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Having a servant leadership style and a vulnerability to leading is the key to success. When people respect you and understand why you make certain decisions, and you're transparent with them, there's a lot of respect that you're going to gain from that because they trust you…I think rather than just being like, ‘fix this, change this to this’, and going a little bit deeper with them is really helpful.

In this episode

Has your team ever experienced creative blocks?

How can managers help their teams remain aligned and productive?

In today’s episode, Melissa dives deep into what it takes to lead creative teams while staying aligned and being a creative unblocker. 

Melissa Rosenthal is the Chief Creative Officer at ClickUp, an all-in-one project management platform – and one of Fellow’s integrations! 

Melissa shared how she defines productivity within her teams and what their creative process looks like. 

She also shares the behind-the-scenes of ClickUps iconic Superbowl ad and how that came to fruition. 

Tune in to hear all about Melissa’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.


03:36

Perceived loneliness as a manager

10:30

Defining productivity in a creative role

13:22

Aligning for outcome

18:26

Coordinating large groups in creative functions

21:59

How to reject ideas to redirect

24:54

Behind the scenes of ClickUp’s Superbowl ad

30:27

Melissa’s go to interview question

36:50

Creating psychological safety

39:02

The key to successful leadership


Resources


Transcript

Aydin Mirzaee (Fellow.app)  00:44

Melissa, welcome to the show.

Melissa Rosenthal (ClickUp)  03:37

Thanks, Aydin appreciate you having me on.

Aydin Mirzaee (Fellow.app)  03:40

Yeah, very excited to have you here. You’ve had a pretty extensive leadership career, you’ve been at companies like chatter and Buzzfeed and today you’re a Chief Creative Officer at clickup. So there’s a lot of things that we want to get into and dive into you with. But the thing that I wanted to start off with was just going back in time, if you remember, when you first started to manage and lead teams, what were some of the early mistakes that you made that maybe you make less of today.

Melissa Rosenthal (ClickUp)  04:07

So my first experiencing managing team I was kind of grown into and maybe that’s the case for others, but the leader of the team at the time, I believe we were about five, he decided he was leaving, and I was asked if I could take over and manage the team and, and grow the team and I’d always wanted to do that. And that opportunity although was very scary because going from kind of that, you know, that icy role to actually growing and leading a team and, and taking people who were once your peers and and you know, managing them I had a lot kind of up against me, I would say in terms of just we’re on an equal playing field one day and then all of a sudden you’re managing them. So you know, it was definitely a learning curve and in kind of how to manage your peers. I’m sure it’s much easier. You know, you come into it already established and you’re given a team or younger, less experienced than you. But that wasn’t the case. isn’t my first experience so? Yeah, I mean, I think at first I treated them very much like my peers, which is something that you would naturally want to try to do to keep that relation and to keep that rapport going. But I think I would have stepped out of that a little bit more quickly and established authority on sort of what we were doing, and really laying the land and the strategy behind kind of how the team was going to work, rather than really trying to just relate to them. And this is a thing that I don’t know if many people talk about, but I think it’s a, it’s a fear of when you’re trying to relate to your reports is like a little bit of fear of loneliness at the top. Because once you become that manager or that leader, you don’t really have the same same people to kind of lean on to talk to about what’s going on. So your you know, your your level of comfort with, with those people changes in a very, you know, a different way the dynamic is different. And I think at first, I was afraid of that, rather than kind of just establishing what what the goal was what I was going to do as a leader and as a team, and really like focusing more on respect and then being liked. And I think both are important. I want to be liked, of course. But I think establishing that immediately would have been would have been something I now default, of course, of course, you want to have them like you. But I think it’s really important to have your team respect to you and respect the decisions you make and how you operate and how you integrate and work with them. Rather than, you know, on a pure basis.

Aydin Mirzaee (Fellow.app)  06:30

It’s interesting, this this, what you said around loneliness, and, or maybe like perceived loneliness. I’m curious. So that probably doesn’t apply to just when you first become a manager that probably applies for every time you take, you know, another step up in the corporate ladder, like have you found what have you done, I guess, to either mentally deal with that? Or maybe it’s a non issue, like how do you how do you think about that today? Just have

