Back to Calibrate

Difficult Conversations As A New Manager

Christian McCarrick
VP of Engineering

As a new manager there will be difficult conversations in all directions where you'll deliver and receive feedback to and from your manager and direct reports. We have varying degrees of experience on this panel and we'll discuss the things that are always going to be hard and what gets easier with time. We'll also share advice and the best tips we've learned along the way.

Are we ready? Excellent. It's right after lunch. So these are super comfy chairs. We're going to try not to fall asleep, but hopefully you won't either. I'm going to get this started. So let me briefly introduce myself. I'm Christian McCarrick. I'm the VP of engineering at auth zero, and I'll be moderating the panel.

Right here, we have T Caldwell senior engineering manager at slack. You have nitty Gupta, SVP of technology at hired. And we have Hassan Corey. So for manager at Amazon lab, one 20 . All right, so let's jump right in. Okay. A former manager once told me that the only things worse than having a difficult conversation was waiting to have a difficult time.

Right. And, you know, avoiding these difficult conversations takes up valuable mental and physical and emotional resources that can cause anxiety, right. It can actually exacerbate the initial problem if you don't deal with it soon. So I have a question for the audience here. How many of you have had a difficult conversation in the last week or are putting one off that you really should be having?

Right. I have a doozy of one coming up next week, so I know all about it. So the other thing is interesting. When you think about hard conversations. I was reading an interesting study that they did in the UK and the, the workers rated their different levels of anxiety around conversations.

Number one was PE two is inappropriate behavior. Three was feedback report performance five was promoted. And then it got down into like family relationships, breakups money, health, but interesting that work conversations caused people more anxiety and they thought that, or more difficult than actually a lot of things in your personal life.

Right. So speaking of hard conversations, I want to hand it over to the panel for a second. Can you share, you know, what was, what has been some of the most difficult conversations you've had in your career? I'll start with you. I would say usually a toughest conversation because

yeah. I think it's become, it becomes easier over time, but it's never easy. I think I still find some difficult feedback conversations. Very, very hard to do. I have to remind myself not to put them off not toys. Yeah. Awesome. Yeah. I think I still have these conversations where there's just really bad news about the project itself that were definitely, you know, you can get a sense early.

You're definitely not going to hit a timeline instead of just upfront saying, Hey. It's probably not going to be feasible. You kind of delay and delay, and it becomes a shock later on instead of just upfront saying it. Yeah. Which I think segues nicely into, I think one of the difficult conversations that we have in that point is, and T I'm going to address this to you as a, as a manager where you have to manage up.

Right. I think that's one of the big things we start learning as new managers is, you know, it's not just managing down or across, but you have to get experience in managing up now to your manager and your managers. So, how do you approach a, a difficult conversation? You're going to be late on a project.

A small messaging company we might've heard of. And you know, how would, how would you approach that what's the best way for you to approach your boss or your manager that you're, you're going to be late or over budget or so I just started this lack of

understanding what you're doing and really cares about how your project relates to the business. And so if I know I'm working on a super high. Product. And I shouldn't be aware of my stakeholders and where they will align. And so when I do have that conversation, doing that homework and research first, where you're not wanting to fire Amanda, but we've also already had that conversation with some of your peers.

So that is a more unified is a better way to have that conversation. When it gets contacted the, the room one-on-one I do say that and we don't the latest, I think the biggest thing you can do if you are delayed is to try and like, be more upfront about this, but then say like, here's my plan. So not just say you have to own it and acknowledge it.

I think they want you to

Absolutely. And I think, you know, as running engineering teams, that's like the number one thing. And I coach my teams that if you come to me right away, there's probably going to be no consequence at all. Right. This is, we can actually fix it. If you come to me the day before, that's a big problem. Right.

And then we're going to have to have a retrospective about how we got there and Hassan you're in hardware too. Right. So that actually, you know, projects for you can, you know, can have big impacts, right. And things specific. You have. Yeah, I think a lot of our conversations are around there's hardware come in.

