Stop asking your employees this one question — it’s hurting them

Trust me, it surprised me too.

“How can I help you?”

You’d think this would be a great question to ask your employees. Surely, I’ve asked this question, as a CEO myself, to my own team countless of times.

Turns out, I’m wrong.

The question, “How can I help you?” hurts employees more than it helps.

Let me explain.

The other week, I ran a workshop. One of the participants — a CEO — was struggling to get feedback from a particularly quiet employee at his company. He asked the other folks in the room for advice about it.

“What if I asked the employee, ‘How can I help you?’ Do you think that’s a good question to ask him to encourage him to speak up?” he pondered.

A few other executives nodded their heads. “Yeah that seems like a good idea,” they said.

Another workshop participant spoke up.

“I hate that question,” she shared candidly (and a bit sheepishly). “When my own direct manager asks me that, I never know what to say.”

Everyone was perplexed — myself included. How could asking to give help ever be a bad thing?

But as she explained, it clicked for me. Despite being well-intentioned, here are three reasons why “How can I help you?” is a terrible question to ask your employees:

It’s lazy.

When you ask, “How can I help you?” you’re not offering any specific ideas or suggestions for how you can be more helpful. Rather, you’re relying on the employee to do the hard (and delicate) work of figuring out how you need to improve as a leader. Expecting that an employee will tell you what you should be doing better without presenting any thoughts on it yourself is, well, lazy.

It puts pressure on the employee.

Can you imagine how daunting it is to tell your boss what she needs to be doing differently? That’s what you’re doing when you say, “How can I help?” You’re asking for holes to be poked, for flaws to be exposed… And the employee can’t tell if you’re really ready or not to hear it. Anytime you’re speaking truth to power, it’s intimidating. We cannot underestimate as leaders the power dynamic that exists between an employee and an employer. There isn’t any incentive for an employee to critique or say something that might be perceived negatively by their boss. As a result, “How can I help you?” puts pressure on the employee to give a diplomatic response, instead of an honest one.

It’s vague.

Now the employee is forced to quickly think through all the potential things that you could provide help with… On what project? On what area of the business? Should they mention communication? Should they talk about about timelines and deliverables? Should they bring up that thing that happened during that meeting last week? Or is the boss asking for something more high-level and strategic? It’s tough to know exactly what you’re asking for as a leader, when you ask the question, “How can I help?”

So what should you ask instead?

If you genuinely do want to know how you can help and support an employee, try this:

Ask about something specific that you can give help on, first.

Point out your own potential flaw, instead of waiting for your employee to point it out. Offer a critique of your own actions, instead waiting to see if it’s something your employee brings up.

The more you go first and share what you think can be better, the more room you’ll give your employee to give you an honest response about what they think could be better.

Here are some examples of specific questions you could ask…

  • “Do you think I’ve been a little micromanaging with how I’ve been following up on projects?”
  • “Have I been putting too much on your plate and do you need some breathing room?”
  • “Am I giving you enough information to do your job well?”
  • “Could I be doing a better job outlining the vision and direction for where we’re headed?”
  • “Have I not been as cognizant of reasonable timelines, like I should have?”
  • “Am I interrupting you too much during the day with meetings and requests?”

I guarantee an employee will feel more encouraged to give you their honest take on how you can help if you ask, “Am I interrupting you too much during the day?” rather than just asking “How can I help you?”

Stop hurting your employees with the wrong question. Start asking the right one.

Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

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Specific questions yield specific answers

Specific questions are our most underrated management tool.

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?

Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

Questioning a purchase

Today I was chatting with someone looking for opinions about project management software. It would have been easy to weigh in with a list of reasons why that person should try Basecamp.

But what if that isn’t the right way to help them?

Instead, I offered the following list of questions that I use when trying out something new. The answers to those questions might lead her to Basecamp, they might not.

What problem am I trying to solve? How does this help me get there?

This question is an old friend. A constant companion as I muddle my way through life. What am I trying to do? Do I know? Child questions spawn, dragging me closer to an imperfect answer that works for now. There is something powerful about the way asking a question reveals flaws in my understanding, or illuminates new avenues to explore. The beautiful thing is, behind each answer I find more questions.

Am I looking for something to help me do my work, or am I looking for something to change how I work?

How often do you really challenge the underlying assumptions about why you work the way you do? Picking up a new piece of software, or looking at a new process is a great time to pause and reflect. Are we doing this because it’s the right thing to do, or has it “always been that way”?

Does using this result in better work? How do I measure that?

This is one of the child questions that comes from asking what problem I want to solve. How am I going to know if making this choice is worthwhile?

If there is complexity, is there a payoff?

Not all complexity is anathema. Taking something complicated and turning it into something simple is a noble endeavour. Deciding not to do something is incredibly freeing. And yet, there is a place for complex processes, if they make life better at the end.

