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Our most underrated leadership tool: Specific questions.

Of all the tools for effective leadership we think we need — a good system for tracking progress, or clear metrics around hiring — specific questions are our most underrated.

Ask the right question… and you’ll learn that your company’s most valuable employee doesn’t feel challenged by her work and is thinking about leaving.

Ask the wrong question… and you’ll hear the same employee tell you she enjoys the work environment and is confident about executing her work. You only learn she’d been considering leaving when she gives you her two weeks’ notice.

The greatest example of a “wrong question” is one I found myself asking to others early in my career:

“How’s it going?”

Nine times out of ten, the other person’s response would be…

“It’s fine. Things are going fine.”

What an empty response! But it’s because I asked an empty question. “How’s it going?” could not be a more run-of-the-mill, vague question to ask someone. So I got a run-of-the-mill, vague response.

Ask a general, half-hearted question, and you’ll get a general, half-hearted response. Ask a specific, carefully thought-out question, and you’ll get a specific, carefully thought-out response.

The more specific the question, the more specific the response.

Sounds easy and obvious enough. Yet in practice, it can be tough to come up with specific questions “on the spot” — especially if you’re asking questions in-person during a one-on-one or over lunch.

Here are a few tactics to help you ask more specific questions that will yield specific answers…

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Pick one thing.

When you ask a question like, “How’s it going?”, you provide no context for which a person is supposed to answer. You’re essentially asking a person to consider their entire time at the company, and deliver an eloquent, precise answer summarizing exactly how they feel about it. It’s no wonder people always answer, “It’s fine.”

To provide more context in your question, ask about “one thing.” As a result, you’re not asking someone to consider or talk about all things — just one thing. It makes answering your question much easier.

Try saying this“What’s one thing that could’ve gone better?” or “What’s one thing that frustrated you?” or “What’s one thing you’re surprised is working as well as it is?”

Anchor your question in an event.

You can uncover a lot more depth about how someone feels about the company if you use an event as the focal point of your question. For example, if you’re curious if the leadership team is communicating well with employees, ask an employee about the last all-company meeting. It could be a question like, “What else should have been brought up by the leadership team at our last all-company meeting?” Doing so can be more revealing than just asking, “What could the leadership team improve?”

Or, say you’re curious to know about an employee’s relationship with her manager. A question like, “During your last project, what hiccups or struggles did you encounter while working with your manager?” is much more specific than simply asking, “How’s it going with your manager?”. A question around a concrete, tangible event will help a person mentally reference that in their head, and provide a much more meaningful answer to you.

Try saying this“What’s something we totally missed talking about during our last meeting?” or “While you were on your last project, what did you observe that you felt were slow or inefficient?” or “What could have been improved about the most recent product release we did?”

Time-box your question.

Possibly my favorite way to ask a specific question is to time-box the question to a specific period of time. For instance, rather than asking, “What do you think we could improve on?” you should ask, “What’s something in the last two weeks could we have improved on?” By asking someone to reflect on the last two weeks, you narrow the scope of what they need to consider to answer your question well. All of a sudden, it’s easier for that person to recall something interesting, pinpoint a specific insight, and share it with you.

Try saying this“What’s something last week that could be better?” or “What’s been most motivating for you to work on this past month?” or “What’s annoyed you this quarter? It can be big or small…”

If you’ve ever caught yourself thinking to yourself, “My employees never tell me anything,” now you know that the solution might lie in questions you’re asking, themselves. And the remedy is simpler than you might’ve thought:

Specific questions yield specific answers. General questions yield general answers.

Which are you asking?

Looking for more detailed guidance on one-on-one meetings? Make sure to check out our 1:1 module in Canopy.
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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.