Succession Planning: Ground, Fruition & the Path

Succession planning seems like something both natural and necessary, and in most cases it is. At the same time, it is not particularly simple, easy, or effective.

Succession planning serves a variety of purposes, ranging from major corporate HR policy to individual founder/CEO contexts. I’m going to focus on the latter.

It is not uncommon — indeed, it’s quite expected — that at some point along an organization’s path, it becomes apparent to the leader (who may be a CEO or a founder, either the original founding CEO or someone who has served in the role by selection and appointment) that a transition is coming. Sometimes succession planning is instigated by an enterprise’s partners or shareholders instead. 

I’d like to share a few reflections that have arisen primarily from my experience as a coach and a student of organizational dynamics.

The Ground

The first question I’d propose to reflect on is: what matters, and why? What is important to the person or people who are deeply invested — not merely monetarily — by their commitment and effort on behalf of the enterprise? This may seem like a straightforward question, but it’s worthy of reflective attention, perhaps aided by journaling or conversation with others within and outside the organization.

The way I suggest approaching this is through what I refer to as threefold logic. Virtually every journey, whether undertaken with intention or arrived at through circumstance, is shaped by three dimensions.

The first is ground — what is the situation now?

What is the state of our enterprise? What is my own state, presuming I’m thinking about my own succession? What is motivating the notion of moving toward transition?

For some of us it may be as straightforward as recognizing who I am — not who I was, but who I am now. Perhaps I have aged, or — more significantly — I feel that I have lost my drive, my energy, my motivation, or some of my capacity. Perhaps I am no longer able to perform as I aspire to. Perhaps I have held the seat of leadership for a long time, or at least a substantial time, and an honest reckoning — holding a mirror up to myself — reveals that I was never really in the role that suits me, or that I have been more than good at. It may also be the case that I’ve been fooling myself, or ignoring what’s going on with me and around me — that my self-awareness hasn’t extended into a more mirror-like wisdom.

But circumstances — results, feedback, consequences, all kinds and types of messages from the world within and beyond the organization — may finally bring me to the point of realizing it’s time, or close to time, to make a shift. I may feel I’m still genuinely good at being the leader I’ve been, but I’m tired. My energy and motivation may have waned. Other circumstances in my life may have changed, sending me the message that this is no longer working, or that my priorities need to shift — illness, relationships, family, other needs that have finally outweighed my ability to focus and deliver as I, and others, should expect. These messages from within and without may not have been within my awareness, or may have been ignored, minimized, or avoided.

Why does this part of the journey matter? Not only because it moves me to action, but because it bears on how I will continue to serve — and even improve — my leadership during this penultimate stage. Almost without doubt, these factors have affected those around me. It’s never too late to step up and lean in, even as I prepare to step out. This part of the leadership journey also best prepares the organization to receive its next leadership, and to be in as healthy a state as possible for what will inevitably be a time of turmoil, uncertainty, and risk on multiple levels.

This is not just about me, however. The ground also includes a host of other factors and dimensions. What is the current state of the enterprise? Where are we along the path and ladder of success? How stable are we? Where do we sit in our market? Where are we going? What is our current strategy, our medium- and longer-term objectives? What’s next for us? What pressures are we facing? What changes will drive our organization through this next period of time — and if not me, whoever is next will have to face these same factors.

If I’ve concluded that part of the challenge is that the organization we built to this point is no longer the organization matched, ready, and needed for our current stage and the world now arriving, I may be too settled or entrenched in familiar patterns to have faced up to, or dealt with, some or many of the transitions we must respond to or anticipate. What will the role need to be, or become?

Over time I have worked with a number of clients who have succeeded parents in leadership roles. The details are always unique, but I can point to some recurring patterns. Both parent and successor are necessarily dealing with a variety of emotions.

