Smart Entrepreneurs Wear Six Hats

Entrepreneurs are necessarily optimistic. You need to be, it allows you to see the possibilities around you and act on them.

However, the downside is that your emotional attachment can blind you to problems that are otherwise obvious to someone who is not as personally invested in the project.

This is why smart entrepreneurs learn to wear six hats: six “Thinking Hats”. Originally defined by psychologist Edward DeBono, the Six Thinking Hats are a structured creativity tool to help you look at a situation from different perspectives, to solve a problem or to foresee and minimize risks before they turn into problems.

When you “wear” a specific color hat, it gives you permission to look at your problem is a specific way:

  • White Hat: Analytical – What does the data say? Look at the available data, both quantitative and qualitative. What are past trends? What can you extrapolate? Where is the evidence to support your assumptions? Where do you need more data?
  • Red Hat: Emotional – How do you feel about this? Access your intuition, gut reaction, emotion. Talk about your feelings about the situation, where you feel good and not as good. How would others feel about this?
  • Black Hat: Pessimist – What could go wrong? Think cautiously, defensively, why it might not work. Poke holes in the idea, look for the weak spots, all with the intention to identify what needs to be addressed in order to overcome any problems.
  • Yellow Hat: Optimist – What if all goes right? Think optimistically, positively. Imagine all the opportunities, the benefits, the advantages. Reach for the stars!
  • Green Hat: Creative – How can we make this better? Use your creative juices to think “out of the box”. Explore weird tangents, unexpected synergies, make it into a “purple cow” (something remarkable that stands out from the crowd).
  • Blue Hat: Process – What do we need to do now? Direct the process of creativity so avoid getting stuck. When in “Blue Hat” mode, step back from the problem and consider if you are giving all of the other hats equal time.

Entrepreneurs seem to do quite well with the Yellow, Red and Green Hat approaches to thinking about an idea. There is more resistance to the White Hat (analytical) and definitely a big block around Black Hat thinking. Could this be because the Analytical and Pessimist are associated with external control?

There is nothing to fear from the Black Hat – it can be your best friend. Wearing the Black Hat gets you out of cheerleader mode and forces you to examine your assumptions up close. From personal experience, I know that when a project backfires, the failure can be traced back to an assumption that was not properly tested. Black Hat thinking gives your project real traction by foreseeing the difficulties and encouraging defensive planning. This makes the plan more resilient and improves the probability of success.

As you explore wearing the various Hats, put on the Blue Hat (Process) from time to time to see if you are considering all the perspectives of your project. Note that the purpose of this thinking exercise is not to assign fault or blame. The mindset of every Hat is to make sure the project succeeds.

It is great fun to dream big and to reach for the stars. But if you want to make any progress, you need to keep your feet on the ground. Practice wearing the Six Thinking Hats as you plan and execute your business project. This mindset will give you the traction to power your project towards real and enduring results.


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