Most strategic planning failures don’t happen in the room — they happen before anyone even sits down.
Leaders often focus on logistics: the agenda, the timeline, the venue, the facilitation. But the true predictors of whether a strategic session succeeds or stalls are conditions that exist long before the meeting begins.
Here are some of the early warning signals I see over and over again when working with organizations.
When everyone arrives with private agendas
If participants walk in thinking they need to:
- protect their territory
- defend their department
- sell their priorities
…then you don’t get strategy.
You get internal negotiation.
Real strategy requires shared viewpoint — not factional advocacy.
When the strategy is already “decided”
Sometimes a planning session is held out of obligation rather than actual exploration. The leadership team enters under the illusion of collaboration — but the CEO or a small group already knows where they want things to land.
Everyone else feels it — and disengages.
A strategy session without true openness isn’t strategy. It’s theater.
When there is no alignment on the “why”
Before any planning begins, there must be clarity around what the session is actually meant to accomplish.
Are we here to:
- set near-term operational priorities?
- redefine direction?
- realign after drift?
- make resource decisions?
- evaluate the current strategy?
When people don’t know the “why,” every discussion pulls in a different direction.
When psychological safety is absent
If team members don’t feel safe to:
- challenge assumptions
- ask difficult questions
- express concerns
- disagree
…they won’t contribute meaningfully.
You’ll get quiet compliance rather than rigorous thought.
When the wrong people are in the room
Who participates matters immensely.
If the people responsible for execution aren’t included — they won’t own the outcomes.
If the people with veto power aren’t included — decisions will be undone later.
If only the loudest voices dominate — insight evaporates.
When no one plans for execution
Some teams treat strategic planning like an intellectual exercise — a set of abstract discussions about theoretical priorities.
Without a structured path from insight → decision → action → ownership, it will die in a slide deck somewhere.
Strategy requires readiness
A successful strategic planning session doesn’t begin with brainstorming. It begins with:
- alignment on purpose
- clarity of roles
- agreement on decision rights
- openness to conflicting viewpoints
- genuine willingness to learn and adjust
When those conditions exist, the session itself becomes powerful.
When they don’t, the session becomes a ritual of wasted potential.
If you want your next strategic session to actually produce clarity, alignment, and momentum I’d love to help you design and facilitate it.
Here’s my direct scheduling link:
https://calendly.com/dianagurwicz/leadership-session
