Wednesday, October 28, 2026
Big-brand positioning is a decision, not a budget. Five questions, a one-sentence position and a five-touchpoint audit you can run this week.
It's 11pm on a Thursday and the decision is still sitting open on your laptop. Hire the second salesperson, or not. Sign the five-year lease, or wait another quarter. Finally let go of the client who pays late and shouts first. You've run the numbers four times and you still haven't clicked save.
If you're stuck on a decision like that, the fastest way through it isn't more analysis. It's a fifteen-minute exercise called a premortem, run before you commit, not after you're already regretting it.
Nine times out of ten, what looks like "I need more information" is actually "I'm scared of being wrong, and gathering data feels safer than deciding." You're not lazy and you're not indecisive. You're human, and you're about to make the decision anyway — this just makes sure you make it with your eyes open.
Here's the villain, and it isn't you: the idea that a confident owner decides fast and a careful one decides slow, so if you're stuck, something's wrong with you. That's backwards. A 2026 Bluevine survey of US small business owners found 68% had delayed or avoided a major decision — hiring, expanding, a big commitment — specifically from fear of getting it wrong. You are nowhere near alone on that laptop at 11pm.
I used to do this with words instead of business decisions. Early on I'd redraft the same email a dozen times before sending it, chasing a version with no risk in it. It doesn't exist. The work doesn't improve in your head — it improves once it's out in the world and you can react to what actually happens. The lesson cost me time I didn't get back: it can't work for you until it's in the public domain. A decision is the same. The fear doesn't go away before you decide. You decide, and then you deal with what the fear was actually pointing at.
Psychologist Gary Klein published a simple fix for this in the Harvard Business Review back in 2007, called a project premortem. Instead of asking "what could go wrong?" — which your brain will wave off with "it'll probably be fine" — you assume the decision has already failed, a year from now, and work backwards from there. It feels uncomfortable. That discomfort is the whole point; it's what gets the real risks out of your gut and onto paper.
"Kevin's knowledge and intellect on all things business — no matter what industry it is — he just seems to find gems that you can focus on. I catch up with Kevin once a week and it is definitely the highlight of my week. He just sees different opportunities so clearly. I would not have considered the B2C market as an opportunity before working with Kevin and now it is a major focus for us. He has opened up so many new opportunities for us."
— John Roberts, Co-owner and COO, Oragene
You can do a premortem solo, and it's worth doing even then. But the real gap isn't the framework — it's that most owners run it once, in their own head, with their own blind spots doing the marking. You already know the two or three risks you're quietly hoping nobody asks about. That's exactly where an outside pair of eyes earns its keep: someone who's sat across the table from a hundred decisions like yours and will ask the question you're avoiding, not just nod along with the plan you've already half-decided on.
This isn't for you if what you actually want is someone to make the call for you, or tell you the "right" answer exists and you just haven't found it yet. It doesn't. What you can get is a sharper, faster, better-tested version of your own judgement — which, once you trust it, is worth more than a hundred more hours of research ever will be.
You already know more about this decision than anyone else in the room. The premortem doesn't hand you certainty — nobody can promise you that. It hands you clarity, and clarity is what turns a decision you've been dreading into one you're actually ready to make.
If the big decision has been sitting open on your laptop for weeks, that's the conversation to have before you spend another dollar on it.
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