· 25 mins · Management Skills

People Leading People: Michael Lopp (AKA Rands in Repose), VP Engineering at Slack on psychological safety

Avatar of Shannon Maloney Shannon Maloney

For our fifth and final episode of Season 2 of People Leading People we’re wrapping up with Michael Lopp, AKA Rands in Repose, VP of Engineering at Slack. We’re learning how he creates a psychologically safe environment for his team.

Listen to the full episode on Apple Podcasts or your favorite podcast network, and if you’re inspired by what you hear, give us ⭐️⭐️⭐️⭐️⭐️. Continue reading for key takeaways, the full episode transcript and more ways to listen to the podcast.

Tell-tale signs you’re not fostering a safe work environment

“It’s just, there’s a sort of a breathing of communication inside of an organism. And when you’re, like the breathing gets weird, you’re like what’s going on here? And that’s, to me, is and it may not be trust and safety in my team, but if there’s something going on there that’s preventing that sort of like healthy flow of knowledge and communication going on.

So, maybe it could be something else, it could be like a bad actor in the organism somewhere, but it’s also usually a sign of like, someone doesn’t feel safe saying something. Someone feels like they’re are going to be repercussions because the products late or blah blah, whatever the excuse is. But it’s always it’s always sort of a surprise and I when I discover something where the soup tastes strange.”

What’s the one thing you do each day that helps you be a successful leader?

“Everyday that I work I have at least 60 minutes in the morning undisturbed to start the day. So it’s, you can’t, you can’t bug me. I get to look at my calendar. I get to prepare for whatever. I get to write a little piece. I get to drink my coffee. The moment my feet hit the ground in the building, it’s go go go go go. And there’s things going, there’s the planned schedule, there’s the things that are going to blow up, guaranteed. So having that 60 minutes at the beginning of the day is just, it’s literally gold to me. It’s literally gold. It’s reading this deck for that meeting that’s three hours later.”


People Leading People: Season 2, episode 5 | Michael Lopp (transcript)

Jillian Gora:  People leading people is a podcast about the stuff that pops up when you lead people at work. Join Brennan McEachran, CEO of SoapBox and Jillian Gora, Customer Experience at soapbox, as we interview the people leaders that inspire us most. 

When your team feels psychologically safe, they’re more likely to share open and honest feedback with you and others at the company.

But as a manager psychological safety can be hard to foster. Michael Lopp will share what he’s learned from his time at Apple, Pinterest and Slack about sharing hard feedback with your team while maintaining an environment where people feel safe enough to say, “No.” Welcome Michael.

Michael Lopp: Great to be here. Thanks for having me. 

Brennan McEachran: Thank you and better known online as Rands. 

Michael Lopp: Rands in Repose.

Brennan McEachran: Rands in Repose. Really appreciate you taking the time. We spent some time together, I don’t know a while ago, and we got into a really interesting conversation about safety. Where, you know, we were looking at if there was a way to measure it. If there is a way to measure, you know, how managers were fostering that, would we be able to kind of predict if managers were doing better than others?

And so, I wanted to kind of resurrect that a little bit and see if we can go into actionable insights for the everyday listener. But before we do that, I’d love for you to introduce yourself to the listeners. And for those who don’t know who Rands in Repose is, the, the quick synopsis of your background.

Michael Lopp: Yeah, so I’m the I’m the VP of Product Engineering at Slack. I’ve been there for almost three years now. And before that, I worked at, was the Head of Engineering over at Pinterest. I was at Palantir and I spent about eight and a half years at Apple around the Apple Store as my last gig there many years ago. During all that time, I realized how hard this leadership thing is, so I started looking for good resources online and books. They were all awful. So I started banging on keyboards and people liked when I started banging on keyboards and they were like, cool keep banging on keyboards. So that turned into a blog and that turned into a couple of books. The one probably most people know is called Managing Humans and I continue to write because I can’t stop.

Brennan McEachran: You get addicted somewhere along the way.

Michael Lopp: Exactly.

Brennan McEachran: We actually, we’re reading your book right now and in the company-wide book club. 

Michael Lopp: Oh nice!

Brennan McEachran: Super fun. 

Michael Lopp: How’s it going? Is it Okay? 

Jillian Gora: Yeah, it’s great so far.

Brennan McEachran: So far, yeah, we’ve got to get the whole company to the end of part 1 before we break for the holiday. But otherwise, yeah pretty good. 

Michael Lopp: Well, thanks for reading it. 