We're the first to actually try to put software on top of it and finding out there's a problem. And knowing that that causes delays in the factory, it causes loss of money and all those types of things. And I think Tina said it well, having alignment with the other teams, like go into hardware, understanding what they can do to fix what they can.

Going to ops understanding what, how much it affects the timeline and those types of things. So that when we go to leadership, we should go to leadership with our plan of what we can and cannot adjust for. Now, did any of you have anything you do to prepare for conversations? Right? Is there anything specific you do?

Did you just go in blind or do you prepare some, how did you, how would you handle it? Of all the four or five different types of difficult conversations you've mentioned. I think the skill that I've developed over time, or I try to, is to put myself in the other person's shoes. Right. So. Whether it's a project delay or whether it's you know, a we're, we're getting rid of somebody it's about making sure.

What, how is the other person going to receive it? Are they going to hear my message? And if it's about upward management, then what is the what's the question going to be? What's going through their head when they are processing this piece of information. So if I'm talking to my CEO, The, the question he's asking or her she's asking is why can I trust you again?

Is it going to happen again? What are you going to do to fix it so that it doesn't happen again? Right? So if I have already thought through what they will go through in their thought process, I can actually tackle it and address it upfront even before they even ask the question. So I think for me, that has actually served me well in terms of making sure that the feedback lands and that the information that I'm providing, I already have answers to.

sort of creating a mental script about how are you gonna, how it's gonna play out. Yeah, exactly. I think that's important. The other thing that giving feedback feedback has been mentioned a lot of times, I think. And a lot of times feedback can be considered a difficult conversation, especially if it's going to be giving maybe feedback.

That's not so positive. So what advice do you have in preparing, especially as managers, a big part of your job is about giving feedback now. And I think that's one of the, the first, most important things that you have to do do up for you. What, what is, you know, how do you give feedback to your direct reports, especially maybe negative feedback.

I do my homework. So I think it's really important for you to have the facts, make it a fact based conversation, not focused on the person as a whole, but on the behavior that you're actually trying to address. And there's a lot of. Hot and out there where you can say here's a structured way, what you go and see, like, what is the one key takeaway that I want this person to understand as it was one of our conversations, but then the part where it comes in and you do have that acknowledging their feelings and trying to figure out a good way.

To problem-solve. How can this be better in the future? And I think that's important in providing that like psychological safety so that you can have these open and honest conversations. And a lot of that psychological safety also comes from having built the trust over the time. Yeah, absolutely. Yeah. So need, if you wanna expand upon that.

Yeah. I mean, I think it, it's still hard. It's still hard to give feedback, I think, but I think it's harder to receive. Not so great feedback, right? So if you go in understanding or remembering the last time you got not so great feedback and how you felt about that that's going to situate you well, because that's the, what you're putting the other person through.

For me, I think feedback is incredibly important. It's not just the duty of the manager, but it's also. It it for all of us to grow, we need to be able to receive feedback. So creating that psychological safety, I think it's very important, but if you've gone through the length of preparing yourself and putting the other person in a place that make it worth their while and make it worth your while for me, the biggest lever is using.

Don't do HR speak. That's just, don't listen to the HR team seriously. It's just because HR, HR speak is just so hard to understand and you do HR speak and they'll be like, whoa, what nigga? You don't collaborate the fuck. Are you talking about, of course I collaborate. Give examples, make it real. And the re the more real you make it.

And the more situations you say. The easier it's going to be for the, for the person to internalize and for them not to be defensive about it. Absolutely. Yeah. How Santa that's something. Yeah. I think the thing I focus on is, so we just had a talk about authenticity and about your leadership. And I try to keep that consistent, good feedback or bad feedback back.

My leadership style is very much like teaching. So I come at it as they're part of my team. They have good intentions about what they're trying to do and how they're trying to go about it. And the thing to emphasize is helping them understand the situation, helping them understand why, oh, in this situation, You went to overhaul the software, but you know, we have these deadlines and, you know, they're expecting these things from us and that's why in this situation that's bad, but in another situation that could be good.

