🚀 Breathe.



“If you don't pay attention to the emotional health of the individuals in your team, you're not going to get the outcomes that you want, you're not going to get good productive work, new ideas, or the trust you need for people to work closely together”.

In this episode

In episode 28, Sarah Milstein reflects on some “bad boss behaviour” she has witnessed in her career… and shares how behaviour affects output.

Sarah is the Senior Director of Engineering at Mailchimp, where she leads and coaches product teams.

In this interview, Sarah talks about why diagnosing the conversations we have with our team matters… and why learning to listen and understand is often better than only reacting and responding. 

Tune in to hear all about Sarah’s leadership journey and the lessons learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Being the 21st user on Twitter


Let’s talk about bad bosses


Measuring teams in remote settings


Diagnosing conversations with your team


When to give advice, and when to just listen


Why distributed teams have higher trust


Common mistakes made when working remotely


Connecting with your team, purposefully


Co-working Zoom calls 


We can’t punish our teams for failing


The thought clarifying process of writing


The power of peer mentorship


Episode Transcript

Aydin Mirzaee 2:35

Sarah, welcome to the show.

Sarah Milstein  2:37  

Thank you. It’s good to be here.

Aydin Mirzaee  2:39  

Sarah, very excited to have you on the show. There is a lot of stuff that we want to talk about. But one of the things that I thought was really interesting, and just doing some research about your background, was the fact that you were the 21st user on Twitter. How did that happen?

Sarah Milstein  2:54  

Yeah, my partner was working for the company that started Twitter, it was a podcasting company called audio. And during a down week, they had like a hack week for their engineers. He was the VP. And a couple of the folks there started what became Twitter. And the company ultimately wound up pivoting completely from the podcasting app to Twitter. And I remember the day he came home and said, You’re not, you need to try this thing. And you’re not going to believe it. It’s super cool. And they’ve been using it internally at that point for a week or two. And I tried it and at that point in time, I’d seen so many different apps, and most of them seem to me like things nobody would really use. And I tried it and thought, Oh my gosh, millions of people are going to use this. And they’re going to use it in ways we can’t even imagine right now. And it is the only time I’ve ever accurately predicted anything that would happen in tech.

Aydin Mirzaee  3:51  

That’s awesome. That’s super cool. That’s, that’s quite the achievement. And what is your Twitter handle?

Sarah Milstein  3:57  

It’s Sarah m.

Aydin Mirzaee  3:57  

Sarah M, they didn’t give you Sarah. Like I feel like that’s a fair thing you could have asked for.

Sarah Milstein  4:03  

I had the choice. I know. It’s so funny. I had the choice. I could have asked for that. Evan Williams, who was the founder of audio. His wife’s name was Sarah. And I thought well, at the time it was just when we joined it was all just friends and people who knew each other I thought oh, that’s a little confusing between me and Sarah, although her last name starts with an M so I’m not sure why I thought this was a better idea. In retrospect, I think it’s good because I would get a ton of messages that are not intended for me if I were just Sarah.

Aydin Mirzaee  4:35  

Yeah, no very wise choice indeed. So Sarah, you know talking about you know, Twitter, you obviously you wrote the Twitter book. And you’ve had a very kind of diverse background because you’re typically when people are engineering leaders, you know, they kind of stick to the engineering discipline today your senior engineer, engineering director of MailChimp which is an awesome company, but you know Before that you were head of sales and marketing at 18. f, and you even founded a successful media company before that. So a very, very diverse experience, I have to ask you, if you were to kind of rewind and take a look back at your history, is your most memorable or favorable boss that that comes to mind that you’ve had that you learned from?

Sarah Milstein  5:22  

Yeah, so my real answer on this is that I don’t like having bosses, I have not in my career had almost any good managers at all, and very few. So it’s part of the reason that I focus on management, I tried to turn those experiences into lessons for me that I can use to become a good manager for other people.

Aydin Mirzaee  5:44  

So let’s talk about bad bosses. And like, was there someone that stood out? Ever, you don’t have to mention by name, but by character, perhaps? And why were they not great?

