MasterStroke with Monica Enand & Sejal Pietrzak

Managing Up

• Season 1 • Episode 5

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Everyone has to Manage Up!  Discover the inner working  of leadership transparency in this episode of the Masterstroke podcast. Hosts Monica Enand and Sejal Pietrzak  dissect the vital role of communication in leadership and how to fine tune the flow of information between a CEO and their Board of Directors. 

You will  hear a story about the importance of creating an environment where team members feel safe to voice concerns. The episode also casts light on interdepartmental collaboration through the journey of a chief marketing officer who embraced the 'first team' mindset, leading to a profound ripple effect on productivity and success across the organization. Join them as they traverse the landscape of leadership, from fostering approachability to encouraging solution-oriented thinking, and learn how reshaping perspectives can unlock the full potential of a team.

Georgianna Moreland - Executive Producer | Managing Editor;
Matt Stoker - Editor


Monica Enand:

I was having trouble with my board. I kept getting feedback from my board that they were really concerned and very stressed about some of the things I was telling them and I kept saying but guys, these are normal things that happen in companies and we've hit them before and we're going to get through them, Don't worry.

Sejal Pietrzak:

Welcome to the Masterstroke podcast with Monica Inid and Sejal Pietrzak. We're going to have conversations with founders, ceos and visionary leaders in technology and beyond.

Monica Enand:

What does your CEO want from you and expect from you, and what does your executive, I guess, or any executive or manager or board even? One thing that I think is interesting is that a lot of people think that CEOs don't have to manage up, but the truth is, everyone has to manage both down and up. Yeah, that's true. Yeah.

Sejal Pietrzak:

That's right, Monica.

Monica Enand:

We have to manage up to a board, right, sejal, and then the board actually has to manage to the investors, and then I mean, everybody has somebody they are accountable to where they're managing up and where. And then everybody has well, unless you're just doing something individually, everyone has people they have to manage with on a team to get something ambitious done. And I think those are two completely different things and sometimes we don't think of them as different skill sets, but they really really are.

Sejal Pietrzak:

Yeah well, there's managing partners, peers, and then there's managing up. Of course, there's managing the people below you, but at every single level. And, by the way, it's not just work, it's home too, right? I mean, so many of the skills that you learn or you think about in terms of management at work are the same in terms of management at home.

Monica Enand:

Although like it's been occasionally y'all's at me at dinner and says please don't put me on a performance improvement month. Are you trying to manage me?

Sejal Pietrzak:

It's so similar in terms of the transferable skills and focus and management of your home and of your work.

Monica Enand:

I'm reminded of a story that conversation I was having with my daughter and she was telling me about friends of hers who have jobs that are easier than she perceives her In terms of shorter hours, like she expects to not work really long hours. She's going to work first startup and she knows she's going to have to be there, you know, beyond the eight hours. You know 10, 12 hours, sometimes weekend work. And she's saying, you know, but it's not fair, because they're making just as much money as I am, or maybe they're making even a little more money than I am. And I tried to tell her, like, if you really view it as investment in yourself which is, I think, what you're saying like the skills that you gain through thinking about how to manage all of the different relationships that you have really help you in all aspects of your life.

Monica Enand:

I had an executive coach once say to me I was having trouble with my board. I kept getting feedback from my board that they were really concerned and very stressed about some of the things I was telling them and I kept saying, but guys, these are normal things that happen in companies and we've hit them before and we're going to get through them, don't worry. And finally my executive coach said to me why are you telling them all of that stuff? And I said I'm being transparent. They said they wanted to know. No, they said it. They actually said, hey, they want to know.

Monica Enand:

And she said, instead of just listening to what they say that they want to know, think about how they need you to show up for them. So her advice was an investor or a board member maybe has their own set of worries and their own stresses, and what do they need from you? How do they need you to show up for them? And so maybe what they need from you in certain times is just steady and confidence. And yes, you're going on a roller coaster up and down and you're stressed out, but maybe you don't need to share all of that with them and take them on the roller coaster with you. Maybe what they need is a little dampening effect and that they need just kind of some steady confidence from you. And so, to be honest, I evolved into that, but I struggled with it because I was concerned of like, what should I be sharing with my manage, with people above me, and what should I not be? How do you think about that or how did you think about it, especially with your executives?

