Stop asking these 4 questions during your one-on-one meetings

If you’re wondering why your one-on-one meetings tend to feel unfruitful, these questions might be the culprit.

Looking at the clock. Staring into the distance. Short, nondescript answers.

A CEO recently told me how he’d frequently see this body language from an employee during their one-on-one meetings. Flat. Disinterested. Preoccupied. It felt lousy to witness, but it’d always been this way. He’d silently concluded that he was wasting both of their time.

“I want to know what’s on his mind and how I can help, but these one-on-one meetings just aren’t working,” this CEO admitted to me. “I’m not really sure what to do except to stop having them.”

To see if I could help, I asked him what questions he was asking. He shared them with me… and then it clicked.

The once hazy picture zoomed into focus: This CEO was asking the wrong questions. All of his questions were common questions, no doubt. But therein lay the problem. Stock questions might be effective once or twice. But ask them during every one-on-one, every week, and over time, and the effectiveness of the question erodes. The person grows sick of answering the question. Or she doesn’t think you really care to know the answer anymore.Before too long, she starts looking at the clock, staring into the distance, and giving you those short, nondescript answers.

To avoid this, you’ll want to avoid the routine questions you lean on. Below are the four most common questions I’ve found used during one-on-one meetings that elicit dead-end, unhelpful responses. Take a look and see which ones you might be asking:

#1: “How’s it going?”

Ah, the perennial one-on-one meeting opener. It seems like a solid way to break the ice and initiate the one-on-one meeting. Yet it’s unusual that you ever get an answer other than “Fine” or “Good” in response. While someone might truly be fine and good in reality (which is great!)… the conversation usually stops there. Anything personal you wanted to learn, any sense of rapport you wanted to create dies with the question, “How’s it going?” This is because, as a society, the question “How’s it going?” has become our automatic greeting to each other, so our answer to it has become just as automatic.

What should you ask instead?

If you’re looking for a casual, open-ended way to kick off a one-on-one, ask “How’s life?” instead. It may not seem like a big difference, but it makes a big difference. “How’s life?” gives permission for someone to talk more personally about life — about what they did that weekend, how their family is doing, how their personal side project is coming along, how they’re managing their workload. “How’s life?” invites the other person to elaborate. Though, quite frankly, almost any other opening question than “How’s it going?” to going to help you learn more about how someone is doing in their life.

#2: “What’s the latest on __?”

It can be tempting to use your one-on-one session as time to get caught up on what’s going on. However, keep in mind that this completely squanders the purpose of your one-on-one meeting, to begin with. A one-on-one meeting isn’t a reporting session. It’s not an accountability tool. A one-on-one meeting is your radar. It’s your metal detector. It’s one of the only ways you have to unearth what’s actually going on in your team, and what an employee is thinking and feeling. You can get a list of deliverables in Slack any ol’ time.Client problems, unforeseen issues with the product, messy team dynamics, unspoken personal frustration — this is only time you’ll get to hear that stuff.

Some of you may be thinking, “Well, Claire, asking this question has helped me get good insights into the team’s problems.” Yes, I’m with you. This question “What’s the latest on X?” can be great if you’re using it to segue into asking deeper questions. For example, perhaps you follow it up with, “What’s most frustrating about how X has been going so far?” Or, “Where do you feel you need more support in working on X?” Merely asking “What’s the latest on X?” falls flat if you use it singularly.

What should you ask instead?

Ask something specific about the project, instead of asking for a general project update. Possibly my favorite question to ask to instead of “What’s the latest on X?” is “Can you tell me about what’s been most surprising about working on X so far?” If an employee has found something surprising, good chances that you’ll find it surprising too. A surprising insight is always useful for you to form an accurate picture of potential issues bubbling up within your team.

#3: “How can I help you?”

The intention behind this question is fantastic. You want to help, you want to get out of their way, you want to figure what you can be doing better. However, this question is the worst way to signal that. Why? It’s lazy. It makes the person receiving the question do all the hard work of having to come up with the answer. It’s also a very hard question to answer, especially on-the-spot and given that you’re a person in a position of power. You’re asking a person to critique you, “The Boss,” across all spectrums and come up with something actionable for you to do. If you do ask this question, answers tend to be, “Nothing I can think of right now,” something vague, or an answer that involves something that you’re already doing. Rarely do you get a precise, thoughtful to-do that you’ll then go implement the next day.

