It’s an uncertain time in the product and tech landscape—and the corporate world at large. Industry leaders Mamuna Oladipo, vice president of product at Shopify, and Lola Oyelayo-Pearson, director of commerce and consumer product at Mysten Labs, share insights to help you navigate career challenges in this episode of the Cornell Keynotes podcast, guest hosted by Keith Cowing, visiting lecturer at the Cornell SC Johnson College of Business and Cornell Tech.
If you are feeling a little lost at work, especially in product and tech, rest assured you’re not alone. In this episode of the Cornell Keynotes podcast, brought to you by eCornell, tech leaders Mamuna Oladipo, vice president of product at Shopify, and Lola Oyelayo-Pearson, director of commerce and consumer product at Mysten Labs, deliver tips to help you pivot during crisis, communicate with clarity and more. Guest host Keith Cowing, visiting lecturer at the Cornell SC Johnson College of Business and Cornell, moderates the discussion.
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Want to hear more from Lola Oyelayo-Pearson and Mamuna Oladipo? Subscribe to their Lost in Tech podcast on Spotify or YouTube.
Join Keith Cowing, Mamuna Oladipo and more industry leaders and Cornell faculty experts for the Product and Tech Leadership Summit, taking place this September at Cornell Tech in New York City. During the immersive learning and networking experience, you will discover how to leverage transformation techniques to build high-performing products and tech teams. Seats are limited – register today!
Learn more in one of 30 online technology certificate programs from eCornell, including Product Management, Product Management 360 and Generative AI For Business Transformation.
Chris Wofford: On today's episode, our friend and guest host, Keith Cowing from the SC Johnson College of Business here at Cornell is joined by tech leaders, Mamuna Oladipo and Lola Oyelayo Pearson from Shopify and Mysten Labs, respectively, to discuss uncertainty in the product and tech landscape. We're going to learn about how to pivot during a crisis, how to communicate with clarity, how to lead with transparency and purpose and how to constantly evaluate why you're doing what you're doing and then figuring out how to do it better.
Chris Wofford: I think many of you will relate to this discussion. Be sure not to miss Lola and Mamuna's podcast called Lost in Tech. And you can see the episode notes for a link to that. And a hot tip for you listeners this September, you can join Keith Cowing and Mamuna Oladipo and more industry leaders and Cornell faculty experts for the product and tech leadership summit, which takes place at Cornell tech in New York City again, this September.
Chris Wofford: So see the episode notes for more details. And now here's Keith, Mamuna and Lola.
Keith Cowing: Mamuna Lola. So excited to have you. Welcome to Cornell Keynotes.
Lola Oyelayo-Pearson: Pleasure to be here.
Keith Cowing: Awesome to have both of you here. You have tremendous experience and perspectives globally across different companies, across different cultures. And today we're talking about change. We're talking about people or companies that have felt lost and how to find your way. We've had a ton of change, a global pandemic, a market crash, AI, all at once.
Keith Cowing: It's a lot to deal with. And so I want to hop right in. Fun story, Lola, I was looking for things that were not on your LinkedIn profile, and of all places, I found a story about you hurting your knee, and instead of going home and sobbing, you ended up in a magazine. Tell me about this story.
Lola Oyelayo-Pearson: Yeah, this is a funny one.
Lola Oyelayo-Pearson: So, uh, this is uh, few years ago, I was working, in an agency. And we were, we called ourselves like the V1 agency. So we, rather than kind of hiring a design team or an engineering team, we were like a product bundle and we would come in and help you do digital transformation. So figure out your process, figure out your product.
Lola Oyelayo-Pearson: So we had a lot of in-house fun because we always wanted to be aware of things ahead of our clients and we wanted to be kind of playing with opportunities and then, you know, we create these internal projects that allowed us to do an end-to-end and then be able to talk about it credibly with the client.
Lola Oyelayo-Pearson: So I was running with my trainer. And I'm hyperflexible, hypermobile for people who know that, which, you know, I think we used to just call it double jointed and I managed to do something really awkward when doing a sprint drill and I snapped my anterior cruciate ligament, so ACL, which is a very common sport injury and I was given this mechanical brace that didn't do anything, but it prevented my leg from hyperextending whilst it was healing because there was no ligament to prevent that. And so I walked into the office one day and everyone was like, Robo Lola. And I was like, it's mechanical, like, what the hell?