Brennan McEachran: Thank you for writing it. Thank you for being here. What I, what I wanted to kind of jump down was, you know, we talked about a few things. One of them was safety and why you thought it was an important thing to foster within a team. Do you have any, you know, off the top of your head insights on why that that popped up as, you know, your, your first instinct. 

Michael Lopp: Yeah, it’s I mean from a distance, I think it’s really obvious in my human perspective like you want people to feel safe and they when they’re at work, they’re like, they’re not worried about, you know, low things, low on the Maslow’s hierarchy.

They’re just, they want to like, you want them to do all they want, to feel like they can get all their work done and there’s not like this impending like impending doom and that’s just like the obvious. I think that’s the obvious way, but it’s actually really, it’s actually really a competitive advantage because folks who feel safe, like they tell you the hard thing.

They say that thing that is, that is complicated or the thing that they’re worried about telling you because you’re the boss, this sort of thing. And that just, that signal moving around whether it’s high signal or a low signal is just better than like, no one’s telling me these things and it’s like whoa, what happened there? Like where did that come from? So it’s just I mean from a very basic perspective, It’s just encouraging of like signal moving around the organism as opposed to you know, it kind of being condensed in this one team that’s worried about this other manager or this other team where but that blah blah, it’s too big. Everything just turns into politics and all this other, other crap. So that’s the basic thing is just getting communication flowing around whether it’s great news or bad news 

Brennan McEachran: And people feeling safe enough to share that with you. 

Michael Lopp: Yeah exactly 

Brennan McEachran: And without fear. 

Jillian Gora: What’s a tell-tale sign, if you’re managing managers, what’s a tell-tale sign for you that there’s a lack of psychological safety on a team or on someone’s team that you’re managing?

Michael Lopp: I had this really horrible boss. Who will go unnamed and he said this thing to me, he was like “No surprises Lopp.” And it was, it was horrible advice because but I turned it around in my head. He was just saying like, make me look good. Like I don’t want to look bad because something’s going on in engineering and I don’t know about it.

So I don’t like him, but let’s turn that advice around into sort of being like what is the leading indicator that you’re asking about which is, when you kind of are just going through the day and you just always like the signals just my day, my job is soup tasting. I’m just tasting soup all day. What’s going on with this soup? What’s going on with this soup?

When I know something’s, some trust or some safeties weird is when some signal gets to me and I’m like what? Like, what, what is this soup? Like, where did this come from? Right, so it’s that sort of thing and it’s not like I need to know everything.

It’s just, there’s a sort of a breathing of communication inside of an organism. And when you’re, like the breathing gets weird, you’re like what’s going on here? And that’s, to me, is and it may not be trust and safety in my team, but if there’s something going on there that’s preventing that sort of like healthy flow of of knowledge and communication going on.

So, maybe it could be something else, it could be like a bad actor in the organism somewhere, but it’s also usually a sign of like, someone doesn’t feel safe saying something. Someone feels like they’re are going to be repercussions because the products late or blah blah, whatever the excuse is. But it’s always it’s always sort of a surprise and I when I discover something where the soup tastes strange.

Jillian Gora: Yeah and you’ve written about the power of saying no and having your employees feel like they can come to you and say no. What are some concrete ways that maybe a less seasoned manager can build enough trust with their team or create that psychological safety to make them feel like they actually can say no?

Michael Lopp: It’s, when you’re saying no, it’s not just a power move, right? It’s not like no, we’re not doing that. What the real, when I when I’m talking with someone who’s kind of a pleaser the person who really wants empathetic, and kind and like, “Of course, whatever. How can I help you?” This thing that I have no time to do, I will sign up to do that. I’m going to not do well at it because I’m just a nice person trying to help you out. I should have said no, I should have said no, right? Because I don’t have time and you’re a great person, I really want to help but I just, I have to say no.

Why do I say no or how do I say no? Here’s the thing. You’ve got to have something before that, which is your vision or your strategy. These are the things I’m working on and I’m really really clear about those things and at Slack, like I tell you what they are is like five things right now and it’s five big huge things.

And I know what they are and I can tell you the story about why they’re important and when you come to me and say, “Hey blah, blah, blah. This thing it’s gonna be a lot of work.” I go in my head I’m like, do you really believe these five things are the most important thing? And the answer is yes, I do. Well maybe I don’t. Maybe the thing you’re asking is more important than that, but that is how I start with the no, is being really clear about what are my objectives, What are the things I’m trying to do and when I when I say no to you, I say no. I don’t say “No, I’m the boss.” I say, “No and here’s why. These five things and the thing you asked me to do is gonna take a week. These five things are far more important, do we agree? And if not, let’s have that debate.”

