You Don't Need Every Decision to Be Right

A typical $5M-$50M business makes roughly 10 strategic decisions a year — product launches, pricing changes, sales motions, VP hires, facility expansions, vendor switches, an acquisition target, a marketing channel. Of those 10, 5 to 7 will work. 60% is a good year.

In baseball, an elite hitter bats .275. He's playing against a pitcher whose entire job is to drive his average down, in conditions where wind, crowd noise, and stolen bases are all variables he doesn't control. Twenty-eight percent and he gets celebrated. 60% in business is treated as failure. The math is upside-down.

The more expensive error isn't expecting perfection. It's how we evaluate. Teams fixate on the 4 that didn't work, hire a consultant to ratify the thesis, cycle through vendors, and lose the year to the failures — while the 6 wins compound unattended — the same trap turnaround strategies are built to break.

Here's the Modern portfolio theory analog. A Venture capital fund — say 2 seed bets, 5 Series A, 3 growth bets in a typical year — sees 2 liquidations, 6 stagnations, and 2 fund-returners across 10 investments. The 2 liquidations don't define the year. The 6 stagnations don't get dwelled on. The next 10 investments get made. The GP isn't fired because the next LP meeting is about the 2 fund-returners, not the 2 misses.

A trader might run 100 positions in a year, 60 winners and 40 losers. The 40 losers don't define the year. The P&L does. The trader who obsesses over the 40 losers will underperform the trader who treats them as the cost of doing business.

It's not about being right. It's about making enough bets, sized correctly, with kill criteria written down in advance.

Bet sizing, written down. Any single decision can fail without sinking the company. 6 wins out of 10 is explicit, not accidental. The team agrees in advance that 4 losses are expected. Not a crisis. Just the math.

Kill criteria, written down before the bet goes on. The team names the conditions under which each bet should be exited — customer count below X by date Y, revenue below Z by date W. The day the criteria trigger is the day the team exits, regardless of who made the original call. Judgment at the trigger is mechanical, not personal.

Both artifacts get written when judgment is still cool — before the bet is on, not after the loss is obvious. Most teams write the second artifact under the first set of conditions, which is the whole problem.

Three artifacts make the portfolio view real.

First, the decision log — every strategic bet gets a one-pager: the bet, the size, the expected outcome, the kill criteria, the trigger date. The one-pager forces specifics on paper, and feeds straight into capital allocation planning. (I went down this rabbit hole once — built a whole template system, three iterations, six months. The thing that actually got used was a one-page Google Doc. The rest was decoration.)

Second, the monthly variance report — green, yellow, red, no spin. A yellow bet two months running triggers a kill-criteria conversation at the next leadership meeting. Not a referendum on the executive; a portfolio review.

Third, the annual review. Of the 10 bets we made, how many worked? What did the wins share? The losses? Were the kill criteria useful, or did we override them? The team that does this every year improves its hit rate. The team that skips it runs the same bet-and-blame cycle.

Look at 10 decisions as a portfolio, not as 10 separate verdicts. 6 work, 4 don't. The 6 wins compound. The next 10 decisions get made — sized with the same logic, kill criteria and all.

Stop treating 60% as failure. Nobody hits 90%; anyone who claims to is lying or new to the role.

You don't need every decision to be right. You need the portfolio to work.