Melissa Rosenthal (ClickUp)  06:57

to deal with it, if it’s what you want, I think I think there are levels of finding other people and other companies that you can talk to, and finding, you know, friends and mentors that are outside of that circle. But of course, they don’t understand the way that you know, anyone within the organization one. And I think, you know, I think it’s just a natural part of progressing in a career, like, there are certain aspects of that that are that are lonely. And I think everyone feels that way. Rather, maybe maybe most people don’t talk about it, some do. I’ve seen it. But I think it’s just an expectation of what comes along with the territory. And it doesn’t mean it needs to be a completely lonely ride. But sometimes you’ll feel alone in the decisions that you need to make and, and the strategy that you need to lay out and the you know, the reception to that and the meetings that you have with individuals on certain topics, like it does feel lonely, because you’re driving that and you know, the only people you can talk to are kind of outside of that circle. But yeah, I mean, I think there are ways to combat it. Just it, I think it really is the reality of it, or it has been my reality through my career. And I talked to other people about that, too. And they asked me like, what’s it like going going into management or a leadership role? You know, I’m honest, I say that dynamic becomes very different. And you know, it can be a bit lonely.

Aydin Mirzaee (Fellow.app)  08:06

That makes a lot of sense. I mean, I hear this all the time, especially, you know, founders of companies.

Melissa Rosenthal (ClickUp)  08:11

That’s the loneliest place to be, I mean, my husband is starting a company right now. And he’s working with a few people, but they’re, you know, they’re overseas or are in different parts. And he feels like that as well. And kind of, you know, we talk about that often, because I’m in a very different, you know, a very different position than he is, but he feels the same, same way.

Aydin Mirzaee (Fellow.app)  08:29

Yeah, and peer group certainly like, again, it networking with other people at other companies can help. In this situation, I did want to dig in on another thing you said, which was, if you could go back, you would, you know, maybe establish your authority more or you know, indicate that you are no longer peers, if we were to play it very tactically, step by step. What are some ways that you could do that if you were advising someone that just today got, you know, promoted? And they were peers, and now they’re leading the team? What should they do?

Melissa Rosenthal (ClickUp)  09:03

I mean, I’m all about just like transparency and visibility. And I think like having those honest conversations and saying, I’m in this role now, and you know, things will change in the way that we we kind of interact on certain levels, but in others, nothing will change. And I’m here like for you, as an advocate of you, and you know, the biggest success would be to have this team, be successful and have this team win awards and do amazing creative work and amazing work in general and have the company be successful. And that’s my goal. And my goal is also to make you successful. And I think like having that and sharing very, very clearly what your goals are, both for the company for the team, but also for individuals, I think would at least given them a sense of comfort that you’re in it for them. Because I think when people are all kind of in this very same arena of what they’re trying to achieve, there’s healthy competition, but as a manager you almost are no you’re you’re a servant to kind of their their success. So I think like laying out my goals and my intentions, is to really up level them and make sure that they’re successful would have would have been really great. And I would give that advice to anyone, you know, make your team comfortable and make them feel like they have an advocate, and that they have someone that champions them. And that, you know, I would have done my previous experience.

Aydin Mirzaee (Fellow.app)  10:20

I think that’s very well put. And that’s, that’s a line that I think folks can rehearse. And, you know, of course, make it their own. But But I think that’s the framework is, is the right approach, you have been, I mean, you spent the bulk of your career doing, just like in the creative space. And so today, you know, when I think about clickup, clickup is a, I would, you know, as an external observer, I would say it’s a very productivity or an oriented company. And so, I’m very curious, because, you know, some roles are easier to feel productive in. And I feel like creative rows, roles can potentially be less. So it might be, it might be more difficult to define what productivity means for creative roles. So I’m just curious, like, you know, as a leader of creative teams, you know, how do you think about productivity? And when people come to you, and ask you about that, like, how do you advise them about like, just the relationship between, you know, creative roles and, and productivity

Melissa Rosenthal (ClickUp)  11:19

in a very tactical way, I attribute productivity within creativity, to and within creative teams to really like that, that ability to get the best and final product with efficient communication and efficient workflow throughout. And I think like, I’ve been in many situations where there’s, it’s chaotic, there’s lots of things going on, there are a lot of stakeholders, nothing is streamlined. And the end product ends up looking a lot different than what was discussed, or what was, you know, decided on. And I think the ultimate like way of feeling productive within a creative unit is when things flow well, and you come out with an amazing, amazing product, or an amazing piece of creative that everyone had aligned on, right, it’s coming going from point A to like point z, with like, minimal, you know, turbulence. So I think it’s like coming out with something that everyone thinks everyone is proud of that performs really well. And then but taking a look back and seeing like, Well, what did that workflow look like? Was it efficient? Are people demoralized? Because they just went through hell to put it out, right? Like, I don’t see that as productivity? I see that as like, how do you solve those pain points? And it’s through a more streamlined process through that, which ultimately becomes kind of that endpoint of like, where are we productive with this project? Or did we just get it done? And that’s how I look at it.

