In 2014, I started working primarily with CEOs and board members of publicly-traded companies. You know these companies by name, their ads are everywhere and these people get asked to speak on just about every panel and TV news show that ever existed.
At first, I was scared out of my wits. “Who am I to be hanging out with these people,” I wondered.
I’ll probably never forget the moment one of them told me he admired me. “Are you kidding?!” I screamed in my head, “You’re a rock star, don’t you realize I practically worship the ground you walk on?!”
Fortunately, within a few months I calmed down and it became my new normal. I realized that I got along with those kinds of people really well, better than I did with, shall we say, others.
I don’t know why I got along with them. I just did, and in the years since, I’ve made a business out of serving that cohort.
I think the ease with which I get along with them has something to do with the fact that I’m naturally curious about pretty much anything. It didn’t matter whether the conversation was about hiring consultants to do due diligence on the acquisition of another company, or maybe looking at Google Maps and Wikipedia to learn about the source waters of the Nile River (yes, those are both real-life examples, and the clients I did those things with are both regular readers of this email, so they probably recognize the examples).
I thought it all was endlessly fascinating, and I think that’s why those clients tended to keep me around for years and years.
One of the first lessons I learned in working with that cohort was don’t ever pretend to know more than you really do. That group has an uncanny ability to size people up, so they tend to know way more about you than you think you’ve shown them. No matter what you do, they’ll know the truth. If you try to pretend you know more than you really do, they’ll see you coming from a mile away. So just say “I don’t know” and learn together.
Another skill I learned was how to have difficult conversations with someone who outranks me many times in pay grade. I had to learn that skill because in my capacity as coach, I occasionally found myself encouraging them to do something they were nervous about doing.
So some years ago, I wrote up some tips for having difficult conversations with someone above your pay grade. This is a subject that will probably interest some of you, so for what it’s worth, I pasted my tips in here:
Asking difficult questions…
You know the kind of questions, the ones where you wonder beforehand if you dare ask them, the ones where you stop first and think things like is that question too forward, or too bold, or is it too early in the relationship, etc.
Yes, asking questions like that is risky, but the upside payoff is huge. People almost never make it to the C-suite unless they’ve shown they can ask difficult questions well.
So knowing how to do it well is an important skill to have.
Here are three tips for doing it well:
- Keep your eyes lower than the other person’s eyes. Not lower as in “look down at the floor, away from the other person” but lower as in slightly below the other person’s eyes in elevation. In fact, to avoid confusion, let me restate that: Keep your eyebrows a little lower than the other person’s eyebrows. And it doesn’t have to be a lot lower — in fact, keeping your eyes a lot lower would probably seem funny. And if both people are playing the same game, there will be a ridiculous-looking competition where both people will slouch lower and lower towards the floor until both people are practically falling out of their chairs to see who can get lower.
- Keep your body loose. Remember mirror neurons and the tendency of people to act like people around them? You want the other person to stay loose and relaxed when you ask them the difficult question, to keep their defenses down, so you need to do the same.
- And probably most importantly, use the other person’s words and phrases, not your own. For example, if the difficult question is how do you achieve “A” and “B” at the same time, even though they are mutually exclusive, get the other person to say “A,” and then to say “B,” and then you say, “Wait a minute, I don’t understand something, a few minutes ago you said A, but you also say B, and those seem like they are kind of contradictory, so how do you do both?”
Once you’ve asked the initial difficult question and a couple followup questions, and no one has died, you can relax a bit and begin digging deeper into the difficult subject, knowing that you’ve been accepted into the club that gets to talk about that stuff.