5 tips for a more meaningful 1–1

One of my most striking observations as a leader at a fast-growing startup has been that the most real, pressing problems in your organization often live in the shadows. And, unfortunately, such problems can remain in the shadows for months until one day they burst into the spotlight when it’s a principle cause of a material, negative event such as a surprise departure of a high-performing team member or a costly operational slip-up. Yet, every single day, these shadow problems are hurting productivity, morale and culture. Examples of such problems are product strategy misalignment, people pain-points, and process annoyances.

So, as a manager, how can you actively seek out these shadow problems? I would argue that 1–1 chats with each of your direct reports is a critical starting point. However, as I’ve learned, the challenge with 1–1’s is that it’s pretty easy to do them poorly. In fact, my hunch is that most 1–1’s have a lot of room for improvement.

To help, I’ve put together a list of 5 simple tips to help you have a more meaningful 1–1:

  • It’s their time, not yours. OK, OK. I’m sure you’ve heard this rule before.
    “A 1–1 is not for you.” It’s for your direct report. But it’s SO easy to violate this rule, right? Your calendar is stacked. Their calendar is stacked. That leads to “Hmm let’s use our 1–1 time to chat about X”. I know I’ve said that so many times. Bad. How can you avoid this? Schedule separate, recurring time to discuss operational stuff with your leads. Call it a “Weekly Project Sync”, “Departmental Update”, whatever makes sense. But doing this will help to squash the bad habit of using 1–1 time for operational issues that YOU want to discuss and help reinforce that 1–1 time is separate and distinct.
  • Don’t skip. Shadow problems are, almost by definition, not urgent. They come out only once you peel the onion back a bit. So if you ask your report, “Do you have anything you want to talk about..otherwise why don’t we skip this week?” there’s a good chance they’ll respond with something like “Nope. Yeah totally let’s skip. I could use the extra time today”. Furthermore, shadow problems are also uncomfortable to talk about. So, even if your report has it in the back of their mind as something to talk with you about, they may jump at the chance to postpone the conversation a week. Finally, skipping 1–1’s sets a tone of 1–1’s being an as-needed, optional time. Skip it once and you’ll soon find yourself frequently cancelling them.
  • Ask short, open-ended questions. An old manager at mine would always start every conversation with “So what’s exciting?” Back then I never thought too much of that question, but in retrospect I realize how effective it can be to kick off a 1–1. You could also choose something simple like ‘What’s on your mind?” After the first answer, continue by asking “..and what else?”. I’ve found that repeating this a couple of times often leads to topics that are more personal, deeper and, often, more shadowy.
  • Make a conscious effort to listen. While this rule is good advice for any conversation, it’s especially true for 1–1’s. You’re not going to learn anything new by talking. Remember, it’s their time not yours. As a loquacious person myself, I’ve struggled with this quite a bit. 2 things to try: (1) Take note of the ratio that you speak vs. your report. Ideally this should be a 3:1 ratio if not better. If you’re not sure, write TALK and LISTEN in your notebook and, every 5 minutes, put a tick mark besides each verb you did most of during that time period. It might feel weird at first — and it is pretty weird — but after a few times doing it you can track this mentally without writing it down. (2) Another trick to listening well is to make a conscious effort to pause for at least 3 seconds before replying. Silences feel uncomfortable but they will give you time to think of a reply instead of formulating a reply when you need to be listening.
  • Finally, The Lunchroom test. One simple piece of advice I received a while back is if the conversation you just had in your 1–1 could have been done in public, you probably didn’t have an effective 1–1. Think about the last 1–1 you did. Could the conversation you had have been done in the open..like on a bench in your lunchroom? If so, it probably wasn’t intimate enough. Not intimate enough = shadow problems remain in the shadow. One simple trick is to go for a walk. There’s something naturally intimate about a walk. Plus, if its sunny outside you’ll both get a bonus dose of Vitamin D.

Well that was a bit longer than I intended. :) If you’re still reading, congratulations! I suspect that it means that you are motivated to make your 1–1's more meaningful. Even if you’re not a people manager, you are likely engaging in 1–1 conversations every single day with your peers. In either case, I ‘d encourage you to jot the above tips down in your notebook and give them a try. If you do, please drop me a note and let me know if you found this list helpful!

I play with blocks. :)