For example, on the parental side, “Who am I if I’m not CEO of…?” And for the successor, “Did I earn this, am I ready, what are others thinking of me, and/or how will everyone within and beyond the company act in light of expectations? On top of these psychological dimensions, there are issues, challenges, and transitions calling for attention within the organization. In one case, my client (the son succeeding his father as CEO) quickly came face to face with many untended issues- including a variety of deeply embedded sinecures, with senior executives living in comfortable, lax, or autocratic fiefdoms, including inappropriate self-serving patterns of operation. In this and similar situations, evident problems can be ignored for a long time if the company is still successful and can be accepted as ‘just the way it is’. My client was not insulated from a long period of hard decisions, difficult changes, and winning over the support among the body of employees and passive support of the ‘retired’ parent who has, in many cases, still exercised considerable influence, if not authority, on an ad hoc basis. 

I have encountered a parental successor who soon after taking the reins came to recognize that his original ‘aspiration’ to succeed his parent was driven by feelings and expectations that were not actually in his own sphere of joy. He realized it was now time for him to begin exploring who the next CEO — not himself — should be. He had learned and worked through many things that helped him understand how to be and act as a human in leadership — a primary piece of the ethos within Reboot: the best humans make the best leaders. But as a leader, precisely by paying close attention to his own well-being and the company’s needs, he realized he was no longer the right match.

All of these things, and innumerable more, may be part of the ground upon which the interest in, or need for, transition and succession comes to the fore.

Fruition

The next stage in the consideration I’ll call fruition. Fruition is about how we know the transition has succeeded. We can’t know in advance — we may not even be present by the time it’s possible to take stock of the new leadership’s emerging success — but we can hold some clarity about what success would look like. I sometimes phrase it as an image: I wake up in three years, and even before my eyes are open, I can’t believe this is my life. I’m interested not so much in what I’m doing, but in the characteristics and attributes of that life that would allow me to feel that way.

It’s much the same with an organization, though it’s a different type of being. An organization has outer and inner characteristics. On the outer level, those attributes are largely quantitative and measurable — growth, recurring revenue, size, expansion, steadiness, and a number of others. But an organization is more than its outer characteristics.

This is something that is core to how we understand it within Reboot: an organization also has an inner being. Inner being speaks to elements, attributes, and difficulties that touch on culture, behavior, degrees of collaboration, and — overall — the way an organization treats itself and all the people within it. It affects the nature of the people we seek to hire, and, in time, the people we ultimately need to un-hire.

It is possible, of course, to succeed on the outer dimensions even when the inner dimensions are not fundamentally healthy, or aligned with the values, practices, and approaches that I know are most important to me and to the organization as a whole — the things that make us not only good at what we do, but good in the way we are and the way we do it.

Some of my greatest joys as a coach have been to work with clients through lengthy journeys and ultimately transition. When a small startup grows over years to realize a successful ‘exit ’, there are inevitably many twists and turns, ups and downs, inner struggles, challenges, choices and actions, in both the company’s and the leaders’ personal paths. It is particularly satisfying if the path of building from idea to match to market and beyond has proceeded with allegiance to core values and cultural attributes. 

My summary: humanity intertwined with focus, clear-eyed fairness, discipline and openness, listening within collaboration, and persistence and respect in every direction. At the time of transition, which may be a sale, but in at least one personal experience as the co-founder’s coach, a new owner kept the original founders in their leadership roles. The succession ‘hand-off’ was not between leaders, but into a new corporate universe. Maintaining the essence and key components of the established and successful culture (and perhaps even influencing the new ‘mother ship’ culture) is yet another opportunity amidst uncertainty. 

When you consider succession, regardless of its specific nature, how much of the intended outcome should include characteristics like these — or any characteristics you’d consider the tuning forks of your enterprise?

The Path

That brings us to the central part of the journey, which is well named the path. The path is about how you will intend and act to get from the moment of now to the time of fruition, and it bears — in every important way — on both who and how you select as candidate leaders, and how you make the choice and handle the transition with them in the handing off of the baton.

Handing off the baton is not necessarily as simple and final as it sounds. Sometimes the baton doesn’t quite pass smoothly.