Sejal Pietrzak:

Oh yeah. So when you said that, let me ask you, monica, as you think about what, I agree you want to be transparent and I agree you want to make sure that you're sharing with the people who are managing you, or the people above you, what's happening. And so, while your executive coach asked you, why are you sharing that? My question would be is it better to share? But then say these are the solutions we've come up with, this is the challenge and this is the way we're addressing it? And rather than sharing the ups and downs, more sharing the I've got this. I'm Monica, I've got this, you know that kind of thing. Is that the way you ended up coming to?

Monica Enand:

Slightly. Actually it's very close. What I ended up realizing was I need to pause. If I quickly solved the problem, then it actually wasn't worth telling them anyway. I mean, I think you know you have to adopt this idea that like you want them to be proud of all the things and great things you do, but you really can't like go for the gold stars like all the time. You can't some things you just gotta solve. Solve them and just let it move on. And they know that the job is hard and they know that there's crap coming up all the time and you don't have to share all of it. So I think I did start to filter, Like, if I quickly solved it and it wasn't a long-term problem and I didn't think it was recurring, I just stopped sharing those problems.

Monica Enand:

If it was something that lasted where I thought, gosh, I have a solution, I'd wait to share until I either had a solution or had an idea of how I was gonna get a solution, or also until I could scope the problem. And so even just the pause of like, just pause, evaluate how big of a problem it is. Is it recurring? Is it existential threat? Is it? What is the downside risk? Is there pieces of information you're gonna quickly know and so it's not worth sharing until you have those pieces of information. I started going through those kinds of that was my thought process. After a while it was like, okay, Just pause and and and don't share everything immediately. Put a pause in so that you can think about these things. I don't know, was that how you, how did, how did you think about it? Say you know?

Sejal Pietrzak:

I'm pausing. It was good advice. I Think about it not only as a CEO and talking to your board. I think about it even as anyone who worked for me. How would I want them to Address or share a challenge if it was a one-time thing and they solved it? I actually would want to know, really, and, and just so that, so that it but it's also valuable to know how they think, how somebody On the team is thinking, and also, in case it happens to come up in a different, different format, if it was important enough Right, it was absolutely inconsequential, doesn't matter.

Sejal Pietrzak:

But if it was important enough, even if it was a one-time problem, I'd want to know. But I'd want to know. Hey, fyi, this is in the past, but this was the problem, this is how we solved it. We did it. Great, didn't? Didn't you need to bring you into it? Fantastic, but good to know in case a it happens. Again, learning from me, potentially learning for the others on the team and and then be, it's also valuable in case you get asked about it, or or if it ends up being something that's not a one-time thing, but that's only if it's consequential, yeah, and then, and then if it's something that is ongoing, I think? Yeah, I would want to hear about it, but I always, always recommend coming with solutions and ideas rather than coming with just the challenge or the problem.

Sejal Pietrzak:

Yeah, and Oftentimes, this is the solution and I've already Tried it and it's okay to not do it. Right, right, try the solution. You, you've you've addressed it. You're a leader. You have the right to be able to go and Make a mistake, it's okay. But you've tried it and, and you know, did it work? That's great. We're moving forward. Did it not work? Okay, good lesson learned. We're gonna pivot fast and we're gonna find another solution, and that's where communication is really important with those above you, and so for me, I utilized it. The same way. I don't think I ever would, you know, bring a board or bring manager into the ups and downs. I think that's good advice. You know, you always want to be that steady eddie. You want to be the person who comes with solutions and is a common cool, cool and collected, rather than you know, bring them along because, you're right, they, everybody above you, knows that your job is not easy.

