Difficult conversations for engineering leaders range from telling someone they have lettuce in their teeth to delivering life-changing bad news. Learn to level-up your ability to handle difficult conversations with a few techniques, practice and hopefully a little humor from Sarah Clatterbuck's personal experiences.
Sarah Clatterbuck joined Google in 2018. She currently leads four teams focused on Alternative Monetization for YouTube Creators. Prior to joining Google, she was a Sr. Director of Engineering at Linkedin focused on Application Infrastructure. She previously held roles at Yahoo! and Apple while progressing in leadership ranks. Her undergraduate degree is from the University of San Francisco and her graduate degree from San Jose State University. She is passionate about getting girls interested in technology and from 2013 until 2018, she served on the board of Girl Scouts of Northern California, leading the board STEM task group.
Your discomfort is less important than your colleague's embarrassment
- Sarah Clatterbuck
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Can I give you all some feedback?
Actually, maybe this is feedback for me too. Us engineering leaders are terrible at difficult conversations. I think the only kind of difficult conversation we're actually prepared to have is to say something like, "I really think you've painted yourself in a corner "with the singleton pattern here." In writing, on a code review.
But anything involving human emotions, or things that make us feel uncomfortable, where we might have to look someone in the eye and deliver a difficult message, this is where we are woefully prepared, ill-prepared.
Okay, so I'm gonna age myself here substantially. How many of you had an NES growing up? All right, phew, I'm not the only one. When I was in the sixth grade, it became my ambition to obtain an NES after having played on the weekend at a friend's house. And my parents, who were actually quite skilled at difficult conversations, sat me down and informed me that I would not be receiving one from them, but I was free to earn one with my own money if I wanted to.
So, it took me about a year to save up enough and buy a system, which then led to what was my first video game addiction, Super Mario Brothers. And, today videogamers have kind of a nice advantage. You know, they can just go on YouTube and look for tips and tricks and moves that they can use to pass through the levels of a game.
But back in the day, we didn't have that. You had to know somebody who lived on your block who might be willing to come over and play with you, and show you how to beat all the different levels. So, we're gonna go back in time, and I'm hoping that I can be that person for you today, walking you through the different levels and worlds of difficult conversations.
So, first up, we have awkward conversations. Now, what is this? This is, you know, your colleague has lettuce stuck in their teeth right before they're gonna give an important presentation. Or maybe someone on the team has a horrible gum-smacking habit that's driving everyone nuts, but nobody wants to tell them, right? That's an awkward conversation.
So, I had an experience with this. I was at a company event, and myself and three other colleagues were preparing to give a presentation in front of the company. And we were all backstage, pacing back and forth, going over our lines before the whole thing started.
And it was three dudes and me because… you know... that's how we roll in tech. And so I'm walking back and forth, and I'm about to pass one of my colleagues, and I notice that his fly is like super obviously open. And I'm like, "Oh man." So, I figure, well we've got 15, 20 minutes. One of the other two dudes is gonna take care of this. But no. We get to like two minutes 'til go time, and we're still in the same situation.
So I'm like, okay. I'm gonna have to have the awkward conversation here. So the next time we pass each other doing our pacing bit, I kinda lean in and quietly say, "Hey man, your fly is down." Crisis averted. He didn't have to go in front of the company that way.
But basically, every gamer will tell you that there's the self-talk that you have to do in addition to knowing the moves to get through the level. So the self-talk that you need to give yourself when you're preparing for an awkward conversation is that your discomfort is less important than your colleague's embarrassment, right? You're gonna be saving them from a much bigger discomfort than you're about to have. So that's the self-talk.
So what's the script for this? Well, it's really simple. You're just gonna tell them. Ideally, you're not gonna tell them in front of other people because that would defeat the whole purpose of having the awkward conversation. So you're gonna be discreet.
And, my sort of power-up tip here for this level is that you can practice on friends and family. It's a lot less awkward to tell your spouse or your kids or your friends that they have lettuce in their teeth. So do it all the time. Be that person that's gonna have that conversation. And you know, this actually wins you a lot of points with your friends. 'Cause you save them embarrassment, your colleagues appreciate it. This is like instant trust-building. Like that guy knows I have his back if we ever work together. He'll never doubt that.