Sarah Milstein  5:55  

Well, certainly, I have had a number of people who were very focused on yelling as a way to get things done, which usually has the opposite effect, or people who were focused on, you know, the phrases on output rather than outcome. So cared about whether you were sitting in the seat rather than whether you were meeting your tasks, people who were not attuned to interpersonal dynamics, and, you know, early in my career, certainly a handful of folks who were abusive or bullying, that that’s become less true as I become more senior, which is a whole other conversation, really like the range of bad boss behavior?

Aydin Mirzaee  6:41  

Yeah. So it sounds like I mean, it’s very interesting, because I think a lot of what you said is relevant. And I guess it’s potentially less possible to be a bad boss, maybe if you can’t really watch people sitting in their seats, perhaps since everybody is now or a lot of people are now working from home. 

Sarah Milstein  7:00  

Yeah, I think that’s actually a particularly hard transition for managers who are used to being able to measure people in some way. And I say, measure sort of, in scare quotes, measure people in some way by seeing, are they at work? Did they show up whatever we consider on time to be are they taking, you know, the right number of breaks or too many breaks? I think a lot of people even unintentionally use those sorts of non metrics to figure out whether their folks are actually working. I think one thing that happens in a world where everybody’s remote is the people who do measure their reports on that kind of physical presence, even if they’re doing it unknowingly have a hard time adjusting to a remote setup, and start to want people to do things like be available on slack at all times, or have some very clear times that they’re checking in, like, as if they were stamping a timecard kind of thing. And I think that actually, you know, that’s to the detriment of those folks. And they often feel without any evidence that things aren’t getting done just because they can’t see the people. So I do think for some people, this is for some managers, this is a really hard transition, and requires a pretty fundamental refocusing of how they understand their role.

Aydin Mirzaee  8:28  

Yeah, yeah, no, that makes a lot of sense. It’s interesting that like, those bad behaviors can actually still follow you. So if you watch people in their seats, you still have the ability, I didn’t actually think that you could measure when you respond on Slack, and so on and so forth. And those bad behaviors can continue. They shouldn’t. But there is the opportunity there. So I guess so you’ve obviously been, you know, it sounds like again, like as a founder, and, you know, early employee in your career, and you just mentioned, you haven’t had a lot of, you know, bosses and you tend to to avoid them at what was the first time that you started leading a team? And what were kind of some of the early mistakes that you tended to make?

Sarah Milstein  9:06  

Yeah, so the first time I led a team was early in my career, but it wasn’t until a little later that I started to be much more intentional about it. So I tend to think about the time when I worked at O’Reilly Media, I had several different roles. And the first role was managing a group of editors who were developing book series to make it much bigger and have a much bigger impact. And I, the team, was distributed before there was a video call. So we made a lot of phone calls. And one of the things that happened is that somebody on the team worked often with freelancers, and she tended not to know how to manage the freelancers and so she would come to me and talk about her frustration with it. And I would turn around and try to solve that. So sometimes very directly, like, I remember once she was talking about a freelancer who was frustrating her with like too many questions, and I called the freelancer and said, You have to stop asking so many questions. Now, the person who was reporting to me was horrified. It was undermining her relationship, it was not the outcome she wanted. Even if it stopped the questions, it was not what she was hoping to get from that conversation with me. And I remember that so clearly, because she was first of all able to tell me that which was great into her credit, but it really made me understand that my role as a manager is not just to take in what somebody says and turn around and solve the problem, regardless of the situation, it’s to really understand if the person coming to me is, first of all asking for that kind of help if they’re venting. And if I can coach them to solve the problem. And certainly inserting myself into a situation like that was not the right answer. And I remember this story in particular, because it was one of the first examples I had of self awareness that I couldn’t just keep acting the way I did normally, and be effective as a manager, or, as a team leader, like my team couldn’t get things done, if that’s how I behave.

Aydin Mirzaee  11:18  

Yeah, no, that’s super interesting. So say, someone comes to you and starts to, I guess, talk about a problem or a situation. So what is the playbook? Like? What do you start doing? When you hear that first?