Monica Enand:

Yeah, no matter what level you're at. I actually I'm so glad you added that, no matter what level you're at, usually when you're working for someone it's important I find, say Jill, to remember that that person has either been in your shoes or managed someone in your shoes, and so they're aware that it's not an easy job and you don't need to prove it to them. And when things go right, they know you had it hand in it, like, so they don't need you to Sort of promote yourself or think about the credit for things going right. What you said about come with solutions, that was something I also struggled with, giving guidance to my team, because I absolutely did want them to come with solutions, but I also needed them to surface problems but we did not have a solution for Because I actually had a time we introduced a new product actually, and the product, the way we built it initially, actually wasn't scalable for the way we ended up using the product, and I didn't actually become aware of this because it was not an easy problem to solve, because we actually got users and Customers started using it and we started having all these problems. You, but the team, was very much focused on bringing me solutions, bringing me problems and bringing me solutions. So they were kind of trying very hard to figure out what to do.

Monica Enand:

And then a new person entered the team. They hired a new guy onto the team and he actually pulled me side at a Christmas party and he said do you know that our monitoring software alarms multiple times an hour, like sometimes 10 times an hour, and that the team is now scheduling on call rotations and every always somebody's up trying to keep the system running? And I said no, I did not know that. And he said it shouldn't be that way, something's wrong. And I said yeah, ok, thank you for letting me know.

Monica Enand:

And he kind of said it kind of on the down low, like don't tell my manager, I told you. And I said no, no, no, don't worry, thank you for sharing that with me. This was like over a drink at a Christmas party. And then I chose, you know, when I got back to work, to start digging in and just seeing like hey, what was our stability, what was the alarm rates Like, how often were on call people being? And I found that we had a massive problem that if we didn't fix it we weren't going to be able to scale this product. And so.

Monica Enand:

I actually had to kind of stop the team and rethink how we were going to solve this big problem. And that problem wasn't surface to me because my team members really didn't have a solution, Like they didn't have a solution that met the current schedule that we had and the current resourcing that we had, and but it was really a threat. So I don't know. I really asked myself later, like did I cause them to not bring me the problem because I said bring me solutions? I don't know any thoughts on that, Sejal, I don't know.

Sejal Pietrzak:

Monica. I mean, first and foremost, I think it's really cool that the new person felt comfortable enough to come to you and say, hey, this isn't right. Yeah, and because everyone else was like, well, this is the way it is, this is the way it always is.

Monica Enand:

It happens slowly.

Sejal Pietrzak:

Yeah, and sometimes it takes a new person to look at something with fresh eyes and a new perspective and ask the question why? Why are we doing that this way? Why are we getting woke? Why do we have somebody up all night and they take turns being on call to shut off the alarm? Why are we doing that? And so I think that's fantastic, and it took a lot of courage for him to come to you on that.

Sejal Pietrzak:

So, monica, that's the first thing I would say. The second thing is it's actually a really interesting point. That's probably a scenario where I would go back on my come to me with solutions. I'm just surprised that they didn't come to you and, like you said, because it happened so slowly maybe it was once a day that the alarm was going off. So they're like, oh, we'll shut it off, it's not a problem. And then it just maybe crept up to multiple times an hour, but by the time that was happening, they were like, well, this is the way it is, it is what it is, and so we don't, we don't fix it. Is that what happened? I think?

Monica Enand:

yeah, I think that was part of it, Sage. I think there were a few things. One, I think it was this boiling of a frog thing, or whatever you say, oh yeah yeah, yeah, the frog you know the saying.

Monica Enand:

The saying is, I know, slowly raise the temperature, the frog never jumps out. But if you raise the temperature too fast the frog jumps out, so you broil a frog slowly. I don't even know if that's actually true, but you know, we've all heard that saying. It's a terrible, it's just a terrible image, but anyway it's the same.

Monica Enand:

So it possibly was that. I'm sure that was a part of it. I think the second part of it was the leadership is the one who got us into that situation. So they made some architectural choices early on in this new product that weren't scalable and weren't easily changeable, and so it would be a very, I guess, embarrassing or maybe they were nervous to tell me that they had made a bad choice and that it had resulted in this. So they felt the ownership and the responsibility. I think that was the second thing. And then the third thing was yeah, they did not know what to do.