Right. And so I keep that consistent. Also when they're doing something good to tell them why it fits with what we're going, where we're going. And I think it's important to that feedback. Can't be something that you just suddenly spring on people like you haven't done it for six months and suddenly you go to a caliber conference and suddenly the next week you're dumping Quebec and everyone, and they're like, what's going on.

But I think. To engender a culture of constant feedback so that when you give feedback, it's not out of the world, it's not like a crisis for them. It's just part of your culture. I think that's also important. Now the other part of feedback is when, like when and how often. Right? So Husson, let's just talk it again.

You know, what is the time like? Is it, when do you do immediate versus is it weekly? Is it monthly? What's the cycle for that? So most of my direct reports I have every two weeks we have one-on-one and I will Keep most general things to that. If there is a specific issue, I would just go by and say, Hey, can we talk real quick?

Right. Cause I do think like you've said that it's about the situation about it being. And that's most easy to do when you have that conversation very soon after this situation has happened. Absolutely. Yep. Great. Yep. And just to add to that, so I do something very similar Sometimes, you know folks will tell you, Hey, if you observed a behavior, pull that person out of the meeting or right after the meeting, talk to them.

I don't do that. That's personal. That's my personal preference. I want us to let the situation cool down, have them absorb it assimilated, but I take copious notes through the duration of my week and at my next one-on-one I will bring that topic up. Closer to the situation is easier for, for, for you to deliver the feedback and for the other person to be able to receive it because it's still fresh in their minds.

Yeah, absolutely. And you, you brought this up a little bit maybe before, not only as a managers, giving feedback really important, but the ability to solicit and receive like active solicitation and receiving a feedback is super important to you, for you, any tips you have for managers that they can help to, you know, solicit that feedback from their employees.

Yeah. I mean there's two things. I'm talk about me because I heard this story from Cooper when I bought at slack and she's thinking people of color in particular, it's really hard for people to deliver to feedback because it's all this client and perception one hot moving act. And so allowing ourselves to be open, like checking your emotions.

I indoor is actually like a good thing. I think one of the things that I try and work with on my temper people of color and minority. So they're saying like, how do you get them doing and just bring it on me and then try and say like, Hey, I did this actual thing, like, and looking at this presentation hadn't how did we get I haven't to improve this?

And so that helps out with the receiving portion and making sure there's nothing unusual. And similar to what Laura was saying in terms of receiving feedback I would say.

the doors. That's the most important thing. I don't know how you can prepare for that and an indictable conversation. It's easier said than done. I now try to neutralize, like instead of having like this space, or even coming up to somebody saying like, Hey, we need to talk to just now trying to be just like more approachable and understanding where they're going to.

And I think it's okay to admit and bring it out in the open that, you know, this, this feedback you're getting might. Affect you. And it might be okay to say, Hey, let me process this. And we can have this conversation again in 10 minutes or tomorrow I wanted to add one thing. So I heard this phrase  public that they would take in private.

And so I try to actively, never do repeat in like a group setting. I'm trying to take COVID and talking about it. One-on-one. And one thing you brought up to you, I want to focus on for a second too. Do you think being a member of an underrepresented group affects how you would approach a difficult conversation?

Yeah. I, yeah, I don't know. It's the reality of situation. A lot of people go on with biases in terms of like how you react. And so I was having an authenticity conversation on, do I feel like I'm being much, you love yourself at work? No, I feel like I'm actually the president of, because I don't want to have this stereotype of him.

Black woman go out a little bit more. And you know, no one really knew, so yeah. Very true. Very true. Yeah. I mean, I think, look we talk about biases, biases exist and we've faced them on a daily basis. Right. Make, I just gave a great talk in terms of, you know, all variety of different types of biases.

So yeah, I, if I have to ask a question of an engineer. Him a feedback. I'd be like, maybe I don't know this, but like, I sort of have to suppress my technical side or some side because I'm giving him feedback and I want him to be able to accept it. Yeah. Happens all the time, but that's unfortunately the reality of the world and our industry.