Right? So it’s not just no power-trippy. It’s no this is less, I believe, using my judgment that this is less important than these other things. And it’s still hard. You still want to be nice and whatnot. But when it’s backed by the vision and the strategy, it’s a lot easier. 

Brennan McEachran: Do you find it works the other way as well? So if you have your priorities you might have, like an idea for a particular tactic to get some of those things done. Someone on your team, also a people pleaser, might not necessarily agree with the tactics you just threw out but as a people pleaser, and maybe that’s not like the always most common role in the team, is there anything you do that lets them say like, “No, no Michael, like chill out. You’re wrong there.” Anything you do that makes them feel safe to say that to you?

Michael Lopp: I feel like it’s the same thing as when, like someone tries to push some process on you, right? You’re like, “Hey, by the way, we’re big company XYZ,” and you go “Hey, I want to get this thing done” and someone says, “Well, here’s the process.” And, what I tell my team, have told my teams in the past, is if someone can’t explain to you why you don’t do the process that way, why we do the process that way, you don’t have to do it.  What is it, how is it similar to what you’re saying?

It’s, whether it’s no, or whether it’s I disagree. It’s not that it’s no or I disagree. It’s why. Like what is, what is behind this? That’s the actual interesting part, not that I’m saying no that we’re having that conversation about priority or tactics or whatever that certain thing is. And it’s my job just like it’s your job. The contract is we must use respect, charisma, whatever it is to actually, you know, convince each other whatever the heck that is. And that’s the piece that actually, that’s the piece you’re actually working on there. And oh by the way, you do this a lot of times, you have these arguments these discussions. You want to know where trust and safety come from? It’s us going through that thing and coming out the other side and being like, “Well I disagree with you, but I understand where you’re coming from.” So look, that’s good. One of my favorite people at Slack right now, we argue 70% of the time. Like it’s really almost like, I guarantee like, argue like errrrrrr and then we’re done and we’re like, “Cool. See you tomorrow. That was fun.” 

Brennan McEachran: Pick this back up on Monday.

Michael Lopp: No, and like if you were watching us you’re like, “These people don’t like each other.” This is literally one of my favorite people at Slack and we argue all the time. 

Brennan McEachran: But you get clarity out of it. You get clarity out of, out of those arguments, out of those different viewpoints.

Michael Lopp: It’s, but it’s hard. I mean it’s work. The first three times you do that, you’re like, “Is this person going to like me after this? Because I’m like, I’m like we are at it right now.” But you do it, you know, 40 times, you’re like, “No. Cool. This is how we work.”

Brennan McEachran: Is that, is that person, not to out them, do they report to you? Or are they a peer?

Michael Lopp: No, they’re in a different org. 

Brennan McEachran: I was kind of thinking that they were, they were a member of your team. How do you, you know, achieve and maybe you, maybe your goal isn’t to, but to jump back to where you started with, you know, that, that terrible not-to-be-named boss who said, “Michael, no surprises.” How do you achieve the same result without creating that environment on your team? If like, someone doesn’t want to invite you into the process to have that debate to have that conversation?

Michael Lopp: It’s, this is why the third book’s called Small Things Done Well, by the way. The answer is, you kind of behave how you’d like to be treated 50 times in a row. You do it over and over and over again, and I’m sure you and I have talked about this before. It’s like, one-on-ones I almost always finish with, “Do you have any feedback for me?” And new folks who start working for me, never in the history of ever have they ever had any feedback because they’re like ahhh I don’t know who you are. And finally two months later, after I keep on asking every single week they go, “He’s not going to stop asking.” So they say something lightweight like…

Brennan McEachran: They have to or you’re gonna get them in trouble at some point, like come on.

Michael Lopp: And they say something and I’m like, “Cool!” And like that, that’s like the first moment on that sort of entering the safety zone where people, you know, where it starts to feel a little bit more like not the boss, and the manager’s kind of flattening things out. 

