Leadership Mechanics: Asking Difficult Questions

I was a Boy Scout as a teenager, and my first scoutmaster was an incredible man we all called Mr. P. He was one of my earliest leadership role models, so I want to start the discussion of Leadership Mechanics with him. Mr. P was a powerfully quiet man - one of the few people I know who possessed the ability to silence a room of 40 teenage boys simply by standing quietly and waiting.

In Boy Scouts, for each new rank you achieve, there are a number of requirements - earn this many badges, go on this many campouts, and so on. The final requirement for each badge was to go through a "scoutmaster conference" - sit down with your scoutmaster, talk with him for 30 minutes or so, and then he signs off for you to get your badge.

When I first started working on my boy scout ranks, I had a notion that the conference would be just a pro forma conversation, something along the lines of "tell me what you learned while earning this rank".

Mr. P's conferences, though, were nothing like my expectation. They rarely had anything to do with the requirements of the rank. In his calm, respectful demeanor, Mr. P would drill in on a line of questioning that was, more often than not, pretty challenging.

A quick aside: it should be no surprise that, as a teenager, I was a first-class nerd. My idea of a good Saturday afternoon was winning a math competition followed by writing programs to find prime numbers, and I lacked any awareness that other people didn't have fun the same way. That my parents allowed me to spend weekends in the woods with a hoard of teenage boys was either a sign of great trust in my ability to take care of myself or great foolishness. The bottom line was, I was a constant target for the other scouts - they called me names, filled my shoes with shaving cream, threw buckets of sand into my tent, all typical teenage stuff.

To this day, I can remember sitting with Mr. P. in the scoutmaster conference for my Second Class Scout rank, and him really exploring with me the topic of why I didn't get along with the other boys. It had nothing to do with the rank, or what I had learned, but it did have a big positive impact on my future in scouting.

What really stands out in my memory was that Mr. P. was very pleasant and even caring throughout these conferences, but he would also keep asking questions, the kind of questions that made me reconsider some of my basic beliefs, until I could give a thoughtful answer.

"What does it matter what names they call you?"

"Um, I don't want to be called those names..."

"What part do you play in triggering them to do these things?"

"What did I do??? I didn't do anything. I was just around. OK, maybe I might have made some jokes about how I was smarter than they were, but a joke is not even close to the same as what they did!!"

"Why do you even react to having my shoes filled shaving cream?"

"Why do I react? They filled my shoes with shaving cream - what else would I do?"

"Does that do anything to discourage them doing it again?" 

"Not really, I guess...."

"So why not choose just not to react?"

"How would you even do that??"

Throughout this conversation and many others like it, Mr. P. pushed, gently but firmly, to ensure that I was really learning and growing as a young man.

Here's why I think this is so powerful as a leadership technique - a great leader is someone who is pushing everyone on their team, kindly, firmly, and consistently, toward ever-better performance. Too often we think of performance feedback as falling in the polar opposites of "Everything's great, keep it up, chief!" and "Oh you really screwed that one up, you better not screw up again," but I think a really strong leader can say, "You're doing great, but I want you to explain this situation to me in more detail."

So this is what I want to call the first of the key tools in Leadership Mechanics: you need to be comfortable asking really difficult questions, and you need to hold people to giving you an answer.

I use this tactic every day with my teams; for example, when things go wrong, I want to make sure we learn something and improve. I don't need to cast blame or chastise people, but I do expect that the situation provides an opportunity for learning. If someone doesn't give an answer that holds water, I ask again. I collaborate on ideas for what we can learn, but I make sure the answer comes from the person who really needs to learn the answer.

You see a similar philosophy in the Toyota Total Quality Management approach of "Five Whys" - in which a problem is debugged by asking why it happened, and, for each reason provided, you ask why that happened, the idea being that by the time you get five levels deep, you've discovered the real root cause.

I developed a huge respect for Mr. P. during our scoutmaster conferences. His commitment to asking very challenging questions, and his expectations of getting genuine answers, pushed me to grow in ways I still appreciate.

As leaders, I think we can all grow our teams and earn their respect in the exact same way: challenging everyone around us to develop genuine thoughtful answers to difficult and uncomfortable questions.