What should you ask instead?

Suggest something you think you can be doing to help. Then ask, “What do you think?” For example: “I was thinking I’m being too hands-on on this project. Should I back off and check-in with you only bi-weekly? What do you think?” By being targeted in what you suggest — and suggesting it yourself — you make it easier for that person to share the exact ways in which you can support them. You help your employees by suggesting what you think you can do to help, first.

#4: “How can we improve?”

This is the vaguest of questions. The problem with vague questions is they invite vague answers. You prompt the person to offer broad suppositions and knee-jerk assumptions, instead of exact details and practical examples. Ask an employee “How can we improve?” and they think, “Hmm, from a business development perspective? Marketing perspective? Leadership perspective? Where to even begin?” Now, some employees you work with will be able to craft a distinct, rich answer from this question. But it’s infrequent. And it’s probable they spent a good chunk of time thinking about the answer ahead of time. For most employees who you ask this question to without any warning, you’ll receive a variant of “I think things are pretty good right now” about 90% of the time.

What should you ask instead?

Focus your efforts on asking specific questions, instead of defaulting to general ones. For instance: “What do you think is the most overlooked area of the business?” or “Where do you think we’re behind in, that other companies are excelling at?” Notice how specific each of these questions are. The more specific the question, the more effective they are.

You may have cringed while reading this list. Many of you (including myself!) have found yourself asking all four questions, at one time or another.

No need to panic or be hard on yourself. You haven’t inflicted irreparable harm to your team. Your sins are not unforgivable. Rather, I hope sharing the unintended consequences of these four questions nudge you to evaluate the questions you ask during your one-on-one meetings a little more closely.

The questions do the heavy lifting. The questions determine the path to which your one-on-one meetings will take. Ask thoughtful, sincere questions, and there’s a higher likelihood your answers returned back to you will be thoughtful and sincere too.


P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

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…

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?

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew).

Ask these 19 questions on your next employee survey

Specific questions that’ll help you get the actionable feedback you’re looking for.

Most of us run some sort of employee survey in our company… But how often is it that we learn something surprising from them? Or how about something actionable? Our research has shown you will get more honest, actionable feedback when you ask specific questions rather than general questions like, “How’s it going?” which is unlikely to yield any meaningful insight.

After all, the more honest and actionable feedback you receive, the better decisions you’ll make. If you can unlock how employees feel about the work they’re doing and the company as a whole — you can figure out what projects to put them on, where you need to focus your attention, as a leader, and how you can improve your team’s overall performance.

To help you ask the right questions in your next employee survey — ones that will elicit meaningful feedback — we pulled 19 of our most popular Know Your Team questions, so you can use them in your next employee survey. Enjoy!

Our 19 recommended employee survey questions

  • Have you seen something recently and thought, “I wish we had done that?”
  • Do you think the company is the right size?
  • Are there are any rumors you’re hearing about the company or about employees that you think I should know?
  • Is there something we should measure in our company that we’re not?
  • Is there something we should start doing as a team?
  • Is there any part of the company you wish you could interact with more?
  • Are there any benefits we don’t offer that you’d like to see us offer?
  • Have you seen someone do great work that goes unnoticed?
  • Have you ever been afraid to share an idea because you thought it would get shot down?
  • Do you feel you’re spread too thin right now?
  • Would you like more or less direction from your manager?
  • Do you get enough feedback on your work? If that answer is no, what additional feedback would you like?
  • Is there something you want more help and/or coaching on?
  • Do you generally think management makes it clear why we’re doing what we’re doing?
  • Is there an area outside of your role where you feel like you’re contributing?
  • Do you feel connected to the company’s success or failure?
  • Do you feel like customers directly benefited from the work you did this week?
  • Have you met the last person we hired?
  • Is there any red tape you’d like to cut at the company?

The 9 questions that uncover the most surprising feedback from employees

I’m sharing three years-worth of findings, based on data from 15,000+ employees in 25 countries through Know Your Team, on the best questions to ask employees for feedback.

When’s the last time you had a one-on-one meeting or performance review with an employee… and you learned something completely new?

Don’t think too hard 🙂 If you’re like most CEOs and managers, getting new, surprising insights from employees doesn’t happen very often. Oftentimes, when we’re asking for honest feedback, we simply receive a confirmation of what we want to hear.

We learn, “Oh okay, it seems like everything is fine” or “I already knew that was an issue, so it’s all good there.

