How to Have an Effective One-on-One with an Employee

Six ways (and 12 questions) to get honest feedback from an employee during a 1-on-1 meeting.

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“I can handle the truth. I’m pretty tough, Claire.”

My CEO at the time told me this during our one-on-one about five or so years ago. The year was ending, and he wanted to know what the company could do to improve, how he could improve as a leader — and he wanted to know the truth of what I actually thought.

Yet despite him saying he could “handle the truth,” I couldn’t bring myself to tell it to him.

Truth was, I wasn’t confident in the company’s overall direction. And I was troubled when I learned a few employees felt they were treated unfairly in the company… But it felt futile to mention these things. I couldn’t imagine that our CEO would take my feedback to heart and change anything in the company. If anything, I could more easily imagine that I’d provoke a negative reaction from him. Telling him the truth just didn’t seem worth it.

I’ll never forget that feeling of holding something back — choosing not to vocalize what I was thinking because I felt nothing in the company would change. To be clear: I’m not proud of my silence. Now knowing what I know about giving feedback to a manager, I wish I’d spoken up. Today as a CEO myself, I can only imagine how utterly frustrating it was for him to have that one-on-one with me… and then a few months later learn that I was leaving the company.

Having experienced this, I’ve thought deeply about the one-on-ones I do with my own team here at Know Your Company. I never want a teammate of mine to feel how I once did on the other side of the table. And I don’t want to be like my former boss, blindsided by how an employee is actually feeling.

To encourage honest responses during a one-on-one with an employee, here’s what I keep in mind…

Make empathy your mission.

Every time I have a one-on-one, I have a single mission: to understand how the other person is feeling. Everything else comes second. I don’t use the time to focus on critiquing an employee’s performance, nor do I use the time to get a status update on a project (those are separate, secondary conversations). A one-on-one is invaluable, sacred time to uncover the truth of how an employee is actually feeling.

When you make empathy your mission, the entire landscape of the conversation changes. You start listening more. You start asking more thoughtful questions. You start to level with employees, admitting you don’t have all the answers. Employees notice when an effort is being made to empathize with them, rather than pass judgement or get your own message across. The one-on-one becomes less intimidating to an employee. And when an employee is less intimidated, they’ll be more honest with you.

I’ll oftentimes make my mission of empathy clear upfront during a one-on-one to further diffuse any sentiment of intimidation. For example, I’ll say:“Today is for me to listen and truly understand where you’re feeling on things – that’s it. This isn’t a performance review or status report. This conversation is for me to understand what I can be doing to make this the best place you’ve ever worked.” When you explicitly let your employees know that empathy is your mission, you give them consent to tell you something that they might not have told you otherwise.

Ask questions to uncover two things: tension and energy.

To get to the bottom of how someone is feeling — particularly the negative stuff — I’ll ask questions around specific moments of tension, and specific moments of energy. Specific moments of tension are situations when someone felt angry, frustrated, bored in, etc. Specific moments of energy are situations when someone felt uplifted, excited, and motivated. You want to uncover what these situations have been so you understand how to create more positive situations for an employee that give them energy, and how to avoid and resolve the negative ones that create tension for them.

When you ask someone about specific moments when they felt disappointed, confused, proud, etc. at work, they can reference their emotions to something real that happened, not something ephemeral or imagined. For example, ask the question, “How’s it going?” and nine times out of ten your employee is going to say, “Things are fine” or some other vague, over-generalized response. You’re never going to hear the real stuff. Versus, if you were to ask: “When have you felt frustrated in the past year?” you’re asking an employee about a specific moment, situation, and emotion. You’re forcing them to think in more literal, concrete terms, and giving them permission to talk about how they feel about working at your company (something that doesn’t always happen all too often in the workplace).

Here are some examples of questions you can ask an employee around specific moments of tension so you know what to avoid:

- When have you been frustrated in the past year? What can I do to help make things less frustrating for you, or get out of your way?

- When have you felt dejected or demoralized this past year? What can I do to better support you, and make sure that’s not the case going forward?

- When have you been disappointed with a decision or the direction that the company has gone in the past year? Was there an opportunity you think we squandered? Something you think we mishandled? How would have you preferred we proceeded?

- When have you been annoyed, peeved, or bothered by me and something I’ve done as a CEO? Why? What would be helpful for you for me to change my behavior going forward?

- When have you felt bored in the past year? How can I create situations going forward so you don’t feel that way?

- When have you felt stressed or overworked in the past year? What can I do to create a better work environment going forward so you don’t feel that way?

Notice that when I ask about a specific moment of tension, I follow up with a question about what I or the company can do going forward. This way, your one-on-one doesn’t devolve into a complaining rant, but becomes a productive conversation about how to resolve, avoid, or fix a tension point in some way. This doesn’t mean you need to solve the issue right then and there (very rarely will you come up with a resolution on-the-spot). But a follow-up question about what future action can be taken will get your mind and theirs thinking in a constructive direction.

Here are some example questions you can ask around specific moments of energy — the positive stuff — so you know what to create and do more of:

- When have you felt excited about what you’ve been working on in the past year? What can I do to provide you with more opportunities so you feel that way?

- When have you felt most proud about being a part of the company this past year? What can I do to make sure that we do things that continue that feeling?

- When have you felt most motivated about the work you’ve been doing?What can we do to create an environment so you feel like that more often?

- When have you felt most “in flow” or “in control”of what you’re doing during the past week or so? What can we do to give you more space and time to feel that way?

- What have you been wanting to learn more of, get better at, and improve on? How can we here at the company support you in doing that?

- When have you felt that this company was one of the best places you’ve ever worked? How can I make this place the best place you’ve ever worked?

If this feels “touchy-feely” and not really your style because you’re talking too much about emotions – I understand. Try peppering just one or two questions about a specific moment of tension or energy into your next one-on-one. I guarantee those one or two questions alone will shed more light on an employee’s level of morale, more than anything else.

And, keep in mind that touchy-feely isn’t a bad thing. The way employees feel about their work affect how well they do their work.

Explain why you need their input.

One of the keys to making it safe for your employees to be more honest with you is explain why their input is valuable. I often forget to do this myself. But I find that when I do, it shows an employee that I’m not asking questions out of vanity or to “check a box.” Rather, I’m explaining how their feedback impacts the success of the company, and their own career development.Professor Amy Edmondson who coined the term “psychological safety” in workplaces recommends to “make explicit that there is enormous uncertainty ahead and enormous interdependence.” In other words, because the future is so uncertain and there’s much to still figure out, everyone’s opinion and input matters. For instance, you could say something like this to your employee: “Hearing your thoughts really matters to me because we haven’t figured ___ out. There’s so much unknown, and we need your input in order to get to where we want to go.”

This isn’t easy. Every time I do a one-on-one, I still feel a little nervous when I ask about a specific moment of tension… And I always take a deep breath to keep myself from reacting defensively when they share their answer. Navigating a one-on-one well requires discipline and a dose of courage.

Most of all, it requires a real desire for the truth. What fuels me to seek out honesty in a one-on-one is because I know that seeing the current reality for what it is — how our business is doing, what our employees think of the company — is the only way I’ll build a better company and become a better leader. Without knowing the truth, I’m squandering a chance to move the company forward, or even perpetuating a valuable employee to leave the company.

Holding an honest one-on-one with an employee is one of the few yet most effective ways to get that truth. Let’s double down on doing it well.

Should you ever ask questions like this anonymously in order to get feedback? Read our next chapter on “Does Anonymous Feedback work?”.

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