No more awkward 1–1s: make them good, make them work for you

Courtesy Pexels (Christina Morillo)

Thanks to those who checked out starter wisdom for new managers! Loved that it resonated and getting follow-up questions.

One that came up a few times was advice on how to do effective 1–1s.

Although it sounds mundane and obvious, the art of 1–1s is worth obsessing over. How you approach 1–1s has a big signaling effect on what you value and how you operate as a leader. And you can’t afford for it to be a waste of time.

So, you know, don’t slack on this part.

Here’s what I found works in high-intensity, demanding environments, and you should craft and customize for the individuals on your team.

Pick a weekly time and make an effort not to reschedule too much. Being consistent and committed is a strong signal your team is important. If you find you’re too busy for your own team, adjust your priorities or org structure stat. Trust me, your team is paying attention to this.

Set the expectation that it’s up to the individual to decide how to use the time. Give them the reigns as much as possible. That said, I’ve found the following pattern ultimately emerges and tends to be productive for 30 min 1–1s:

  • ⅓ Share an insight that is useful to that person (e.g. new information from executive meeting or partner conversation). Be generous in passing along business context that they don’t otherwise have access to.
  • ⅓ Check in on the person, not the work. Ask how he / she is doing. This is especially important during new hire on-boarding or new relationships. Pulse check their overall wellbeing and demonstrate that you care.
  • ⅓ Listen and problem solve for what’s top of mind for that person. Help them walk out of the 1–1 with a concrete “win” like a better state of mind, a solution or an action.

When things get intense, expectations are high and everyone is busy, it’s tempting to use those precious 1–1 moments as a tactical catch-up. If you have to occasionally use a 1–1 to exchange critical project updates, that’s OK but try to not let this become the new normal. Be vigilant that your 1–1s don’t turn into a tactical crutch. Protect that time to focus on the person and the important things that need to be discussed one-on-one.

Ok, this is the really tough one. Put down that phone (screen side down) and actually listen. I find this challenging some days when I have a jam packed schedule and my mind is still processing the last meeting I was in 1 min ago. Try to consciously tune in, and if you’re overwhelmed, just name where your mind is at that moment, and let the other person drive the discussion.

Have you noticed how 1–1s can get needlessly awwwkward just because of the room dynamics? Like when you’re sitting across from each other in a quiet, formal conference room? This is why obsessing over 1–1s is worth it. Pay attention to how the setting affects the conversation dynamics and see if you can get the energy level right. Walk the block, get a coffee, pick a sunnier spot, etc. Whatever works, but make sure it’s working for the two of you.

Courtesy Pexels (Pepe Tapia)

There is a ton of literature on this topic but I find that 1–1s are more art than science. Pro tip: being authentic and open will allow others to enter that space as well, so don’t create power distance where it’s not needed.

Hope this helps! Feel free to share your ideas and tips in comments below.

Investor, Board Director, former Tech COO and Business Development Exec. Hypewoman for Female Founders & Funds. Glass 3/4 Full. My personal views only.

Investor, Board Director, former Tech COO and Business Development Exec. Hypewoman for Female Founders & Funds. Glass 3/4 Full. My personal views only.