How I ask questions in 1:1s that get honest answers

Being the CEO of a ~20-person company is a bit strange. The company is big enough that you're probably not directly managing many people anymore,  but it's still small enough that you'd be silly not to try to have a direct relationship with everyone.

This is where I'm at. I still meet with each employee periodically, but not in the way a manager would. I'm not giving them performance evaluations or assigning them work. Instead, it's more like a dentist visit. I want to check in and make sure they're getting what they need from the company, and identify any company-wide issues before they become a real problem.

I don't think my process is flawless, but it has improved a lot over the years. In this article, I want to share my approach.

The main reason 1:1s can fail

If you're not careful, check-ins with employees will go like this:

You: Hey $FirstName, how's it going?

Them: Good! How are you?

You: Good! So, what's up? are things ok? Any issues I should know about?

Them: Nope, all good!

Then two weeks later they quit because it turns out there was something bugging them that they never told you about.

Almost all major problems start out as tiny sparks. If they're given enough time and oxygen, they smolder and grow into a forest fire. If you can identify them early enough, you can normally resolve them without too much drama.

Unfortunately, this means that the only way for the meetings to be useful is for them to be uncomfortable. It sucks hearing negative feedback, even if it's constructive. When someone tells you everything is fine, you want so desperately to believe them.

Even worse, people don't like giving negative feedback. All the stuff you'd rather not hear, they'd rather not say. If you give people the option of letting problems smolder, most people will gladly take you up on it. These meetings need to force the uncomfortable topics into the open.

The setup

My routine is to meet with everyone at the company twice per year. Before the meetings, I send a company-wide email with some questions I'd like them to answer. Normally I send about 5 questions and ask them to answer at least 3. This way they feel a sense of control (they don't have to answer anything they don't want to) but they still have to answer something.

It's important for everyone to have a chance to think through their answers in advance. Not only does it give them time to prepare quality answers, but it allows them to psych themselves up for a potentially hard conversation.

The questions

Here are some questions I've asked in the past:

  • Addition by subtraction - If you had to improve the company by removing something (a policy, a project, a commitment, etc.) what would you remove?
  • What's an example of invisible work in your job. Something you do that's important, but you don't get credit for?
  • What one thing do want to be true about the company 10 years from now?
  • When talking about your job with friends and family, what's something that you don't like to tell them because it's embarrassing?
  • What is one thing (a person, process, etc.) that is hindering your work the most?
  • What's something that we should be discussing in internal meetings that you don't think we're talking about?
  • What's something work-related that you think would be fun to work on, but that you aren't currently working on?
  • What is a decision the company has made that you don't understand the reasoning behind?
  • If in two years you don't work here anymore, what's the most likely reason why?
  • What is an idea that you or someone else at the company has suggested that you don't think was taken seriously enough?

The main thing that you'll notice about all these questions, is none of them allow for "no" as an answer. There's a huge difference between asking, "is anything bothering you?" vs. "what thing is bothering you most?" The first one won't get a meaningful answer from most people because it's so easy to cop out. Every question above requires a real substantive answer.

You might think the questions are all too similar. Yup. Repetition is an important part of management. Fundamentally, most of the questions are asking, "what's wrong?" but by asking them over and over and mixing up the wording a bit each time, I keep uncovering new things.

The discussion

I would get very little out of this exercise if I just wrote down their answer and moved on to the next question. These are conversation starters. I normally expect each question to take about 15 minutes to fully discuss.

When an employee answers a question, I have two natural instincts that I have to fight against:

  1. If they bring up a problem that I think is valid, I want to immediately go into solution mode. Here's an idea, let's take action now!
  2. If they bring something up that I don't think is valid, it's often because I have information they don't (e.g. I know the reasoning behind a policy and they seemingly don't). So I want to start explaining things to them.

Both of these instincts are bad. There will be plenty of time later on to take action. This is a unique opportunity to learn as much as possible and to make sure the employee feels heard.

What this normally means in practice is that I'm asking a bunch of follow-up questions. When was the first time you had this thought? How did you handle that situation? What would you like to see done about this? It is a conversation so I do share my own thoughts and ideas, but only as a way to get the employee to share more.

I plan on writing another post with more info on how this meeting fits into the bigger picture (e.g. how I take this feedback and use it to shape the next 6 months) but for now, I'll leave it at that. I ask questions, listen, and learn.

Ideas for the future.

By no means is my current approach perfect. I mentioned this topic on Twitter and Lesley shared an idea I love: Ask employees what is the greatest value they bring to the company.

What I love about this is that it's very different type of question (positive rather than negative) but it's still something that employees probably won't volunteer on their own because it's uncomfortable. People don't like praising themselves any more than they like sharing negative feedback, so I need to put them in a position where they feel comfortable doing so.

I want to explore other topics that people are uncomfortable sharing, but that are important to discuss. Anything in that category is a good fit for this type of 1:1 approach.

Setting that specific idea aside, the key is that it's important to keep experimenting and improving. My 1:1s have improved a lot over the years, and I will keep experimenting and learning so they can continue improving even more.

Have thoughts on this post? I'd love to hear from you! I'm @TylerMKing on Twitter.
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