Lola Oyelayo-Pearson: And I'm in a lot of pain and I was really grumpy for ages. And one of the co founders, he came to me and he was like, Hey, what if it wasn't mechanical? And we basically invented a project where we looked at the data that I needed, my physio needed, my surgeon needed for my knee. And we built a basically wearable knee brace.
Lola Oyelayo-Pearson: And so it was basically tracking the range of movement I would have every day, the number of steps, and then it uploaded it to this webpage. And then I could take that webpage to my Physio. And then she would look at it and then we would figure out how to adjust my exercises and then my surgeon. And so I had a pre surgery period that I had to do.
Lola Oyelayo-Pearson: And so while we were awaiting the surgery, we built the leg and, you know, the team was really like, we had Meccano bits, we had a raspberry pi. You know, we bought sensors ourselves and we welded and put the whole thing together in the office. And then after my surgery, we used it as a live experiment.
Lola Oyelayo-Pearson: And so everyone would get a weekly data update on how I had been that week up until the point at which I was discharged. And so the runner's world approached me because a physio had been talking to somebody else and wanted to do a profile. And so I ended up in runner's world with like a photo shoot.
Lola Oyelayo-Pearson: It's very weird. I was very awkward. I'm not okay in front of a camera in that way. But it was a really great experiment. We got to have some great conversations with people like Adidas. We spoke to the company that manufactured the leg brace and talked about wearables. We learned a lot about the wearables market, the, you know, pricing of physical devices, especially tech that's like always connected.
Lola Oyelayo-Pearson: And you have to think about batteries and stuff. And we never did get any work out of it for various reasons. I, there's a lot of, long term investment involved, and it's very difficult for a startup to enter the wearables market. Actually, that was one big takeaway is the market was locked in, but it was a fun exercise for our team in building something like that and seeing it come to life and then having a real use case. Like I did genuinely use it post surgery as part of my like recovery and data sharing. And I've been obsessed with wearables since, and you know, I'm now part of the Apple family, although I resisted for a while.
Keith Cowing: I think there's a great metaphor in there around falling down and bouncing back, getting back up, finding a learning experience in something. I love the saying, "never let a good crisis go to waste". What else did you learn from going through this about yourself?
Lola Oyelayo-Pearson: I mean, I think there was a lot of resilience on a personal level, the actual fall wasn't a great thing. My husband was planning to propose two weeks later on a holiday in Santorini, which if anyone has been to that island... well, I didn't quite blow it, but he was very annoyed that he had to carry me on the beach the morning that he ended up proposing.
Lola Oyelayo-Pearson: I wasn't aware, but I should have just, it should have been a lovely walk along the beach. He was not happy with that. But I, you know, I think never let a good crisis go to waste is a really good way to put it. I definitely felt much more empowered through the process because I got to build a thing. And I'm one of these people, like I love hard problems and I love kind of going head first into something that I haven't done before.
Lola Oyelayo-Pearson: And, you know, it made it easier to think about this scenario where I felt a little bit like a victim with physios and doctors. If I could go in with data that I had collected myself and say, Hey, here's what my range was. And this day and I tripped and I stumbled. And so I felt, you know, I know myself well enough to know that if the more informed I am, the less nervous I am.
Lola Oyelayo-Pearson: And that process actually really helped to kind of validate my approach to how I try and go through things in general, which is just, give myself more information so I'm much less nervous and much less anxious about the situation. Just also to have a lot of fun with stuff that goes wrong it was a very interesting six month period, put it that way.
Keith Cowing: And Mamuna, I heard a story on your side, actually about getting laid off and how that impacted how you think about yourself, how you think about risk taking walk us through that, what you learned from it.
Mamuna Oladipo: Yeah, so when I worked at, it was the Orchard, but it had been acquired by Sony Music. I was in this role for about four and a half years or so.
Mamuna Oladipo: Very just settled in the role, kind of looking for the next thing, but just like, you know, head down doing the work. And I came in one day and they laid off, myself and a bunch of people under me and I was completely blindsided. I hadn't prepared anything. It was just, oh no, what is this? And that moment, I think the day of, it was like just drowning, like all the fears, all the emotions, everything just hit me all at one time.
Mamuna Oladipo: And it's like, I don't know what to do. I don't know where to start. It's like all the things I'm sure that a lot of people today are feeling just with the current climate. And so I remember like a week into it, I was like, it's just very down, like trying to. I was panicking, like, okay, how do I find the next thing?
