Types Of 1-1s

This is a post about the different types of 1-1 I have encountered in my life. It is almost as if 1-1s were animals in a zoo. Seasoned managers will quickly identify a member of each species and know how to deal with them. Newer managers might mistake a tiger for a house cat, and lose a limb in the process. As a manager with plenty of scars (yours truly made nearly every wtf mistake in the post below), I hope to help newer managers not get mauled when they misidentify a 1-1 animal.

A quick aside: this post is not about the reason for 1-1s, or why you should have them regularly, or why you should have a 2-way agenda, or what you should discuss in them, how to give and receive feedback, etc. There are a plethora of articles on that, including a whole app to help you run them better. Instead, this post is about real-world situations managers encounter, for which an app can’t tell you what to do. If you’re interested in learning more about the mechanics of 1-1s, drop me a line, and I’ll write it out.

If you’ve been managing people for a while, these 1-1 types will appear familiar to you. I’d love to hear about ones that I missed to add to the zoo. Comments and feedback appreciated - @radoshi on Twitter.

🐶 No Agenda Chill

Engineer: “Hey, boss, what’s up? I thought we could just hang, I got nothing on the agenda.”

I’m a type-A organizer. This message is my kryptonite. A meeting without an agenda? Say what? Why are we even meeting? Should we cancel?

The obvious answer is no. But it often takes me a few deep breaths to get there. Me: “Sure, let’s hang.”

25 minutes of conversation into the “no-agenda” 1-1: Me: “And how is X going?” Engineer: “Oh, it’s a total disaster, and the team is really clowny, and I’ve been super stressed about it and not sleeping, but didn’t know how to bring it up, because I’m so stressed, what should I do?!?”

Well, that escalated quickly. Let’s get into emotional support and problem-solving in the last 3 minutes.

As a manager, the no-agenda-chill 1-1s are the second-worst (Quitting is the worst). You never know what to expect - it might be a waste of time, you might have to prompt the engineer to write an agenda next time, or you come out with some scars because you were in the dark and didn’t ask enough probing questions. 🤷🏽‍♀️

Approaching the No Agenda Chill:

Go really broad on topics, ranging from how they are doing, personally and professionally, and probe for areas of concern. When you find a problem, follow it up with the immediate help solving the problem. Think of ways to avoid surprise next time.

🧯Everything Is On Fire

Engineer via email or slack, sometime before 1-1: Hey, I’m really concerned about Thing. Can we spend 5 mins in our 1-1 talking about Thing?

5 minutes. Yeah, right. This Thing is going to take up the rest of your 1-1. If you got anything else, get it done before you talk about the Thing.

These 1-1s are amongst my favorites. As a manager, I don’t have to dig around for where the fire is. Staring at a blazing inferno, being asked to point the firehose. My help! Yay, I feel useful.

The natural response, of course, is to jump into problem-solving mode immediately. I am an engineer (well, I was an engineer, but self-delusion is a powerful thing). This is what I do best. I solve problems. Let’s go.

The fly in the ointment is that, as a manager, you don’t really know what the problem is. One thing it most definitely isn’t: the thing your report tells you it is. Not because they aren’t smart; au contraire, they are better than you at their job. If they knew what the problem was, they would have likely solved it by now. By immediately jumping into solution mode, you’re probably just pointing out the obvious.

Approaching the Everything Is On Fire:

Do a lot of active listening. (If you are not familiar with active listening, I strongly recommend watching a few YouTube videos on the topic. It will change your 1-1s forever.) Ask clarifying questions. Try and understand the problem in multiple different ways. Do not offer solutions in the 1-1. Think about it offline and write some suggestions within 24 hours. Often, the people talking through the problem, with the aid of your questions, will solve the problem for themselves. This is an excellent outcome. Use the credits to unlock the next level in the Manager RPG.

🦨 That Team (or Person) is Terrible

This 1-1 is a variant of Everything Is On Fire, but we are dunking on a person or team instead.

Engineer: “This person is an idiot. They did everything wrong, and now I have this whole mess to clean up. Why can’t we just fire them? I don’t want to work with them again because they’re just so hard to deal with.” Or: “That team has no clue what they are doing, but they won’t let me get my work done. They are blocking my commits, won’t answer my questions. Moreover, their code or API or whatever is just a complete mess. Why are they even around?”

Oof.

This is a dangerous 1-1 and must be approached with care. On the one hand, you must walk the engineer off their rage-fueled, emotionally flooded edge. On the other hand, you must help them put things in context and approach problems constructively. Additionally, there might be an element of truth to the engineer’s rage, and you must investigate things further.

There are two large danger signs associated with this 1-1. Engineer says something overtly racist, sexist, against company values, or deeply offensive, in the heat of the moment. Depending on the severity of the infraction, this can result in a stern talking to and a reminder that certain types of speech are not acceptable, or in the extreme, a discussion with HR that can lead to censure or dismissal. It can also be really tempting to join in on the gossip and slam the other team or person. As a manager, you’ve just made your position infinitely worse by doing this - you’ve sent a message that this sort of behavior is okay, you’ve given the engineer the impression that you agree with it (and they’re definitely telling their friends), and put yourself in a vulnerable position.

Approaching That Team Is Terrible:

De-escalate as quickly as possible. Help Engineer to calm down. Focus on facts. Re-focus the conversation on people having good intentions, but not being capable (everyone is learning/growing), or circumstances conspiring a certain way etc. Dig into the exact complaint. Investigate the engineer’s claims. Follow up with others as appropriate. Follow up with Engineer to close the loop. If appropriate, get HR involved, or escalate to higher leadership.

