The Right to Left Thinking Challenge

At our emerging high growth Company, we are often faced with lots of exciting challenges, some easy, some complex but most require swift decisive action.

To help better attack these challenges and in my continuing pursuit of insight from seemingly unexpected places, I recently read, The Head Game — High Efficiency Analytic Decision-Making by Philip Mudd, former deputy director of the CIA Counterterrorist Center and FBI National Security Branch. “In The Head Game, Mudd sets forth a methodology of guiding principles that help to solve even the most chaotic of challenges.”

One of my areas of focus at our Company is to run the intelligence team, which I explain to people is the team responsible for empowering our internal and external stakeholders to make better decisions by answering tough questions with compelling stories grounded in irrefutable evidence.

Yes, that’s a mouthful, but interestingly (and a pleasant surprise) our methodology is similar to how The Head Game starts and now is certainly be bolstered by the knowledge in Mudd’s book.

Without deep understanding of how analytical processes work, most people in the organizations tend to come over to analysts and say “can you take a look at all the data we have and just cut it up and tell us what we should know?”

My usual response to the “cut the data and give us answers question” is two fold:

  • What is the question we are trying to answer?
  • What is the story we are trying to tell?

Having my team go down an endless pursuit of mining data to come up with answers is akin to running a race but not knowing where the finish line is — is it a 5k or marathon? It’s inefficient.

This is where the Right to Left Thinking Challenge (and HEAD Game) comes into place.

The most basic difference is that left to right starts with the data and right to left starts with the question we want to answer to achieve decision making goal.

Using a Pyramid (as diagrammed below — my interpretation of Mudd’s words) can help you understand the different between left to right and right to left thinking

Using Mudd’s HEAD framework (or adapting a subset of it) we can more efficiently get to our decision making goal. Note: I’ve adapted a subset of Mudd’s Checklist For Playing the HEAD Game Below (see pages 207 -214 in his book)

Without reading Mudd’s book and diving deep into the HEAD Game what can you immediately start doing to challenge yourself to think Right to Left?

  • Per Mudd, be the contrarian in the room, start the conversation in a way that assumes the mainstream position at the table is wrong. Rather than asking if everyone agrees, start at the other end. “There’s a good chance we’re missing something here.” What haven’t we considered? What don’t we know?
  • The next time someone asks you to “cut the data” push them to work with you to define the question and play the HEAD game — By starting with the question we want to answer that meets our decision making goal, we can better define the race we are running.


Here is a subset of Mudd’s Checklist (I’ve adapted) For Playing the HEAD Game Below (see pages 207 -214 in his book)

Getting to the right question

  • Can you use only one sentence to summarize your question? (clear and concise)?
  • When you pose the one sentence to Mom, can she understand it? (simple enough)
  • Is it broad enough to cover what we think we’ll need to cover, but narrow enough to provide a useful answer? (inclusive)
  • Does the question reflect the decision maker’s needs? (are we answering what they are interested in knowing)

Getting to the right drivers

  • Have I created a driver list that appears to cover what I need to cover?
  • Does every driver link directly to the question I’ve asked, or have I added items that are interesting but peripheral

Getting to the right metrics

  • How can I set a few metrics that will help me understand whether or not I’m on the right track
  • How can I come up with at least one rough metric for each driver?
  • When I set metrics, can I attach a time frame to them?
  • If confident today, when should I reconsider?
  • Have I defined the line between capability and intent metrics?
  • Are the metrics measurable in some way?

Getting to the data

  • Have I divided my information into the baskets that correspond with the drivers I identified?
  • Have I distinguished what I know, what I don’t know, what I think?
  • Have I differentiated between hard and soft drivers; capability and intent and Do I know where I might be vulnerable in my data?
  • What is it about this problem I don’t know and how can I close those gaps?
  • Is there data that doesn’t fit the driver baskets? What have I done with this data? Was it important?

Getting to the conclusion

  • Can I summarize the conclusion in three lines?
  • Would my mom understand it?
  • Are the drivers articulated?
  • Have I highlighted gaps?

Originally published at

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