And that's why we talk, we're talking so much about diversity these days. Yeah, I think for me, the thing I focus on is trust. So part of that is consistency of one-on-ones, but the other part of it is as I solicit feedback from them, I write down, I try to make sure that by the next one-on-one I have follow-up.

How were either you're trying to change it for the group or how we do that thing. And then when I have the next one on one, I have the last one-on-ones notes next to where I'm taking a new one on one's notes so I can make sure I follow up. And that creates that I can always say, oh, last one, when we talked about this and yeah, I went through and try to modify that or change that, right?

These creates this trust where they don't feel like I'm just giving them lip service. They feel like if they give me feedback or something, they think about the group needs to change. I take that seriously. Great. Thank you. And I want to go into a hypothetical situation now because this is something I, I always run into, unfortunately.

And as new managers, I think you might, you might run into this. So you're in an open floor plan. You happen to be sitting there and you start hearing a conversation between one or two or three more engines. That concept, that conversation starts escalating. Yeah. At what point is a manager, do you step in to deal with that versus letting it play out?

You know, and now of course, everyone in the, in the, your pod is like never happens. What are you talking about?

So I can actually jump in I'll tell you this funny story. In some company that I started at A company shall not be named. I started in and I think, and I think, and I think a few, a couple of months in, and I think it was 10 o'clock at night, I was working and one of my Em's said, Hey, are you guys following what's happening in the dev channel?

And I'm like, what is happening? And they're like, oh, engineers are going at it. Like, why are you not doing anything about it? And I go in there and literally it was like this mad, you know, everybody ranting against everything on each other on top of everything. And I, I tried to like jump in to just say, Hey guys, let's take this offline.

Let's talk about this. And then one of the Em's he says. Nitty come on. I was just bringing up the popcorn, like kidding me. So the point of the story is yes, it happens. And I think this is where we, as leaders need to jump. Right. And that there's a different expectations. When you become a leader of the organization, you have to shape the culture of the organization.

You have to shape the ethics of the organization. You have to fundamentally shape how our team works with each other, and that's not how you work with each other. And whether it's an in-person conversation, that's happening in an open office set up, or if it's over slack or, you know, whatever you need to jump in.

Yeah. See, because at the end of the day, that conversation must be making somebody uncomfortable and you don't want to promote that. And you don't want to foster a culture where that's accepted. So as a leader, you step in you mediate. If needed, you have people settle their differences and you moderate the conversation if needed and then loop back.

I think the loop back is really, really important. You loop back with the rest of the team or whoever observed that interaction to say this was the resolution and oh, by the way, this is how we resolve our differences. We don't resolve our differences in a public. You make such a great point that the it's a choice, right?

Not to step in as a manager, you're making a conscious decision or you make, you may think it's not doing anything, but not doing anything in a situation where you're seeing a value or a culture of your company. You know, being, you're not being followed as a manager. Now you have that as your point of responsibility to step in and not stepping in is a conscious choice.

And your employees will see that now you tolerate that behavior, whatever that may be. Great Hassan you interesting is a lot of you, I think a new managers is, you know, Katie had you raised your hands, what do conversations become more difficult when you have to have them with former peers? Right? I think some conversations do, but I think the biggest thing is it's kind of like when you go back home and then you're.

No you before you were important, right? They're kind of like I knew you before you were a manager and they, there's always kind of a, a snide comment here and there. And I think the thing you want to do is although you want to stay authentic sometimes you have to learn a lot about having that manager manager.

And I think it's like, oh, I'm a really smiley person, if you see, but I can also be like, so this problem happened in there's an issue here and we need to fix it as a group. Right. And it's about your nonverbal cues about how you talk about how you stand about fidgeting, about modulating, your voice to bring in a common force about how you dress and making that transition smooth and kind of.

Getting that out. I don't want to call it respect, but having them see you in a different light, right. And sometimes you have to help that along. Anyone else it's important to set expectations. I think it's really cool. So you already had a relationship with IRRs coming in and saying like, Hey, ours tip is going to change.

