Why Strategy Meetings Should Plan for What Could Go Wrong

In a recent LinkedIn post, Cicely Simpson discusses how leadership teams can use strategy meetings to anticipate change instead of simply reviewing recent activity. This article reports on Simpson’s LinkedIn post and examines her recommendations; it is not written by Simpson.

“85% of strategy meetings are status updates with a better title.”

Simpson argues that the gap between strategic thinking and planning leaves organizations exposed when conditions change. “Thinking without planning is just ideas,” she writes, while planning without thought can become “just bureaucracy.” Her post offers six signs that a team may be managing the present rather than preparing for what comes next.

Start with the future, not the meeting recap

According to Simpson, a meeting dominated by reports on what has already happened can consume time without prompting decisions. She recommends opening with the next 90 days’ priorities and leaving a shorter slot for reviewing the previous quarter. The shift, she suggests, directs discussion toward choices teams can still influence.

Simpson also urges leaders to ask what might surprise their organization. If team members cannot name potential disruptions, she says, the group may be missing a shared view of risk. Her example is rising supplier prices: raising that possibility early gives the team a chance to consider a response before costs become urgent.

Prepare for more than one outcome

“It works perfectly, as long as nothing changes. But when reality shifts… you’re improvising under pressure.”

Simpson points out that a plan built around a single expected future can leave an organization scrambling when assumptions fail. She recommends sketching best-case, worst-case and most-likely scenarios, then deciding how the team would respond to each. Her examples include a budget increase, a midyear cut or a flat budget.

Make strategy a regular practice

In Simpson’s view, strategy cannot be confined to annual planning season. She advises scheduling monthly sessions to revisit assumptions and look ahead. A regular cadence, her post suggests, can reveal outdated expectations before they shape decisions for too long.

She also recommends auditing how leaders spend their time. By labeling recent activities as strategic or tactical, teams can see whether urgent work has displaced time for longer-term thinking. If the balance is heavily tactical, Simpson suggests blocking dedicated planning time in the calendar.

Review decisions to improve the next plan

Simpson’s final sign is a lack of follow-up on past decisions. Without reviewing what worked and what did not, she argues, teams risk carrying old mistakes into a new plan. She proposes examining three major decisions from the previous quarter and asking what leaders learned and would change.

Her practical starting points are modest: spend 15 minutes a day considering what is coming, hold one monthly look-ahead session and conduct a quarterly review of decisions. Simpson presents these habits as ways to build more consistent strategic thinking, especially as Q4 planning begins.