Sarah Milstein  11:30  

Yeah, well, I have to say, I still think this is hard. I think it’s hard for almost everybody. the first thing to do is usually to ask more questions to understand the situation better. And then start asking questions about what the person who’s talking to you once out of this conversation and out of the situation that you can help figure out to they need coaching, can you coach them through it, are they looking for more direct intervention, which you may or may not choose to do, but really diagnosing the conversation you’re having, in addition to the situation, that’s, that’s more what I love to do now. And then holding back from just giving advice, that’s one of the hardest things I think where everybody falls down is, you know, as a manager, you’ve often been through the situation that the person is talking about. And so it’s very tempting to just give advice or tell them what to do. Frequently, though, that’s not the path for them to grow, or it’s not even really what they’re asking for they’re looking for, they might be looking to vent, they might be looking to bounce their ideas off of you rather than get your ideas. They may need some help thinking through a problem. But none of that is advice and advice can really cut down the more productive conversations that they may be hoping to have.

Aydin Mirzaee  12:47  

Yeah, that’s really interesting. I mean, asking a lot of questions, makes sense. But I really like what you said, which is let’s diagnose this conversation in the sense of like, what are you looking to get here? or How can I best help you? And that just sort of like meta analysis and tagging of the conversation, I think is pretty powerful.

Sarah Milstein  13:06  

Yeah, for sure. And hard. As I say, you have to keep reminding myself to do that. So that I don’t fall into the trap of let’s just give advice, because it seems obvious how to solve this problem.

Aydin Mirzaee  13:17  

Yeah. And it’s very right, like what you said about, you know, as a manager, I mean, chances are that you actually may have been in that situation before. So you might have the answer, it might even be the right answer. And so there’s, you know, you could either get to it very quickly, or you could take the very long, long path. So, I guess my question is, what is your advice on this? Is it ever not true? So, for example, I know that you’ve been in a lot of startups, and, you know, there’s not a lot of resources, there’s often you’re you’re racing against time to beat up the competition, and you know, all this fun stuff. Is there? Is there a time where, as a manager, you can be like, no, go, this is the answer, and move quickly, or should you always be the wise advisor?

Sarah Milstein  14:02  

Yeah, that’s a good question. I would say I think about that two ways. First of all, the more junior somebody is, the more likely the balance of advice is a little heavier, because they don’t have the view yet, or the tools to be able to see the picture or some of the options. So in any situation, startup or otherwise, if they’re more junior, I’m probably waiting a little little more toward advice, and a little bit less on the like, well, you already know the answer to this kind of thing. I will say if it’s if it’s a really urgent situation, which as a manager, an important thing to do is to diagnose that pretty honestly, a lot of times things feel more urgent or you can feel important by making things urgent, but being very honest about whether something can move a little more slowly. When you’ve determined that it’s absolutely critical that something moves quickly. And if you’re going to give the advice you can then go back later and have a bigger conversation about it. How the person could diagnose those things themselves in the future, and how you can talk about them together in the future, so that they can use you more as a sounding board and less for input on direction to take.

Aydin Mirzaee  15:13  

Yeah, no, I think that’s, that’s super wise. I like that. And, you know, speaking of, you know, a lot of this is similar, like managers play relationships, advice and things like that. And even in the beginning, you talked about one of the behaviors, which is not good, is yelling, and you’ve experienced a lot of yelling, in other circumstances. And I think that yelling oftentimes is potentially like a symptom of when you have a team that doesn’t have a lot of trust. And so you just feel like you have to get things done through force. And when it comes to trust, you have this really interesting quote, you’re quite a prolific writer, I mean, I, we’re gonna link to your website, and a lot of the articles you have, but one of the things that you say is distributed teams often have higher trust. And this worked better than CO located teams. That’s a pretty bold statement. Tell us more about that.

