“What problem are we trying to solve?”

It was a simple enough question, but it caused me to take pause over my dinner. We’d just finished a whirlwind day in New York City with the boss, and settled in over a meal and what’s euphemistically called a “hotwash.” As we reviewed the events of the day and discussed those to come the following morning, he posed the question to the small group at the table. Before anyone could answer, he continued: “In my experience, we’re really good at solving problems. But we don’t always take the time to make sure we know what the problem is before we come up with a solution.”

Effective Leaders Know How to Ask the Right Questions

Throughout their book, Leading with Strategic Thinking, authors Aaron Olson and Keith Simerson maintain a steady drumbeat: effective leaders know to ask the right questions. Not just any questions, but the right questions. Through two separate assignments working for this particular senior leader, it was clear that he’d mastered that skill. In my time in uniform and out, I’ve never met anyone as adept at consistently asking the right questions when the answers mattered the most. When it came to gaining insight, driving change, and getting results, no one was better. 

Heilmeier’s 8 Questions that Fueled the Right Opportunities for DARPA

In time, I came to understand that there was a method to his line of inquiry. A formula. A simplicity that defied the complexity of many of the issues we faced. Intentionally or not, his line of inquiry paralleled that of former DARPA director George Heilmeier, whose “Heilmeier Catechism” proved essential to the agency long after the end of his tenure there. In an organization like DARPA, which operates on the principle that risk is a catalyst that fuels opportunity, George Heilmeier posed eight questions that helped to assess and prioritize research proposals.  

1. What are you trying to do?

This was the equivalent of “What problem are we trying to solve?” For Heilmeier, this needed to be expressed as simply and directly as possible, and free of any jargon. In the three years I worked for him, the boss always opened with the same question, and yet people still struggled to answer it. 

2. How is it done today and what are the limits of current practice?

It’s not a difficult question, especially if you’re proposing a change. What’s so wrong with the way it’s done today that it necessitates a change? Oftentimes, we expend an inordinate amount of time and effort on iterative changes that really don’t make that much of a difference.

3. What is new in your approach and why do you think it will be successful?

Again, a very basic question, but one that many find difficult to answer. This is often the trap of iterative change efforts that won’t be met with much enthusiasm or achieve meaningful results: change for change’s sake. Sometimes, a minor change will gain significant rewards; if so, you should be able to articulate that clearly and succinctly.

4. Who cares? If you are successful, what difference does it make?

Many initiatives simply don’t produce change that matters. But we’re not always honest enough with ourselves or willing to admit the truth. If you’re going to invest in something, the reward needs to be worth the risk. 

5. What are the risks?

Understanding the risk involved allows a leader to make informed decisions about how best to mitigate it – avoidance, acceptance, reduction, or transference. Not everyone sees risk the same way; some people would rather avoid it altogether. But, flying blind in the face of risk puts you directly in the “hope is not a method” category. That’s not a good place to be.

6. How much will it cost?

In the broad calculus of strategy, resourcing is often the determining factor. It’s not just the grand vision that matters, it’s what you can afford. It’s what you have the means to achieve. 

7. How long will it take?

Time is as much a resource as manpower and money. But just because you have the other two doesn’t mean you have the luxury of time on your side. Unfortunately, we’re not often forthcoming when it comes to time, and just as often, leaders fail to account for it. 

8. What are the mid-term and final “exams” to check for success?

Assessment is fundamental to execution. What are your assessment tools, measures, and metrics? One of the key roles of a leader is pulling the thread that ties planning and assessment into execution. This is summed up perfectly by authors Larry Bossidy and Ram Charan in Execution:  “As such, [execution] is a major – indeed, the major – job of a leader. If you don’t know how to execute, the whole of your effort as a leader will always be less than the sum of its parts.” If you don’t know how or what you’re measuring, execution will always fall short.

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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.