4 Things Every Leader Should Do Before They Retire

At The Workplace Coach, we’re known for sharing expert insights and actionable strategies that help leaders unlock their full potential—at every level of their career. But today’s article offers something a bit different. It’s not about your next promotion or a leadership pivot. It’s about what comes after.

The truth is, most leaders—especially high-performing, type A professionals—don’t retire well. Not because they failed to save or plan financially, but because they underestimated how much more there is to prepare for beyond the numbers. Retirement is more than a finish line—it’s a transition into a new identity, a new rhythm, and ideally, a lasting legacy.

This piece highlights four essential actions that every leader should take to retire with intention, clarity, and purpose. Whether you’re a few years out or already preparing for your encore chapter, these steps can help ensure that what you’ve built doesn’t just end when your job does—it evolves.

Most leaders have a pretty good handle on what they need financially to retire. Like you, they’ve saved and invested over the years to prepare for the next chapter. It wasn’t always easy, but it came with a straightforward road map. Plus you could always call in professional help if you needed it.

But when it comes to your legacy, the road ahead for retirement is less clear. Few leaders are ready for a structured handoff that ensures their impact will survive after they’ve left the building for good. Yes, there is professional help for this too -- more on that in a bit.

In the meantime, take a look at these 4 key actions you’ll want to take when getting ready to retire. They provide the broad brushstrokes for what a smooth transition and leaving your legacy might look like.

1.        Cultivate Your Successor

Your experience, insights, and relationships are assets that have grown over time. You don’t have to let it all disappear when you leave. Have you had your eye on a promising employee that with the right kind of preparation could do much more than they’re doing now?

Consider having them shadow you at important meetings. Let them see exactly how the sausage is made so you can see if they can help make it. Get them in leadership training now. Because best case, succession planning is an ongoing process; it’s not left until the last minute to fill a leadership gap.

2.        Document Key Processes

In an ideal world, there would already be a user guide of all the work you do. Maybe you’ve already documented a collection of processes that keep things running smoothly. If so, that’s a great start.

What your colleagues will most benefit from – and they can keep adding to – is a knowledge-sharing system so all that institutional know-how doesn’t rely on any one person. It could be simple shared platform or dashboard where people can access the latest and greatest guidance on demand, such as manuals, trainings, templates, and webinars.

3.        Strengthen the Culture

You’re living the company’s core values like collaboration and communication in your daily work. Now is the time to take steps so the culture you’ve helped to shape lives on after you.

Consider formalizing the mentoring process with standard operating procedures. Set up touch-base meetings for a full year out. Write down or record your key insights, reflections, and experiences. All these can help promote a resilient culture with your unique imprint that carries on when you’re gone.

4.        Plan for Your New Life

It’s natural to identify with your job title, circle of influence, and daily schedule. It’s who you are and what you’ve done over pivotal years in your work life.

Retirement means a major shift to a new identity, or at least rebalancing what you focus on and how you spend your time. This happens when you explore an interest more deeply or find ways to share your hard-won expertise. Don’t spend too much time thinking. Make solid plans for how and when you’ll take the next steps, with days and times figured out and committed to.

After the honeymoon period – those first few weeks and months when you do what you want, when you want – those enjoying retirement find they’re spending time learning something new or contributing meaningfully to something important, and sometimes they’re doing both. With a plan.

Support from the Workplace (and Retirement) Coach

Have you got all four actions covered – succession, documentation, culture, and planning? What steps are you ready for, and which could use some support?

The Workplace Coach helps leaders refine their retirement strategy to ensure their legacy will last and their next chapter will resonate. When coaching is part of the process, gaps in preparation can be spotted before they become roadblocks to success.

We specialize in anticipating and finding solutions for the challenges that face today’s leaders in an increasingly complex business ecosphere. Let’s talk about how executive coaching at this important time can optimize your transition.

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