Mamuna Oladipo: What do I do? Just frantically thinking about, you know, those next steps. And I was talking to a friend and he was like, you know, you're lucky. And I was like, what do you mean I'm lucky? What are you talking about? And he's like, you know what it feels like. That's it. Like, you have nothing to fear here. You're done.
Mamuna Oladipo: And I was like, no, like, what does it mean? And after some time I processed, like, what he was saying. And basically he was saying, it's like, you now have gone over, like, that hill of the unknown and it's known. And so from here on out, you have an understanding of this feeling.
Mamuna Oladipo: And so now it's like up to you to decide what you want to do with that. And it just sort of turn a new page for me in that I was able to now say, okay, like, let me take a quick second. Maybe it's not as bad as I think it is. And this is just for me, you know, I'm sure everyone has different circumstances, but for where I was, I wasn't like job hunting.
Mamuna Oladipo: I wasn't networking. I wasn't doing any of the things I probably should have been doing. So I said, okay, like it was close to summer. It's okay. Let me just take some time. Think about, you know, that environment I was in, was it an environment I could thrive in? Was that the right setting for me? You know, if I were to take a new role, what would be good for me?
Mamuna Oladipo: I was feeling burned out and tired. I said, okay, I'm going to give myself some time. I'm going to evaluate just what I want to what's going to be next for me? And that was just a good reset. And I think maybe the dangerous thing about that is that I now have no fear of that. Not to say that I go to work recklessly every day looking to be terminated, then.
Mamuna Oladipo: But I definitely operate in a world where I don't fear that, like, there is no sense of like, oh my gosh, if I don't have this job, there's no me, there's nothing I can do. I know that there is always another opportunity. I know that I can stand on my feet. I, you know, just want to, you know, encourage folks who have been laid off recently who are going through this phase to you know, find their footing and take the moment to see it as an opportunity to kind of reset, understand what you were doing, if that was a good fit to what you want to do, what environments you thrive in.
Mamuna Oladipo: Lola, you always have like a good analysis for opportunities.
Lola Oyelayo-Pearson: The three questions. Yeah. The, my personal three questions that I asked myself, but I also mentor people and I always share it, which is like at any point in your career, whether you're employed, unemployed or what you're looking for, you kind of say like, what is the job that I'm doing day to day? And does it feel good? Am I happy with that? What is the environment that I'm working in? And do I like that environment? Am I happy with that? And what's the growth trajectory that I can see in front of me? And am I happy with that? And the answer to all three questions won't always be yes but depending on the answers, you're checking in with yourself to be like, am I okay to stay or do I need to change something?
Lola Oyelayo-Pearson: And it could just be, here's a conversation I need to have with my boss about, hey, I kind of want to shift what's happening in my day to day, but I love this environment and I feel like there's an opportunity here, or I feel like I'm not growing. In a layoff context, I think it's also like what didn't work for me in that previous environment or what did and therefore what do I need from the next environment in the next role to kind of be in a better position.
Lola Oyelayo-Pearson: And I think whatever happens to you, as long as you're always being honest with yourself about what brings out the best work and the best kind of emotional well being for you at work, then you're always going to gravitate towards something that does long term have, you know, a good outcome for you. But if you're, you know, I think people who, you know, and maybe to tap into like a zeitgeist, I think there are some folks who are almost going through layoffs and it takes them a while to realize that it was a blessing because they actually really hated their job or they read that they were working at a company that everyone was like, oh my God, you're doing so well, but they hated what they were doing.
Lola Oyelayo-Pearson: And so they're starting to realize that If they ask themselves this question, maybe you are a better fit for a different environment, a different brand, a different context. And being laid off allowed you to make, take the time to have that reflection,
Keith Cowing: Let's talk about one keyword I heard in all of that, which was fear.
Keith Cowing: And you talked about having fear, getting past the fear, getting the confidence and the swagger to really have your own agency, have your own optimism. And I see this on organizations too, not just individuals. I coach CEOs and chief product officers and frequently they'll say, oh, we need a new strategy or we're not moving fast enough or the roadmap is broken.
Keith Cowing: But then you dig under the covers and you find actually you're missing collaboration at the team level. And that's the core problem. And why is that? Well, there's no trust. Why is that? Well, because people have fear and when they have fear, it's going to lead to bad decisions. It's going to lead to them being closed, not being open, not having transparency.