Aydin Mirzaee (Fellow.app)  12:37

Yeah, that makes sense. So I think like, just having a framework and a process around getting to an outcome can can really help establish milestones around it. And I like what you ended with, which was, and maybe you could repeat that again, you know, did did we do this productively? Or did we just get it done?

Melissa Rosenthal (ClickUp)  12:54

Yeah. I mean, I think there are things you get done, and you’re like, Wow, we got it done. It’s like we missed, you know, we accomplished check in check the box. But how did we do it? Like, did we spend way too much time on it? Was there a ton of back and forth? Were we misaligned along the way? How do people feel right, and I think there are so many factors and kind of like, establishing whether that that was a productive way of approaching that project, or getting it done or getting it to that finish line. And that’s, and that’s how we think about it.

Aydin Mirzaee (Fellow.app)  13:22

As you were talking, it seems to me that a lot of times where things can go wrong, or if you know, people are not aligned, or they’re, you know, examples or stories of when you’ve seen a situation where, you know, things weren’t aligned and and how you went about getting people aligned so that you can achieve the right outcome at the end.

Melissa Rosenthal (ClickUp)  13:45

There’s so many situations, and I think it’s up front like hitting a lot of the people that need to make the decisions in that room and saying, what are our goals for this? Right, like, who are the stakeholders? How many, how much time do we think it’s going to take? And what is the ultimate outcome? Like, what do we want to achieve here, and getting everyone’s buy in from that? I think it’s like, very, very important. And then understanding, you know, and along the way, kind of like really like being in it with the team, I’ve always found is like, very helpful, because you can then identify like blockers or problems or things that are gonna get in the way of that. I mean, it’s hard to identify a very specific example, because I think it happens pretty fairly often. You know, the best thing you can do is, is take some learnings away from like, what, what didn’t work in that past piece of content or creative that you were working on? And making sure that things change moving forward? I mean, you’re never going to have perfection at first, but I think optimization over time through that understanding, and through that process, iteration is going to be key. And that’s what

Aydin Mirzaee (Fellow.app)  14:46

we do in terms of other sorts of roadblocks that might prevent you from getting to a productive outcome. How do you think about creative blocks in general, if a team is not making You know, the progress that maybe you think they should be and you feel that it might be a creative block? You know, how do you tackle situations like that? And how do you go about unblocking folks?

Melissa Rosenthal (ClickUp)  15:10

I mean, I try to dig into what what is causing it? Is it like a lack of understanding of the goals, and often it’s that it’s we don’t know how to get to this outcome, because we don’t understand what the goals are, or how to actually tell that story. Because like the front half of it, or these pieces haven’t been established, then I try to dig into like, Well, okay, that’s the blocker here. That’s why everyone is feeling, you know, the way they are. How do we how do we like release that? So it’s very, I feel like it’s a very nuanced thing, right, like creative blocks happen in different pieces of the process? And you have to figure out what that piece is like, is it? Is it not, you know, figure like the messaging is lost? Or is it that the visuals do not convey the messaging appropriately? Does the story not resonate? Well, you have to It’s so nuanced. It’s like, I wish I had like a generalized answer for that. But in every project that I work on, sometimes there’s a blocker. And sometimes they’re very easy, and sometimes they involve multiple stakeholders. And I think it’s just figuring that out. You know, it’s being a player coach, it’s understanding, like, what is happening within your projects that you’re working on, and what your team is working on, to understand where you can kind of like, release, and then help those blockers. But it’s definitely like, you know, if you’re, if you’re sitting above everyone, and I know, you kind of go back to this, like managers, I think a lot of them are, you know, or maybe the perception, I don’t know what the perception is today. But perhaps the perception is that they don’t do much, but in my, you know, one of my experiences, like my role is to be heavily involved in all of these projects, understanding exactly what you just said, like, Where are their blockers, and my my goal, and my responsibility is to free up those blockers, and utilize the people around me and understand like, where I can step in to help and free those. So I really believe that that’s its player coach mentality within within the ability to help on that front

Aydin Mirzaee (Fellow.app)  17:00

end. So what are some questions that you would ask again, like getting a little bit tactical here, or there go to questions that you would use in order to help unblock progress on a project?

