Changing the Way the World Thinks about Strategy
Honesty in Strategic Thinking

Honesty in Strategic Thinking

The ninth critical skill in strategic thinking is honesty.  Great strategic thinkers can balance their tremendous creativity with a sense of realism and honesty about what is achievable in the longer term. This ability to balance is not an obstacle to their accomplishments.  Many strategic thinkers refer to themselves as realistic optimists.

How does this honesty in strategic thinking show up?

One of the hallmarks of shortcomings in this area is self-deception.  While many point out – correctly – that many entrepreneurial activities require a certain kind of optimism, great strategic thinkers temper that optimism with understanding.  This means that good strategic thinking may start with an optimistic idea, such as “We can do this”, but works realistically with the issues that exist.

In strategic planning, the capabilities assessment reveals a lack of honesty.

A clear understanding of both the strengths and the weaknesses of the organization is a great clue that some good strategic thinking is going on.  Strategic planning teams sometimes resist this.  It can feel vulnerable to accurately acknowledge weaknesses in a group.  A well-managed team, however, treasures that vulnerability as a sign that the group is both trustworthy and honest.

There are three main areas where honesty can be a huge issue in strategic planning.

1. Acknowledging weaknesses

The first is exactly the problem we see when team members aren’t brave enough to talk about weaknesses in the capabilities assessment.  We do this because, anthropologically, there is a group sentiment that weakness should be avoided and, where noticed, it should be exploited by the alpha in the group.  This is the opposite of good teamwork, but it’s a strong part of primate behavior.

2. Perceiving threats

The second is often referred to as the “ostrich syndrome”.  You have the desire to stick your head in the sand to feel safe from the threats you cannot see.  This is obviously not going to work, but our stress responses often cause us to behave like a small child.  We cover our eyes when the scary part of the movie comes up!

3. Accepting the possibility of bad outcomes

The third area comes from assuming we have a good plan which can’t go wrong.  Of course a good plan can go wrong.  One problem we see in many models of strategic planning is the failure to assess how that plan might cause new problems that didn’t already exist.

All three of these issues arise from the problems many cultures have with pretending things are OK.

This is not unique to western culture, but it is particularly strong there.  Why do we pretend things are OK?  Here are the biggest reasons:

  1. The group tendency to gang up on the weak (which was already mentioned).
  2. The classic management approach of trying to make every peg fit our square holes, which became enshrined in manufacturing management in the early 20th Century.
  3. The normal human tendency to treat different thinking as bad.
  4. The cult of “fake it till you make it” we learn from motivational speakers and sales training.

All of these reasons are artifacts of our history, our evolution and our culture.  All of them are also either created by or sustained by the people involved.  Great strategic thinking requires that we challenge this reasoning.

The underlying thought process here is that we often look at the way things could be and ask “Why not?”.

This is a great approach for strategic thinking.  Unfortunately, our minds – and the minds in our groups – can often come up with easy answers that don’t connect with reality.  The real answers are often the most useful for strategic thinking, but acknowledging them can feel vulnerable and threatening.

How can we encourage brave, honest thinking?

The most important factor here is our sense of safety.  We have to remember that we are actually less safe when we fail to acknowledge the truth, even if it feels like we are safer.  In groups, we also need to take the effort to make everyone feel safe speaking the truth, even when it isn’t what we want to hear – and even if it scares us.

Have you wrestled with self-honesty in your strategic thinking?  What steps do you take to avoid this?

If you’d like to learn more about strategic thinking and more specifically the importance of honesty, Simplified Strategic Planning is a great place to start.  For great ideas on how to improve the quality of your planning, contact me at  Consider holding a one-day workshop on Simplified Strategic Planning.

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Robert Bradford is President & CEO of the Center for Simplified Strategic Planning, Inc.  He can be reached at

Dana Baldwin is Senior Strategist with the Center for Simplified Strategic Planning, Inc.  He can be reached by email at

Co-Author Robert Bradford

Co-Author Robert Bradford

Co-Author Dana Baldwin

Co-Author Dana Baldwin

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