Leadership Succession

A life-and-death question for small organizations

Photo credit: Camilo Jimenez

Recently, the theme of leadership succession has felt pretty ubiquitous. It keeps cropping up in conversations with clients, in colleagues’ work, even with friends. Which got me thinking about the issue of succession in smaller organizations (10–100 employees) — the kind I’ve spent most of my career consulting to and helping to build.

As the leaders who stepped up ten or twenty years ago move on they will create opportunities for others. They’ll open up space for fresh ideas, creativity and learning. Unfortunately — and unintentionally — many of them will also leave crises and mayhem in their wake.

Small organizations often have a difficult time surviving their founder’s departure. And usually, the challenge doesn’t begin with the new leader — though he or she may end up shouldering most of the blame.

Why losing their leaders (and especially pioneer leaders) kills some small organizations

Here are just a few reasons that this happens with some regularity. Often they occur in combination.

  • Critical external relations with backers, major clients or donors are invested in the departing leader. As is their confidence. She goes, and most of the money, support and work promptly dry up.
  • The old leader’s departure sparks an exodus of key staff. Perhaps they stayed for you, and not for the purpose or the work. Maybe they sense trouble ahead. Or just fear change. Whatever the reason, the organization is left empty and incapable of working effectively. It withers away, regardless of new management.
  • Mom (or Dad) leaves and the kids embark on a power struggle to decide who should rule the roost — and control the budget. The ensuing chaos rips the organization to shreds.
  • The founding CEO has one or two skills that no one else in the system possesses, and without these, it can’t go on. This can be as basic as being able to speak and write with real conviction about the work, or as complex as the loss of very scarce skills and the ability to offer a unique service.
  • Insufficient preparation and thought go into the process of appointing a new leader. Someone who looks good on paper, interviews well — or just has ready capital — is chosen. They may not really understand the core business. They may not buy into the culture or values. Their experience might not equip them to run the specific kind of organization that they’ll now have to lead. And then, zero support is offered to them — on the grounds that the old CEO coped well enough, and therefore, so should they. This is a quick and effective recipe for disaster.
  • The owners or board lose confidence in the new leader, or in the capacity of the old staff in the absence of the old management shoring up the cracks. They decide the risks are too great and start jumping ship — one crisis too many for an already fragile organization to absorb. Cue exodus. Lower lights. Sell assets.
  • The new leader can’t win staff over or get to grips with what the old leader has left her to deal with. She throws up her hands and leaves after six months. The next incumbent finds things in an even worse state — he only sticks it out for three months. And so it continues until the system is bled dry by a series of incumbents who find it all pretty unmanageable. (Sometimes this is because of bad hiring practices. It’s also often a consequence of the complex mess left behind by a departing leader who — to be fair — may not have known how to do it any differently.)

There are other scenarios too: death by nostalgia (“We just can’t go on without you” — flattering, but sad); death by missing the point (i.e. the new CEO fiddles with the core process, although it’s working just fine); death by bureaucracy (the new leader feels out of control and imposes a bunch of new procedures and controls that drain energy and alienate both staff and clients). Or the organization literally makes the new CEO sick, so he’s absent all the time. Or the new leader goes crazy with frustration and decides to channel Josef Stalin… After the second purge of dissidents, there’s nothing left to save.

And so on. The variations are probably endless.

But, none of this is necessary. It may be that a little slump in effectiveness is inevitable — leadership change is significant, and it does affect the whole organization. But it need not produce a life-threatening crisis.

What’s the alternative?

The fairytale version

You might be really fortunate, or really skilled, or possess a simply sterling combination of wisdom, foresight, and good luck.

The perfect new leader may emerge fully formed. She may even be an existing employee. So, the transition goes seamlessly: she is loved by one and all, as well as being excellent at her job. And everyone thinks fondly of you, the departing leader, and wishes you well on the next stage of your journey. This story ends with everyone living happily ever after — at least until the next economic, environmental, technological or political disruption comes along.

I’ve never actually seen exactly this happen, but I’m sure it’s not impossible. Still, although fairy tales are nice, preparation is probably better.

The pragmatic version: prepare for succession

This is a topic to which I’ll return in future posts. For now, three thoughts:

1. See the whole system

In order to prepare for leadership succession, you have to deeply understand what it is that you, as a leader, have been holding. What you have done for and to your organization. (Every leader shapes cultural norms in one way or another.)

And get to grips with how the whole system is actually working, in context. (Many top managers lose contact with the heartbeat of the day-to-day work, or with parts of the organization’s ecosystem. Now’s the time to reconnect, so you really know what you’re handing over.)

Getting a handle on all of this, as well as working really hard to see your people (with all their gifts and challenges) and your organization (with all its assets and blind spots), is the basis for making a workable change plan and orchestrating a responsible transition.

2. Don’t do it alone

You probably can’t (and shouldn’t) do this alone.

It’s practically impossible to see a system that you are so intimately connected to with any objectivity at all.

Get help — certainly from your board or partners, perhaps from your senior team, and preferably also from someone with a little more distance: an OD person, a consultant you trust, or a colleague with wide experience who understands the dynamics of change, and thinks systemically.

3. Design a holistic change process

Once you have some help, be aware that the change process that needs to be designed is not just about who will ‘replace’ you. (Those scare quotes acknowledge the impossibility of simply replacing anyone.)

This is an excellent opportunity to look at where the organization is going and what it will need to get there, to look at the culture and ask if it is serving your larger purpose, and to think about what is realistic and desirable, not just what is needed.


Approaching leadership transition and succession could be an opportunity to seriously strengthen and future-proof your organization; to ensure its relevance and effectiveness for years to come. Or, it could a harbinger of disaster if the wrong choices are made — or, even worse, if key choices are left unmade.

The legacy of your leadership should not be the failure of whoever comes after you — or of the organization you’ve spent years building. But avoiding the complexity of leadership succession can unintentionally set everyone up for precisely that outcome.

Based on a post published on https://warrenbanks.co.za on May 29, 2019. The original version focuses more narrowly on the South African civil society sector.

The Startup

Get smarter at building your thing. Join The Startup’s +800K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store