An established international services group with a newly formed three-region board had aligned on the headline goal, a trade sale within the next two to three years, but had never sat in a room together to translate that goal into a clear north star, defined roles, and an operating model that could carry them through to exit. Two days off-site changed that.
The business had reached a moment that called for a board retreat. The founder was preparing to step back from operational leadership, and the business was setting a two to three year horizon to a trade sale at a defined valuation target.
The board itself was new. A global leadership team had been stood up the year before, and the board now spanned three regions. The strategic priority was clear, but the operating model behind it was not. One regional leader had near-complete autonomy. Another was running a region under closer scrutiny. The group CFO had visibility on the financials but was carrying real concern about whether surface-level alignment on the sale was matched by alignment on how to get there.
Pre-call work with each board member surfaced consistent themes and the tensions underneath them. Profitability as the north star. The need for clearer roles and responsibilities across the regional leaders. A succession gap behind one of them. The board's tendency to spend meetings on quarterly numbers when it needed to be on long-term strategy. A live question of whether the founder would genuinely step back this time. The brief was to use the two days to put all of this on the table and leave with a shared answer.
I designed the retreat around Playing to Win as the spine. Five interlocking questions: winning aspiration, where to play, how to win, must-have capabilities, and enabling management systems. The structure gave the board a way to move from north star down to operating implications inside a single conversation, without losing the thread.
Day one was about team dynamics and north star. I opened with each board member sharing what they were bringing into the room and what they needed from it, drawn from the pre-calls so nobody had to expose the conversation cold. I then worked the winning aspiration question explicitly: not just the number, but what winning meant for the founder, for any future buyer, for the leadership team, and for the staff who would carry the business through to transaction.
Where-to-play work followed. The board worked through current and target client mix, with regional differences placed alongside each other rather than forced into a false consensus. The conversation surfaced where each region's commercial reality genuinely diverged and where the business needed a single global answer.
Day two turned to roles, responsibilities, and the route through. I built out a simple business plan structure with timelines and defined ownership, used the golden triangle to pressure-test financial assumptions against strategic and operational commitments, and surfaced the unresolved questions about succession and structural gaps in the leadership shape. The conversation about how the founder would genuinely step back was the hardest of the two days, and it happened.
The board left with a shared north star, a clearer view of the route to a trade sale, and an honest read on the operating model gaps that would need closing in the time between now and a transaction.
Specific outcomes worth recording. A defined business plan structure with named owners and timelines, including work to make a future exit payout feel tangible to the leadership team beyond the board itself. Explicit agreement on a regional client focus shift. A surfaced and acknowledged set of operating model gaps, succession chief among them, with a route to closing them. And a clearer statement from the founder about how the step-back would actually work.
The board was given the structure to keep doing this work without external facilitation. A quarterly review cadence, a defined agenda that protects strategic time from operational drift, and the language to challenge each other when meetings start sliding back into the numbers.
The most useful thing about Playing to Win for a board at this stage of life is that it forces the conversations the business has been avoiding. The framework does not let you off the hook. If the winning aspiration is a trade sale at a defined multiple, the where-to-play and how-to-win answers have to be consistent with that, and the must-have capabilities and management systems either are or are not in place.
For a long-established business, the absence of a previous board retreat is itself the most telling part of the brief. The work in two days was not new strategic content. It was making explicit, in the same room, what people had been carrying separately. That was the value, and it is the work most established mid-market boards are quietly avoiding.
Most work like this starts with a 30-minute call to understand the team, the context, and what good would look like. From there we agree the shape of the work together.
