Ten Things Your Leadership Team Should Leave Strategy Planning With

1. An honest review of last year’s objectives

Before agreeing what comes next, a leadership team needs a clear view of what happened to the last set of priorities, including which objectives drove impact and where execution stalled. Without it, new priorities are built on assumption, and the same bottlenecks tend to reappear under different names. This review opens From Strategy to Execution, so that the priorities agreed on day two are grounded in what the previous year actually showed.

2. Tensions surfaced rather than smoothed over

Every leadership team carries disagreements about priorities and about how the work should be done. Planning agendas designed to produce a coherent plan tend to set those tensions aside, and they then travel back to the office and resurface during execution. The most valuable conversations in a planning session are usually about things that have been true for a long time but never said out loud. Those conversations depend on deliberate design and a facilitator who sits outside the team’s dynamics.

3. Confirmation that everyone means the same thing

Agreement is relatively easy to reach in a well-run session, whereas alignment, where every leader understands each priority in the same way and has worked through what it implies, is considerably harder. Without alignment, each part of the organization reinterprets the strategy through its own lens as it cascades, a pattern described in Why Annual Planning Seasons Produce Alignment Theatre. A useful test before leaving the room is to ask each leader what a given priority will change in their own area next month, and see whether the answers fit together.

6. Measurable OKRs and KPIs for every objective

An objective without a measure is difficult to manage and easy to reinterpret. OKRs define what the organization is trying to achieve and how progress will be judged, while KPIs track the ongoing health of the business. Translating each priority into both gives every team a concrete way to connect its work to the strategy. This translation is the focus of day two of the workshop, where leadership teams move from agreed objectives to draft OKRs and KPIs.

7. A named owner for each objective

Shared ownership often turns into no ownership once the operational pressures of the year take hold. Every objective that leaves the room should have one named leader accountable for it, someone who reports on progress and makes the trade-offs when priorities collide. That person also becomes a visible signal to the rest of the organization, because people read where leaders spend their time and attention as the most reliable guide to what the strategy really values.

8. A map of how every team connects to the strategy

Company objectives only improve performance if each team can see how its own work contributes to them. Before leaving the room, a leadership team should be able to show how each objective translates into team and function goals, so the line from strategic intent to day-to-day work is visible rather than assumed. Where that line cannot be drawn for a particular team, it is usually a sign that the objective needs sharpening or that the team’s current priorities need revisiting.

9. A realistic view of who carries the message

An org chart shows who holds formal authority, but strategy travels through the informal network of who people trust and go to for advice, and the two rarely match. It is worth the leadership team asking, before the cascade begins, who colleagues genuinely listen to, because those people are often two or three levels below the executive team. For organizations that want to measure this rather than rely on judgement, organizational network analysis can map it, as in our work with a European FMCG manufacturer.

Few leadership teams will have all ten in place, and the list is most useful as a check on where execution is most likely to stall. Most of it is covered across the two days of From Strategy to Execution.

For some organizations the larger risk sits beneath the leadership team, in whether the wider organization is structurally able to carry what has been agreed. Where that is the concern, Organizational Performance Insight can add an evidence base to the planning process, with a baseline before the session and a way to re-measure progress once the cascade is running.

We recently ran From Strategy to Execution with the senior leadership team of a Middle Eastern defence services provider. Following a leadership transition, direction was clear at the top, but alignment varied across teams and priorities tended to multiply as the year went on. Over two days, the team agreed four company objectives for 2027, each with drafted OKRs and KPIs and a named owner. They also agreed a model for cascading them through the organization and a weekly and quarterly check-in rhythm to keep them on track. You can read the full case study here.

If your leadership team has a planning session on the horizon, we would welcome a conversation about how to approach it. Start a performance conversation with us.

A note on how this piece was written

This article was written with the assistance of AI. The thinking and professional judgement draw on Inspirational Group’s published work and client experience. AI was used to structure and draft the piece based on that material.