Part 2 of 2
Part 2 of our series on judgment: the habits that turn good instincts into a repeatable practice.
Last issue, we looked at why even smart, experienced leaders get big calls wrong — not because they're careless, but because the brain is wired for speed over accuracy, and few decisions come with the certainty we wish they had. We also looked at the real cost of waiting for that certainty to arrive.
This issue is about what to actually do about it.
Don't Judge Decisions by Their Outcome
Annie Duke is a former professional poker player turned decision strategist and author. And she has a name for one of the sneakier habits in business thinking – and that is judging a decision by how it turned out instead of by how sound the decision actually was.
To illustrate… let me provide two examples. Coca-Cola ran roughly 190,000 blind taste tests before launching New Coke in 1985. The new formula consistently beat both original Coke and Pepsi in those tests. With that much data, Coke was assured of a winning move. The result? The rollout flopped so badly that the company brought back Coca-Cola Classic within three months.
The research was sound. The outcome still failed.
Flip it around: Sara Blakely had no market research and a patent attorney who thought her idea was bad enough to be a prank. She built Spanx into a billion-dollar company anyway, on little more than a hunch and $5,000 in savings. The process was thin. The outcome was massive.
Neither story proves what it looks like it proves. Outcomes get shaped by plenty that nobody in the room controls: the economy, competitors, timing, luck.
So if we judge every call purely by its result, we will draw the wrong lesson almost as often as the right one. Therefore, the better question is: given what we knew at the time, was this the best decision we could reasonably have made?
Think Like a Meteorologist
Philip Tetlock spent decades studying people who consistently made accurate predictions. He expected to find experts. Instead, he found thinkers.
The best forecasters rarely spoke in absolutes. Instead of “this strategy will work,” they'd say, “given what we know today, there's about a 70 percent chance this succeeds.”
It's a small shift in language, but it changes what happens afterward. Say a strategy “will work” and you leave yourself no room to be anything but right or wrong.
But if you say there's a 70 percent chance, you've built in room to learn no matter what happens. The best leaders are comfortable saying “I might be wrong” — which is a big part of why they end up right more often.
Invite Someone to Disagree With You
Most of us don't have an information problem. We have a confirmation problem. We naturally seek out people who reinforce what we already believe.
That's comforting, and it's dangerous. Before your next major decision, ask someone you respect one question: What am I missing?
It's also one of the reasons an outside perspective earns its seat at the table — a colleague, a board member, a partner who isn't buried in your day-to-day. A second set of eyes has saved companies real money simply by asking the question nobody inside the building thought to ask.
Build Review Dates Into Your Decisions
One reason leaders hesitate is that decisions feel permanent. Most aren't.
Jeff Bezos built an entire decision framework at Amazon around this distinction. In his 2015 letter to shareholders, he described two kinds of decisions. Type 1 decisions are one-way doors — consequential, hard to reverse, worth the slow, careful process most leaders default to. Type 2 decisions are two-way doors: if you don't like what's on the other side, you can walk back through. Most decisions, Bezos argued, are Type 2. The mistake most organizations make is treating every decision like a one-way door — the same heavyweight process, the same drawn-out deliberation, whether it's actually reversible.
Instead of asking “should we completely rebuild our digital presence?” ask “what can we test in the next ninety days, and what would tell us to walk it back?” A new campaign, a redesigned page, a pilot channel — most digital decisions are two-way doors. Commit, measure, adjust, and save the slow, careful process for the handful of genuinely permanent decisions.
To Get Better At Making Decisions – Ask These Five Questions
Before making an important decision, take five minutes and ask:
- Which decision tool should I be using — intuition, rules, analysis, or creativity?
- What evidence would convince me I'm wrong?
- Am I thinking in probabilities or certainties?
- When will I deliberately review this decision?
- If this fails, what lesson do I want to learn?
None of these guarantees success. That's not their job. Their job is to make your thinking sharper.
One Final Thought
Leadership isn't about making perfect decisions — nobody does. It's about becoming the kind of person, and the kind of organization, that makes thoughtful ones consistently.
Most of what determines whether a business succeeds isn't one brilliant call. It's hundreds of ordinary ones: the hiring decision, the pricing decision, the platform decision, the decision to finally rebuild the website you've been patching for six years.
If you're sitting on one of those right now, we're glad to be the second opinion in the room. That's most of what we do. Connect with us here.