Melissa Rosenthal (ClickUp)  17:12

Sounds? So textbook, if I say it that way? You know, it’s like, it’s like, how can I help you? What are you dealing with today? Where are you blocked? I mean, I, you know, we have we have, if we’re working on a big project, we have daily calls. So we’re pretty in lockstep on where everyone is in the process. And across the the key stakeholders or the squad that’s working on the program, or the or the piece of creative, we kind of understand where we’re blocked, right? So I think it’s if they’re less, it’s less questions, and it’s more like going through where we are and what we’re dealing with and what we’re each working on. And understanding like, well, that’s being held up, why is that being held up? And then understanding like, you know, and also brainstorming together, I think, like, collaboratively, we free up a lot of those blockers as a team and as a unit, but it’s really not about asking specific questions. I think it’s about listening. And I think it’s about like, understanding, like, kind of the flow and where we are on something and seeing storyboards or, or like mapping it back to like, where we should be, it’s more listening and then stepping in, but it’s also around like, I mean, at least that’s not my style,

Aydin Mirzaee (Fellow.app)  18:18

I would imagine as, as clickup has grown, and, you know, the company’s grown a lot in the last few years. So how has the like, have you found that you’ve had to change your approaches on the creative process, as you’ve involved a lot more, you know, people, you know, for example, to get people aligned, very tactically, like, do you create strategy docs before things are, you know, started? And how does that all work today? How do you organize so many people?

Melissa Rosenthal (ClickUp)  18:46

I mean, when when we were a team of like, you know, only a few, and the team was, the entire company was 60. People, you know, you’re you’re making unilateral decisions, for the most part, and you’re like, we’re off to the races. This is a team, this is what we’re doing. You know, now we’re about I guess, about 1000. So it’s very different. There are tons of stakeholders involved in everything that we’re doing. So you know, the key is like creating a systematized way of actually operating on different projects, and understanding who the key stakeholders are creating a briefing process. All of this is great because it’s automated and done through clickup. So when someone submits or we’re working on a campaign, a lot of these things are filled out for us so we can ask those questions that we need to ask up front. And then basically the goal is to align on it before we get to the prop prop, you know, to the actual project and then have steppin points along the way when we’re checking in making sure we’re still alive. We’re still alive, we’re hitting that finish line, and we’re where we need to be. You know, of course, there are cases where that doesn’t happen or, you know, things change along the way you have to you have to reset but building those systems as you scale is just a necessity. But the funny thing is you can’t build a system from day one. So you just have to understand where you are and where you should be. If you step into a company that 60 people in your you know your creative team of three years. For and you’re creating robust process and systems people are gonna be like, What are you doing? You know, this isn’t this isn’t Amex? So you know, I think it’s a, it’s a balance of understanding where the company is, what’s the maturity level of the of the organization as a whole and of the team, and then understanding where you can put processes in, that can help and not block. Because there’s always like, over processing things, too, is my worst nightmare. Like, there’s just this now there has to be this Healthy Marriage of like, how does this help us do our job, but not block us. And there’s like, a very, I think, middle ground of what that looks like. And it definitely also pertains to the size of the organization, you know, I’ve never worked at it. Well, I actually have worked with a company that big, and that was very challenging. When like, when Chandra sold to Altice, the company was 15,000 people. So you know, when we went from a company of 200, to 15,000, of course, like the just the, the way that they went about things was so so different from a company that size. So it’s all about you know, where you are at your stage, how big you are, what you’re working on.

Aydin Mirzaee (Fellow.app)  21:02

Okay, they’re just a quick note, before we move on to the next part, if you’re listening to this podcast, you’re probably already doing one on one meetings. But here’s the thing, we all know that one on one meetings are the most powerful, but at the same time, the most misunderstood concept in practice and management. That’s why we’ve spent over a year compiling the best information, the best expert advice into this beautifully designed 90 Plus page ebook. Now, don’t worry, it’s not single spaced font, you know, lots of text, there’s a lot of pictures, it’s nice, easily consumable information, we spent so much time building it. And the great news is that it’s completely free. So head on over to fellow dot app slash blog to download the Definitive Guide on one on ones. It’s there for you. We hope you enjoy it. And let us know what you think. And with that said, let’s go back to the interview. I’m curious to dig into a little bit of the creative process. You know, and I don’t know if your your team is involved in I assume it’s your team that produces a lot of the videos and campaigns. And I mean, I’m a big admirer, I think I think the work is fantastic. To talk about the you know how you get to some of those ideas, I would imagine, sometimes people might come up with ideas that maybe you don’t agree with? Or maybe you have a very strong feeling that you shouldn’t approach it that way. I’m very curious, how do you reject ideas? Or like, how does how does that process work? It’s so tough, because

