Examples of Smart Questions

As leaders, we often find ourselves in a meeting where members of the team brief us on their business plan.   I want to share with you a few things I’ve picked up that can help those meetings become more valuable for both you and the rest of the team.  My message isn’t for you to “ask questions” (I leave the simple answers for other blogs.  We’re into smart content here!).  The key, I believe, is to formulate the right questions. Smart questions.  Let me explain.


Why an image of this book? Keep reading…

How might you describe the meeting I’m referring to?  You know the one.  Each member has 20 to 60 minutes, they’re supposed to deliver a presentation on how they plan to hit the targets you’ve set for them as part of the overall objective, and they have a prepared slide deck.  Here are a few ways I would describe how these tend to go from the presenter’s point of view:

  • They’re nervous (maybe).  At least they want to look competent.
  • They probably haven’t been looking forward to this, and will be happy when it’s over.
  • They know that, most of the time, there will be a couple basic questions asked during the presentation.  They are prepared for these questions (this is important – we’ll come back to this).
  • They are inclined to portray more understanding or confidence in their material than they might actually feel.

On the flip-side of the same presentation, let’s think about how one of these presentations might be received from the leader’s point of view:

  • You’re trying to look like you understand all the details.  You might do this by furrowing your brow and nodding your head in what you assume to be a sage and very leaderly way.
  • You actually know what’s coming, but you work to stay focused out of deference to the presenter.
  • You are trying to listen but have ten other problems that are competing for your mental attention, not to mention you are behind on creating your own presentation to present to YOUR boss at an upcoming executive staff meeting.

In short, these meetings can follow a script that makes everyone feel like they’re playing a role, but no insights are uncovered.

I have found that a great way to break all this up is to ask what I’m going to call the “smart question”.  Here’s what characterizes the smart question:

  • It is unexpected.  The presenter has to stop and think.
  • It’s non-threatening.  In fact, it puts both parties on the same side.
  • It taps into imagination.  There is a “fun” element to it.

I recently read Team of Teams by General Stanley McChrystal (along with Tantum Collins, David Silverman, and Chris Fussell).  I highly recommend the book.  (If you enjoy considering how leadership lessons from the military can be applied to your personal life, check out this and this and this and this.)  Gen. McChrystal writes about visiting units in the field and being impressed by how a senior commander named Mike got to the heart of the matter:

We were visiting a unit that boasted of having more than 250 intelligence sources (Iraqi civilians recruited to pass information to U.S. forces).  I was deeply impressed.  Mike then asked a simple question:  “Can you describe your very best source?  I’ll assume that all the others are less valuable.”  The unit admitted that the best was new and unproven, and in an instant it was clear that their source network had little real substance.

Was that question unexpected?  I’ll bet!  Was it non-threatening?  Mostly, although I suspect there was some nervous clearing-of-throats and looking-at-boots happening.  Did it tap into imagination?  Somewhat.  It certainly forced the unit to think differently about what success looked like (e.g. 250+ sources isn’t impressive if they’re mostly unreliable).

Here’s a question McChrystal himself would ask when he was in Afghanistan:

I later used a specific question when talking to junior officers and sergeants in small bases in Afghanistan: “If I told you that you weren’t going home until we win – what would you do differently?”  At first they would chuckle, assuming I was joking, but soon realized I wasn’t.  At that point most became very thoughtful.

Was that question unexpected?  You bet!  Was it non-threatening?  Yes (once they gulped and realized he wasn’t delaying their return home, I’m sure).  Did it tap into their imagination?  Yes!  In short, that is an example of a very, very, smart question.

Let me pass along one more that I learned from being in a few executive briefings during my time at IBM.  I heard this question asked a couple times and I have used it myself on a number of occasions.  Note – you can’t use the same smart question over and over, otherwise it won’t be unexpected anymore and immediately become less “smart”.  The question is: “What resources do you need to double your results?”.

I have usually found people are initially in some sort of stunned silence, but as you coax them, they unfreeze and think about it.  On the face of it, the task is impossible – even if we hired 10 more reps there’s no chance we’d get them hired, trained and productive fast enough to double the growth, they might say.  Which is fine.  But….sometimes you get thoughtful replies about how if you gave them more resources here or there they could increase results by a smaller – but still impressive – margin.  When you’re confident in what you hear, then you may have found two things:  where to put a few extra dollars in the budget, and who the next leader of your group might be.

Smart questions.  They can change the game.

Good luck!