Rule No. 6 📔 Your first idea is rarely your best.

Executive insights 👥 Let me tell you how that played out in my company.

Have you ever moved forward with the first idea that seemed right, only to later realize a better option existed? What did you learn from that?

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the Rules matter.

“The greatest originals are the ones who fail the most, because they’re the ones who try the most.” — Adam Grant

The surprising habits of original thinkers | Adam Grant | TED

The first idea is also usually the most obvious one. That’s why you should always question it. The businesses that break through are willing to ask, “What if we’re wrong?” or “What else could we do?” and keep looking, long after everyone else has stopped. Breakthroughs rarely come from the first answer. They come from the discipline to ask more and better questions. As leader, being the person with the answer isn’t nearly as important as being willing to question your own answer. Your first idea may be good. It may even be right. But don’t let your position, your experience, or your ego keep you from asking, “What else?” Give your team permission to challenge the first answer. Give yourself the same permission. The better idea may just be one conversation away.

A) As a decision-maker, how do you balance the urgency to act with the discipline to challenge your first idea, especially when others are ready to follow your lead?

B) Think about a big decision your company made in the past year. Did you choose the best idea, or the first idea that seemed workable? Would you do it differently today?

C) Why, or in what area, does your team tend to settle on the first idea? Is there a possibility that your are the bottleneck in the process?

D) What strategies do we have that could change the decision-making process to consistently bring more alternative ideas to the table?

🥊 challenge the Rules | take the contrarian view

Go with your gut. Your first idea is often your clearest, and overworking it could reduce speed, conviction, and competitive advantage.

  1. Are you really improving the idea, or just delaying the decision because you’re uncomfortable committing to it?

As a group, could we come up with 3-5 actionable strategies that put Rule No. 6 —Your First Idea Is Rarely Your Best into practice and help each of us turn this Rule into a habit?

One last word, before we wrap for the week…

In business, there will always be pressure for you to decide and execute quickly. Over and over you’ll hear “speed is a virtue”. It is, but speed applied to the wrong idea just makes a bigger mistake. Your real strength, as the leader of your team, is having the discipline to stop for a second and ask, “What else?”. Don’t build on the obvious (that also could have been the name of this Rule). We don’t build on the obvious because the stakes are high and, as the leader, people are going to rally around the first idea that you say out loud. If you don’t intentionally open the door for second and third opinions, and various options, no one else will.

This week isn’t about slowing down your business. It’s about sharpening it. Here’s the advice: treat your first idea like a rough draft, not a decision. Write it down, set it aside, and force yourself to come back with two more approaches. The discipline we build by comparing ideas is where our better judgment comes from. The first idea often wins just because it’s convenient, not because it’s the best. It sounds decisive. It feels productive. Everyone nods, and you move on it. Remind your team to think deeper. Ask them if everyone thought of this idea. That probably means your competitor did to. Stop. Think deeper.

See you next week. Take this Rule back to the office.

Keep going. Take a deeper dive into this Rule and see what it looks like in the real world. Hear how other business leaders have approached the issue, look for red flags and green flags in your own organization, and explore the additional terms, links, videos, and resources we’ve assembled.

  • When to Apply | Red Flags
  • Rule Overview
  • Ask the Right Questions
  • Contrarian View
  • Actionable Strategies
  • Real World Scenarios
  • Leadership Team Discussion
  • Rules to Results Workshop
  • The Right Track | Green Flags
  • Key Terms
  • Book Summary
  • Author Links
  • Executive Insights
  • Worth Watching
  • Related Reading

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Here are 5 warning signs you and your team may be ignoring Rule No. 6:

⚠️ Fast Consensus– Teams quickly agree on the first idea presented, with little debate or exploration of alternatives.

⚠️ Idea Fatigue – Leaders discourage “too many” suggestions, signaling that efficiency is valued over creativity.

⚠️ Fear of Rework – Projects push forward even when flaws emerge, because revisiting the concept is seen as wasted effort.

⚠️ Overconfidence in the Pitch – A strong initial presentation is mistaken for a strong long-term solution, without deeper testing.

⚠️ Lack of Iteration – Products, strategies, or campaigns are launched without pilots, prototypes, or scenario testing.