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Planning for success(ion)? Identifying your successors is only one piece of a long-term exit strategy

HBO is revered for its authentic portrayals of times and places throughout history, from Band of Brothers’ harrowing journey woven through the events of World War II, to the crime-ridden streets of ‘90s Baltimore in The Wire. Yet it feels like none of its series based in reality (sorry, Game of Thrones) have captured the attention of the zeitgeist quite like Succession, acknowledged for its realistic, and all-too-relatable, encapsulation of a leader who has trouble letting go.

The series follows Logan Roy, the aging CEO of a massive media conglomerate called Waystar Royco, and his four children, as he loosely attempts to hand down power and step away from the business world. If you haven’t watched it, I implore you to do so – it’s a deliciously dark, debauched trainwreck that part of you wants to look away from – so you can best understand what not to do. It’s better than any material I’ve read on the subject and if you’re in Logan’s position as a leader who is too integral to lose, even in a small business, it might just get you to think harder about your own long-term plans.

So what does succession planning actually entail, and what else should go into your exit strategy, beyond figuring out who’s picking up the mantle once you’re gone?

Succession, S03E04, credit HBO


Identifying the motivation for your succession plan lays the foundations for the other questions set out below – if you don’t know why you’re doing something, it becomes impossible to execute that something to the best of your ability.

Joe Maier and Bob Schneider of Johnson Financial Group wrote a brilliant article that succinctly ties up motivation and frames it in the context of Succession’s Logan Roy:

“When working with business owners on succession, I always start with happiness: what makes you happy and how does the transition of leadership and ownership help maximize your happiness? The answer to this question results in what I refer to as the “succession purpose”:

  • Legacy (keep the ownership and leadership of the business in the family);
  • Loyalty (transition ownership to insiders); or
  • Liquidity (sell the business for top dollar to outsiders).

Logan Roy’s purpose is clearly the first: he almost views the business as his favorite child and wants to keep control in the Roy family as part of his story or legacy.”

They’re absolutely right. Legacy, loyalty and liquidity serve as the three cardinal directions a leader would look to head in with a succession plan. No single one of these directions is strictly better than another:

  • legacy relies on succeeding family members being interested and engaged with the business, and able to replicate (or improve upon) what you bring to the table
  • loyalty aims to transfer control to senior team members who have proven themselves a worthy fit, but may leave the departing CEO with less cash in their pockets
  • liquidity usually means the biggest individual payout, but “ends the legacy” that some leaders would almost literally die for – just look at Logan Roy – and may end up with other fundamental players at the company departing, leaving it in the hands of people who don’t know what they’re doing.

So, knowing that there’s no one-size-fits-all solution, which direction would you go? And once you’ve chosen a direction, how do you plot the course?

Succession, S02E10, credit HBO


Understanding how best to grow your company to capitalise on your key motivator is what will determine how your succession plan unfolds. I have set out this section under the “Legacy, Loyalty, Liquidity” framework laid out by Maier and Schneider, because each direction requires different, sometimes conflicting choices to be made, and because I cannot put it better myself.


Legacy is the bread and butter of Succession’s narrative, and where better to learn what not to do than by watching Brian Cox’s veins bulge from his temples as he ruthlessly eviscerates his offspring, having led them, and the viewer, to believe that they might just be his choice for succession.

In a Forbes article written by Edward Segal, he spoke to Nicholas Creel, an assistant professor of business law at Georgia College and State University, who unpacked why the fictional Roy legacy was crumbling:

“It becomes painfully clear how the lack of an articulated succession plan can lead to incessant chaos within an organization. The many potential heirs apparent on the show are constantly trying to betray one another for their own gain rather than working together for the good of the company… [Had Logan] given his children a clear answer as to who is next in line… they could instead focus their time and energy on building up themselves and the company rather than on tearing one another down.”

