Designing You and Your Team for Success: Navigating Leadership and Organizational Dynamics

Mamuna Oladipo at UXDX USA. Video: https://youtu.be/C-67vQB2wJY

Readable transcript: edited from the recording's captions for readability (fillers and false starts removed, punctuation and section headings added). Wording is the speaker's own. Timestamps are positions in the video. Names marked [?] could not be verified against the audio.

Introductions and the team today

[00:00:00] Ryan: Hey everyone. My name is Ryan, and as Joe just mentioned, I'm the head of design at Priceline. I'm also the brand ambassador in New York City for UXDX, so I'm really excited about today. I think we have two days of really great content lined up, and I'm super excited to talk to Muna today. I think this is going to be a really good one. Taking a look at your LinkedIn, you have a really impressive background. Maybe we could just start with you telling us a little bit about yourself and how you got to where you are.

[00:00:29] Mamuna: Sure thing. Currently I'm VP of product at Shopify. I've worked across a number of smaller and larger companies, from Bloomberg and Sony to small startups in LA and here in New York. I've led engineering teams, product teams, product managers, product design, data, research, you name it. It's been fun. So I'm here today with you, Ryan.

[00:00:59] Ryan: Awesome, great. Why don't we start with today? Talk a little bit about the team that you have today. What size team are you working with?

[00:01:08] Mamuna: I recently went through a change of team. I went from a 700-person team down to about 100, just a different shift in the organization. So about 100 people, 150 or so.

[00:01:21] Ryan: Wow, that's a big team. Could you talk a little bit about the composition of that team?

[00:01:29] Mamuna: It's a cross-functional mix of engineers, designers, product managers, and delivery managers or project managers.

[00:01:37] Ryan: Great. Just before we move on, show of hands here: how many of you are in person, or remote, at work?

[00:01:48] Mamuna: At work, at work.

[00:01:50] Ryan: Good point. How many of you are here right now with us? I'll be honest with you, I did piece that together; I knew you were all here. How about hybrid, at work, not here? Uh-huh. Okay. And how many are fully remote, at work, not here? Okay, show of hands, great. And what are you doing today?

[00:02:15] Mamuna: Shopify is fully remote. We have the concept of bursts, so in the event your team wants to get together to discuss a problem or work through something together, there are in-person locations where your team comes together and puddles [?].

Building culture in a large remote team

[00:02:34] Ryan: In terms of building culture on your team, you have a large team, so I think there are a few pieces to this. One, how do you approach building a good, strong, positive culture with a large team? And how do you do that being remote, compared to when you were in the office?

[00:02:48] Mamuna: It took a lot of trial and error for me. Today I focus a lot on one-on-one relationships, interpersonal relationships, understanding the needs of the team, keeping in mind that cross-functionally there just are different needs and different touch points. Everyone's just not the same. When I think about the touch points my design team needs during the week, versus potentially my delivery managers or PMs or even engineers, it varies completely. The types of problems they want to come together to solve or discuss are very different, so I'm very cognizant of that need, and I make sure that I carve out sufficient time.

[00:03:33] The thing I found, especially when you're building teams remotely, is that everyone wants to feel seen, and they want to feel that they are plugged in to anything that's impactful. They want to feel like not only are they telling you something, but they're getting something back in return. So a lot of my time is spent not just having them come together and tell me things, but me also coming to the table with information to share with them, so they feel like they are part of and plugged into the bigger organization. A lot of it comes down to team touch points, smaller group touch points and one-on-one touch points, but in each of these different groups making sure that there's a different meaning or purpose behind each one.

[00:04:15] Ryan: Great. Being a larger team, and now a remote team, have there been breakdowns in communication, or in how you want to scale the team? Could you give an example?

[00:04:25] Mamuna: There certainly have been breakdowns. For me the biggest one was in the transition during COVID, which I'm sure a lot of folks here experienced: transitioning from in person to remote, and how to do that meaningfully. In that world we were all thrown in and trying to figure out, okay, what does this mean, what is the shape of this thing? The teams were freaking out: how do I connect, how do I meet with people on Zoom all day? And I think we all had a bit of fatigue after some time.

