Rule No. 5 📔 Make Fewer, Bolder Moves.

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the Rules matter.

Your insights will appear here, along with your name, title, company. Be the first to add your insights to Rule No. 5 —Make fewer, bolder moves, or the book Playing To Win.

“Strategy is about making specific choices to win in the marketplace. It requires making explicit choices, to do some things and not others, and building a business around those choices.”

Are you accomplishing a lot? Or just attempting a lot? Spread yourself too thin and you’ll probably do most things half-ass. Too many companies are mediocre across the board, because they’re chasing ten things at once, every day. You can’t do everything well. You can’t chase every new idea; jump on every opportunity; or try to fix every problem that comes along. You can, but if you want to play the long game, you shouldn’t. The leaders who win pick fewer bets, but go all in. Pick the things that matter most and do them really, really well. Commit to fewer initiatives, but back them fully, and win where it matters.

A) Tell us about a time when your organization was trying to do too much. What finally made you realize that focus, not more effort, was the answer?

B) Looking back, what is one initiative your organization should have killed sooner? What did that experience teach you about making fewer, bolder moves?

C) What is the boldest strategic decision you have made as a leader? What did you have to say “no” to in order to make it happen?


Roger Martin on How Strategy Really Works

🥊 challenge the Rules | take the contrarian view

In a volatile market, making fewer, bolder moves can be reckless. Diversifying across many smaller bets is the smarter path. Let me push you, as a group, to wrestle with this:

  1. Are you calling something “bold” when it’s actually just concentrated risk?
  2. Are you hiding behind diversification to avoid making a real strategic commitment?

As a group, let’s try to list 5 practical, actionable strategies that could make this Rule a habit, not just something that gets talked about once a year.

One last word…

The older I get, the more I believe that business isn’t won by the “hustle and grind”, by just doing more. It’s won by knowing what really matters and having the guts to put your time and money behind it. Making fewer, bolder moves means you going to have to say no. It also means you’ll have to be willing to accept that some people are not going to like it. Some good opportunities will also pass you by. Oh well. That’s the price of focus and discipline. But if you can leave this discussion with one thing, this is it: you don’t need more on your plate. You need more conviction behind the things that are most important. Win where it matters.

Now, it’s time to take this discussion back to the office. We’ll see you next week.

There’s more to this Rule than these few sentences.

October 2026

This Master Class is in development.

Help us build each of the 50 Master Classes, by adding your insights and sharing your entrepreneurial stories.


Class begins Monday, January 4, 2027, with each Rule being built out as we go. Each will contain the study sections listed above and will continue to evolve through your contributions. As business leaders continue to challenge these ideas, the Institute becomes more and more valuable, not because it’s finished, but because it never will be.

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Here are five eye-opening warning signs that signal your organization is ignoring Rule No. 5 —Make Fewer, Bolder Moves. These are the kinds of issues leaders pretend aren’t problems…until they’ve already cost them years.

⚠️ 1. Everything is labeled a “priority.” When every project is “critical,” none of them are. This is the classic sign of a leadership team that lacks the courage to choose. Busyness replaces strategy.

⚠️ 2. The roadmap keeps expanding, but nothing meaningful gets finished. If initiatives pile up while outcomes stall, you’re not being bold—you’re drifting. A bold move has a finish line. A bloated list is just avoidance dressed up as ambition.

⚠️ 3. Leaders defend pet projects instead of killing them. Old initiatives stick around because no one wants to pull the plug. That’s how companies end up with dozens of half-alive efforts draining energy and morale.

⚠️ 4. Resources are spread so thin that teams are constantly “starting over.” People jump between five projects and make progress on none of them. This is the operational death spiral that comes from refusing to commit.

⚠️ 5. The company talks about “innovation” but only pursues low-risk tweaks. If your boldest move each year is a new feature, a new tagline, or a new flavor, you’re not innovating—you’re decorating. Real strategy requires stakes.