Brennan McEachran: So I think that’s a fun way. There’s a really senior leader who talked to me at one point and said like, you know, “How do you react when someone gives you,” and she was doing this, she was saying, You know, “Do you have feedback for me?” and “I’m open to feedback, do have feedback for me?” And the first piece of feedback she got on this new team, she felt it was like a personal attack. You know, she was always late for things right and they didn’t have empathy for her and she asked me, “How do I, how do I react to that? What do I do?” And, but you alluded to it a little bit of saying like, oh cool like you’re excited if someone you know, a new hire hits you right off the bat with something that’s a gut punch. What do you do? 

Michael Lopp: Well, it’s interesting because your brain really wants to mess with you on that. You can tell, you can tell when someone’s about to give you hard feedback because they’re like, “Hey Blah, I have some feedback for you.” And it’s like the hair in the back of your neck stands up and you know, and by the way you know, and I’ve received a ton of this in my career, you know, this is going to be something which is going to be a gut punch. So the goal and this, it takes training and practice.

You can tell it’s coming. It’s usually never a surprise because they’re nervous or they say those words or they’re just holding themselves in a way, You’re like, oh shit. I just, I just, I just sit there and I remind myself first off, I see it coming. I just put my feet on the ground. I clench my hands together or on my knees like I’m doing it right now. And I just sit there and remember this is going to be, your reaction is totally normal because you’re literally, your brain is about, is feeling like it’s about to get punched. And what do you do? You like freeze up and get ready to be punched, right?

Brennan McEachran: And defend yourself.

Michael Lopp: But that’s not what’s going to happen. I mean, it’s going to feel that way. You just gotta remember feedback, however, good or bad, or misinformed or like spot-on, even though it’s coming in hot it’s good, it’s a gift. There’s a signal there, and all I’m doing when I’m walking up ready for this, so I’m like, “Okay. What’s the signal, like there’s something here, even if it’s a complete rumor packaged as a lie that’s designed to make me mad.” It’s like, “Okay, someone’s really mad at me,” or like, “that’s really interesting that that rumor exists.” Like being sort of vulcan objective about it and not letting that instinct to like punch back be the thing. And it’s, I make it sound easy because I say these words but it’s really, I mean, I just have to sit there and go like, “Okay I’m breathing here, we’re just gonna, okay, where’s the signal?” Yeah, they’re not, I mean don’t take it personally. It’s just because, even if it’s personal, it’s not personal to me, I’m just looking for the signal. Like, how to, what, what am I going to learn from this?

Brennan McEachran: Get more clarity. Don’t defend. Ask more questions and listen.

Jillian Gora: And like, yeah, part of giving feedback I think too from an employee’s perspective is they give the feedback and then you know that was hard for them to do also and they expect to see some sort of change or reaction in the days to come sort of like leading coming out of that session. How do you kind of work around that because sort of again speaking of like signal and the noise, like just because somebody is sharing feedback with you doesn’t necessarily mean that they have the full picture and that it’s something that you’re going to go and change how you’re doing something because of it. So, how do you, how do you maneuver that? How do you deal with situations where you’re like, I’m not really going to change this?

Michael Lopp: Yeah, there’s two steps to that. Number one is, let’s just make it kind of really hard feedback like, like one that’s like, got a motion to it or whatever the heck’s going on there. Number one is making sure what they’re saying is what you’re hearing. This is the power move of the day. Someone comes in and they got the same “I want to punch you, blah blah blah.” Okay, I hear it. Got it. What I hear you saying is this: blah blah blah blah. And like 50% of the time, 50% of the time, like cut the coin, they’re like, “No what I meant was this..” and by the way, it was like two words different, but it was important to them that those two words were there.

So that’s number one. We’re not even into like fixing whatever the problem is. The number one is: Do we agree? Are we cool here? 

Jillian Gora: Are we understanding the same thing here? 

Michael Lopp: That’s right. So like, “but what I heard you say is this.” And I always do that, especially when I know that the stakes are high. And number two is once we figure out if it’s appropriate. Sometimes it’s just the job to listen. Sometimes that’s the job. But if it’s like, okay, what is the thing I need to do here? I use very deliberate language. I use very deliberate language. Okay, we agreed this is it. I’m committed to blah. I’m committed to blah and that’s my contract. That’s the thing that I’m saying and I’m sitting there taking it, but I’m agreeing I’m saying to you this is the thing that I’m going to go and commit to do. And that’s, again, this is like hard feedback coming in. It diffuses it. They feel heard. They understand and they understand the path forward. And of course, the most obvious advice is meet the commitment.  Do the thing that you said you’re gonna do which should be obvious, but it’s really the sort of, to me, a lot of it is really traversing that moment that the conversation’s occurring that’s really the important part.