Sarah Milstein  16:05  

Yeah, so I had an interesting experience. Earlier this year, I, as you noted, I worked for MailChimp, which until March was largely an in person company, we had the companies headquartered in Atlanta, and I run the satellite office in Brooklyn, there a couple of other satellite offices and a handful, there were a handful of remote people. And up until that time, there was a big emphasis on working in the offices. And my career has mostly been working on distributed teams. So I was a little surprised by that and heard myself saying to a colleague some months ago, that I liked working on distributed teams more because they tended to have higher trust. And then I thought, I wonder why I think that it’s definitely been my experience. But I hadn’t even fully been aware that that was what I thought until I heard those words come out of my mouth. And so I started to do a little research about why I might have found that to be the case. And I think there are a few things that contribute to that situation. One of which is simply that people who are drawn to teams that are inherently remote, so right now everybody’s remote. So it’s a little bit of a different situation than when I first started investigating this. But teams that are set up to be where you’re going to not work in person with your folks all the time, I think tend to draw people who have a higher propensity for trust. So there’s some research that shows that people just have some innate propensity for trust or a propensity to not to mistrust people, but to need to build up a reserve of trust before they really see the need to observe you doing things that will make you make them trust you. Versus people have propensity for trust, start at high trust, and you can do things that would undermine the trust. And I think that remote teams tend to draw the folks with a higher propensity for trust. So you kind of show up in your zoom meetings, with a little bit of reserve before anything’s even happened. I think that’s actually quite meaningful, and different from companies where the assumption is that I can only trust you If I see you doing things. And that’s not to judge folks who have a different propensity for trust. But I think it’s a different set. There’s also many software companies in particular, and I think startups especially have the dynamics of something called swift trust was identified about 25 years ago by a group of psychologists looking at workplaces, where people have very distinct roles and come together on an ad hoc basis to create an identified product, and then they disband and do something else. The canonical example is movie sets. But software teams tend to operate like this a lot, and especially in startups, where there’s a lot of change and transition all the time. And you’re re forming and regrouping and one of those conditions there is that you care about your own work, and you’re collaborating with other people who have other kinds of expertise. And that translates really well into remote work, and generates a certain kind of trust as well, because you’re not stepping on each other’s toes, and overlapping. So those are some of the things I started to look at that suggested that remote teams might actually be more productive and higher trust than in person teams.

Aydin Mirzaee  19:24  

That’s very interesting. So he called it swift trust. And I guess it makes sense. You’re on a movie scene. stuff needs to happen. You don’t have time almost not to trust each other. Yeah, yeah. So it’s very interesting. So I guess like the, you know, the question becomes the people who tend to work remote, I think it makes sense what you’re saying which is like they would have had to have a propensity to trust more because otherwise they would have, you know, not operated in that sense or when you’re a manager and you’re looking to hire and you’re okay with hiring remote. Like maybe you have that propensity. Do you think that now that largely a lot of companies have been almost forced to be remote that they would have had To develop this swift trust,

Sarah Milstein  20:02  

Well, certainly some have, what the research at this point shows is that a huge percentage of people would prefer to be able to be remote much more often than they were previously. Like, people want to come into the office, one or two days a week or a week, a month or something like that, rather than every day. But that’s a different question of whether managers are feeling that they can dress people or teammates feel that they trust people. What I do think has happened is people have recognized that you can be productive in a distributed setting that probably trust is like a lagging indicator their first people could see you could be productive. And so now they recognize Okay, I can trust folks when I can’t see them a little bit more. I think it takes some intentional nurturing of that as well. It’s not just like, Oh, I’ve recognized that it’s okay. I think it takes some work to be able to keep maintaining.

Aydin Mirzaee  20:58  

Hey there before we get to the next part of the interview, quick interjection to tell you about one of the internet’s best kept secrets, the manager TLDR newsletter. So every two weeks, we read the best content out there, the greatest articles, the advice, the case studies, whatever the latest and greatest is, we summarize it, and we send it to your inbox, we know you don’t have the time to read everything. But because we’re doing the work will summarize it and send it to your inbox once every two weeks. And the best news, it’s completely free. So go on over to fellow dot app slash newsletter, and sign up today. And with that said, let’s go back to the interview. Other things that you talked about in the remote context are also things you’ve talked about in the past. So what is a drama situation in remote companies?

Sarah Milstein  21:50  

Yeah, this is so interesting. I remember I mentioned before, I used to work for O’Reilly Media. And O’Reilly was at the time, this was in the early 2000s, had an office in Sebastopol, California, north of San Francisco, and office in Cambridge, Massachusetts, and a whole bunch of remote folks all over the country. And I had the opportunity to work remotely for a while, spend a lot of time in the Cambridge office and then work from the Sebastopol headquarters for a couple of years. And one of the things that I observed was that when I was working remotely, I was just focused on my work like that was what I was doing and the gossip and drama of the company. And he was not very visible to me, it was very muted. When I was in the Cambridge office, which was a satellite office, it was a little bit more pronounced, because there were more managers there. And there were more people gathered. When I was in the Sebastopol headquarters, it was a huge topic of conversation, what did the leaders care about most of them were there, you could see that they were meeting together, they would meet in person in rooms that everybody could see, you could see them interacting with other people. And the level of drama and gossip was much, much higher in that office than anywhere else. And since that time, I’ve observed in many other companies the same pattern, if you’re in the office, and you’re seeing the other, the way leaders interact with people, everybody tends to really key into that and spend a lot of time. What did it mean? The CTO was laughing in the kitchen with one of my peers? or What did it mean that I heard yelling in that meeting of the executive team? And there’s a lot of focus on the opinions and behaviors of the leaders and a whole lot less focus on the actual work and customers?

