The Strategic Exit: Leading Well Includes Leaving Well
Turnover is inevitable. Including at the top table. How we meet those exits says a lot about who we are, as leaders and as an organisation.
My observation, broadly speaking, is there are two types of Chief exits.
The first is the star performer: The one offered a bigger role, or broader scope, greater influence etc.
It makes sense. It’s a progression move.
The second is a less happy exit: The Chief whose momentum or sense of purpose has slowed. Whose frustrations - sometimes within the ExCo itself - have remained largely unspoken but now become the tipping point to exit.
On the surface, these two resignations look very different. But in reality, both are defining moments of leadership:
for the Chief themselves,
for the CEO and CPO,
for the culture and business as a whole.
Because how someone leaves tells the organisation who you really are.
Either way, when it finally happens, it’s tempting to rush the process - to tell the cursory ‘good news’ story and quickly focus sights on the ‘what’s next’. Ignore the rocking of the boat and carry on.
But I’d suggest that these moments are actually opportunities to be seized, to demonstrate who we really are, as a Chief and as an organisation. This can be a moment of affirmation - of our culture, our purpose, our ambition and, ultimately, our success.
The Star Performer: A Story of Growth
When a high-performing Chief leaves for their next development opportunity it can feel destabilising and perhaps even a failure on the part of the business to retain top talent.
Rather than assume failure, let’s look instead to roles and accountabilities for all concerned.
For the exiting Chief it’s a test of maturity. A strong Chief does not simply “take the opportunity.” They steward the exit. Their responsibility is to:
be transparent early,
invest fully in succession.
leave the team stronger than they found it.
avoid rewriting the past to justify the future.
This is a story of growth, and growth does not require disowning where you came from.
For the CPO, the moment is equally important. It’s easy to slip into scarcity thinking: “We’re losing one of our best.” But what if this is proof of strength? If your Chiefs are in demand externally, it says something about the quality of leadership you cultivate internally. What if this is:
progression, not abandonment;
our culture of growth working;
part of how we develop leaders here.
Handled poorly, a star exit creates organisational doubts and politics.
Handled well, it enhances your employer brand and strengthens your bench.
The Unhappy Chief: Leaving as Last Resort
The more destabilising exit is often the one that’s been forming quietly: Loss of impact. Unresolved friction in the ExCo. A sense of being blocked or unfulfilled. Political fatigue. Challenges outside of work. Personal burnout.
Often the Chief themselves cannot fully articulate what changed. They just know the role and the place no longer fits. To everyone’s detriment, they’ve either done a great job of presenting “okayness”, which may have led to things simmering out of sight, or they’ve become a ‘source of negativity’ within the team, expressing a general disquiet without being able to constructively engage with the real problems.
In this scenario, the Chief has responsibility:
to surface concerns early,
to own their part in team dynamics,
to reflect on issues outside of work what may be adding pressure,
to avoid silent disagreement and disengagement,
and to seek clarity before defaulting to departure.
Leaving may still ultimately be the right choice. A positive choice even.
But without this kind of personal accountability, their exit can weaken both their own brand and the integrity of the system they’re departing.
But the CPO has responsibilities here too. This is where their leadership really counts.
Can you detect the drift before the resignation letter?
Can you create a space safe enough for the truth?
Can you help your Chief parse the critical “is this time to develop - or to depart” inquiry?
When frustrations are named constructively, particularly at the top level, things can shift for the better. Sometimes the Chief can rediscover their momentum. Or, if not, the clarity can make their exit more strategic - positive even.
In both cases, the business - and everyone involved - benefits.
What rarely serves, tempting as it is, is the swift and neatly packaged shimmy out the door, but which leaves unexamined the real grounds that led to exit.
Exit is Our Culture in the Spotlight
Chief exits are visible moments. They signal whether:
you confront issues head on or gloss over them,
your values are integrated or performative,
you genuinely want the best for your people,
leadership here is genuine, mature, growth oriented.
Your organisation is watching. Future talent is watching. And your ExCo is having to visibly re-calibrate, on behalf of the whole organisation. Handled consciously, exits at the top can be a moment of strengthening, not de-stabilising.
The Strategic Exit
A strategic exit then, whether progression-driven or dissatisfaction-driven, is one where:
the narrative is honest,
the succession is visible,
the ExCo remains aligned,
the departing Chief feels respected,
the organisation feels strengthened.
And what you cannot do is fake it. How your people leave, and your response to it, is a reflection of the system in which you’re operating. There’s little point pretending things are one way when in reality they are another. The Chief exit is an opportunity to live and to demonstrate your values - who you really are.
A Concluding Tip For Success
Often, what makes the difference is whether there’s been space before resignation for deep reflection. When Chiefs are given room to explore their desire for impact, their frustrations, their ambition and how they experience fulfilment, two outcomes tend to emerge:
Renewed commitment and increased impact.
Or, less often, a conscious and strategic departure.
Both are healthy, and good for your organisation.
What is unhealthy, and expensive, is silence… and then departure.
For CPOs, the question is not simply how to retain talent. It’s how to ensure that when Chiefs stay they stay energised, and when they leave they leave in a way that strengthens the business.
The strongest organisations do not cling to leaders, they develop them.
And when the time comes, they let them go… in a positive exit.
Because leading is also how we leave, and how we leave is also who we are.