Melissa Rosenthal (ClickUp)  22:37

you know, I mean, I’m emotional about creative ideas, creative people are emotional, emotional about creative ideas. I’ll give you a very, like specific instance. So our Superbowl ad, we went into this group brainstorm with all of our team, and we came out with a bunch of like, ideas, we were laughing, and we’re like, these are this is it, this is it, these are the ideas. And of course, you know, specific people had written these ideas and come up with them. And, you know, as we started to go through the process of like, actually thinking about execution, given the timeline that we had, given all the resources, the limited budget, we were like, we can’t do this, well, this will be a disaster. And we workshop, and we workshop, and you know, at first and then you know, at some point, we were like we’re trying to fit, you know, a round peg in the square hole. And this is just not going to work. And you know, it’s hard because people get very emotionally attached to the idea. And I think you have to take them out of the fact that it’s their idea and have to say, the idea is that, like, we need to win and be successful as a company. If this idea that you’re very attached to doesn’t work, like it doesn’t work. So you know, as a team, we need to be aligned on everything, you know, and I think when the team is aligned, and we’re taking a vote, or we feel collectively about something, it’s much easier, but yeah, it’s very hard to reject ideas. When I reject an idea, I will typically say that it’s not aligned to kind of the objectives or where we’re looking to go. At first, I will not, like do that. Because generally, like, the ideas are good, they’re just, they just need a little bit of massaging or tweaking into, into what I think can become the version of the idea that actually goes out the door. And that’s, I mean, that’s how I work typically, like, a lot of the ideas that come to me are in a rough, they’re rough, right? And it’s like, okay, this could work, why don’t we try this, this and this, let’s think about this. And then they mature, and they get to a position where they’re, they are what they are. But yeah, I mean, sometimes I have to say, No, we have limited resources we have, we have to, you know, keep our focus. So there are times where it’s like, I like this, but not right now. Or this isn’t, you know, our priority at the moment, you know, maybe in the future, but you know, you have to have a backbone and reject ideas sometimes and, and just, you know, feel like you have to take your ego and emotion out of it. And I’ve done that and or I tried to do that. But, you know, if it’s helped the team to do the same thing.

Aydin Mirzaee (Fellow.app)  24:55

What was the process of coming up with the original ideas for the Superbowl ad?

Melissa Rosenthal (ClickUp)  25:00

We had a bunch of people in a brainstorm, we had done a ton of research, you know, none of us have been involved on commercials before. But we’ve never done a Superbowl ad. So we, you know, did a ton of research on what has worked well, statistics. And then we came up with concepts. And you know, it was just coming up with concepts that we thought were funny, that can bring our brand message to life in a really unique and humorous way. And, again, it was a great, great meeting, we walked out of there everyone feeling like we have like four solid ideas. And then you start to think about execution, and things fall apart, you start to write a narrative, you start to write a script, that has to be exactly 30 seconds, that has to tell a story. And, you know, if you’re moving from vignette, to scene to scene to scene to scene, you know, you lose a lot, because those scenes are each two seconds. So it’s how to convey a message in several scenes that are each two seconds long that tie back to an overarching brand message that feels cohesive as a story. You know, it’s a complicated process. And we were only we didn’t work with an agency, we only did it with our internal team, there was a lot of a lot of emotional tension, I would say, because people were locked in on ideas that, you know, in reality, we just couldn’t execute in both, you know, they didn’t make sense or timeline or budget or feasibility, they wouldn’t have worked. But you know, that was it was a lot because people have left that feeling really good.

Aydin Mirzaee (Fellow.app)  26:22

Or people tasked with doing the research, I suppose ahead of time coming up with concepts like everyone comes to the meeting with concepts in advance.

