The Art of the Awkward 1:1

You probably do a lot of one-on-one meetings at work: with your manager, teammates, folks from other teams. Unfortunately, most people totally waste their 1:1 time. The problem: the 1:1s aren’t awkward enough. Here’s how to make them better.

The 1:1 is a sacred space. It’s intimate. It’s dedicated to just you and the other person. It’s super high bandwidth for complex and uncertain content, especially emotions, hopes, and fears. It’s also the most inefficient way you can devise to disseminate non-controversial info.

Very often, people waste most of the 1:1s potential. You might make a little agenda, and then give some updates, some light feedback, and share some complaints. It’s helpful and valuable and nice. But, ask yourself: is the conversation hard? Are you a little nervous or unsure how to get out what you’re trying to say? Is it awkward?

Because if it’s not a bit awkward, you’re not talking about the real stuff.

You’re not talking about your challenges — how you’re a little burned out and started daydreaming about other jobs and why. Or that you’re scared about not making progress on a growth area, whether because it seems a bit B.S. or just because you don’t know how. You’re not confessing that you have to plan for an hour for each of these 1:1s and be super careful not to say something wrong. You’re not saying you know you’re both frustrated about the project, but you really want to work it out.

You don’t tell them the good stuff , because it feels silly. Like how they made your whole week with a simple “Great job!” after the talk you gave. Or how you went home and bragged to your partner about it. Or, how you’re so grateful how their care and empathy got you through a really rough patch. Or how they inspire you with how good they are at a skill. You’re not asking: “Why do I totally flop when I try to copy what you do? What am I missing?”

All of those things would be really awkward. So you don’t say them.

Obviously, not every minute of every 1:1 can be like this. But make no mistake — you should have enough awkward in you to use up a chunk of each meeting. This is what solves problems that otherwise go unsolved. It breaks the cycle of repeated issues or an impasse. It lets you be you and let down your guard. It builds trust and relationships. It creates growth for both of you.

Change and growth are always awkward — embrace that.

Embrace the Awkward

A few years ago, as an engineer, I used to dread and avoid awkward conversations like the plague because they were very uncomfortable. Then, very slowly, I realized I was wasting a rare precious resource: one-on-one time with another person. Now I instead dread bland, vapid, cookie cutter 1:1s. I fear that we’ll talk for a while but never get to anything real.

I made the change by committing to be awkward. Here are the two rules I use for every 1:1, many times a week:

1. Don’t talk about any topic that you could discuss in the open, among your team desks or in the cafe. If it’s safe enough to be overheard — it’s not the right content for a 1:1. Email it, send it in Slack, discuss among the desks, say it at a meeting, anything but a 1:1.
2. Commit to saying one rather awkward thing every 1:1, and get the other person to commit too. Agreeing in advance and getting permission makes it feel way more safe. Committing creates peer pressure to be real. It works.

Of course, I hate to have to say this, but I will: don’t be awkward in the wrong way. Nobody wants to hear your TMI story or off-color joke. It’s awkward, but it doesn’t count.

These two rules are transformative. Following them is oddly liberating and effective. We’ve had great success teaching this to whole teams, breaking them up into pairs, and sending them off to come up with one awkward thing each to say to each other.

The Awkward Awakens

If you want to join me and get going on this, here’s some tips to help you unleash the vast sea of awkwardness that resides within each one of us (maybe especially so in tech), just waiting to be released.

• Get started and commit. A common complaint is that setting up the agreement to be awkward in a 1:1 series itself feels really awkward. Great! That satisfies your quota for the next meeting. Commit to awkwardness to someone (your peer, manager, a friend) and follow through.
• Fix your other communication. If it’s hard to get to the real stuff in 1:1s, your other communication channels might suck. Get all your updates, easy questions, simple feedback done some other way: email, team meeting, Slack msg, text, whatever your company does. Whatever you do, don’t waste the 1:1.
• Plan to be awkward. Spend a few minutes at the beginning of the week thinking what would be great to get off your chest and what you’d love to hear about from your coworkers. Plan how to be awkward rather than how to avoid it.

If you’re not sure you want to take the risk to get started — ask yourself: “How often am I too awkward vs. not awkward enough?” and check out Make The Other Mistake.

The Awkward List

Awkwardness is hard at first, but it really does get easier. As with anything, the key is slightly uncomfortable practice. But, there’s something that makes that practice easier: whenever you succeed getting something awkward out and survive, it creates a huge feeling of satisfaction and relief. It’s deeply positive to have another person hear you and understand you better.

So, to aid your practice, here’s a long list of guaranteed awkward and positive things to help you get started. I hope that majority of these will work with most of the people you have 1:1s with!

Meta & Feelings (Occasional)

• Talk about emotions. Label one you’re feeling, or what you sense from other person. Boom, instant awkward and great discussion.
• Any meta-conversation about your conversations. We never talk about Topic A, we just always talk Topic B. Why is that? When I tell you about Topic A, you always react like this, and that’s why I don’t tell you that stuff. When I bring up Topic B, how do you feel? Why is that?
• Ask for their fears. What are they afraid of (for their career, the project, an upcoming tough meeting)? Why? Share your own.
• Trust check. How easy is it for both of you to share intimate things with each other? Why? What would make it easier? Discuss.

Extra Honest Feedback (All the time)

• Are they acting like the best manager / report / partner you could wish for? Are you? Why or why not? Discuss.
• What have you already told someone else about this person (or heard others say)? Share with them. Discuss.
• What is everyone around neglecting to tell this person? What’s the work equivalent of this person having mustard on their face after lunch? Be a good friend / coworker and tell them.

Humble Advice Seeking (All the time)

• Tell them a growth area you’re working on currently. Tell them why you picked it (even if it was one of those “not-really-optional” ones!). Ask for advice.
• Check for your own role in a weird situation. Pick a thing you’ve recently complained about. Ask them — “What could I’ve done differently in that situation?”
• Ask for feedback on how to be better. Then, skip the fluffy answer and ask again until you get something real.
• Admit a fault or a mistake. Ask for support and advice. Ask them if they noticed you making it or not.

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