So moving on to level two, alignment. We get in misalignment a lot in the industry, in companies, in organizations. It's just a natural part of doing business. And misalignment can occur because teams are working on different metrics that all of a sudden start to clash into each other and cause friction. Maybe one team is depending on another for something, but the priorities are misaligned, so the other team's not gonna deliver in time for that team to do their work. And, these are just natural occurrences. And we have to be able to have the conversation when misalignment happens.
So, there's self-talk here too, for this type of conversation. The first thing is, you need to be able to walk in your colleagues' shoes. This is often gonna happen with peers, most likely, where you're gonna have a misalignment. And you need to be able to phrase the argument from their standpoint, not just from your own standpoint. And you also need to realize that it's not personal. While you may feel a great deal of frustration, and your team may feel a great deal of frustration, because you're unable to move this conversation forward, this is just a natural part of business. And it's not like this person is trying to sabotage you and your work, they're just trying to meet their metrics.
So the script goes in three parts. Basically, you're gonna state the misalignment openly, you're gonna empathize with your peer, and then maybe you're gonna seek to get some input. So it might go something like this. Here's a typical misalignment over technical direction. And I find that it usually helps to state their position first, to demonstrate your empathy.
So I might go to my colleague and say, "Hey, you've actually been optimizing on this project "for developer ergonomics, "and I've been optimizing for performance, "and these are different trade-offs, "and they're both really important, "but they've led us to make different recommendations, "and we seem to be at an impasse. "What can we do to try to get into alignment?" And then you can kind of wrap the conversation up with, "Hey, if we're unable to reach alignment, "maybe we can go together to the next level "to get more input on our decision." So that way you're kind of suggesting that it's okay to escalate and get input, together, if you need it.
So the next level is a type of difficult conversation that I don't think we have enough. We aren't really known for our humility in technology, especially here in the valley. And this is the apology. And, you are gonna make a lot of apologies when things go wrong in business, and otherwise. And, in case nobody's told you, you actually own accountability for everything your team does, in addition to everything that you do. So even if your team screws up, maybe they do something you're not even aware of, you're actually in charge of that. You have accountability for it. And so you're gonna get used, as you grow in leadership, you're gonna get used to making apologies a lot. One thing to realize is that if you are willing to apologize and do it quickly, it'll actually diffuse a lot of negative emotions that might be happening. That's the self-talk.
So what does the script look like? Well, you're gonna own it on behalf of your team, and you're gonna own the remediation for the problem. And then we'll talk about a power-up move here. So, something like this might happen. "Hey, we disabled those integration tests "because we thought they were flaky, "and now that caused a huge production issue, "which has really negatively affected our users. "What I'm gonna, "I'm really sorry about the impact to the business. "What I'm gonna do "to make sure that this doesn't happen again "is that when our team encounters flaky tests, "we're gonna fix them right away."
So, there is a power-up move here, and this is to actually ask for forgiveness. And this power-up is actually reserved for times when you've actually caused personal harm to someone in business. So, let's say you're running a team meeting, and a micro-aggression happens at the table, and you, as the leader, just sit there, kind of in stunned silence, and let it go by. And then later, you realize that actually, someone on your team has been hurt by this, and you've caused them harm by not doing anything. This is the type of thing where you can ask for forgiveness. So in that case, you're gonna own what you've done or not done, in that case, what you're gonna do better in the future, and you're gonna say, "Hey, I hope you'll forgive me. Will you forgive me?" And that can be incredibly powerful in remedying things that have gone wrong in relationships in business.
So now we're to feedback. And I think this is the one where everyone associates difficult conversations. This is where someone in your business up here, someone on your team has a behavioral thing that's holding them back and you'd like to give them feedback.
So the self-talk here is that, especially in the US, we are very tempted to do this thing, it's called the shit sandwich. It's basically where you put the feedback between two compliments. I'm happy to report that the Europeans do not suffer from this problem. They go directly to the negative feedback. But what happens when you do this is that it dilutes the message, and it leaves the person totally confused as to whether they were like, totally awesome, or need to fix something, right? And, when you're giving feedback, your whole goal is to help them be better at what they do. And so, you really wanna focus the conversation on that feedback that you'd like to give them that will help them improve.
And so there are three parts to this script. I actually learned these in my very first management course, and they have served me incredibly well. Basically, you're gonna note the behavior that's holding them back, you're gonna explain why that behavior is causing an important problem, and you're gonna ask them to reflect back the importance of that behavior. And then you're gonna let that person actually own the remediation to the problem.