In one assignment, I was supporting a CEO who had upleveled existing senior staff to the CEO-COO positions. During pre-handoff months, the founding CEO recognized that he was still taking the lead in recruiting, hiring, and onboarding for two significant go-forward C-Suite roles – part of his ‘special sauce’ abilities, but ultimately concluded that the timeline of his departure and these recruitment priorities were not likely to be completed successfully by his long-announced ‘final day’. He raised the question, “what is the distinction between abdicating and delegating?”, concerned that staying on, if only to complete these two processes, would collapse his succession boundary. We explored a nuanced perspective, the distinction between abdicating and completing, and the possibility of exploring and defining with clarity a short-term, narrow ’completion’ process with his successors. 

In yet another situation, I was working with a founder-owner of a mature company (still growing and expanding) trying to redress a transition that didn’t seem to be working with the replacement CEO — about eighteen months in. He hadn’t given up on it, but in essence he concluded that it wouldn’t, and could not, work — not a good match, without the right skills or attitude. I’ll leave the end of that story incomplete. In situations such as this, the final decision to change again would have impacts and implications from having made an unsuccessful choice the first time — how it could have gone differently, and how the process needs to unfold if it has to start over. Willingness to meet the moment, and to live through the discomforts of consequences never expires. Retaining our steady leadership stance when the seas are rough, and the storm doesn’t relent, is always our leadership aspiration and practice. Every sailboat captain knows that. 

I’d like to lay out some additional dimensions of the succession path:

Internal or external?
Do you have a preference, requirement, or judgment that your successor should come from your current group of employees, or are you open to, interested in, or feel it necessary to recruit from outside?

Modeled on you, or built for what’s next?
In either case, do you believe the incoming successor should closely resemble you — in levels of expertise, skills, experience, and style — or do you judge that you need someone who can pick up from where you are now and carry the company toward its next, longer-term future? If it’s the latter, an honest look at your own gaps is warranted. You may well want to include your current executive team, advisors, board, or other outside voices in that assessment.

If you visualize where you’ll be — let’s say over the next three years or longer — what will you need that you don’t have now, or that you’re no longer energized to deliver? I’ve often experienced and seen that hiring a successor also involves a broader leveling-up of your current leadership structure. Generally — though not always — it’s not helpful to make new executive hires before the new CEO has had the chance to arrive, settle in, and gain experience and perspective, and only then make adjustments to her or his executive team. Ask yourself: what does this role need to become, in the short term and soon after?

If internal: what are the skills and experience levels you judge critical for the next generation of leadership?
If there are one or more internal candidates, what are their individual strengths and the areas they’d need to strengthen — and is there time to provide the support, training, coaching, and guidance that could make that development realistic?

If external: you’ll need to address the whole separate journey of recruitment, which probably deserves its own exploration.
But one thing needs to be clear and well communicated to everyone involved in the search: the full spectrum of capabilities, experience levels, and values fit that’s needed, and why.

Decision-making process.
This, too, could be explored in depth on its own. Key questions: who needs to be involved, who needs to have input, at what stage, and to what extent? To what point is confidentiality imperative, and what level of transparency will serve the candidate and the culture?

Communication and collaboration.
There is no formula that can dictate how and to what extent to communicate and solicit feedback or input from internal and external stakeholders during the process of executive transition. All I suggest is to recognize that internal communication can be a significant benefit – to morale, alignment, preparedness, and contribution to recruitment, selection, and the departure/arrival runways. And simultaneously point out that too much communication – if not thoughtful (or at worst random), contained within boundaries, and without purpose, can backfire. Communication with, feedback, guidance, or active participation from impactful or governance positions (board, investors, key advisors and perhaps a few key clients) may be essential. The extent to which the recruitment and hiring plan/process will include (and how) broader leadership or stakeholders is also an important decision. 

Emotional and political dynamics.
Any organizational — or personal — change carries emotional dynamics, and there may be political dynamics within the organization as well. That’s another discussion in itself, but important to name here.

Runway.
How much runway do you actually have? This isn’t just about time — it includes effort and resources, yours and others’.

Compensation and boundaries.
Bringing in leadership at that level, or any executive level, must balance against the market for the talent that meets your requirements. Recruiting and hiring a new CEO is one of the most significant investments an organization makes — not merely a cost, but a question of value, in the context of the results and outcomes that can make or break the next arc of your organization’s journey.

