In the outdoors, pausing to reassess your route isn’t a sign of weakness — it’s a core safety practice. Hikers routinely stop to check weather, daylight, trail conditions, energy levels, and new information from fellow travellers. Those dynamic assessments — and the willingness to change plans — have undoubtedly saved people from injury or worse.

The workplace should treat planning the same way.

Why the analogy fits

Unpredictability: Just as weather can shift on a ridge, markets, customer needs, and internal capacity can change overnight.
Stakes: On the trail the stakes are physical safety; at work they’re business viability, team wellbeing, and careers.
Information changes: New data can indicate that a plan is no longer optimal. The smart move is to adapt, not to double down blindly.

What dynamic assessment looks like at work

Scheduled “pause and check” moments: Regularly built-in reviews during a project where teams evaluate assumptions, risks, and progress against outcomes.
Trigger-based reassessments: Clear triggers (missed milestones, new competitor moves, budget changes) that prompt immediate re-evaluation.
Open information flow: Encouraging frontline employees to flag issues early — like a hiker reporting unexpected trail damage.
Psychological safety: Leaders should foster a culture where admitting a plan needs changing is respected, not punished.

Practical steps leaders can take

Build checkpoints into plans: Treat them like trail markers — mandatory moments to reassess.
Define decision rules: When do you continue, pivot, pause, or stop? Make the criteria explicit.
Normalize course corrections: Share stories of successful pivots so teams see reassessment as competence.
Train for flexibility: Develop skills for rapid scenario evaluation and small-scale experiments to test alternatives.
Celebrate responsible changes: Reward those who identify the need to reset course before costs escalate.

Leaders who model pausing and recalibrating reduce risk, preserve resources, and keep teams aligned and resilient. Flexibility is not indecision — it’s informed stewardship. In uncertain environments, the most effective leaders are those who combine clear intent with the humility to update the route when conditions demand it.

A simple challenge Before your next major milestone, schedule a deliberate pause. Ask: What has changed since we started? What assumptions no longer hold? What’s the least risky next step? Treat the answer like choosing the safest trail — and be willing to change course.