[00:05:00] At the same time, a lot of companies were saying, what is this COVID thing, how are we going to shift strategies, how do we plan for the unknown? So there was a lot of change. For myself, the breakdown was that I was adjusting to remote, I was also adjusting to the new strategy, and I had forgotten that the team was steps behind where I was, because they weren't as plugged in to the changes. In a lot of instances where I had already digested the change, the team needed time and space to understand and digest the information for themselves.

[00:05:40] So today what I generally do is make sure that I'm scaling information as I'm getting it. If I learn something, I make sure my managers know, and I make sure they have time to ask questions and time to digest, and then they can scale it downward to the next group. So it's not just on me to share information; now it's myself, my managers, and whatever leadership group or team I have beside me, and we all feel accountable for making sure that the teams are caught up to speed. In the beginning I felt it was on me to do that, and that was my point of failure.

[00:06:16] Ryan: That's interesting. With such a large team, you're mainly communicating through managers down?

[00:06:24] Mamuna: Sometimes. I still will communicate directly to a team in all-hands and several meetings, but I realize I'm not going to get time with each person one-on-one for them to meaningfully ask questions as I would want. So it's being mindful of the fact that information may travel faster than me, and that's okay.

Leading cross-functional teams

[00:06:44] Ryan: Right. And now you have a cross-functional team, so you're managing a lot of different disciplines. In the past I think you've managed designers. For me, my background is managing design teams and research teams, and maybe some strategy sprinkled in. What would you say are the different challenges you face with a team of cross-functional disciplines compared to design teams?

[00:07:08] Mamuna: Initially I would oftentimes pull the different groups together, have meetings and share information, without really thinking about the needs of each of the different functions individually. And that did not work out so well, because different functions have different questions, they go into different depths, and they want to meet amongst their peers. So what I do differently is this. If I am just leading a team of PMs, or designers, or engineers, whatever it is, I know that I can focus on sharing the information in the way that I know they want to take it in. But if I'm leading cross-functionally, I may want to share the information broadly first, but then I need to meet with each of the functions separately, which is what I do today.

[00:07:57] If I share a change in strategy, I'm then going to sit down with my PMs, my delivery managers, my engineers and my designers, share the information, and give each of them space to ask those questions. I've found that a lot of times some functions are more vocal than others, and some personalities are more vocal than others, and it's easier for people to ask questions if you carve out their spaces, their niches. Then I can tailor my message or my feedback to the group as I know they need to hear it.

Advancing through different companies

[00:08:30] Ryan: That's great. Let's pivot a little bit here and talk about how you've navigated your career and changes in your career across various companies. What have you learned about advancing and maturing your career as you've progressed through different companies?

[00:08:49] Mamuna: I have learned that there are some things that are similar, but most of them are different. For me, I think I've found success in acknowledging that when I am starting in a new company, or a new team within the company, I start as if I know nothing, and I embed myself across the different teams. I engage with individuals, not in any type of hierarchy, but I just shadow, creepily watching people do what they do. But I enjoy it, and it helps me build empathy for what they do day to day. So if a person is complaining about a process, I don't just shoot it away. I know, okay, that is a challenging process, it takes six hours, and I wish we could improve it, and hopefully we'll get to do that. But I've felt it with them, so I know what that problem is.

[00:09:43] I think that has been helpful: sitting down, building empathy with the teams, understanding what their processes are, and then slowly working my way up to a point where I feel like I can start to give recommendations, give guidance, and then start to manage and lead the team. I've also built trust along the way. Oftentimes in the past, when I've come in and said, "Hey, I'm your new leader," and started to say things, people were like, "I don't know you, and I don't know why you are telling me to do these things. You don't understand what I do." And I find that there's more friction there. So it's a slow build for my teams.

[00:10:24] Then for myself, I spend a lot of time networking within the company. I will meet with folks across legal, finance, policy, whatever; I meet with everyone, and my goal there again is to build relationships. The worst thing I've found for myself is to meet a person for the first time during a moment of duress or stress. It is not a good time to ask a person for help or to tell them something is wrong. But if you know their dog's name, or you can talk about something, and then you say, "Hey, listen, this is not working out," they are more inclined to help you and support you, which is good.