Aydin Mirzaee  23:35  

Yeah, that’s really interesting. And I mean, would you say that, like, I be, you know, at a company that, like, do you think that the drama also, I guess, will also disappear? So I guess, like most of us will start to notice that there will be less drama. If we are now suddenly remote too?

Sarah Milstein  23:54  

Well, what I’ve noticed is that if the drama is muted, if everybody’s remote, it doesn’t not happen. But what I’ve noticed is when I talk to people about this phenomenon, almost everyone says, Oh, that’s true, but they haven’t noticed it until I pointed it out. I think we’re pretty especially if you come from a company where there’s a fair amount of in person interaction, people are pretty keen to those dynamics already. So it takes a little bit of adjustment.

Aydin Mirzaee  24:17  

Yeah, no, that’s very cool. I feel like after this, I’m gonna go do some digging and start asking people, do you feel that there is less drama now? No, that’s, that’s awesome. And something very cool to be observant about. On the topic of remote work, what are some things that you feel and especially now that everybody’s remote? Like? What are some common mistakes that you feel people make that they should really be aware of? We kind of mentioned, you know, just a little bit earlier. You’re not measuring by, like, how responsive you are on slack and like focusing on output, but what are some other things that people tend to do wrong?

Sarah Milstein  24:54  

And well, in some ways, I think the biggest thing is assuming that our in person habits are the only way to address a need, whether that’s a need to be able to brainstorm or ask quick questions or be aware of each other’s lives. If you think instead about the purpose of your interactions or the purpose of the systems that you’ve had set up, and then brainstorm new ways to meet them, teams and individual managers and teams can come up with a lot of ways to make remote work really effective. And sometimes, in some cases more effective. That’s not to say there aren’t trade offs. But in some cases, you may hit on solutions that you find are better than what you had in person and the things you were doing in person, were just habitual rather than actually addressing a true need. So I think it’s that assumption that what we did before was the only way to do it, or the best way to do it. And is there like an example of that, like some habit that maybe we we have been doing and that we shouldn’t be doing going forward? One thing I find teams often do is when they’re in person, they have a regular stand up, or some kind of regular check in. And it tends to focus on kind of what’s the status of things. So we can all stay connected, especially at smaller and younger companies. And when you’re distributed, that tends not to work as well. It’s like a boring zoom meeting when you all get together. And that information can be shared pretty easily, asynchronously. But if you cancel the meetings, then it feels like well, now there’s no connection between us. So one of the things to think about is what was that the purpose of that meeting was the meeting, not only helping you share information, but if it was also helping you connect, then it’s worth thinking about what else could replace that, whether it’s a stand up that focuses on other kinds of things, on lessons learned, or on questions that you have for each other, if it’s a sense of personal connection, and that might be then you want to spend a little time with each other’s kids and pets, or talking about how your weekends when or sharing pictures from your life. If you can identify the underlying needs that that meeting met, then you can start thinking about other solutions. And I think that the standup is a really good example for where that’s often doing a lot of silent work that you can find good ways to meet.

Aydin Mirzaee  27:23  

Yeah, so I guess like, the sense that I’m getting is like, we can’t just, you know, sit back and relax. It’s almost like we’re re architecting things all over again, like, we might start with all the same habits and all the same meetings. But it’s really time to ask, what is the real purpose of this meeting and potentially re architect new solutions, you know, on the list of like, common mistakes that people make and some other things, some other habits that you recommend? You have like this long post actually have a list of habits and things that you can do. But one one really interesting one that you mentioned is this concept of setting up co working time together would love for you to elaborate, like what is that? You know, what context can people do it in,

