Here are the two rules that you can 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 safer. 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.

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.