Building trust

[00:11:06] Ryan: Yeah, I really appreciate that, in terms of coming in and taking your time and moving slowly. I think that's one mistake I've made in the past: coming in with ideas, and you're just excited to push forward, and then you realize it's not really the right thing. And then another big piece of it is trust. So how about strategies for growing trust within the team, which I think today is increasingly more difficult than in the past?

[00:11:29] Mamuna: The biggest thing is you put yourself in everyone else's shoes. The biggest thing I always ask myself is: why should I trust this person, or why should I listen to or engage with this person? In order to do that for myself, I have to know that they understand who I am and what I'm doing, and they have to speak to those Maslow's hierarchy of needs. It creates a space of safety for me. They have to let me know that, hey, if I make a mistake, it's okay, they're going to support me through it, and they're going to give me feedback, whatever it may be.

[00:12:03] So I'm really mindful of how I am as a manager. In my earlier times as a manager, people could see whatever it was on my face, and then they'd be scared to say, "Hey, I messed up," or "Can I get some help?" But in meetings I model what I expect. I'll be the first one to say, "I don't know, can you explain what this is?" And the team's like, "Oh, okay, great, they're telling me there's space for me to ask the question, or I can do this as well." So modeling for the team, but then also creating space for them to do the same thing, is important. I don't really react much in meetings. I'll just let people say whatever it is: "Okay, great, let's talk about how we can improve that," or "What do you think we could have done differently?" It's giving people space to share. And as a leader it's great, because you learn more about what's not working across your teams, versus finding out from wherever.

[00:13:00] Ryan: Yeah, and I think it's also good because it's not saying, "Hey, I'm the smartest one here because I'm the manager of the team," but "I also want to learn from you." I think that's the best way to really get work done.

[00:13:10] Mamuna: Yeah. And the day would be pretty boring if we knew everything.

Managing strategy shifts

[00:13:15] Ryan: Agreed. How about strategy shifts, which again I think is another relevant topic for today? Something happens, and we've been working really hard going in one direction, and now it's time for a pivot to do something new. It's often difficult to give out that type of news, and also hard to get that type of feedback, especially when you've invested so much time in doing something. Do you have any examples of strategy shifts, or times you've had to manage through change, and how have you gone about doing so?

[00:13:52] Mamuna: This one I feel is more common now, during this period post-COVID and during COVID. Personally, in the beginning I would just say it, rip the Band-Aid off and keep moving, and I wouldn't think about the impact that the shift would have on the team. If a team has to throw away work, which is a hard one, there was a lot of pent-up anger that would be stuffed in somewhere and would come out in different ways, especially in all-hands.

[00:14:29] But what I found is you have to take whatever it is and start to break it apart for the team. I may again pull my managers or a small group together and say, "Okay, this is the direction that we're going to be going down. Can you all talk me through your concerns?" That's the first layer I start to gather concerns from, and I will start to adjust my messaging, add things, take things away based on the feedback I'm receiving, and craft the messaging from there. Then I will work with those leaders to communicate it out. If it's a shift that is significant, I won't put it on my leaders to say it first. I'll say it first, and I'll take the brunt of whatever it is, and then my ask is that my managers, or the leaders around me, echo everything that I say. My hope is that they'll have a sense of what has already been asked and what has already been shared in terms of feedback, so they're prepared for their own conversations.

[00:15:31] After that happens, what I tend to do is have smaller group sessions. I start to do groups of three or four, depending on the size of the team. It takes a while, but I've found it's worth it. If people don't understand, or if they're not bought into a shift, the shift won't matter, because people won't do the work in any meaningful way. So you have to get them bought in. It can be time consuming, but it is worth the investment.

Q&A

[00:16:03] Ryan: I love it. I love your approach to communicating with your team. I have a lot more questions for you, but I know that there are audience questions coming in, so let's open it up. I know it's over here; I'm always the one who can't see that screen, so I'm going to look up here. How do you handle disagreements between product and design?