The takeaway here is that you need to decide early and reinforce often those in the “line of succession”, so that those family members you want to replace you are aware of their role in the future of the business. Both they and you can work towards nurturing their strengths and reinforcing their weaknesses before the time comes to hang up your hat. It may well be the case that your familial successors do not possess the expertise or training that senior members of the business have worked to acquire, so the sooner you get them involved and understanding how things work, the stronger a candidate they will turn out to be.

Looking at Succession, both Kendall and Siobhan show aptitude for leadership and a reasonable, albeit untested, ability to negotiate, whilst Roman oozes a somewhat slimy charisma but lacks the fundamental acumen to make good strategic decisions. With training and experience, any one of them could meet or even succeed their father’s ability to run a modern-day conglomerate, but he doesn’t give them the time of day.

As Maier and Schneider put it in their article, “in a legacy based plan, business success almost has to be the top priority”, but that holds true for any long-term exit strategy. There needs to be a fundamentally robust business for people and other businesses – family, senior team members or companies looking to acquire – to care about before you plan for the future.


Loyalty is more commonly seen as a logical successional direction to take, especially in the SME world due to the fact that there’s less of a legacy at stake. It also requires a lot less legwork to ensure the continued success of your business if it’s being managed by long-serving senior team members who know the business intimately. That’s not to say it’s easy, but there’s a lessened subjectivity when you’re elevating existing team members as opposed to picking favourites between your offspring. There still is a subjectivity bias, of course: even though Gerri has worked for this company longer than anyone else, or Frank is your oldest friend and a hard worker, that doesn’t mean that either of them are naturally suited to run the company well.

There is a wealth of research defining the process of loyalty-based succession better than I ever could so I will avoid drilling down into fine detail. It ultimately boils down to recognising what is required to replace you, deciding upon impartial metrics by which to assess key team members who may be suited for the role(s) and then assessing those people. Once you’ve pinpointed those worthy to wield your equivalent of Thor’s hammer, Mjölnir – presumably, some form of supreme executive power within your business – you can then set about preparing them for the transition.

Given that, unlike family, colleagues are not forever, you are at risk of these candidates moving on before you’ve stepped back from the business, so giving them reasons to stay is crucial. Providing incentives to both contribute to the direction of the business as well as profiting from its success, through the use of government-backed tools like the Enterprise Management Incentive (EMI) scheme, can make all the difference. Even just letting them know of your retirement intentions early so they’re aware of what the future could hold for them can be enough of a motivator for those on the fence to hop back off.


And this is the field where the cash cow grazes. If your family are disinterested in inheriting the business, and you want to make some big money, liquidity is a natural fit. That being said, selling your business isn’t a straightforward process, nor is it easy for CEOs with attachment issues. Once you sell, there’s no turning back, and the buyers can do what they want with your company. Just look at what happens to Vaulter in Succession, a fictional social media start-up purchased by Waystar Royco, which is unexpectedly dismantled, to the chagrin of the original owner.

What you’re looking for with liquidity is to make your business attractive to external investors. Whether this involves growth through acquisition, the restructuring of the business (holding companies, anyone?), the streamlining of shareholdings or just a steady profit is ultimately determined by the investors themselves.

Crucially, however, is the fact that you will likely no longer be involved, and will therefore lose agency within the company, immediately after completion of the sale. With either other style of succession plan, you have time to pass on your expertise to others who you trust to continue on the right path, which means you can slowly untangle yourself from the business to a point where you’re no longer essential. As counter-intuitive as it sounds, if you’re looking to sell, you will need to make yourself obsolete. If you’re not, the business will inevitably struggle or fail without you. A lot of business sales split the sale value between an initial payment, followed by a subsequent performance-based pay-out and if the business isn’t performing because you, the lynchpin of its success, are gone, you’ll end up out of pocket.


So, we have established that there are many ways to plan for your succession, and no single correct answer. My personal conclusion is that only the CEO will truly know which path they want to take, and will need to consider everything well in advance to succeed in succession planning. If you need a hand planning the future of your business, feel free to get in touch with our team and we’ll see what we can do.

In the immortal words of just about every character in Succession: “Now, f**k off.”

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