How to ask difficult questions?

A reader asks, “How can I ask 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. Also, if you’re an outside consultant, your clients will almost never see you as a trusted advisor unless you know how to ask difficult questions.

So knowing how to do it well is an important skill to have.

Here are three tips for doing it well:

1. 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.

2. 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.

3. 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 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.

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