Brennan McEachran: If you’re to say the common commitments that you’re going to pull out of your utility belt. And in that scenario…

Jillian Gora: Your commitment hat. 

Brennan McEachran: Yeah your commitment hat. Are they you know, I commit to fixing it? Obviously not.  Are they, what are you offering them back in the moment? You know when you’re a little bit caught off guard.

Michael Lopp: Well, I mean it really it depends on how the feedback is. Because, really like I just said a second ago, sometimes it’s just, they want to say it. 

Brennan McEachran: Yeah.

Michael Lopp: Because they’re mad. Like really there’s nothing to do other than to be like, “Hey, I feel like the team is super political. Here’s the thing that’s going on here blah blah blah.” And I’m sorry it’s a plain boiled wall. It’s like, whatever they’re saying is a big deal, but like very often, it’s just like, be heard, you know. I want to be heard. So that’s, that’s number one. Number two is like, there’s another piece which is sometimes it’s not the time to actually, that moment where you’re like, it’s kind of tense, it’s not the moment to figure it out. Like, okay, it’s Friday. Let’s, let’s meet on Monday and let’s see what happens after 48 hours of sort of stewing in this thing, and doing that later. So I mean, there’s like, it really so depends on the person, your relationship with them and what the feedback is.

Brennan McEachran: All right. So there’s a couple common things I heard. One is like every single one on one, every week sit down and say “do you have, you must have feedback for me? Please Give me feedback, do you have feedback.” They’re gonna punch you. It’s going to happen. Someone is going to swing for you and come back to them with what I’m hearing is. 

Michael Lopp: Yeah. 

Brennan McEachran: Yeah what I just heard was, and then think about a commitment, right? Come back to them and say, “Hey, here’s a couple things I’m going to actually commit back to you.” And that doesn’t have to be the same day, doesn’t have to be the same meeting. You can I guess, I guess you commit to saying I, you know, I’ve heard you. I will come back with something, say on Monday, right? Let you know you’re heard here.

Michael Lopp: Yeah, I mean another one is like, this is really complicated, I need to talk to some other people. Let me gather some more signals and I’ll circle back with you. 

Jillian Gora: Cool. Okay. Well, we’ve reached the point in our in our show where it’s time for the secret question. Very exciting. So if you could please choose a number between 1 and 3.

Michael Lopp: Three? I want to know all three questions. Let’s go with 3. That’s my favorite number. 

Jillian Gora: All right. Hey, that’s good. My favorite number is 5. Fun fact.

Brennan McEachran: Fun fact of the day

Jillian Gora: Fun fact of the day. Okay. So what’s the one thing you do each day that helps you be a successful leader?

Michael Lopp: Ohh. Everyday that I work I have at least 60 Minutes in the morning undisturbed to start the day. So it’s, you can’t, you can’t bug me. I get to look at my calendar. I get to prepare for whatever. I get to write a little piece. I get to drink my coffee. The moment my feet hit the ground in the building, it’s go go go go go. And there’s things going, there’s the planned schedule, there’s the things that are going to blow up, guaranteed. So having that 60 minutes at the beginning of the day is just, it’s literally gold to me. It’s literally gold. It’s reading this deck for that meeting that’s three hours later. 

Brennan McEachran: Is that like 8 to 9 a.m. Is that not, is it the same time every day or is it…

Michael Lopp: It is. Yeah. As long as I’m not traveling it’s exactly, it’s exactly the same time. My team now knows about this and they know that my response time in slack is legendary. If as long as it’s a short thing. So I get a lot, people try to figure out like that time is like sacred they’re  like, “Hey, what about this?” And I’m like, “Yes, blah.” So I get like, my slacks at a time certain spike, which is fine as long as they’re not like, trying to like, pull me into these, like huge things. But yeah, 60 minutes a day no matter what.

Brennan McEachran: First thing.

Jillian Gora: And are you doing that kind of like off-site from home? Because you mentioned when your feet get into the building. So is that something that you’re doing before you actually arrive to work?  

Michael Lopp:  Exactly. Exactly. 

Brennan McEachran: Wow.

Jillian Gora: Cool. 

Brennan McEachran: Very cool. 

Jillian Gora: Great. Well set tous mes amies. We are done.

Brennan McEachran: Awesome. Thank you for the time. I really appreciate the, the advice. 

Jillian Gora: Yeah, it was a pleasure to talk to you.

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