On Leaving well…
In September 2026 was invited by Oliver Puddle who runs the OXEO network of Oxfordshire-based employee-owned companies to do a talk on what I’d learned from selling and stepping down from di:ga Communications. On a sunny morning at Kellogg College, University of Oxford, I enjoyed sharing some thoughts on how to leave well and set your successor up for success. The article that follows is a version of what I said.
A change of leadership is a moment of jeopardy for any organisation, but particularly when the person stepping down also founded the company. Seventy percent of private, family-owned businesses fail after the first handover of leadership. Even in bigger, publicly owned companies, or SMEs, it’s a tricky transition to navigate without turbulence. Profits usually dip.
Employee-owned companies buck this trend, with around 90% surviving the change of leadership from founder to new CEO or MD. In my view this is because everyone feels they belong, and everyone has a stake in the organisation’s future success (including the exiting founder).
But this doesn't mean the transition is easy. Having a debt to repay can put pressure on a business, and it can be tricky for staff and clients to adapt to new leadership - and for that leadership to step up to their new responsibilities.
Having founded then sold and exited my own agency, di:ga Communications, I have a few reflections and lessons on how to leave well. I was a founder exiting a business I had sold into employee ownership but I think many of these lessons probably stand for other sorts of leadership transitions.
Start planning early. Give yourself at least a two-year run-in between deciding to sell, selling, and exiting. In my case, it was about 18 months after deciding to sell that the sale took place, and another 18 months till I stepped down.
Communicate clearly and manage expectations. Decide who you will tell when. Avoid uncertainty and gossip. Tell the people who are critical for the success of the transition early.
Prepare your business to be sold. Make sure the company is profitable, the systems work, are understood by everyone who has to use them, and are not too idiosyncratic. Do everything you can to shore up the new biz pipeline so the team has a good runway after you’ve left.
Loop clients in early, especially trusted ones. Focus on creating a feeling of continuity for them. There should be no difference in feel or quality of their experience from your last day to the first day under new leadership. Hand over the relationships properly (without secretly hoping people still call you once you’re gone). Be generous and equip the person you are handing the relationships over to to win trust and respect.
Make yourself the least important person in the business. I had a coach who I worked with to prepare for the sale and I remember him telling me that this is what I had to do. Two years on, when I walked into the office in my last week and no one looked up, let alone asked me anything, I realised I’d succeeded. It was a bittersweet feeling: on the one hand I realised I had succeeded in removing reliance on me, and that was good. On the other, I felt a pang of irrelevance.
Do the work on yourself so you can leave well. Stepping down as founder (or a purpose-driven leader, with an emotional connection to the business) is hard. It will bring up all sorts of questions about identity, status, purpose. Make sure you don’t know just what you are moving away from but what you are going to. Have things planned that will give you a sense of excitement, and make you feel needed so your team can move forward without you. Coaching can be really helpful at this stage. Lean on family and friends outside the business too. It’s an exposing, emotional journey: don’t overestimate that.
Prepare your new leader and be clear about succession. Set your successor up to succeed. Communicate in advance so others know what is happening and can support the new leader to thrive. Be careful of bias when appointing. Run a fair, transparent process - even if there is only one candidate. Give others in the business a degree of involvement and the chance to input their thoughts. Consider offering coaching to your replacement too - to help them prepare and then do the job when they step into it.
Allow for evolution. The new CEO is NOT you! They will make different decisions. This is ok. In fact, it is necessary. They may even make mistakes. Decide carefully how and when to intervene. You will have rights that protect you while you are still owed money but use them wisely. Ultimately, it is in your interests - and the company’s - that the new CEO learns to run the show without you.
Don’t be a shadow CEO. Define your role in or alongside the business clearly before you go - and stick to it. Will you be chair, or an advisor, or are you stepping back entirely? How will your involvement change once the debt is paid off? You don’t have to tie your hands completely but you do owe the new leadership team clarity around what you’re planning. If you are tempted to intervene, ask yourself why - is this ego, or a reaction to lost status, or will what you’re about to do really help them?
Support the team through the transition. It’s tough for them too! Some people will feel worried when they hear you are leaving. Some will have deep loyalty to you as the founder and might find it hard to adjust to a peer stepping up to lead, or someone coming in from outside. Others will feel excited about what might change under new leadership. Consider working with an external consultant to support the team and give them the chance to air their concerns, expectations or grievances.
Be realistic about money. Design a payment schedule that is realistic and flexible and doesn't put too much pressure on the business. Keep decent reserves in the bank. Think about how soon you will pay dividends to staff (we designed the repayment schedule so that we could do this in the first year that the company became employee-owned). Communicate clearly about the money side of things and manage expectations, including about what happens if the business has a less profitable year.
Be transparent but don’t feel you have to share everything. Leadership is lonely. The new CEO will discover this. Make sure they have the support of senior colleagues to decide when and how to share information with staff, and what ‘employee engagement’ looks like in the new structure. Be extra careful about how you communicate sensitive or confidential HR decisions, such as redundancies, and how you let staff know if business is not doing well financially. Think about what people need to know, what will benefit the business to have them more involved in. Under employee ownership, an organisation's culture will probably evolve, but it doesn’t need to transform overnight.
Plan for the long term. The risk is not over or even at its greatest the day you step down. The team will need support to thrive for years after you leave. Think about how they can access this - and what it is appropriate for you to do vs when someone else would be better placed to help them. Expect bumpiness. Stay the course.
