Got an upcoming one-on-one meeting with your manager? Consider a few of these tips in preparation for it.

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, Iâve heard countless managers, CEOs, and business owners say a version of this to me:
âDuring a one-on-one, Iâll ask a question and thereâs silence on the other end. Or theyâll use it as a complaining session and itâs clear they havenât been thoughtful about what feedback theyâre offering. The lack of preparation just kills me.â
As an employee, this may be somewhat surprising to hear. We often underestimate how vexing it can be for a manager when we donât come fully prepared for a one-on-one meeting.
I know I didnât 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 didnât think about what I wanted to say in the weeks (and days) leading up to it. â Was it really worth putting in the energy to do so? NahâŚâ I thought to myself. So I decided against it. As a result, when my boss asked me, â What do you think could be better in the company? â my answer was vague and not meaningful.
At the moment, it felt like a 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 Iâd approached those one-on-one meetings differentlyâââwith less passivity and more positivity. I wish I wouldâve seen those one-on-one meetings as an opportunity instead of an obstacle. I wish I wouldâve 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, Iâve since learned the power of preparing for a one-on-one. Itâs not just managers who should be preparing for them, but employees too.
Knowing what I know now, hereâs what I wish I wouldâve considered when preparing for a one-on-one meeting with my then bossâŚ
Share whatâs been most motivating to you.
Managers crave to know what they should be doing to help you do your best work. After all, a managerâs 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: Whatâs been your favorite project? Who was someone you really enjoyed working it? Why was what you were working on so invigorating to you?
Reveal whatâs been draining and demotivating to you.
As an employee, itâs always tough to bring up a critique of the companyâââespecially if itâs about your own managerâs habits and actions. Youâre worried itâll be misinterpreted as âcomplain-y,â that your manager will take it personally, and that it could affect your career progression. Or perhaps worst, youâll 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 donât talk about it, our managers will never know about it. The little thingsâââwhether itâs your manager interrupting you during meetings or always asking you to stay lateâââadd up. They gnaw away at your ability to feel energized about your work. If you donât 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. Itâs a hard, delicate path to travel. But itâs 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 youâd like to be further pushed and challenged in your role (or outside your role). Take time to reflect on what youâd like to improve or work on professionally. Perhaps itâs something broader, like learning to be more patient and strategic in your thinking. Or maybe itâs much more about gaining a specific skill, such as becoming a better writer. Suggest potential projects for how youâd 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 youâre looking for.
Highlight what youâre grateful for about the company, work environment, or how your manager has treated you.
Giving feedback during a one-on-one isnât just about zooming in on the bad. Itâs the perfect time to point out the good, especially the good things your manager has done or said. Think about what your managers do that your previous manager at another company never did. What are the things you want to make sure she knows you donât 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 whatâs 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 about 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. Itâs much more challenging to try to bring it up those questions outside of a one-on-one meetingâââso 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, itâs a good and helpful thingâââand something to prepare for. To help make the conversation easier for you both and to show that youâre actively looking to improve, offer some thoughts yourself about moments you wish you wouldâve handled differently. This could come in the form of goals, such as, âI want to find ways to ask more questions when interacting with customers,â or observations of areas you want to strengthen, such as, âI have a tendency to rush some of my projects, and I want to find ways to focus more on quality instead of speed.â
Prepare 3 to 4 questions to ask, to help you better understand how to focus your efforts going forward.
In case your manager doesnât ask questions that cover everything youâd like to cover, youâll want to have a few questions prepared. Here are some examples of questions you can ask thatâll 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 Iâm doing? An area you think I could be pressing a bit harder in or exploring deeper?
- Whatâs been frustrating or confusing about working with me? Where do you see the greatest opportunity for me to improve?
- Whatâs 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 has 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?
This may feel like a lot. I might recommend taking 30 minutes or so to reflect on some of these items, and even writing out some questions, yourself.
But keep in mind that the more you put into a one-on-one, the more you can get out. While a thirty-minute or one-hour meeting doesnât seem like much, itâs an opportunity to create a better relationship with your manager, to improve the work environment around you, and be plain happier in your job.
đ Want to put these tips to use? The easiest way is to use our One-on-Ones Tool in Know Your Team to prepare for your next one-on-one meeting. Use our hundreds of suggested questions and agenda templates to write a shared agenda with your boss â and they can add their own questions and topics too. Try the One-on-Ones Tool (or recommend it to your manager) in Know Your Team today.
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