How to know when overthinking is good

How to know when overthinking is good

For years, my business coach has been telling me to stop overthinking things, trust my judgment, and keep going.

He’s not wrong.

The funny thing is, I wouldn’t consider myself a deep thinker. Instead, I prefer to think strategically and balance these ideas with a predominance of acting.

In the coaching I do with sales professionals, the first step we typically take is to assess what kind of thinker the individual is.

From my experience, there are three different categories of thinkers:

Strategic thinkers: Those that think about a situation or idea but rarely think too deeply, as their preference is to balance thinking with action.

During strategic planning sessions that I facilitate, participants consider the state of the business and progress towards critical objectives. Then as a group, we determine what we should start, stop, or continue doing to achieve the business objectives.

Strategic thinkers have a well-rounded view. They seek clarity around their current circumstances and use the information collected to move forward and achieve their goals.

Activity-based thinkers: Those who prefer acting overthinking and believe that they will figure things out as they go.

These are individuals who rely heavily on their intuition to help them progress their plans.

My boys are both involved in hockey, and I often remind them that they have little to no time to think while playing a game. They need to trust their intuition (built through hours of practice) and act; otherwise, the other team will gain the upper hand.

The greatest weakness for activity-based thinkers is that they spend considerable time attempting to resolve or recover from actions that require more thought.

Deep thinkers: These are people that think deeply about a situation or problem, taking their time to consider all angles and subsequently determine what the right path forward might be. Their solutions and ideas are often very robust; however, the downside is that it can take some time for them to conclude.

I still recall doing some consulting work for a deep thinker many years ago. During our first meeting, I walked into his office and asked, “how is your day going?” His response began with, “how is my day… that’s a great question. Let me think about it for a moment.”

After a long pause, he highlighted critical parts of his day, which took about ten minutes.

I was a bit taken aback. As I got to know him, I realized just how intelligent he was. However, if you don’t know him well, you might wonder why he takes so long to respond to any question or statement you make.

This is when I began paying closer attention to the different approaches to thinking. As you might imagine, there are pros and cons to each method, and as a result, I encourage the leaders I coach to consider flexing their approach to thinking based on the situation at hand.

When faced with an urgent situation like a fire, there is no time to step into deep thought or even think strategically about what to do. Instead, the best course of action is to collect your team and then leave the fire scene as quickly and safely as possible.

Strategic thinking is the best approach when faced with a situation that does not require an instant response. For example, this is a good approach for selling when faced with finding or converting target accounts. By taking time to weigh the pros and cons of the situation, contrasted against your capabilities and capacity, you’ll identify the best possible course of action.

Deep thinking is appropriate when you encounter a complex situation that is not time-sensitive. For example, it might be deciding your next career move, identifying a new product or service to launch, or even how to best support the development of your team.

Deep thinking allows our subconscious to engage in the process, often resulting in ideas that we might otherwise not have identified.

While writing my third book, The Unstoppable Sales Machine, when I reached a point in a chapter that I couldn’t write, I skipped the section and engaged in more profound thought, often returning a week later with fresh ideas and examples to share.

The benefit of deep thinking for high performers is that the process can present options, ideas, and solutions that would have otherwise not have arrived, engaging a much deeper level of our conscious awareness.

However, it’s essential for those who are naturally deep thinkers to consider flexing to include both activity-based and strategic thinking when the opportunity presents itself.

Another strategy to overcome a natural tendency to divert to deep thinking is setting time limits or milestones around your review, prompting yourself to move forward with some element of your plan.

So the next time you have a decision to make, avoid the tendency to fall into old habits. Instead, consider what the best approach might be to achieve the best possible outcome.

I’ll admit that changing our natural tendency around our thinking isn’t easy, but self-work is some of the best work we can do.


Shawn Casemore is a speaker and facilitator who works with entrepreneurs and business leaders to align their teams, “wow” their customers, and grow their businesses.