But what about the stuff you don’t know? How do you discern if an employee has an idea to improve the company that she hasn’t brought up yet? How do you figure out if an employee is frustrated with her manager? Or, how can you tell if she’s thinking about leaving?

That’s where we at Know Your Team come in. We’ve spent the past three years researching, writing and refining hundreds of questions across 15,000 manager and employees+ in 25 countries.

From our 312+ Know Your Team questions, below are the best nine that we’ve found to yield the most interesting insights for companies…

#1: “Are you afraid of anything at work?”

Our findings: 67% of employees said, “Yes, I’m afraid of something at work” (753 employees answered this across 89 companies) when asked through Know Your Team. This result caught me off guard (almost 70% of employees are afraid of something at work!) but it goes to show the importance of showing vulnerability as a leader and digging deep to uncover the areas of the company (or people in the company) that employees may feel intimidated by.

#2: “Have you seen something recently and thought to yourself ‘I wish we’d done that’?”

Our findings: 75% of employees said, “Yes, I’ve seen something recently, and thought to myself, ‘I wish we’d done that’ (1,338 employees answered this across 221 companies) when asked through Know Your Team. Clearly, employees are noticing what competitors are doing and may have ideas for you to improve the business. Asking this question helps bring to light what those ideas are.

#3: “Is there something we should measure in the company that we currently don’t?”

Our findings: 78% of employees said, “Yes, there’s something we should measure in the company that we currently don’t” (286 employees answered this across 78 companies) when asked through Know Your Team. This reveals a need to more closely examine the metrics we use to run our businesses, and ask employees if there’s anything not being measured that should be.

#4: “Is there any part of the company you wish you were able to interact with more?”

Our findings: 81% of employees said, “Yes, there’s a part of the company I wish I were able to interact with more” (507 employees answered this across 72 companies) when asked through Know Your Team. An overwhelming majority of the employees we surveyed feel silo-ed. By asking this question, you’ll learn exactly which parts of the company they’d like more interaction with, be it a specific department or office.

#5: “Are there any benefits we don’t offer that you’d like to see us offer?”

Our findings: 76% said “Yes, there are benefits we don’t offer that I’d like to see us offer” (1,807 employees answered this across 179 companies) when asked through Know Your Team. You may be thinking, “Ugh, of course most of my employees want more benefits”… However, what’s most revealing with this question is which benefits your employees are looking for. Many of the companies who asked this specific question have added key benefits that have helped retain employees, or even gotten rid of benefits no one is using. You never know unless you ask.

#6: “Is there an area outside your current role where you feel you could be contributing?”

Our findings: 76% of employees said, “Yes, there’s an area outside my current role where I feel I could be contributing” (814 employees answered this across 135 companies) when asked through Know Your Team. This result is surprising, considering that most managers feel their employees are slammed and are already at capacity. Thus, this question all the more important to ask: You’ll learn very tactically where your employees want to contribute more to help push your business even further.

#7: “Is there anyone at the company you wish you could apprentice under for a few weeks?”

Our findings: 92% of employees said, “Yes, there’s someone at the company I wish I could apprentice under for a few weeks” (2,217 employees answered across 190 companies) when asked through Know Your Team. This shows how much employees crave learning and developing their skills — especially from others within the company. Asking this question will expose to you if this is similarly the case within your own company.

#8: “Have you seen someone here do great work that’s gone unnoticed?”

Our findings: 76% of employees said, “Yes, I’ve seen someone here do great work that’s gone unnoticed” (1,485 employees answered across 209 companies) when asked through Know Your Team. Based off this data, it’s highly-likely that employees in your company may feel under-appreciated. The answers to this question can help you discover which exact projects or areas of the company that employees would like more gratitude and recognition shown in.

#9: “Are there things you don’t know about the company that you feel you should know?”

Our findings: 55% of employees said “Yes, there are things I don’t know about in my company that I feel like I should know” (3,197 employees answered this across 702 companies) when asked through Know Your Team. Employees want to know more about the company — the company’s vision, people’s roles, why certain policies exist, etc. When you ask this question, you quickly get to the core of what those things are.

How many of these 9 questions are you asking in your own company? The next time you go grab coffee with an employee or have a quarterly one-on-one, consider asking one (or all!) of these questions. I guarantee you’ll learn at least one insight that is completely new and surprising.

P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)