How to prepare for a one-on-one meeting as an employee

Many managers say flat-out that their biggest frustration is when employees are not prepared for a one-on-one meeting.

Yikes, really?

Over the past four years, I’ve heard countless of managers, CEOs, and business owners say a version of this to me:

“During a one-on-one, I’ll ask a question and there’s silence on the other end. Or they’ll use it as a complaining session and it’s clear they haven’t been thoughtful about what feedback they’re offering. The lack of preparation just kills me.”

As an employee, this may be somewhat surprising to hear. We often underestimate how vexing it can be for a manager when we don’t come fully prepared to a one-on-one meeting.

I know I didn’t prepare for any of my one-on-ones, six years ago, when I was an employee. Out of fear, anxiety, and a bit of dread for what the conversation was going to be like, I pushed my impending one-on-one meeting out of mind. I didn’t think about what I wanted to say in the weeks (and days) leading up to it. “Was it really worth putting in the energy to do so? Nah…” I thought to myself. So I decided against it. As a result, when my boss asked me, “What do you think could be better in the company?” my answer was vague and not meaningful.

In the moment, it felt like the safe and comfortable thing to do. But truth is, I only hurt myself. I bungled my opportunity to influence real change. And, I only further frustrated my boss, who was perplexed that I seemed dissatisfied but never vocalized my concerns outright.

Eventually, I left the company. But I dearly wished I’d approached those one-on-one meetings differently — with less passivity and more positivity. I wish I would’ve seen those one-on-one meetings as an opportunity instead of an obstacle. I wish I would’ve seized those one-on-ones as a moment to engage and dig deeper with my manager, instead of using them to create distance and fester in apathy.

In the six years since being an employee, now as a CEO myself, I’ve since learned the power of preparing for a one-on-one. It’s not just managers who should be preparing for them, but employees too.

Knowing what I know now, here’s what I wish I would’ve considered when preparing for a one-on-one meeting with my then boss…

Share what’s been most motivating to you.

Managers crave to know what they should be doing to help you do your best work. After all, a manager’s ultimate job is to create an environment that enables you to tap into your own intrinsic motivation. During your one-on-one, make sure you share what tangibly has been most motivating to you while at the company: What’s been your favorite project? Who was someone you really enjoyed working it? Why was what you were working on so invigorating to you?

Reveal what’s been draining and demotivating to you.

As an employee, it’s always tough to bring up a critique of the company— especially if it’s about your own manager’s habits and actions. You’re worried it’ll be misinterpreted as “complain-y,” that your manager will take it personally, and that it could affect your career progression. Or perhaps worst, you’ll put in all the effort of sharing your feedback and nothing will happen. While all of those scenarios might be possible outcomes, what we must remember is that if we don’t talk about it, our managers will never know about it. The little things — whether it’s your manager interrupting you during meetings or always asking you to stay late — add up. They gnaw away at your ability to feel energized about your work. If you don’t say something, then who will? When you do speak up and vocalize tough feedback, look to approach the conversation with care, observation, fallibility, and curiosity. It’s a hard, delicate path to travel. But it’s a worthwhile path if you want your work environment to become better.

Explain how you want to stretch and grow.

Your one-on-one with your manager is your chance to let her know how you’d like to be further pushed and challenged in your role (or outside your role). Take time to reflect on what you’d like to improve or work on professionally. Perhaps it’s something more broad, like learning to be more patient and strategic in your thinking. Or maybe it’s much more about gaining a specific skill, such as becoming a better writer. Suggest potential projects for how you’d like to grow in those areas, and see if your manager has any ideas around it. Ask your manager for advice on what books, classes, or people you should be talking to help you pursue the greater learning you’re looking for.

Highlight what you’re grateful for about the company, work environment, or how your manager has treated you.

Giving feedback during a one-on-one isn’t just about zooming in on the bad. It’s the perfect time to point out the good, especially the good things your manager has done or said. Think about what your managers does that your previous manager at another company never did. What are the things you want to make sure she knows you don’t take for granted? Be specific, and say thank you. Not only will it help boost the morale of your manager (who needs the positive support, as being a manager can be a thankless job in some ways), but it helps guide your manager to double down on the things that you appreciate.

Consider what’s been confusing or concerning to you in the company.

Are you concerned that the company is growing too fast, and losing some of its original culture? Are you confused why the company decided to change its vision midyear, when things have been going so well? Consider leveling with your manager about what uncertainty is weighing on your mind during the one-on-one. It’s much more challenging to try to bring it up those questions outside of a one-on-one meeting — so take advantage of the fact you have dedicated time to discuss bigger questions about the state of the company with your manager.

Suggest one thing you see as your greatest shortcoming, and what you want to do to actively compensate for it or improve on it.

During your one-on-one, your manager is bound to share some constructive feedback in an area you could get better. While intimidating at times, it’s a good and helpful thing — and something to prepare for. To help make the conversation easier for you both and to show that you’re actively looking to improve, offer some thoughts yourself about moments you wish you would’ve handled differently. This could come in the form of goals, such as, “I want to find ways to ask more questions when interacting with customers,” or observations of areas you want to strengthening, such as, “I have a tendency to rush some of my projects, and I want to find ways to focus more on quality instead of speed.”

Prepare 3 to 4 questions to ask, to help you better understand how to focus your efforts going forward.

In case your manager doesn’t ask questions that cover everything you’d like to cover, you’ll want to have a few questions prepared. Here are some examples of questions you can ask that’ll help you better understand how you can improve as an individual contributor, and help your manager understand what she can be doing better as well:

  • Do you see any untapped potential in the work I’m doing? An area you think I could be pressing a bit harder in or exploring deeper?
  • What’s been frustrating or confusing about working with me? Where do you see the greatest opportunity for me to improve?
  • What’s the biggest challenge you feel you face as a manager? In what ways can I be helpful in overcoming or facing that challenge?
  • What worries you most about the team?
  • What are you most proud of the team having accomplished?
  • In what ways have I saved you time or made your job easier? What can I be doing to do more of those things?
  • Where do you see the team or company a year from now, and what I can do to help make sure we achieve that vision?
  • What are the biggest challenges you foresee the team or company facing in the upcoming year?

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