What is expected of you? How can we do this together? And that can be difficult for you having that upfront conversation will help like shape the way I'm a leader on the team. And so  yeah, you make a really good point. I think a lot of MIS you know, misunderstandings happen because of a lack of explicit expectations.

I think a lot of people have talked about that today. The manager read me's I think is a good way to do that. And a lot of times I found it's just these difficult concepts. You can prevent difficult conversations by just having more explicit than implicit things like you are working on this. This is my racy, this is my kind of span of influence.

This is yours. It's when you know, it's ambiguous when lots of conversations like that happen, and then you have to go in and unwind them. Right. Now an interesting point as new managers, I think you should all feel that you're not necessarily alone in what you do. Maybe for a small startup, you might not have as much resources, but at what point until both of you, well, you'll work at companies that have pretty good HR organizations, but at what point does the conversation become beyond just your ability to take, like at what point does the conversation become too much that you have to get someone else involved?

Like your manager or HR. Oh, yeah. I could, I have a person that's going through this experience right now by a one on one one-on-one because the performance would use even, and a lot of emotions are high. And so one of the things there is this spectrum of like, are you in there yet? Am I here to do this?

What am I not qualified for? I think it's great to start off a conversation and say, how are you doing? But if somebody starts just crying, Every waking second, where you feel like there's something wrong. I actually had to be like that. Like I'm not falling. Like, and it's probably something deeper going on where I'm not allowed to ask.

Yeah. Yeah, yeah. Yeah. I mean, I think so I will modulate what I said earlier, in terms of not listening to your HR team in this situation, please do they are there to help you. And yeah, I think if a person is crying, I think if your plan, if you are not happy with it, Performance, it's better to loop them in sooner, rather than later, they can guide you through the process.

If there are individuals who are throwing red flags in terms of it's going to it's like litigation a territory, or what have you you know, I've had this individual who at the right point in the right conversation, we'll throw in some word, which sort of makes me nervous. And I would loop in HR and legal.

So. With HR and legal aid, if any of these red flags go off, look them and sooner rather than later because you definitely don't want to get into a Yaki situation. Correct? Yeah. And I think too anything where people talk about maybe hurting themselves or hurting other people or anything like that, you really have to take seriously because you think it's funny, but I've been in conversations where, you know, we've, I've had to call the police, right.

I mean, it's just, it gets serious and you have to take things seriously and not to put it down. You know, as a manager, you have a responsibility to yourself, the person in front of you and the rest. Yep. Right. You didn't put the time, much time and a half. Cause I just want to. Okay. Right. So the other thing, and you know, did he, you were like a manager of managers.

Okay. As you coach other managers, what, what, what do you coach your managers and how to handle their teams? Like how do you coach them to handle difficult conversations? So that's a great question. I think the force thing for me, and this is, I think I've, I've sort of developed this POV over time is, you know, as Katie gave her talk in terms of being real right, being authentic to me, being authentic is truly just talking to an individual when I'm giving them a difficult, when I'm having a difficult conversation versus a not difficult conversation.

I think it comes most new managers and most, you know, most managers and directors that I work with. They're not comfortable with that. As a manager, it is okay for you to have a real conversation when you're having a difficult conversation as a manager. It's okay for you not to know everything about your team that I actually taught for the longest time that I should know everything about that my team is doing.

Okay. Completely stupid. And now I guide them otherwise. Right. So I think it's about to me, all of this boils down to you're just being real. And where that comes from is I was once in a feedback conversation or promise of your conversation and the person that I was giving the feedback to, they stopped.

And they looked at me and they're like, nitty, can you just talk to me like a human. And that was a turning point for me because it's like, oh shit, you're right. I am just speaking the HR vernacular. I am not talking to you like a normally would. So anytime you catch yourself doing that, and I think typically we all, as managers resort to that language, When we are faced with a difficult conversation because it doesn't come naturally to us, I would say practice that I do a lot of practice sessions in the bathroom.

So do that. And with my new manager, with my managers, that's the guidance I provide. And the other guidance I provide is if you haven't delivered this, or if it's really hard for you, let's pray. So I do practice sessions with them sometimes where I'm like, okay, I'm the recipient. Talk to me how you would deliver this to me.