Sejal Pietrzak:

I would say sooner is always better to share bad news right Nothing, ever no. Bad news ever gets better with time.

Monica Enand:

Yes.

Sejal Pietrzak:

You've heard that saying right.

Monica Enand:

That's true.

Sejal Pietrzak:

And it's so important and that's part of being communicative and you think, oh, I don't, this is not that important, it's just something that we have to shut off every few minutes or six times an hour or 10 times an hour. But it actually is really important because that's affecting the company and so it's really interesting to hear that kind of a story because I think it touches on so many things where people may be afraid to bring up something that's concerning. But in fact it's always good and if you can come with a calm, you know, before it blows up, right, because for you it's not like anything had negatively happened yet. But can you imagine if something and you couldn't turn off the alarm one time or something, then you would have been really, really upset because you'd say, hey, I'm the founder of this company, I should know when this kind of stuff is about to happen. Absolutely.

Monica Enand:

I think what you said is don't your manager is not. If you are higher in the organization and you are reporting to somebody who's an executive, your manager is not the first person you talk to. The problem about the first person is, you know, gotta be somebody on the team that can help you find the solution.

Monica Enand:

Yeah, you first try to solve the problem and then come to the manager and say we had this problem, here's what. I think the solution is just FYI. But I think you have to do your diligence at saying, like, is it a real problem? How big? Can we find a solution before you're bringing it to a senior level executive, would you say?

Sejal Pietrzak:

that I agree 100%, yeah, absolutely. And it has to be quick. You can't just be like, oh, I'm gonna try to solve this thing for a month, yeah, but this just moves too fast, yeah. So, as you think about managing ups, one of the things we talked about just now was, you know, transparency, and how much should we come with solutions, versus how do we address and be transparent, versus being calm and cool and collected. What are some of the things that you think will help you find a solution?

Monica Enand:

úsica called nothing can prevent security but for online simopr and who's been here for?

Sejal Pietrzak:

two years.

Monica Enand:

That means this big change of usage has a challenge in reporting to others. Yeah, really collaborated well with their peers and so that they were in lockstep. I had times in the organization where I felt like we siloed. You know the opposite of kind of managing across Everyone, kind of siloed. And I don't know if you're familiar, did you read or participate in Patrick Lanzioni's like first, the idea of a first team?

Sejal Pietrzak:

Yes.

Monica Enand:

Yeah, so that actually really resonated. The the first team concept really resonated with me really well once the organization got larger. Because I think initially when we hired people we wanted those people to be really good at their domain. So, like our chief marketing officer, she knew demand gen brand marketing, she knew marketing inside and out right and she was great at it and she had a.

Monica Enand:

She viewed it as her mission to manage her team really well and so she kind of I guess the phrase I might say is she was a little bit of a mama bear about her team. So she protected them, she wanted to make them productive. I mean, all sounds like great stuff, right. And when we went through that Lanzioni training and realized about the first team, I think she realized her first team couldn't be her direct reports and that she couldn't first only think about the mama bear of that and that she had to really think about the productivity and what was needed across to the organization with her peer group. And when she got kind of like wrapped around oh we're her first team, they are not your first team her behavior completely changed and she became much more collaborative with sales and customer success and with engineering, with product and you know, the entire team became more productive because she was kind of now mama bearing, caring for all of our product, all of the team's productivity, if that makes sense, I don't know. Does that resonate?

Sejal Pietrzak:

Yeah, the totally agree. It's it's that's really insightful and it's really interesting that it worked so well to have that change happen, and and then collaboration across the functions is so critically important. Well, it was great chatting with you today, monica, and I think hopefully all of this advice will be useful to anyone who's listening.

Monica Enand:

Absolutely Well. Thank you so much, sejal, and thank you to our executive producer, georgiana Morland.