Asking Questions

I'll always remember two of the most powerful questions a former colleague, a senior partner at a global consulting firm, would ask of clients. After the small talk had played itself out, he'd say: "How's business?" Later on, after rafting the tributaries that flowed from that initial query, he would follow up with: "How are you?"

These two questions were profoundly generative, and I've often thought about why. What are the design principles that made them so effective? Most obviously, they are wide open. They create maximum space to roam. But I think they also avoid three common pitfalls:

Pitfall #1: Triggering defensiveness

Open questions are surprisingly nuanced. Word choice really matters. A well-known hack is to ensure you never start a question with anything but the words 'What' or 'How'. In many instances that feels unnatural. Why did you change your strategy? seems like a perfectly reasonable thing to ask. In truth, it's not exactly a bad question.??

It's just that it could be better. Because there's something mildly, subtly, obliquely confrontational about the word 'why'. It can trigger a subconscious need to defend oneself. It can feel more accusatory than exploratory. How/What questions elicit dialogue, whereas Why/Is/Do questions stake out positions in a debate.

Rather than Why did you change your strategy?, it might be better to ask, What are the most important elements of your new strategy?

Pitfall #2: Shutting down authenticity

People often manifest the response they're looking for. This is most annoying when the anticipated answer is tucked into the question itself: How you doing? Good? It's a particularly egregious display of obliviousness.

But the problem can be less blatant than this. Hey, how are you feeling today? seems like an open question, but it's not. There are all kinds of cultural reasons why people feel obligated to affirm things are hunky-dory all the time, especially in a professional setting. The inevitable answer — Doing great, thanks. You? — becomes entirely performative.

A former colleague managed someone who was going through a rough patch in her role. In their weekly one-on-ones, he had a ritual of using a quantitative variation of How are you? He'd say: OK, on a scale of 1 to 10, how are you feeling this week? She started at a 2 and gradually moved up the scale, because he explicitly made it his mission to brighten her perspective over time.

Pitfall #3: Front-loading the personal

Notice how the consulting partner always asked "How are you?" in the later stages of the conversation. This is the opposite of what we tend to do. We are inclined to get the personal stuff "out of the way," typically as part of small talk.

Again, it's not that this is inherently wrong. It's just that the moment of interpersonal connection could be intensified. There's a palpable shift that happens in a business conversation when the agenda items have been satisfactorily addressed. Suddenly, you have a more unobstructed perspective on the other person. You see them more clearly.

That is the moment when a deeper connection is possible. It was the moment my former colleague relished, and it became the most productive wellspring of trust in his client relationships.?

There are creative ways to accentuate this moment. For instance, you can prime the positive with a question like: What are you currently most excited about? Or, slightly more cheesily, What's making you feel most alive these days?

Good listeners demonstrate interest, empathy, and affirmation. Great listeners do that as well, but through skillful questioning.