Sarah Milstein  28:06  

I’ll talk about how I’ve done it. And then some other ways I’ve seen it done. So my job before MailChimp, I worked on a team at 18 F, which is a startup inside the federal government. And I was on a team where everybody had a fair amount of heads down work that we had to do every week, in addition to a lot of meetings that we had to have with each other or with other teams. And one of the things that we found was that the heads down work was hard to get to because of all the meetings and a little bit hard to focus individually once we were in it. And sometimes we wanted to just have that feeling of like there’s other people around us working. So that would help us focus. And so we would set a couple of two hour blocks per week when we were all going to be on zoom together, but basically muted on zoom together and doing our heads down work. And it provided that sense of co-presence of the feeling of co-working. It was easy to unmute and ask a question or ask Is this a good time to ask a question or to just chuckle at something and let everybody else know what you were thinking about? And helped us feel a lot more connected in a pretty lightweight way. I mean, it also had the benefit of preventing a lot of meetings from getting booked over every minute of the day for everybody. But I’ve seen teams take that to some real extremes. There are teams that basically especially in small, early stage teams, where you need a lot of contact with each other. I’ve seen teams have setups where they’re basically on video with each other all day every day, and might have like a separate screen that you’re using for that might have a dedicated camera for that kind of thing. But where the assumption is that you’re going to be with each other over video, basically, for a good part of the day. And I would say if you’re going to do that, and truly in any video meeting A key tactic for not running yourself down is turning off your own view of yourself. Looking at yourself all day is exhausting. It’s far, far, far less tiring to be on video all day. If you’re not looking at yourself.

Aydin Mirzaee  30:15  

Yeah, like, just get into the habit of turning that off. And you know, it’s really interesting. Obviously, you’re in the discipline of engineering. And so pair programming, I guess, like pair programming could possibly even be easier. If you’re doing this remotely, right?

Sarah Milstein  30:30  

Yeah, it’s so interesting we have at MailChimp in Brooklyn, we have some pair programming stations that we’ve set up for in person. But most of the people who do pair programming, do it with people who aren’t in the Brooklyn office. So for sure people have found good ways to do it remotely and make it as you say, lends itself to remote work.

Aydin Mirzaee  30:51  

Yeah. And so just like a very tactical thing, if you’re doing this coworking setup, so you mentioned that everybody is on mute, or do you kind of like leave it? unmute. So you can just be, you know, snarky remarks from time to time.

Sarah Milstein  31:03  

It really depends on the team. I think, as I recall it, 18 if we actually did some experimentation with all mute, all unmute. But I think that actually raises the important point, which is, one of the things that I found most consistently, is that when you’re creating new systems, when we’re saying, okay, the way we did it in person isn’t the default, you have to do a ton of experimentation to figure out what works. And you have to check in every couple of weeks or every couple of months, depending on the thing you’re testing to see. Is it still working? Is it meeting our needs, like putting a date in the calendar to figure out, okay, mute and unmute is something you can figure out, just checking in with each other over the course of a couple days. But if you’re trying the whole idea of a coworking thing, you might say, let’s try it for three weeks, and then check in and put a date in the calendar and say, do we actually like this? Is it meeting the need, we thought? Or do we need to keep trying different things?

Aydin Mirzaee  31:56  

Yeah, no, that makes sense. And you know, another tip that you have is doing video calls when you can versus just approaching everything as like text based communication. So how do you do that? Like, what does your day look like? Do you randomly call people? 

Sarah Milstein  32:09  

Yeah, you know, it’s interesting. Part of the reason I noticed this is because at 18 F, which was when I was there was about 200 people, it was the norm that people would slack you and say, do you have a sec for a quick call, and then you jump on video, and we I think use three different video platforms there. So you’d have to sort out which platform but it was the norm, you would get on a two to five minute video call all the time. At MailChimp. It’s not at all the norm. It’s the norm that all the meetings are scheduled. And it’s rare that people sack each other and say, Can we just jump on video, but I find it’s useful. So I try to set that with folks who report to me or work with me closely. I tried to do it often enough that they know they can do that with me, they can always hit me and say can we have a quick call. And really the main barrier to it is having enough space in your day for that to be possible. But being intentional about it and saying this is something I want to do rather than I have to like, wait until there’s a meeting scheduled or book a meeting, I think is the biggest thing. It doesn’t require new technical systems, it just requires a little bit of different habits.

