After a difficult quarter, a senior manager updates their CV late one evening. A month later things feel calmer, and the CV goes back in a folder. Three months after that, the cycle starts again. They have been “thinking about leaving” for two years.
Deciding whether to stay or leave a job is one of the biggest career decisions most people make, and one of the least structured. It is often made on a bad day, or postponed indefinitely on a good one. At senior level the stakes are higher: your reputation, your finances and your relationships are all bound up in the role, and a poor move is harder to undo.
This guide offers a practical framework for making the decision well, so that whichever way you go, you go on purpose.
Why this decision is so hard
- Mixed feelings are normal. Most jobs have parts you value and parts you don’t. Very few decisions are clear-cut.
- The known feels safer than the unknown, even when the known is not working.
- Bad days distort the picture. So do good ones.
- Senior roles come with golden handcuffs, such as bonuses, pensions, status and relationships built over years.
- Leaving can feel like failure, particularly if you have invested a lot in the organisation.
The aim is not to remove the difficulty, but to replace a cycle of frustration and relief with a clear, considered decision.
Separate the problem from the role
Start by writing down exactly what is making you think about leaving. Then sort each item by how changeable it is.
| What’s wrong | Could it change if I raised it? | Is it likely to change within a year? |
|---|---|---|
| A difficult relationship with my manager | Possibly | Depends on the organisation |
| Workload and hours | Often | Often, with a direct conversation |
| No route to the next role | Sometimes | Depends on structure and timing |
| The organisation’s values or direction | Rarely | Rarely |
| Lost interest in the work itself | No | No |
Problems near the top of this table can often be fixed without leaving. Problems near the bottom usually can’t, and staying in the hope that they will change tends to lead to years of frustration.
Five questions to test the decision
- If you were offered your current job today, would you accept it? Knowing everything you now know about the role, the people and the organisation.
- What is the cost of staying another two years? To your career, your energy, your health and the people around you.
- What specifically would you be moving towards? If the answer is only “anywhere but here”, more thinking is needed first.
- Have you genuinely tried to fix what can be fixed? Have the conversations been had, clearly and directly?
- What would you advise a respected colleague in your exact position? People are often wiser about other people’s careers than their own.
A simple scoring framework
When your thinking keeps going in circles, putting it on paper helps. Score your current role and a realistic alternative against the things that matter most to you. Choose your own factors and weight them by importance.
| Factor | Importance (1–5) | Current role (1–10) | Realistic alternative (1–10) |
|---|---|---|---|
| Interest in the work | 5 | 4 | 8 |
| Relationship with leadership | 4 | 3 | 6 |
| Financial security | 4 | 9 | 7 |
| Growth and next steps | 4 | 3 | 7 |
| Time and flexibility | 3 | 5 | 6 |
Multiply each score by its importance and add them up. The numbers won’t make the decision for you, but they often show clearly where your instinct already lies, and where your worries are about one or two factors rather than the whole picture.
Be careful to compare against a realistic alternative, not an ideal one. Every new role comes with its own frustrations.
The conversation to have before you decide
Many people leave jobs over problems their employer never knew about. Before you decide, it is usually worth one direct conversation with your manager, or with a trusted senior sponsor if your manager is part of the problem.
Keep it constructive and specific:
- Say what is working. It shows you are raising this because you want things to work, not because you have already gone.
- Name the issue clearly. “The scope of my role hasn’t changed in three years, and I’m not developing the way I want to.”
- Say what would make a difference. Be concrete: a different remit, a timeline for promotion, a change in workload.
- Ask for their view, and listen properly to the answer.
- Agree a next step and a date to come back to it.
You don’t need to mention that you are considering leaving. The response will tell you a great deal: whether your concerns are taken seriously, and whether change is genuinely possible. Either way, your decision becomes better informed.
Getting the timing right
Even once you know the answer, timing matters. A few practical points are worth weighing:
| Consider | Why it matters |
|---|---|
| Bonus and pension dates | Leaving a few weeks earlier or later can make a significant financial difference |
| Notice period | Senior notice periods are often three to six months, which affects when you can start elsewhere |
| Projects in progress | Finishing a major piece of work strengthens your reputation and your next interview examples |
| The job market in your field | Some sectors recruit in clear cycles; others are steady year-round |
| Your energy | If you are exhausted, a period of recovery before a search may lead to a better decision |
None of these should keep you in a role that is clearly wrong for you. But a well-timed move is usually a better-paid, less stressful and more successful one.
If you decide to stay
Staying can be a positive decision, not a default. Make it one:
- Have the conversations you have been putting off, about workload, scope, development or your next step.
- Agree what would need to change, and by when, for staying to remain the right choice.
- Build a plan for the next stage of your career where you are. A Career Development Plan for Senior Professionals shows how.
- Set a review date, perhaps six or twelve months away, to check whether things have moved as you hoped.
If you decide to leave
Leaving well matters at senior level. Your reputation travels with you, and your former employer may become a client, partner or referee.
- Don’t resign before you have a clear next step, unless your health or circumstances genuinely require it.
- Search quietly and professionally. Use your network rather than broadcasting your plans.
- Prepare for interviews properly. Panels will ask why you are leaving. Answer positively, focusing on what you are moving towards.
- Hand over thoroughly. How you leave is remembered longer than how you performed in your last few months.
- Stay in touch. Former colleagues are among the most valuable relationships in a senior career.
If your next move is into a different field altogether, Changing Career in Your 40s or 50s covers how to plan it with less risk.
Talking it through at home
A decision to stay or leave rarely affects only you. Partners and families feel the impact of your work, and they will feel the impact of any change. Involving them early usually makes the decision better and the transition easier.
- Share your thinking before you have decided, not once you have. People support decisions they have been part of.
- Be honest about the money, including the worst realistic case and how you would manage it.
- Ask what they have noticed. People close to you often see the effect your work is having on you more clearly than you do.
- Agree how long you will take. A defined decision period is easier on everyone than open-ended uncertainty.
If the people around you have different views, that is normal. The aim is a decision you have made together with your eyes open, not unanimous enthusiasm.
Common mistakes
- Deciding on a bad day. Or postponing on a good one. Make the decision over several weeks, not one evening.
- Leaving to escape one person. Managers move on too, and the next role may bring a different difficult person.
- Accepting a counter-offer without fixing the underlying problem. More money rarely solves a values mismatch.
- Staying out of loyalty alone. Loyalty matters, but organisations make decisions about roles for their own reasons, and you are entitled to do the same.
- Never deciding. Years of ambivalence take their own toll on energy and career progress.
Not sure what you want next? The free Career Clarity Assessment maps your interests, work values and preferred ways of working, and takes about fifteen minutes.
Weighing up whether to stay or go?
I work one-to-one, online, with mid-career and senior professionals who want clarity about what comes next. Wherever you’re based, sessions are scheduled around your time zone.
Career Development Coaching helps you get clear on direction, understand your strengths and gaps, and build a practical plan, with accountability while you act on it. Where it’s needed, it also includes CV and LinkedIn improvement and interview preparation.
If you’d like to think it through with someone outside your organisation, book a discovery call and we’ll look at the decision clearly and confidentially.