Have awkward conversations with your manager
Beware of falling into the routine of status updates and empty one-on-ones
Time Commitment: ~4 minute read
We all have one-on-ones with our managers. It’s common to meet regularly with them. Most of us waste this time. We might make a neat little agenda, dance around with some small talk, maybe give some execution updates, sprinkle on some surface level feedback, and voice some run-of-the-mill complaints. Then it’s over and we come back to do the same thing again next time.
If you want to leverage your manager and use these conversations to drive your career forward; stop making your one-on-ones a “check the box” exercise every week. Sure, doing this has some value, but if the conversation isn’t somewhat challenging and you're not a little nervous, it’s not truly helping you grow.
A good one-on-one is where you lean into the awkward.
You’re wasting your one-on-one time by not discussing the struggles you're facing — feelings of burnout that might have you fantasizing about another job. By not expressing fears about not making progress in areas that were called out as constructive feedback a few months ago. By not admitting that you’re carefully preparing for each of your one-on-one meetings because you’re worried you’re not making a good enough impression.
By not asking your manager to do more to encourage you because it feels childish to do so. By not sharing how relieved and excited you were when they pinged you saying “you did great,” after that high stakes product review.
These conversations might seem too awkward or you might feel like you’ll look unprofessional, so you stay silent and go back to the routine one-on-one.
Not every one-on-one can or has to be “awkward.” Some will just be the standard updates, blockers, feedback, and other day-to-day topics. But you should aim to make at least a chunk of each meeting awkward. These are the conversations that get the ball rolling. These awkward conversations are what makes light bulbs go off and unlock growth. They build trust and lasting relationships. They create an environment for both of you to grow and get better.
Change and growth are always awkward — lean into the awkward.
Four ways to enable the awkward
Here are some ways you might start the awkward conversation. Be easy at first, it takes time to build a relationship and get comfortable. But you have to start if you want to break the routine of mundane and low value one-on-ones.
Voice your emotions. Counterintuitive right? There isn’t supposed to be emotion at work! Wrong. Get right into the awkward by talking about how you’re feeling. Or, highlight what vibe you’re getting from your manager. Do they seem worried? On edge? Call it out and ask how you can help. The awkward will start flowing like no other making for a great discussion.
Highlight a mistake you made recently and how you learned from it. Getting comfortable reflecting and doing retrospectives with your manager is such a career unlock. Most of us want to hide the mistakes we make so that our managers don’t think less of us. Fight this urge and lean into sharing your blunders. This is awkward, but creates an environment of authenticity. And usually, you manager will reciprocate and share some of their own experiences.
Give your manager direct feedback. Is there a perception of your manager that they may be completely oblivious to? Share it with good intention. Invest in their growth and they will want to invest so much more in yours.
Share your hopes and desires and recruit your manager to help with them. Most of us don’t bother openly sharing our goals with our managers (not just the “I want to get promoted,” but where you see your career and/or life going in the long run). If you keep these things a secret or are vague about them, how can you expect your manager to help you achieve them? They can make things happen only if they know what success looks like for you. When you share where you want to go they can find opportunities for you. The truth is you could probably do your job without your manager but it is unlikely your manager could do their work without you. Making you successful is their job. Help them do that job — even if, to you, it feels awkward.
Embrace awkward conversations with your manager. Even if they are just a few minutes at the end of every one-on-one. Doing this builds a strong, authentic relationship rooted in vulnerability and that is a huge career unlock.