Melissa Rosenthal (ClickUp)  26:30

We structured it, where we did a kind of just, we had a meeting with our CEOs. And the goal was to come to that meeting and brainstorm. But we wanted to ahead of time have have ideas and have concepts and, and loosely written narratives. So we came up with like five different ideas and had come to that meeting, prepared to brainstorm on them. But the concepts went over so well, that we really didn’t brainstorm, we just thought started talking about the concepts. So leaving that meeting with like, these three solid concepts, you know, we were, we were excited about. And it was also we, you know, we didn’t have much time, so we really needed to figure out what we were going to do in the next week or so. So, yeah, I mean, for that meeting, specifically, like we came prepared, but we walked away, and we thought we’ve made a ton of progress, and we moved back, like, you know, then we tried so hard to make some of those ideas work, I would say we lost, you know, a bit of time trying to do that. And I think that’s again, like, it’s hard to shut people down. But I think taking the emotion out of it, it allows you to move quicker, when you’re not just like attached to something an idea, but it’s hard. It’s a you know, if you’re a creative person, that’s a part of it, you want to be attached to ideas, I think that’s also a huge positive and people that are passionate right there, they get attached to things that they’re, they’re passionate, and they’re proud of that they want to see it come to life. But um, yeah, it’s always the natural, creative tension. But yes, tactically, we came prepared to that meeting with several concrete ideas.

Aydin Mirzaee (Fellow.app)  27:51

Switching gears for a second and talking more about, you know, the hybrid workplace, a lot of companies, I mean, basically, everybody was all remote for a while, how are you all playing it going forward in terms of offices and hybrid, and

Melissa Rosenthal (ClickUp)  28:05

when I came on board, I brought a few folks with me, not immediately, but I hired them shortly after, and I had to move out to San Diego. You know, when you’re in a highly creative role producing things, you know, people will argue that the hybrid workplace is the workplace of the future. And I’ll agree, you know, I think like something as as large as a pandemic that made us like, see that we can do work a sync, and we can be productive. I think that’s 100% accurate. I think in certain creative roles, it’s very hard to do that, because you need to be with those people and work with them closely. So the majority of our team is located in San Diego, and we work together every day in person. There are people that are remote, you know, designers and people that are writers, which which makes sense. And they’re remote most of the time, but they do fly in for specific meetings, because it’s really, it’s hard to brainstorm a sync, it’s hard to align, it’s hard to like, get on the same page sometimes. So I think that for creative people, specifically, it’s important to at least have some of that in person face to face. How do I think it’ll shape out in the future, I think it’ll shave out that way. The teams that need to kind of be together, will, will be together or see each other more frequently. And the workplace will become hybrid, in most regards, though,

Aydin Mirzaee (Fellow.app)  29:17

is that specifically for your teams, or everybody in the company? Largely everybody’s coming back to work?

Melissa Rosenthal (ClickUp)  29:22

Yep. To headquarters in San Diego and Utah. And there were a lot of people in the office on the days that we would do a three day three day home today at work. But you know, there are a lot of people in all the time we come in every day, but you know, except today head on. Most most times were actually in the office and I would say there are a lot of people there which is great. I mean, I love it. I mean I’m that person that like kind of needs that like I love that interaction with my both my peers and other teams and I feel like sometimes you know, you lose that was just completely a saint hybrid work. But yeah, you know, where we do it effectively and I think obviously like a lot of that is owed to clickup If I don’t know, like without a sense of like that, if we would be able to be as productive, like, we’ve also had this kind of beautiful like organization of all of our process and our projects and steps and approvers. And we can do things just as well, a sink outside of physical productions, which you need to do in person, but everything else happens, you know, via the platform. So it’s really the, you know, the face to face brain storming creativity, actual production work that’s done in person, but everything else is done, you know, via clickup.

Aydin Mirzaee (Fellow.app)  30:27

I also did want to I mean, you mentioned you, you brought some, some people and hired hired them in afterwards, one of the one of the things that, you know, I read you posted on LinkedIn was, you know, a question that you typically ask during your interviews, which is asking candidates to share a situation where they’ve been wrong. Why do you ask that question? When? And what kind of insights do you get from it?

Melissa Rosenthal (ClickUp)  30:51

Because there have been experiences in my career where I’ve dealt with people that they don’t necessarily say that they’ve never been wrong, but they can’t admit when they’re wrong, or they they can’t say that they don’t know something. And I find that like, impossible, because everyone, you know, there are things you don’t know, right? And I think it’s an important question to ask, because you see, kind of the vulnerable side of that person. And like, you know, what were they wrong about? And like, why, and how did they How did they approach that? Right? And I think, you know, depending upon how I like to see who they mentioned, I like to see like what they were wrong about I like to see like how vulnerable they are in an interview to to admit that, and I like to see how they course corrected, there are a lot of benefits, I think, to understanding that question. But you know, I think everyone is wrong. And you know, to kind of have that insight into how they think about what that means and being able to be open. I mean, I’ll admit, when I’m wrong to the team, or I made a mistake, I think that shows that I’m human, and I’m vulnerable. And that like, you know, we all make mistakes, like we all do, and that’s okay, as long as we fix them moving forward, and we create a process or a system where they don’t break or something doesn’t happen again. But I do think it’s like, you know, I value that leadership, I’ve always valued that leadership. And I think it’s important.