Does using this save me time?


This doesn’t do X. Does that matter? Could we do without?

When considering a move to something new, I often catch myself discounting a product because it doesn’t do something I’m used to. I’m trying to get better at ignoring that impulse, and being more open to changing how I work.

Are there any questions I’ve missed? Do you have a personal favourite you ask when looking at a new piece of software, or a new way of working? Let me know!

At Basecamp, we’ve got so many questions, and we’re having a blast trying to find the answers. We love questions so much, we built automated questions into the latest version of Basecamp. If you are looking for a calmer way to work, why not grab the questions above, and see if Basecamp 3 is the answer?

What are questions?

An unexpected answer from Clayton Christensen.

A few years ago I was fortunate enough to spend about three hours with Clayton Christensen. Clay, currently a professor at Harvard Business School, is best known for his book, The Innovator’s Dilemma. His latest book, How Will You Measure Your Life, has some wonderfully insightful business and life lessons.

His books, thinking, and approach to life, business, — and now, teaching — have influenced me greatly. I recommend reading everything he’s written and watching any videos of him you can find. Clay’s site is a good place to start.

What impressed me most about Clay yesterday was his clarity. He’s a very clear thinker and communicator. His genuine interest for helping other people discover clarity comes through with every patient word.

This one thing thing he said

Spending time with Clay leads to lots of interesting insights, but for me, there was one that stood out among all the others.

You’ve probably heard it said that someone can’t be taught until they’re ready to learn. I’ve heard it said that way too. It makes sense, and my experience tells me it’s mostly true. Why though? Why can’t someone be taught until they’re ready to learn?

Clay explained it in a way that I’ve never heard before and I’ll never forget again. Paraphrased slightly, he said:

“Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question — you have to want to know — in order to open up the space for the answer to fit.”

What an insight. He continued to talk about the power of questions. Questions are your mind’s receptors for answers. If you aren’t curious enough to want to know why, to want to ask questions, then you’re not making the room in your mind for answers. If you stop asking questions, your mind can’t grow.

That day had a profound impact on me. It’s so easy to think you know, but most of the time you’re really just being defensive — protecting yourself against the truth about something you think you’ve already figured out. Make room, make room. It’s a life-long pursuit.

(Special thanks to Bob Moesta for inviting me to meet Clay)

If you liked this article please click the ❤ below. It’ll let me know you’d like to read more articles like this, and it’ll help other people discover the article as well. Spread the love! And then please check out my labor of love, Basecamp 3.

Don’t pose the question if the answer can’t change your mind

There’s an undeniable appeal in seeking broader consensus from your customers, employees, and partners in decisions big and small. When your direction has the legitimacy of a wide backing, it’s invigorating and enabling. Making progress together is more fun and effective than making progress by edict.

But you should temper your temptation to pose questions to which you aren’t really interested in hearing an opposing answer. Seeking legitimacy is a double-edged sword. When it “works”, and the asked reaffirms your preferred choice, it’s great! But it often doesn’t, and they don’t. This is where problems arise.

And it’s true whether you query for opinion or fact. If you ask your customers what’s most important for us to work on next, you better be prepared to build a faster horse. If you tap the data oracle to see whether your redesign worked, you better be prepared to revert if it didn’t.

The problem is that it’s really hard to formulate a question without falling in love with one of the possible answers. In fact, many questions arise from the infatuation with one of those answers, and serve more as post-hoc justifications than genuine inquest of inquiry.

Say you already have a destination mapped out on your mind’s road map, but you want to be seen as being “responsive to customers”. Or you’re already loving the redesign, but you just want to cover your ass in case business was to drop.

We instinctively know that simply picking a direction based on gut alone is hard to rationalize, both to ourselves but especially to others. So we seek to dress up the instinctual pick in more neutral, objective clothes and pass it off as just an innocent pursuit of the “best answer”. But it’s often baloney and the whiff travels.

Better then to simply admit when your gut is going to be in charge and own it: “We’re doing this because I think it’s the right thing to do, and that’s that”. When you say that out loud, it’ll surely feel a tad uncomfortable, but at least it’ll be congruent. Everyone knows when the leader is just seeking reaffirmation of a choice already made anyway, so dressing it up as a question is merely a ballroom dance of charade. We nod, we smile, but we know.

The other advantage of owning up to the discomfort is it will serve as a natural check on the number of gut moves likely to be made. Few people, however bold, are happy freezing at the top of the mountain alone, even if they get an unlimited stack of edict paper to fill out in return. We all want to be loved and accepted, not merely be effective. Well, most of us anyway.

By the same token, some times you really just need someone to pick a path and go with it. There’s nothing inherently wrong with that. Embrace it (judiciously).

The strong leader is neither someone who makes all the choices or none of them, but the one who knows when to do either.