Andy: There’s a moment every boss has and it’s not a fun one. It’s the moment you have to tell someone: We have a problem here, and it’s not fine. Things need to change, starting now, and improve steadily, ideally quickly, or we’re going to be having a bigger, badder conversation in the very near future.
Emma: I think it’s one of the hardest parts of being a manager. We know it’s human to make mistakes. There’d be no medical dramas on TV if we weren’t messing everything up all the time. No ER. No House. No The Resident. Have you seen The Resident? It’s truly terrible, and also full of people who keep screwing up.
But mistakes exist on a teeter-totter. On one side you’re messing up and that’s okay, and on the other side you’re messing up and it’s a problem. For example, you flub intubating a patient, but you’re an intern and it’s your first week and you’ve only done it once before while under close supervision, plus you haven’t slept in 34 hours! That’s okay.
But if you’re an attending and you can’t intubate your patient because you’re trying to hide an undisclosed hand tremor: It’s a problem.
Andy: Both the teeter and the totter require prompt, articulate, helpful feedback. But those conversations sure feel different, don’t they?
For me, light, casual and no big deal comes naturally. “We can work on this! It’s totally fine!” It’s an instinct that I have to fight with my entire being. If I don’t, I say something like this:
Hey, Nick, it’s fine that you messed up the anesthesia amounts this time, but next time you need to make sure they are right.
Let’s dissect that sentence.
Hey, Nick — opener that starts the conversation
it’s fine that — downplaying
you messed up the anesthesia amounts this time — identifying the problem
but — we have to negate the downplaying!
next time you need to make sure they are right. — weird vague consequences
I go back to my desk and realize: It’s not fine. And “next time you need to make sure” is not the solution I actually want.
Emma: In the course of any relationship, you are going to need to say things that are closer to Real Talk than small talk — things that are not easy to say. A lot of managers (I have been one of them, more than once) delay it, often for so long that we skip straight to the bigger, badder conversation. All of a sudden poof! there’s a PIP and a record on file and HR has been notified. We’re all aware this is not the way to do it. Nevertheless it happens all the dang time.
Andy: Do not delay! Your worst most fumbling attempt at having this conversation is better than not having it at all.
Telling Someone What’s at Stake
There is no rule for when a more-than-just-feedback conversation needs to take place. The teeter-totter can be tipped by a lot of things: how many times the problem has happened before, how egregious it is, your person’s level of awareness and complacency, how long they’ve been in the role, what their goals are. That said, the earlier this conversation happens, the better for everyone.
We’ll walk you through how.
Prepwork
We do not recommend having this conversation on the fly. Give yourself some time to plan how to clearly articulate these four key pieces of information:
- The problem
- Why it matters
- Your expectations, including timeline and consequences
- Immediate next steps
We recommend writing out those four things so you can email it to your report directly after your conversation. More on that in a moment.
This conversation should happen in a 1-on-1. (If you don’t have one on the books, set one up.) As a practical matter, try to book the room for a bit longer than you think you’ll need — this will give you space to go over, or for either of you to decompress without getting kicked out.
Broaching the subject
Sometimes, your report will surface the issue on their own. This is an ideal scenario and it almost never happens. Most of the time, you’re going to have to bring it up. Try one of these segues:
When it’s the elephant in the room
- Let’s talk about [event] yesterday…
- I’d like to talk about…
If they’re oblivious
- I’ve noticed a pattern…
- I wanted to point out how [behavior/action] comes across…
- I don’t think you mean it this way, but from the outside [behavior/action] seems like…
- Can you help me understand…
If you learned of the problem from someone else
- I want to share some feedback with you…
- I got some feedback I need to share with you…
State the problem
State the issue and why it matters. Keep it clear, concise, and neutral — we’re talking two or three sentences.
I’ve noticed you’ve been coming late to your shift at least once a week for the past month. When you’re late, there’s no one to answer customer calls.
I got some feedback I want to share with you: Your Photoshop files are so disorganized that other designers can’t work with them. We collaborate so much on our team that it’s a problem we need to fix.
Set expectations
Again, keep it short and clear. Think of it as geo-locating this conversation in the larger course of events: What needs to happen, by when, and what’s next. (Dwight does a pretty hilarious job of this in an episode of The Office.) Lots of people will interpret this as “getting in trouble,” so it’s nice to remind them that you’re there to help.
I’ll continue tracking your timesheets to see that you’re clocking in by 9am. If you don’t clock in by 9am every day for the next two weeks, the next step will be a Performance Improvement Plan, a formal and highly documented plan I’ll put together with HR — because, unfortunately, a pattern of tardiness is grounds for termination. That’s not where I want this to end up, and I’m here to help.
I’d like to work with you to improve the organization of your Photoshop files by the end of the month — that’s the timeline we’re on. If your files aren’t consistently accessible to other designers by then, we’ll have to move to a formal Performance Improvement Plan.
Make it a conversation
You need to confirm that your teammate understands what you just told them, answer their questions, and receive their reaction. Lots of times, this will all be a fairly neutral exchange: You deliver clear information, they are mature and take it professionally, and everyone continues to carry on. Make it easy for them to respond.
In most cases, a simple question will do the trick:
Do you have any questions for me?
For under-reactions — arrogance, ambivalence, shrugging it off — ask them to summarize the situation:
I’d like to make sure we’re on the same page about this. Can you recap what we just talked about?
For overreactions — maybe shock or tears or panic — you can reassure them that this is solvable.
I know how hard it can be to hear something like this. The good news is we’re addressing it early and I’m here to help.
One thing you definitely don’t want to do is undercut the seriousness of the situation. Some phrases to avoid (even though you’ll definitely want to say them):
- Don’t worry about it
- It’s not a big deal
- This is just a heads-up
- You’re totally fine
- You don’t need to worry about it hurting your performance review / promotion / etc.
- I’ve never fired anyone over something like this
- I promise we’ll figure it out
Explain next steps
Follow up with an email recap of what you discussed — update the draft you started in your prepwork with additional notes or clarifications that surfaced in real time.
After that, it’s up to you. You might want to have a second conversation after they’ve had time to digest, or set up time to build a plan or have a training session. You can also simply mention you’ll talk again in next week’s 1-on-1.
In the next hour or so, I’m going to email you a recap of this conversation. It’s just so you have something to refer to if you have questions — no need to respond. I’d also love to regroup mid-next week to see how things are going, so expect a 20-minute meeting invite to come through today as well.
As a next step, I’d like to spend some time working with you on simplifying your design process to create cleaner files. Let’s start next week with two hour-long sessions. Please find time on my calendar that works for you and set up those sessions by the end of this week. I’ll also recap everything we went over today in an email as well, so you’ll have it as a reference.
End the meeting
Quick tip: Don’t leave the room at the same time. Hang back by at least a few minutes to give them some much-needed breathing room, or if they’re not looking ready to get up, let them have the room and let them know how long you’ve booked it for. If you sit near each other, camp out somewhere else for a bit.
