Friday, September 04, 2026

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Most strategic plans for next year don't fail in June. They fail on the day they're signed off — in the half hour between finishing the plan and feeling pleased with it, when nobody in the room is willing to ask what could go wrong. If you're locking in your 2027 numbers this month, there's a ten-minute exercise that catches a plan's fatal flaw before you've spent a dollar executing it: the pre-mortem. Kevin has run it with businesses from seven-figure operators to companies turning over $100m a year, and it is almost always the cheapest insurance a growth plan ever buys.

Why Confident Plans Fail Quietly

The enemy here isn't a bad strategy. It's the planning session itself. The whole format rewards optimism — you build the plan, you sell it to your team, you sell it to yourself, and by the time it's finished, pointing out a weakness feels like betraying the work everyone just did. In 1989, researchers Deborah Mitchell, Edward Russo and Debbie Pennington found something simple and useful: when people were told to assume a future event had already happened and then explain why, they generated roughly 30 percent more reasons for it than when they were only asked whether it might happen (Journal of Behavioral Decision Making, 1989). Certainty opens up thinking that mere possibility keeps shut. Gary Klein built that finding into the technique he named the premortem in a 2007 Harvard Business Review article, and it still works for the same reason: assuming the plan has already failed gives your team permission to say the thing nobody said in the meeting where it got approved.

The Pre-Mortem, Run Properly

This isn't a brainstorm. It's a structured exercise, and it works best with the same people who signed off on the plan.

  • Declare the failure as fact. Tell the room: "It's December 2027. This plan has failed completely." Not might fail — has failed. The tense change is what unlocks the honesty.
  • Write reasons alone, then share. Give everyone five minutes to write down, individually, every reason they can think of for why it failed. Collecting them before anyone speaks stops the loudest voice in the room setting the answer.
  • Sort for the ones with teeth. Group the reasons. Most groups land in four places: the market moved, the team couldn't deliver it, the cash ran out before it paid off, or the owner stayed the bottleneck. Rank them by how much damage they'd do, not how likely they feel.
  • Build the one or two moves that defuse the top risks. Not a response to everything — a response to the two or three reasons that would actually sink the year. That becomes the first entry in your 90-day plan, not an appendix to it.

This is the backbone of how we open Know Your Future, Simple-Growth's strategic planning programme: the pre-mortem runs before a single number gets locked in, not after.

"Talking with Kevin the first time was so valuable and we were learning so much. Within an hour Kevin had us thinking about our business and our goals in a totally different way. In fact we were supposed to be catching a flight but we decided it was more important that we continued the meeting with Kevin."

— Angus and Cameron, The Flatpack Co

Why Owners Skip the One Exercise That Would Save Them

Here's the real obstacle: most owners already know this is worth doing. What stops them is that running an honest pre-mortem on your own plan means being the person in the room who says "what if this doesn't work" about your own idea — and most owners have spent years training their team to follow their confidence, not question it. That's a hard switch to flip solo. It's one of the clearest reasons an outside voice in the room changes the outcome: a coach can ask the question an owner can't ask of themselves without it looking like doubt.

Key Takeaways

  • Assume failure, don't predict it. Treating the outcome as certain, not possible, is what makes people think harder about why.
  • Write before you talk. Individual reasons, collected silently first, surface risks a group discussion buries.
  • Rank by damage, not likelihood. The risk that would do the most harm deserves the first move, even if it feels unlikely today.
  • Build it into the 90-day plan. A pre-mortem that doesn't produce an action is a nice meeting, not a safeguard.

If your 2027 plan hasn't been pressure-tested by anyone outside your own head, Kevin will pressure-test it with you.

Be the owner who walks into 2027 knowing which risks your plan has already beaten.