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How to stop sabotaging your team (and yourself) by over-thinking

I knew this guy who seemed to have most of the answers, in detail.

He covered nearly every base.

He anticipated conversations and had most of the solutions ready to go.

He was respected for this. It brought him more rewards and responsibility.

He was happy.

Happy to work 12 hour days.

Happy to support his team by having all the answers and contingencies resolved.

Happy to meet every deadline, barely.

He was a thinker.

Along with his thinking style came worrying, doubting, perfecting, and hyper-analyzing.

All these characteristics served him and his success.

Until they didn’t.

Checking and rechecking work drove his team crazy.

Hesitancy to make recommendations frustrated his boss.

His wife and family resented the long hours and late meals.

I can also say I know this guy really well.

It’s me.

There were clues along the way.

One boss handed out humorous gifts at an appreciation party, mine was the T-Shirt with the Scotty from Star Trek saying “I need more data!” boldly across the front.

“But he wasn’t thinking properly. It was as if the thoughts were chasing each other round and round his head without managing to catch up to each other.  – Isabell Hoving, The Dream Merchant

Often when I’m introducing myself to a new group, I say I’m a “recovering engineer”.

People seem to know what that means. 🙂

It would be more accurate to say I’m a “recovering over-thinker”.

Much of my personal and professional development has been about becoming more decisive; allowing emotions, values, and intuition to be a part of my decisions and actions.

The change in me has been extremely fulfilling.

As a result, I feel more complete, more connected to myself and everyone I know, and more in love with living every moment.

It is part of the foundation behind my Purpose Statement.

My purpose: I help leaders create and achieve their visions. – Ken Roseboom

Leaders in analytical industries like engineering, IT, software, manufacturing, accounting, and construction often struggle in new roles where their analytic, problem solving, and execution focused skills are not enough.

Leadership is a role where you can’t simply think your way to success. (Ask me how I know!)

Something else is needed.

In this article, I will share several ways people over-think and ways to overcome it.

But first.

Why do we over-think in the first place?

The simple answer?

Because it feels good.

We have been rewarded and recognized throughout our lives for our thoroughness and thoughtfulness. It’s possible we felt the most loved as a child when we were smart, acted perfectly, and pleased everyone.

We want more of those rewards even if the context of today’s challenge is different.

So, we over-think, over-analyze, and over-deliver.

And while we are chasing perfection, we miss opportunities.

“Perfection is the enemy of progress.” – Winston Churchill

Or maybe we over-think because we fear moving forward will be more painful.

We over-think when we believe the only two options are “bad and worse”.

The stakes are high, and the outcome is uncertain. Stakeholders are not going to like your recommendation or action.

It feels better to delay, avoid, and over-work the issue than to “pull the band-aid”.

How do you know you are over-thinking?

The first clue to knowing if we are over-thinking is that it feels good.

Over-thinkers are comfortable when thinking.

Going forward, completing (or starting) the project, or having the difficult conversation is far more uncomfortable than gathering more data or analyzing the problem one more time.

But there are better clues.

Look at the situation. Sharpen your awareness and notice:

  • Are you missing deadlines and working late nights and weekends (both you and your team)?
  • Are you over-delivering? The task called for a 1-page summary response, and you delivered a full analysis.
  • Do you embrace “risk management run wild”? (Stacking what-ifs on top of what-ifs.) Have you thought through every known contingency and objection, but still doubt if you are ready or if you will be successful?
  • Do you search for more data when it will not change the decision or outcome?

Dig a little deeper. What’s happening on the inside?

  • Are you avoiding criticism? (Maybe you have never received feedback for missing a consideration in your recommendation or action plan.)
  • Do you think of yourself as a skeptic? Do you frequently doubt or not trust others’ accepted opinions?
  • Having trouble sleeping? Spending too much time worrying, doubting, and generally being anxious?
  • Is it possible you fear change?

If you answered yes to many of these, you’re probably an over-thinker.

If so, you’re in good company.

And like me, you may also be a “doer”, so let’s get on with the “what to do” section!

How to stop over-thinking

Check your optimism/pessimism balance.

Be careful about pessimism masquerading as “realism”.