This process triggers real tension.
It’s hard to recognize, much less say out loud: “I’m not the person for what this organization needs to become.” Nothing good comes from failing to lean into how this change will affect your identity, your ego, and — in ways you may not anticipate — the story of your life. It will likely also change your financial relationship to, and access to, the capital you’ve accumulated. If you’re working with mentors, guides, or a coach, this period of transition is one of the most fertile and demanding, emotional and psychological parts of a life journey.

What you can’t see on your own.
Looking honestly and openly, and getting input from colleagues, mentors, and friends, may illuminate some of the changes that are hardest to see. Growing organizations that are scaling naturally shift — in most or all dimensions — from a founder-centered structure to a diverse, layered one. It has always been a myth that a founder-CEO is supposed to “know everything,” or even act like they do. The wiser path is to draw on collaborative wisdom at every level to generate the best choices — often surfacing steps and directions the founder wouldn’t have arrived at alone. That requires the consistent evolution of systems and approaches to delegation. Looking at your successor, consider what particular attributes, skills, and demonstrated capability have been missing, and are needed.

Succession doesn’t mean disappearing.
Very often, particularly in founder-led businesses, the outgoing CEO still has a large and significant stake in the company’s future. So the question isn’t only about leaving or stepping aside — it’s about stepping into what.

Sometimes it works very well for the former CEO to step into a governance role — often as board chair. But there’s a major difference between governance and management, and understanding and being willing to make that shift is critical. Very few things are more challenging than a founder who can’t let go to the extent senior management needs, in order to sail the ship forward. In parallel, it’s entirely possible for a founder to transition successfully into a governance role that recognizes and works the intersection of strategic direction and execution — another story for another time. I’ve also seen former CEOs transition well into an active operating role well matched to their particular strengths — perhaps as the external-facing voice, even an evangelist, or the lead product visionary.

The two keys are: does that role take advantage of your unique strengths, and can it be done without impinging on executive leadership’s overarching management responsibility? Very few things create more friction than a governance role that dives into the weeds, particularly by whim. Few executive leaders — and especially CEOs — benefit from a former CEO stepping into actions or decisions and exercising unwarranted authority. None of this suggests leaving entirely is the only acceptable option. We can all name both famous and infamous corporate leaders who either continued to add important value, or, conversely, undermined and even damaged their companies by trying to run things from behind the curtain.

The handoff.
This could be its own chapter. It’s something like a relay race — unique in every circumstance — but it has to attend to questions like: how long is the runway before leaving? Will there be overlap, or, in the case of an internal hire, a period of working in parallel and stepping back gradually? Is there a life after the official transition, where the relationship continues in a different form for a while? I’m familiar with an institution I’ve been on the board of for many years, where the new CEO came on, and the old CEO stepped down, yet both agreed the former CEO would retain an office on the executive floor for six months, engaged only on particular, discrete matters where his expertise and loyalty were still invaluable — while both understood that this contribution was never to be confused with the decision-making process.

Existential pieces including legacy and identity.
Many founders have never honestly leaned into or examined this. But this can be quite material — the founder’s named intention perhaps has always been to exit successfully and let go, reaping optimal benefits, whether short, medium, or long term. But ultimately an owner/leader may realize that company legacy is of significant meaning. In other cases, the organization has been held by the founder as a link in an ongoing family legacy, whether or not the family retains actual control.

What is the company going to mean, going forward? Will its brand continue to be identified with the founder? Is it intended to be a training ground for the next generation of family, even while — at least in the interim — an outside CEO holds the effective, actual leadership torch? Perhaps even more deeply and personally, as an impending former CEO, the unknown future may trigger a strong fear of irrelevance, or of loss of a long-relied-upon identity, or hold the belief that the company couldn’t possibly survive without you. These aren’t simple or easy matters, but they are important. It doesn’t work to ignore or pretend these dimensions are not present. Ensuring personal and professional support will never have been more helpful.