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Your Worst Decisions Are the Ones You Stopped Thinking About

  • Writer: Jerry Olson
    Jerry Olson
  • 5 hours ago
  • 3 min read

Leadership Team discussing Data generated by AI

Author, Jerry Olson, is a Business Advisor with The Resultants.

To learn more about Jerry, visit our Team Page or connect with him on LinkedIn.



One beautiful autumn day, I had a long break between meetings. Perfect chance for fresh air and a quick workout, so I jumped on my bike and headed out on one of my regular routes.


About halfway through, I approached a stop sign at an all-too-familiar, seldom-used, totally obscured driveway.


Decision time. Slow down and stop? Or blow through it?

Like hundreds of times before, I blew through it without slowing down.


As I entered the intersection (much too late to stop) a car appeared from behind the trees. I face-planted onto the hood, tumbled across the car, and landed in the ditch on the other side of the road.


That collision was a dramatic reminder of something every business leader eventually learns the hard way:


The decisions that hurt you most are rarely the ones you agonized over. They're the ones you stopped thinking about.


Are you confidently creating a blind spot?


Every time I ran that stop sign and nothing happened, my confidence grew. This worked before, so it will work again.


In reality, each pass just brought me closer to the eventual outcome. I wasn't building judgment. I was building a blind spot.


Businesses do this constantly.


The pricing model nobody has revisited in four years. The hiring process everyone complains about, but no one owns. The customer segment you know is your best (because it was…in 2019.)


What decisions, assumptions, strategies, and tactics should you be rethinking?


I love biking. I spend many hours on my road bike each season. I set seasonal goals and weekly targets. I have an app that tracks my progress in real time.


Sound familiar? It should. That's a vision, a strategy, and a set of growth metrics. The same three things that make up the Plan side of any healthy business.


I had a plan and I was measuring against it.


But here's what I missed: a plan tells you where you're going. Measurements help you track your progress. Neither of these tell you what you've stopped questioning along the way.


Familiarity is where the risk hides.


Good leaders continually and critically question assumptions, especially in familiar territory. So, ask the uncomfortable questions:


  • Is the market really what we assume it is?

  • Is our technology as robust as it needs to be?

  • Are the teams we depend on as engaged and aligned as we believe?

  • Is our sales pipeline truly what we think it is?


What past experiences have you leaned on too heavily?


Marketing strategies? Sales processes? Staffing projections? Customer expectations? Supply chain?


The fix isn't more caution. It's better rhythm.


You can't white-knuckle your way to good judgment by trying harder to pay attention.

What catches blind spots is structure. The discipline of surfacing the right questions on a regular cadence (even if nothing “feels” wrong.)


This is one of the reasons we spend so much time on Meeting Management when we work with clients.


It sounds like the least interesting part of the Accelerate Your Business™ model, but a well-built meeting system is where uncomfortable questions are asked before they turn into problems.


When that rhythm is in place, you don't have to remember to question your assumptions. The system asks for you.


What it cost me


On that beautiful autumn day, my biking season ended abruptly with a broken neck.


After ambulance and helicopter rides, an intense encounter with 25 members of a Mayo Clinic emergency trauma team, multiple x-rays, MRIs, and a day in the intensive care unit, I was sent home in neck and body braces with a long list of restrictions.


I was very lucky to be alive and walking.


Most business blind spots don't end that dramatically. There's no ambulance. No trauma team.


Just a slow drift you don't notice until you're already in the ditch.


Operating on autopilot?


The Accelerate Your Business™ model is built to catch the things you've stopped seeing. A clear plan, the right people in the right seats, and an execution rhythm that keeps the hard questions on the table. If that sounds like something your company needs (hint: most do), send us a note and we'll set up a conversation.

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