There is a large body of knowledge supporting the fact that being optimistic creates better outcomes faster.

Martha Washington once said, “I am determined to be cheerful and happy in whatever situation I may find myself. For I have learned that the greater part of our misery or unhappiness is determined not by our circumstance but by our disposition.”

Accept the leadership challenge to move forward in the face of uncertainty and ambiguity.

Remember how a clue to over-thinking is “that it feels so good’?

Leadership requires getting comfortable with the discomfort of uncertainty.

Trust, vulnerability, and courage will be required. This is masterful leadership territory.

Stop trying to manage the unmanageable.

You can’t control what other people think, feel or do.

Stop trying.

Sure you can influence and be influenced by others’ thoughts, feelings and actions. But be aware if you are in fear of them or are seeking approval at all costs.

Your focus on being likable might be at the expense of being less respected.

The weather, competitors’ actions, and customers’ choices are all unmanageable.

“There is only one way to happiness and that is to cease worrying about things which are beyond the power of our will,”
Epictetus, Greek Stoic philosopher

Focus on your actions and responses, not on trying to control the uncontrollable.

Think of decisions as “experiments”.

Move forward with your idea.

Experiment and learn. Adjust the course as you learn more.

Know the difference between irreversible decisions and reversible decisions. More decisions are reversible than we think.

The consequences of a regretful decision are often less than we imagine they would be.

Know that one decision opens the door to many more decisions. You can’t answer them all before you start.

Make the first decision, learn, make the next decision, learn…..

Are you neglecting the wisdom of your heart and gut?

We are “heady” people.

I’ve seen people over-think as they grapple with logistics, risk, and uncertainty.

Sometimes the real issue is “that head logic” is at odds with their emotions and intuition.

Yes, our emotions are logical!

They drive behavior and actions.

The emotions of fear and love are the two most powerful human forces. Ignore your emotions at your own peril.

Become friends with your feelings, learn the nuances of their logic and story, and become skilled at navigating to emotions that help you get more of what you want.

“The head thinks. The heart knows.” Rasheed Ogunlaru

True, some people trust their intuition when a bit more thinking and analysis would support a better decision.

However, our gut feeling about a situation is an awesome guide.

Intuition is best accessed by accessing core values and vision for the future.

No need to over-think an action if a possible solution isn’t congruent with your vision and values.

Consider the cost of indecision and over-thinking.

Delaying a decision is a decision.

Overthinking and overanalyzing take precious resources from everything else you could be doing.

Opportunities are lost when decisions are delayed.

Allocate the appropriate time and resources to thinking and analysis. But be aware when the time and resource budget is consumed.

The bigger picture may well require an action or a decision on less than perfect information and analysis.

Overused strengths become weaknesses – what got you here won’t get you there.

Many of my clients are great risk managers.

They are knowledgeable and experienced. They are paid well to apply this knowledge and experience.

They create the likelihood for the best outcomes of decisions and projects.

And when they over-think they drive everyone else crazy.

Desiring respect and admiration for their knowledge, they delay decisions and actions by “connecting every dot”, analyzing, and having plans for every risk.

Over-thinkers solve problems they don’t have yet and may never have. – Ken Roseboom

They try to manage the future rather than lead creatively into it.

Over-thinkers love complexity and solving complex conundrums. Masterful leaders appreciate complexity and then communicate with simplicity.

When you’re an over-thinker, simplification requires new skills, new mindsets, and new actions.

You can’t think your way out of over-thinking. – Ken Roseboom

Would you like a guide?

Someone who understands the over-thinking challenge and is living the brave world that exists outside our heads?

Let’s get on a call to see if I’m the right fit to help you to create and achieve your visions.

Click the link: Book a Call with Ken.

Don’t over-think it 😉

“Be decisive. Right or wrong, make a decision. The road of life is paved with flat squirrels who couldn’t make a decision.” – Anonymous

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Ken Roseboom

Ken Roseboom is the President of Thinking Partners. He partners with leaders to increase impact, create aligned teams, and deliver better results. He leverages the Alignment process, assessment tools, expert coaching, and years of front line leadership experience to support his clients.
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