We’ve all had 1x1s with bosses where conversations go badly, or one party has the wrong idea about what was to be discussed. Such conversations are unproductive, of course, but also sometimes frustrating, mortifying, and demotivating. Here’s how to get back on track.
Note: a bad 1×1 with a generally good boss is not the same as having a difficult 1×1 with a problematic boss; I address that here. (Here’s the post on how to have a good one.) If you don’t see an answer to your question about this topic here, you can email me at firstname.lastname@example.org or find me on Twitter @akrook.
Find out what went wrong. The first thing to do is find out what went wrong. Unless your boss told you specifically (“I wanted to go over projections for the new product in our marketplace, and you didn’t bring any data with you”) you need to ask: “Did I misunderstand what you were expecting? I thought you wanted [this], but you wanted to discuss [other thing].”
You can address the problem as it comes up (best), have this conversation at the end of the 1×1, or later, casually, in the hallway, for example, or later, formally, in a dedicated conversation. Which you pick depends on how much of an issue it was and how chronic the misalignment is. Ordinarily you should not wait more than one business day to address a problem like this; sooner is better before everyone gets overwhelmed with other work and forgets the actual cause.
If the mistake is yours, apologize. “I apologize for misunderstanding; I understood you wanted two-year projections, not three-year ones.” Don’t pre-emptively apologize before you find out what the problem was, because you want to apologize (if you need to) for a specific mistake, not for your overall work (!).
On a related note, If you tend to excuse yourself, apologize for things that are not your fault, or say “I’m sorry” all the time, in email or in speaking, check out my tool for how to identify that and do less of it.
Find out where it went wrong. This is the single most helpful thing you can do to make sure your next and subsequent 1x1s don’t go badly for the same reason the last one did. Did you agree on what your boss needed from you, and then miss an email with an updated request? Did such request come in time for you to get the new information? Did your boss simply change what s/he wanted from you and forget to tell you? Communication breakdowns are often at the root of bad 1x1s, and the important thing is to articulate them and fix them before next time. If you discuss what you believe was the cause in a factual, non-defensive way, and where you got your information about what you believed you were to discuss, you are likely to identify the cause much faster and fix it sooner.
Focus on the problem, not the person. This classic piece of advice is classic for a reason: it works better than almost any other tactic. You should focus on what you and your boss need to discuss and solve together to make your next 1×1 better, not on whether your boss likes you, which is often the underlying fear during and after a tough 1×1. So you focus on the specific issue, not on yourself or your boss personally or on problems generally: “I missed the email because I had meetings from the time you sent it up to our 1×1” not “If you didn’t ask so late, I could get you what you want” and “I’ve been backed up with [projects] and need your guidance about what to prioritize” not (just) “I’m overwhelmed and behind.”
The person is the problem. Sometimes, unfortunately, the person is the problem, or at least the person’s interactions with you are. In cases where your boss is focused on a personal trait of yours (“You sound whiny when you presented at that meeting”) try to refocus on an addressable part of the comment: “Where did you notice that? Tell me how it hurt my presentation so I can improve.”
Very often asking about inappropriately personal or generally unhelpful criticism makes the person improve it into something you can address (“You sounded defensive when people asked you questions”), but sometimes it doesn’t (“I just hate squeaky voices”). If you find inappropriate or unhelpful personal commentary coming repeatedly from your boss, you need to approach that in a different way, which I address in this post.