It may be one of the most frequently asked (and least meaningfully answered) questions in the workplace. We say it when we join a Zoom call, walk into a conference room, or wait for the rest of the team to arrive. The exchange is almost automatic:
“How are you?”
“Good. How are you?”
“Good.”
And then…agenda item one.
There’s nothing wrong with the question itself. The intent is usually genuine. We do want to know how our colleagues, clients, employees, and friends are doing. But somewhere along the way, “How are you?” became just more of a greeting than a question.
Framing the question
I was reminded of this while watching Matthew McConaughey talk about communicating with his teenagers on The Drew Barrymore Show (13:00).
Instead of asking “How are you doing?”, he received some advice to widen the lens by asking: What’s it like being a teenager these days?
It’s a small shift with an important distinction. Rather than asking someone to immediately explain themselves, you give them permission to talk about the world around them—the pressures they experience, what frustrates them, what excites them, and what has changed.
And somewhere in that conversation, you start learning how they are actually doing. There’s a lesson there that extends well beyond parenting.
Are we asking questions or checking boxes?
In business, we spend a lot of time asking questions.
“How’s the project going?”
“Any concerns?”
“Does everyone agree?”
“How are customers responding?”
“Anything else we should know?”
They’re reasonable questions. But they are also questions that make it remarkably easy to give a safe answer.
“Fine.”
“No.”
“Looks good.”
“Pretty well.”
Sometimes that’s the whole story. Often, it isn’t. If the goal is to truly understand someone’s experience, we have to create space for them to explain.
Instead of “How’s the project going?”, try: “What has been harder than you expected?”
Instead of “Any concerns?”, try: “What are we not talking about that we probably should be?”
Instead of “How are customers responding?”, ask: “What are customers telling you that has surprised you?”
Instead of “Any feedback?”, ask: “If you could change one part of this experience, what would it be?”
Those questions invite stories and explanations rather than status updates.
Curiosity is more than a soft skill
We tend to think of curiosity as a personality trait: some people are naturally curious, others less so. But professionally, curiosity can be a discipline. It means resisting the urge to assume we already understand the problem.
It means asking the follow-up question.
“Tell me more.”
“What makes you say that?”
“Can you walk me through an example?”
“What would better look like?”
It also means becoming comfortable with answers that challenge our original assumptions. That is especially important when talking with customers. If we only ask questions that validate what we already believe, we may leave the conversation with plenty of responses, but very little insight.
And then comes the hard part: listening
Of course, asking a thoughtful question only works if we are willing to hear the answer.
If someone raises a concern and we immediately defend the process, explain why something cannot change, or race back to the agenda, we’ve communicated something too…. next time, “Good” is probably the safer answer.
Real engagement requires leaving a little room for the unexpected. That applies in a customer interview, a project meeting, a performance conversation, a workshop, or at the dinner table.
Maybe we don’t need to stop asking, “How are you?”. We just shouldn’t stop there. Because whether we’re trying to understand a teenager, a customer, a colleague, or an entire market, deeper understanding often begins in exactly the same place.
Ask a better question. Then be curious enough to hear the answer. In doing so, you instill trust and retain access to the most critical pieces of information people can provide.
– Leah McQuillan, Consulting Manager