Aydin Mirzaee  33:17  

Yeah, it’s super interesting. I mean, it’s you know, just like tapping someone on the shoulder. So it kind of replicates that any probably provides a lot of the other stuff that we talked about, you know, for example, connection, and so on and so forth. You know, it is FaceTime. So, yeah, it definitely helps in a lot of those ways.

Sarah Milstein  33:37  

I think you’re really right. And actually, the reason I think it was the norm at 18F, is that was a fully distributed company, or it was remote first, basically. And MailChimp has been an in person company for most of its life. So the idea of the tap on the shoulder still needs a little bit of translation time.

Aydin Mirzaee  33:53  

Now that that makes a lot of sense. You know, the other thing like as we’re talking about teams, and obviously how to manage in this environment and get them to connect, and you’ve definitely written a lot about you managing when a lot of things are going wrong, when the morale perhaps isn’t as high. And there’s this quote that I grabbed from you that I thought was really interesting. And I was hoping that you could maybe explain it a little bit more. So you said that when your team equates project failure with defeat, many will intuitively address the problem by narrowing the scope of new projects in order to make them more likely to succeed. And that sounds like a bad thing. So we’d love for you to know, explain and like how you do not let that be the case?

Sarah Milstein  34:41  

Yeah, so it’s a bad thing. If you’re in a mode where you’re trying to hit on new ideas, which is certainly true for a lot of startups, you’re still figuring out what’s going to take what do our customers need, who are our customers, and you’ve got to try a lot of things. It’s a little bit less the case if you are fine, too. Doing something. But most of the time, we want our folks to take risks and to be able to try new things. So that we have new opportunities. What I found is that in companies where you’re trying a lot, and you’re failing a lot, if people are at all punished for the failure, or really feel like they wasted time and trying something, they’re going to take as many steps as they can to avoid that feeling. Nobody wants to feel failure, nobody wants to feel shame. So as a leader, one of the things you have to do is work really hard to help people understand failures, as lessons that contribute to the company, as things that you can learn from that help you focus and help you take new direction, that build on your knowledge, rather than like building a mountain of shame. And people naturally feel a sense of failure when things don’t go as hoped or expected. So that’s one of the cheap tools that a leader can provide is rerouting some of those feelings into understanding, productive failure, and in framing and building the work in that way. And it’s almost always a question of talking about what we learn from this? And how can we do things differently or shift based on what we’ve learned?

Aydin Mirzaee  36:21  

Yeah, that makes a lot of sense. And you also have another tip that’s kind of related to that, which is creating projects where you can win, especially when there’s a lot of stuff that’s uncertain with a high degree of failure. 

Sarah Milstein  36:33  

Yeah, I have a one of my reports right now is on a team, she’s running a team that has just launched a product that’s been in development for nearly a year, at this point, whether that one succeeds or not, you could imagine those engineers just need time to do some quick things that they know are going to work. So the new launch is still new, we don’t know what’s going to happen yet. There’s lots of room for it to go really well and some room for it to fail. And what they need is just some time to do some small things that they know are going to win and contribute to what the company needs. And so it’s sometimes that idea of the small wins applies, even when you’re not quite at the failure stage. Just when you’ve been in a long slog, and need to help people refocus and get some morale. 

Aydin Mirzaee  37:26  

Yeah, it’s so interesting. Like, when you think about all the things that managers have to do, there’s also this this concept, it seems like you’re always paying attention, is this team having too many failures, are they having enough wins, and they’ve been on this long thing, and maybe it’s time to switch them to this. You’re always thinking about all the various scenarios. And no wonder management is hard.

Sarah Milstein  37:47  

Yeah, right. Right. And I think, you know, if you don’t pay attention to those things, to the emotional health of the individuals in the team, you’re not going to get the outcomes that you want, you’re not going to get good productive work, you’re not going to get new ideas, you’re not going to get the trust, you need for people to work closely together or raise new ideas or flag things that might be damaging. So that layer of emotional health is always important to pay attention to.

Aydin Mirzaee  38:14  

Yeah, that’s super valuable advice. I have to ask you, in meetings, and especially now that we’re all remote. What is your favorite meeting? Or like which meeting Do you look forward to?

