Should You Stay Or Should You Go?

Sierra Leadership Blog

It’s common for senior executives to think about leaving their jobs, more so than you might imagine. In 2022 a Deloitte survey found that 70% of C-suite executives were contemplating moving to a job that would allow them to have better well-being. So if you have been wondering if you should leave, you’re in good company.

Those feelings can be attributed, at least in part, to the extreme pressures of executive roles: the long hours, frequent travel, and high stress. Executives who lead large organizations often feel the weight of the world on their shoulders because their actions can have an enormous impact on people’s lives.

If you’re trying to decide if now is the right moment to leave your role, here are four strategies to help you create the best path forward.

Delve into who you are, and what you want. As I point out in 10 Tips For Finding Your Next Executive Role , the path to a new role (or deciding to leave) involves getting to know yourself better.?

Take time to reflect on who you are now. You can do this with a journal, in conversations with trusted confidants, or simply by reflecting. Try to paint an accurate, up-to-date picture of yourself, your needs, and what ideal work looks like for you. It’s worth doing this periodically, to refresh your understanding of your evolving experience, perspective and dreams. There are numerous approaches to finding your true north . You might start with questions like:

• What are my biggest strengths and passions?
• What do I already know about what satisfies me most in work, and what doesn’t?
• What are some times I’ve been the most happy and productive? What was happening during those times?

The more you know about who you are, the better able you’ll be to chart a course to a decision. Self-awareness is your internal compass.

Learn what’s out there, and how you’re positioned. While spending time learning about yourself, you also need to learn about the job market. After a few (or many) years in one role or company, you might be surprised to learn that you have some new options. And how can you decide if you want to leave when you don’t have any idea where you might be headed?

Getting to know the job market requires caution of course. It’s a small world, and the more you reach out to people, even “confidential” recruiters, the more likely your manager, board, or other stakeholders will find out you’re looking. Limit this risk by talking only to trusted colleagues or recruiters about your interest in the job market. Let them know the confidential nature of your exploration.

Improve your current work situation. You’re thinking about leaving because life is not great in your current role. But so long as you’re there, are there ways to improve things? Write a list of the biggest pain points in your current job. For each one, brainstorm possible mitigations (you can also do this with a friend, coach or AI). Where is the low-hanging fruit?

Another strategy is to isolate yourself from the source of pain. Perhaps the job can be somewhat limited by drawing more boundaries around it—through stricter work hours, restricting email at home, or keeping communication with a toxic manager only to what’s essential. Just be aware of potential downsides and strike a balance that doesn’t harm your work product or reputation.

Invest in life outside of work. If work isn’t great, why not look towards creating more joy in parts of your life? You’ve spent a lot of your time on work to get to where you are. Maybe this is a good moment to double down on your family life. Or playing guitar. Or going to some museums. Whatever you enjoy, that you’ve been putting off.

A happy life outside of work brings benefits beyond just making you a more satisfied, well-rounded person (reason enough to invest in it!) It also makes you more resilient and energized for work, and better able to navigate your decision and potential job search. One rule of thumb is, when possible, try not to make big decisions when you aren’t feeling good or thinking clearly. You want to bring your best thinking to your biggest life moves.

These four strategies work together. Each one lightens the load, and enables you to be more to be more successful as you proceed. While you take these steps, something may change, or the path ahead may suddenly become clear.