So it might go something like this. "Hey, I've noticed that you're often off "by an order of magnitude on your estimates, "and, as we all are at one point in our careers. "But the latest time this happened, "it actually delayed our launch of the new app, "and we had to cancel all of our PR, "and it means that the company "has to maintain the old app longer. "Do you understand why this is so important "that we were off so dramatically?" And then, you let that person reflect back, and then you ask them, "What's your suggestion "for making sure that this doesn't happen in the future?" And I've found that if you let the person kind of reflect and own how they can make it better in the future, they're more likely to stick to a change in behavior, than if I suggest to them what I would do, right? It's an ownership thing.
So last up we have agonizing conversations. And these are conversations where you're gonna have to deliver news to someone that's going to negatively impact their life, even if it's just for a short time. And, I hope many of you have not had to do these kinds of conversations yet, but you're almost certainly to encounter them in a career, as a leader. And this is something like you're gonna lay someone off, you're gonna fire them, maybe there's gonna be a major reorg that's gonna completely change what they're working on, or their pay grade, or something crazy like that.
So, the big thing here, in terms of self-talk, is to really empathize. And I think most of us faced something like or another in our careers. If you haven't, congratulations. I hope things stay that way. But you probably also know someone who's been affected by one of these situations, and you can kind of feel those feelings that you had for someone close to you or that you had yourself before you have this talk.
And then the script is gonna go as follows. You're basically gonna acknowledge that the news that you have to share is gonna be something that they don't wanna hear, that's gonna be incredibly difficult. And then you're just gonna stop talking after you deliver the news. And you're just gonna let the person respond how they respond. And I think listening is very underrated as a conversation skill. But give space for the person to react too. Maybe they're gonna be silent, maybe they're gonna be angry, maybe they're gonna be sad. You don't know. And then, once they've had time to process, you're gonna offer to help, and you're gonna mean it.
So, I have a happy story coming from an agonizing conversation in my past. Basically, I had a big reorg going on, and I didn't know exactly how the reorg was gonna come out, but I knew that several of the folks on my team, that the roles that they had were not really gonna be the same anymore. And one person, in particular, had a role that just wasn't gonna exist in the new organization. And so, I had to deliver this news, and fortunately, we had the luxury of time, where I could deliver the news and offer to help, and actually extend that help over a period of weeks.
And, it turned out that in talking with the engineer, we felt that a change of ladder might be interesting. There might be another ladder where they could really apply their skills. And so, I was able to go to leaders in the organization, on that ladder, and say why I thought this engineer would be amazing in that role, and would they be willing to mentor the engineer? And so, when the whole reorg went down, that's the transition that took place. And I'm really happy to report that the engineer has actually achieved at least one promotion since switching ladders in that transition.
So these things can come out well in the end, if you offer to help, and you mean it. So I hope I've given you some tools to rescue Princess Toadstool and save the Mushroom Kingdom. Or maybe just to survive the different levels of difficult conversations. Thank you.
Thank you, Sarah. This one from anonymous. "Do you have any advice on how to get people "to express themselves about topics? "I have a report who does great work, "but the response to any question is, 'Whatever.'"
So, one of the things that I've suggested for people who aren't able to express themselves, and, you know a lot of us are introverted, as engineers, is to start writing. So, that was something I didn't mention in the asking for forgiveness. If you're not comfortable doing that face to face, sometimes you can do it in writing. And so, if I have folks on my team who feel sort of cornered by a question, and aren't able to sort of express themselves on the spot, I might suggest like, "Hey, why don't we start a document "where you can write down your different opinions, "and then we can share it with the team." And sometimes that helps people move into expressing their opinions when they can't do it verbally for whatever reason.
Wonderful, thank you. Another question from anonymous. "How do you talk to somebody who's a step four, "who doesn't admit to any faults, passes blame to others, "or does not admit that there is any performance problem?"
Yeah, this might be a power-up. So, I was actually doing this talk for a friend last night, and she asked me the same question. I think it's basically, repeat yourself at least three times first. So if the person hasn't heard you in the first conversation, make sure to have that same conversation at least three times, 'cause sometimes repetition will stick. And then if it doesn't, sometimes it can help to bring other opinions to the table so that that person knows that you're not alone in that opinion, but maybe there are others who have the same feedback to share with them. So more of like an intervention style of feedback. That's what I would recommend starting with.