🐰 It’s Urgent

Engineer: “Hey, can I chat with you urgently?”

Uh oh. This one is important but seldom good.

If we are lucky, this urgency is about a time-sensitive decision that needs to be made. However, most decision problems get sent over slack or email, and there is usually no need to be coy about the agenda.

This is the 1-1 where the dire stuff comes out. Someone got sexually harassed, someone found something deeply wrong that violates company guidelines or is straight out illegal, anything else that is just Serious.

Approaching It’s Urgent:

Make time for this asap. If you need to get out of a meeting, do so. If the report is serious, escalate to HR or senior leadership as appropriate. If in doubt, check with HR, they are here for precisely this reason. Follow up with engineer (there are some circumstances where HR or legal would require you not to, but those aside, you should follow up to make sure the issue was addressed.)

🦘Feedback Hour

There are two flavors of these - the conversation after the formal performance review, and the ad-hoc feedback conversation. The former is more mechanical: prep beforehand, send the recipient a writeup that they can read and digest beforehand, then spend time going over it in person.

The ad-hoc feedback conversation is more interesting.

“Do you have any feedback for me?”

🤔

Approaching Feedback Hour:

Rookie version: “Sure. Here are 3 things you could be doing better.”

Battle scar version: “How do you think you’re doing with area X, Y, Z? What things are going well, and what aren’t?” You have a list of things they need to be working on (right? RIGHT?), and this is your opportunity to check their self-perception on their growth. “I agree with X and Y, think you could be doing more on Z, here are two specific ways I would have approached it if I were in your shoes.”. ✅

Remember: you don’t have to diagnose, create, and deliver feedback all on the spot. It is perfectly fine to follow up over email or slack or another 1-1 in 24h, as long as you do actually follow up.

🦡 Promote Me

Engineer: “What do I need to do to get promoted?” or even better: “Reviews are coming up. Are you going to promote me?”

Side note: I love working with people that are bullish on themselves and straight up ask for a promotion. That being said, remember that there are a lot more people who are shy, who have cultural issues against asking for a promotion, who suffer from imposter syndrome, or a bad case of Dunning-Kruger. Care about these people, possibly more than than the ones that ask you to get promoted.

Back to regularly scheduled programming.

The decision tree here is straightforward. You believe your report is ready for a promotion. You are genuinely going to fight for your report in whatever promotion process your company has (unless you’re Google, in which case managers have little say 🤷🏽‍♂️.) You don’t think they are ready for a promotion and are not willing to put them up or fight for them.

In either case: Inviolable Rule: Be Honest. There is no better way to break long term trust than to make things up.

Approaching Promote Me:

If they are ready for promotion, go into expectations management in case the promotion does not happen: “I think you’re close and are crushing it on many fronts. Here are two areas that are still questionable. I’m going to get feedback from other senior people at the company (or whatever the promotion process is) and make a good call.”.

If they aren’t ready, let them know: “I’m not sure you’re ready yet. We believe in trailing promotions, and you need to be performing at the next level for at least N months. You need to demonstrate more of X and Y for this to be a slam dunk promo. However, I’m going to bring up your case and get feedback to make sure I am calibrated.”

☠️ I Quit

My worst 1-1. And they almost always start innocuously. Engineer: “How’s it going, how’s the family, isn’t the weather great?”. It’s like some human desire to push away talking about difficult things until the last possible moment, even in the very meeting that you’re supposed to talk about it. Once the engineer feels the manager is warm enough, they drop the bomb: “So, I was thinking about doing something else in the future.”

Me, blinking furiously, half my brain telling the other half to keep calm because they’re not quitting: “Okay, what were you thinking of?”

Engineer: “Well, my friend started this company, and I have an offer to go be their CTO. I’m thinking of taking it.”

Me: “Ffffffffff”

Approaching the I Quit:

After a moment of panic, take 5 deep breaths, and let’s unpack this.

1. 🤦🏽‍♂️Manager person WTF! How did you fail to detect that your star engineer is bored, tired, or seeking new challenges? In some cases, there is nothing you could have done - a chance meeting leads to something bigger, and suddenly, they have an offer. But in most cases, you could have seen it coming and knew in the back of your mind that you should do something about keeping them motivated.
2. 💰What is the right thing for the engineer? Sometimes, the best opportunity does indeed fall into their lap, and the best thing you can do is encourage them to take it. People is a long game. If you’re consistently doing the right thing for your people, you’ll work with them again.
3. 🙅🏽‍♂️Some times, the deal they are offered is genuinely not good. CTO might sound great, but the company is going nowhere and has been around for a year. Or Founding Engineer looks excellent; they are getting screwed on equity. In cases like this, I’ve helped my reports actually model these things out and understand how ownership, vesting, and dilution work. Incredibly smart engineers sometimes have a hard time building a spreadsheet, so I create one for them (which they then take and make 100x better and add many complicated factors).
4. ❤️More than sensible advice and help (in the form of spreadsheets), they are also looking for emotional support in two dimensions: 1) knowing that you and other leaders at your company care about them and 2) they have a strong connection to their team and the mission here. Reinforcing these emotional points, along with the rational artifacts 👆🏽, leads to a 50% chance of saving the engineer from leaving your team.

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