Aydin Mirzaee (Fellow.app)  32:14

What are other ways that when you do evaluate candidates, or you look to your career, amazing people that you brought onto the team? What have been your observations on people who end up really succeeding on on the teams that you’ve been on? Or they’re, you know, other questions you ask or traits, you look for strategies or approaches.

Melissa Rosenthal (ClickUp)  32:37

So my number one, like or my number two, like things are passion and curiosity. And I think like, when you’re passionate about something, you know, you are driven and driven people just like, I think a, you create a really solid team, if you have a bunch of driven people around each other. If you have one person that is just kind of like, check in check out and you’re just startup like, it’s just not going to work. So you know, the passion and feeling the passion in an interview with someone when you’re talking about what they love to do, or, you know, like the best project they’ve ever worked on. I think just like getting that sense from them, is incredibly important. The other one is I don’t really ask this, I do ask this. But what do you do outside of work? What’s your passion? What’s your project, your hobby, and one person I interviewed a while ago, he was at my old at BuzzFeed. And he actually he’s very successful, runs his own giant, cool company called mischief. Now, I don’t know if you’ve heard of them, but they, they do. They did the the Jesus shoes with Drake, and they drop all these really crazy things all the time. They’re like, basically, like, culture makers effectively. But when I interviewed him to work at BuzzFeed, you know, one of the questions I asked was, so he was working at a tobacco factory during the day. And I said, Well, what do you what are you doing at night, like, you know, he showed me some of the stuff that he was working on. And he was working on all these kind of like viral interactive sites, and kind of like fun stuff that he was doing. And he would just spend, you know, all of his off time building this and taught himself how to code. And I was like, wow, like, you know, obviously, this person is so curious and so driven outside of what they’re doing on the day to day basis, that like, of course, I’m gonna hire this person. And, you know, he obviously went on to be like, very successful, but I think that’s a really successful trait. And it doesn’t even have to be, you know, like, when I’m out of work, I either, like spend time with my husband or I work or I do something else. But, you know, I think like finding like, you know, my, our video guy, you know, when he’s out of work, he’s like, either spending time with his family or he’s videoing and he’s working on his craft, or our motion graphics guys are teaching themselves on the weekend courses on how to be better. And I think like when you’re so passionate about your craft, that you spend time out of work, honing in on it, or learning other things, you know, that that kind of speaks to that. So it’s that curiosity. I love people that are passionate about their craft, and I think that’s really important and creative like you You have to find people that are like very, very driven, curious, passionate.

Aydin Mirzaee (Fellow.app)  35:03

Those are some really good examples and anecdotes on also asking about what kinds of things people are passionate about outside of work. How do you detect passion, though? Because, yeah, so what like, what would you ask? Is it in the way that people describe something? Or

Melissa Rosenthal (ClickUp)  35:20

when you’re talking to someone who’s passionate about something and what they do? There is a feeling right? Like, I feel like there’s an intuitive gut intuition. You know, when I’m talking to someone, and I’m interviewing them for a design role, and I’m like, what gets you excited? Like, well, when you wake up in the morning, and you’re working on something, what do you want to be working on? And if they’re just like, you know, like, there’s a way of feeling that out, I don’t think there are questions like that, that are leading questions that you can get them to talk about that. But you know, trying to get that person to open up, like, what’s the best project you’ve ever worked on? Who’s the best person you’ve ever worked with? What’s the best team you’ve ever worked with, like hearing those stories are going to allow you to understand like, is this person like driven and passionate, and like, maybe they’re not passionate about one thing, but they’re very passionate about this, or they love working with a team, or they love being an Icee. But there are certain things you can take away. And obviously, it depends on what role you’re hiring for. But I also feel like you can very much tell like if someone isn’t passionate person through just talking with them, and I make my comfort my interviews, like both, you know, I asked questions, but they’re also very conversational, because I think you can take away a lot from someone from just talking to them.