Sarah Milstein  38:25  

The meeting that I most enjoyed at MailChimp doesn’t exist right now. It was a meeting. As I noted, before I run our Brooklyn office, I have two roles at MailChimp, one of them is running the Brooklyn office. And the Brooklyn offices are kind of a startup inside of MailChimp. In some ways, it’s about the company’s about 1200. Overall, the office is about at its three years old, the company is 20 years old for the past couple of years, and I’ve been in the in the role in Brooklyn, I have been gathering the local managers to help identify problems and opportunities in the Brooklyn office in our community in Brooklyn, and how we can solve them. And it was a once a week meeting where we would get a group of people together to really look at and solve problems and just create a space to really think about how we can make things better. And it was very action oriented. And I like that sense of working with a team to make things better. We are now fully distributed. And we don’t need that meeting anymore. There are other things that I work on that are, you know, pandemic related and affect people but it’s not how we make this office work? Well, how do we make sure that people have the resources they need in this space? So those kinds of team meetings are something I really love, and for me don’t exist right now, I’m not the way we’re structured. I don’t have a team that I’m working with. But I will say my experience at 18 F which as I said my team was completely distributed, was very much problem solving as a team together. And we did that remotely. We did it over zoom a few days a week and I found that satisfying and effective, that work doesn’t need to be in person to work well.

Aydin Mirzaee  40:05  

Yeah, no, that makes a lot of sense. And I think like my takeaway there is that that that’s really interesting that when when you have a group of people, in this case, like, I mean, it was in the Brooklyn office, but you could have other sub teams, but sometimes it makes sense to have that meta meeting or initiative where you kind of look at problems and opportunities and like tackle that, you know, from like that group. It could be like the engineering team, it could be like the sales team meeting together making that kind of a call. So I think the spirit of it makes a lot of sense.

Sarah Milstein  40:33  

Yeah, absolutely.

Aydin Mirzaee  40:34  

One thing that I wanted to touch on, you know, as we get too close to the time here is the concept of writing, you obviously write a lot, you’ve written a book, many different articles, what does writing do for you? And is that is it are there lessons or things that that we should take from it that you think it could be useful for other leaders,

Sarah Milstein  40:52  

Writing does a couple of things, probably the most important thing is when I sit down to write out an idea, it forces me to really clarify my thinking, and sometimes open up new ideas. So just the practice of writing makes me a better thinker, and a more thoughtful manager. But I also find that publishing writing means that other people can challenge my ideas sometimes or add to them, which again, makes me a better manager. And sometimes they just become aware of me in ways that are useful that spur new relationships or new conversations that I wouldn’t have had otherwise, I will say that writing isn’t for everyone. And it’s not the only way to have an experience like this. But for people who have the propensity for making the time to do it, which is hard, of course, but making the time to do it can really be valuable and can pay off in a lot of ways.

Aydin Mirzaee  41:50  

That’s very, very useful advice. And I love the clarity of thought. And I think like a lot of this stuff becomes even more relevant, obviously, when you are working in a distributed fashion. Sarah, this has been amazing, so many great insights and stories, and also a lot of tactical tips to take away. You know, one of the questions that we ask everybody as kind of like, the final question is for all the managers and leaders out there looking to get better at their craft, looking to uplevel their management and leadership skills? Are there any books, tips, resources, or words of wisdom that you would leave them with?

Sarah Milstein  42:24  

One of the things that’s been true throughout my career is that peer mentoring has been a huge boost. that’s been true in a number of different settings. But I think we often think about more formal structures, mentors, and sponsors within an organization who are more senior than you are different kinds of classes and articles, things like that. But I actually find that if you can create the magic of finding one or two or three peers with whom you can really share information and honestly talk with each other. That can be one of the biggest boosts to self reflection that’s needed for development. And sometimes you can find those people in the organization you work for, and sometimes you find them outside. And it can be hard to find the folks you really connect with, it could take a few tries. But that can be a hugely meaningful connection. And it’s a sort of thing you can easily do over zoom and over slack. So you don’t need to be in person with each other.

Aydin Mirzaee  43:27  

Yeah. And I feel like your reach is now even broader, so you have even a larger pool to choose from. Exactly. Sarah, this has been amazing. Thank you so much for doing this.

≈ 43:36  

Aydin, Thank you. It’s been my pleasure.

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