I will ask you the questions to prepare you so that you can make sure that it's landing. And that's an awesome one. How many people here have actually gone through any sort of coaching or management training? Anything's right. Did any of you in that, do any role playing you did. Yeah, I think so to your point, I think, you know, it's okay.

It sounds really ridiculous, but in most other sports or anything else that you do, people practice, right. You know, they practice, they get, they have the ability to do that and we're just expected to be perfect on day one. Right? You're not, you're not gonna pick up a new instrument, learn to play it in the first day, nor should you be able to handle difficult conversation, right.

It all takes practice. You don't just the expectations in there that you know that right. I think one thing too, as managers. As you grow in an organization, what you say has greater impact, right. And the higher going in the organization, the more impact that have what you say has, so how do you keep that in check sometimes when you're having a difficult conversation to, to not be like, well, I'm the boss.

So what I say is right. Oh boy, that is really hard. That's very, very hard. I mean, I don't think that I've mastered that yet. I think I still find it odd that I walk into a meeting. I say something and then people's got to get on the treadmill, do that, do it. And I'm like, wait, that's a focus group of one.

That's just my opinion. So So I think I have to caveat that a lot. I have to say, Hey, this is just my opinion. Please push back. Please contribute. More often than not, I try to not articulate my POV. It's hard for me. It doesn't come naturally to me. I try not to do that, to give, to solicit input, but when I do, I try to caveat it.

This is just focus group of one. Let's make sure we're making the right decision. So yeah. I'll start, I think, to add to that as a kind of newer manager. Yeah. I think the thing I focus on is trying, and this is about new manager trying to leave engine direct engineering is moving more toward, this is the goal.

Then this is how you achieve the goal, right? Like, and. Again about educating about this is the situation we're in as a company. This is a situation we're in as an org. This is our goal is our goal to help help with those goals of the broader organization, how you execute it can take many different directions and we should discuss that as a group, but I'm laying the foundation about where we're trying to get to not how we get there.

Perfect really quickly, two for each of you. Any recommendations you have, we had a great one before how to talk to your kids. Well, listen, I think that's, that's actually a really good one. Anything else that you have that we do recommend for new managers to read? So I, I feel like that was like my go-to man.

Your Bible is crucial. Conversations were helpful with that. And we had a lot of interacting and role-playing to get you in courses that are around, but I haven't had drink. Radical candor huge fan feedback, authenticity direct on direct. I love it. It's fine. I don't have a book, but I would say actually one thing that helps as a new manager and talks about, you know, you would learn from coaching is actually going into more meetings with other seniors.

Actually, because they often have conflict with each other and how they deal with it in a respectful way is one of those things where you can try to read it out of a book, but you really need to like see it and hear how they speak. Awesome. And thanks for the feedback is another good one that I recommend to my managers as well, because it's good for both giving and receiving.

Right. I think, you know, overall, I think we've had a panel discussion here. So mastering the art of crucial conversations and hard conversations is going to be so important as you're part of the manager. And it's so important for you when your personalized, like, I think as you step up as a manager, I've found, you know, just having conversations with like my spouse and other things, like it actually helps.

Right. And vice versa. And the one thing that I I'll ask each of you to do here too, Is to find that, you know, you all said you had one conversation, one conversation that you might be putting off. Like, so my task for you is schedule that meeting, you know, today over the weekend on Monday, like habit, like just have that conversation, pick one, get it over with, and it's like a snowball effect.

Once you start doing that, they'll start getting easier and easier. Thank you, everyone in the panel here. Thank you very much. .

About Calibrate—

Founded in 2015, Calibrate is a yearly conference for new engineering managers hosted by seasoned engineering managers. The experience level of the speakers ranges from newcomers all the way through senior engineering leaders with over twenty years of experience in the field. Each speaker is greatly concerned about the craft of engineering management. Organized and hosted by Sharethrough, it was conducted yearly in September, from 2015-2019 in San Francisco, California.