[00:16:25] Mamuna: Oh, that's a good one. It depends. Sometimes I find the disagreement is in an approach, or the disagreement is in the people and how they communicate. So my first approach is: what is the disagreement on? Are you both saying the same thing, and you're just not happy that one person's saying it and the other person's not, or whatever it may be? But if it truly is about an approach, it's subjective sometimes. I hate to use the word "depends," but it really does depend on the situation.

[00:17:05] A lot of times you have to coach people through the conversation, because if you come in and pick a side, and you are leading both of those functions, one function will feel slighted. So you want to coach them through and help them get to a solution. A lot of times I won't come in and say, "Obviously this is the right answer." I will coach them through and help them try to communicate and understand what would be the best approach. Oftentimes it's a little bit of both that we can take forward. But I try not to come in and pick a path, unless there's a blindingly obvious one that we should be taking.

[00:17:46] Ryan: Yeah. And I think sometimes it's also helping people craft that message, because you could say something the wrong way or the right way.

[00:17:52] Mamuna: Exactly.

[00:17:54] Ryan: If you say it the right way, you're going to get a positive response. If you say the same thing not the right way, then all of a sudden it just leads to more conflict.

[00:18:00] Mamuna: Yeah. But one thing I would say on that is that one thing I'm mindful of is how quickly decisions are made. Sometimes it is a very timely decision, and there's not a lot of time to do the coaching back and forth, so you have to be very mindful of the balance there.

[00:18:16] Ryan: Sure. I'm going to go to another question here; it looks like we've scrolled down. How do you measure mood and morale with a team of 700 people, and how do you get the vibe, especially in a remote setting?

[00:18:31] Mamuna: Tools, honestly. Sometimes I do a weekly poll with Slack, and just have a little Slack bot that pops up for people, and people push one through five: how are you feeling, what are you working on? There are a couple of questions that go out to the team on a weekly basis, so I can see whether the person feels connected to a larger mission or project, and I can see their overall morale. And then if there's a question, they'll ask, "Why are we doing this?" or whatever it may be. They can choose for it to be anonymous or they can put their name on it. Most people put their name on it. So I can quickly take a poll of the team and see where I need to spend more time.

[00:19:14] Ryan: Yeah. We have a Donut channel where you randomly get paired with somebody at the company who you normally wouldn't meet. It's interesting, because that's across an entire company, and you could do that on a team with 700 people. How do you define the boundaries or roles between product and research and design?

[00:19:36] Mamuna: I have never been one to carry hard boundaries. I think it's important for teams to build empathy for each function, so I encourage people to pair: product and UX, product and whatever. I encourage all folks to pair, just so you understand what a person is doing and how they're thinking about a problem, so that it doesn't come to you as a surprise. Oftentimes I will have a RACI, where I'll say this person is responsible, this person's accountable for a decision, so there is clarity even though you are pairing. Normally when I'm working with larger teams, there is a RACI that we have where we say, okay, for this type of project, if it's research, if it's the shipping of a product, for the different phases of the product life cycle, I'll have a RACI where each person knows they are the accountable party for moving this along to the next step.

[00:20:28] Ryan: Right. And just a quick time check: it looks like we might be up on time. I don't know if we have time for one more question. Peter's has been up there for a while and then disappeared. What is your perspective on moving design jobs abroad? We'll wrap up after that one.

[00:20:41] Mamuna: I think it depends on the company, honestly. I've worked with companies where we've had design in house, and that's the way Shopify is currently. But then I've worked at companies where we've had design in Ukraine or in other places, and it really just depends on the need of the organization. We had designers in house, but then we would need to scale for a project, and we would go out. Again, the biggest thing there, if you want to be successful, from my experience, is scaling the communication and making sure that they feel like they're part of the team, because they can be unhappy too, and the quality of their work can go down.

[00:21:19] Ryan: Great. Well, it was amazing talking to you today. I know I learned a lot, and hopefully people here got something out of it. All right.