Aydin Mirzaee (Fellow.app)  36:25

I love the questions, too. So I had to tee it up. I think those are some really good, good ways to do that. So basically, these are the the few interesting things you’ve mentioned on on hiring so far. So obviously, finding people who are who are passionate, really passionate about something, the interview question around, just seeing if they have been wrong in the past is another key one. So I guess, on the being wrong part, and you’ve said, uh, you know, I, I’m not afraid of admitting when I’m wrong about things, concept of psychological safety, especially when it comes in a role that is you’re often getting feedback, you know, from other teams, and obviously, there’s going to be differing opinions, how do you kind of encourage that within your teams and make sure that there’s that safety and that trust amongst everybody who’s working together,

Melissa Rosenthal (ClickUp)  37:18

I always like to start off meetings by just saying, like, this is our team meeting, and we’re going to discuss everything and things will be hard in this meeting. And, you know, that’s okay. And we’re all in this together. And just kind of like creating that unity, I feel like the more that you can kind of create that. And also like, you know, I’m I’m right there with them, like I am with you every step of the way on this. And, you know, ultimately, like, the reflection is on me. So, you know, the psychological safety is like, I need to work with all of you to get this to a place where we’re all happy with it, and I feel confident with it. Because I’m never going to throw you under the bus for for something, it’s going to fall on me. So you know, there’s like that, that kind of like, I have to do that. Because it’s the reality of it. And also, I want the psychological safety of like, if you perform, and you do everything, you know, and we work together on this, like, I’m the person that that, you know, this will come back to you. But it’s also I think it’s just the way that you operate within a team, like the way that I work with my team, I speak with my team, it’s never like point and be like, go, go, go go. It’s more like this is the strategy, this is how we’re going to execute it, we’re going to do this together. This is where I’m going to be looking to do X, Y, and Z, this is what I’m gonna be looking for. But establishing that upfront is really important. But yeah, I mean, you know, I feel very strongly about player coach leadership. And I think that’s one way to really kind of keep psychological safety like top of mind, it’s the fact that that person is not like sitting so far above you, that you’re you don’t know what you should be doing. And you don’t feel like you can go to that person for feedback.

Aydin Mirzaee (Fellow.app)  38:52

Yeah, I think that makes makes a lot of sense. And I love the you know, you’re you’re right there with them and doing that player coach role. And I think that that makes a lot of the difference. You know, most of this has been very, very insightful. We’ve talked about hiring, you know, going back to the office, rejecting ideas, productivity, psychological safety. And we even went through the process of how you came about the Superbowl ad. So I think all in all, we’ve, we’ve covered a lot of very insightful things. One question that we ask as a final question for all the guests on the show is, you know, for all the managers and leaders constantly looking to get better at their craft. Are there any final tips, tricks, resources, or just parting words of wisdom that you would leave them with?

Melissa Rosenthal (ClickUp)  39:36

Having a like servant, leadership style and a vulnerability to leading is is the key to success. Like I think when people respect you and understand why you make certain decisions, and you’re transparent with them to the level that you can be like, there’s a lot of respect that you’re gonna gain from that and I’ve honed in on trying to do that more and more, like I’m doing this Because of XY and Z, and I want you to understand that, and having them understand where how a decision is made, it increases that because they trust you, they, they they know that you’re gonna, like, let them know why something is happening, especially on you know, if something was not right, you know, why not. And I think rather than just being like, fix this change this to this, it’s like, kind of going a little bit deeper with them is, is really helpful. So I’m always like, I think growing in my way, as leader and as a manager, I’ve really focused more on that. And it’s, there’s a lot that you sacrifice for that it’s giving a lot of yourself to your team, to make sure that they are successful, and they feel good, and that they are, you know, striving to grow every day and growing them. And at the same point, it’s, you know, not everyone wants to do that, because it is like, it’s tolling on people. But that’s why the right people that are leading teams or want to be doing that, because it’s such a different type of role than focusing on myself, I’m focusing on everyone else. So I’d say if you want to be a leader, you know, and a good leader, like there’s giving a part of yourself as a necessary part of the role. And that that means being an empathetic, strong leader that communicates really well and often and frequently with them and knowing that they’re, you know, they have they have that person that’s there for them.

Aydin Mirzaee (Fellow.app)  41:20

That’s great advice, and also a great place to end it. Melissa, thanks so much for doing this.

Melissa Rosenthal (ClickUp)  41:25

Thanks so much for having me. Really appreciate it.

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