop for fuel. It works until it suddenly doesn't.

When to run a career review

Most people only do this when something forces them to: a restructure, a missed promotion, a difficult conversation with their boss. By then the options are narrower.

Better moments to pause:

• The run-up to your annual appraisal, so you go in with your own view rather than reacting to your manager's
• After a major programme or deal closes
• Twelve to eighteen months into a new role, when the honeymoon has worn off
• Before you start talking to recruiters or executive search firms

The eight questions

Block out an hour, ideally away from your desk, and write your answers down. Thinking isn't enough; writing forces precision.

• What were the biggest challenges you faced, and how did you handle them?
• Where did you genuinely learn and grow?
• What did you accomplish that you're proud of, with specific results?
• Where did you step up as a leader in a way only you could have?
• How did you manage your energy and focus, and where did it leak?
• What's the single most important lesson of the period?
• Does your current direction still serve you, or are you on autopilot?
• What do you want to create or achieve over the next twelve months?

Reading your answers

Look for patterns rather than individual answers. If your proudest achievements all sit outside your core remit, that's telling you something. If your energy consistently leaks into the same meetings, the same stakeholder or the same type of work, that's a design problem you can fix. If question seven makes you uncomfortable, take that seriously.

Turning reflection into a plan

Reflection only pays off if it changes what you do next. Pick no more than three priorities from your answers and decide what the first concrete step is for each, with a date.

Here's the biggest lesson I've learned from my own reviews: goals are fragile without systems. A goal disappears the first time a busy month hits. A system, such as a fixed weekly hour for career development or a monthly coffee with someone in your target sector, keeps moving even when plans are disrupted.

As for the drive home, we did make it in the end. If I'd slowed down earlier, we'd have got there sooner.

If you're weighing up your next move, book a free 20-minute clarity call. No pitch, just a clearer view of where you are and what to do next.