Keith Cowing: I'd love to hear you talk a little bit about what you've seen in companies that can cause fear, micro behaviors, and what you've seen in companies that can get past the fear and generate that optimism, that energy, that agency that really helps companies move fast and deal with, okay, we've been through all these changes.
Keith Cowing: Now what's next? How do we get our swagger back?
Mamuna Oladipo: The foundation is, for me, is Maslow's Hierarchy of Needs. Is it? And that the base foundation is, I think, a psychological safety. And what happens in a lot of environments is that individuals, maybe they don't understand how their jobs fit into the overarching strategy.
Mamuna Oladipo: Maybe they have a manager that doesn't see them or like feed energy into them so that they feel like they're growing. But there's uncertainty in their day-to-day. And what happens in that type of environment, like what Lola was saying earlier, you don't actually know, you know, how you're doing, how you're performing.
Mamuna Oladipo: So there's a lot of uncertainty into just like, do I, am I doing the right job? Am I doing enough? Am I secure in the work that I'm doing? And once you're operating that space, you either are going to burn out because you're, putting pedal to the metal, maybe in the wrong direction. You're not getting that feedback.
Mamuna Oladipo: It's an empty space to drive in. And if you have a lot of people sort of in that same setting, you'll find that your team of individuals are not operating efficiently or effectively. And once I was brought into a company where they said, oh, you know, we have a team of 12 people, but you know, they're not efficient and effective.
Mamuna Oladipo: So, okay, and you talk to the individuals, and they are very competent, very knowledgeable, but it's just that they haven't been given something that they can attach to and say, okay, I understand what is expected of me. I know how you're measuring success of me. I know how I can drive this thing forward.
Mamuna Oladipo: And so in that world, really it's on the company to say, okay, here, first I see you, here's what I need from you. Here's how I'm measuring success. Here's the thing that we as a company need to achieve. And here's how your role plays a part in that. And that level of clarity can do a lot to not only create just align directional thinking, but also for the individual, they understand how to measure themselves within the company.
Mamuna Oladipo: So they know that they have impact. What are your thoughts on that Lola?
Lola Oyelayo-Pearson: No, I would build on that. I think a hundred percent through that. The first point you made about like, what am I contributing to? That I think we've over talked it and people kind of dismiss the value of mission clarity, but it really, helps everyone to understand why am I here?
Lola Oyelayo-Pearson: And you know, we met at a company where the mission clarity was absolute. We knew we were powering entrepreneurship. We felt passionate about that individually. We understood that problem space and it helped to show up for the company. Even when you disagree, you kind of feel that you're able to kind of respond to that on an emotional level and it charges up a lot of the decisions and a lot of the uncertainty you might face, but I think there's 1 additional factor that people do underestimate.
Lola Oyelayo-Pearson: And I think a lot of large companies that diversify or have a lot going on also miss. Personally for me I think I need the north star, but I've also found understanding how we make sure we're doing well or we're meeting our objectives is like so foundational. And a good example of this is in tech. I bet, I don't know, 5 out of 10 people working in a tech company today, unless it's a traditional commerce business that sells like online retail, they do not know how their company makes money.
Lola Oyelayo-Pearson: And the problem with that then is I'm optimizing for the North Star. I am aspiring towards this bigger goal that we have, but I actually don't know how I ensure how the company makes sure I get paid. And so I start making decisions that undermine the bottom line. I start over investing in an opportunity or I don't have any fiscal control.
Lola Oyelayo-Pearson: And then comes the negative impact of that, which is we've got to cut people. We've got to make changes. We've got to do all of these things. And then you reintroduce fear because in not understanding the business model of where you're working, suddenly everyone's attempts at following the mission don't really work because you've got to follow that mission, but you've got to stay on budget.
Lola Oyelayo-Pearson: You've got to make sure the money's coming in and you've got to do the ROI game. And that absence of commercial context I think is undermining a lot of tech businesses today.
Keith Cowing: And can you walk us through some specifics? Put us in the room. You've been in a bunch of different scenarios, Lola. You've been in financial services at Capital One, you've been at Shopify, agencies, blockchain, really different environments.
Keith Cowing: Tell us a behavior or two that you've seen specifically in a Zoom room, in a conference room that bred fear, even without the leader understanding it, or that got rid of fear and help the team really be informed and empowered.
Lola Oyelayo-Pearson: Yeah, so I'll give you an example of my time at Capital One, which I really enjoyed when I was at Capital One in the UK, I used to lead the design organization.
Lola Oyelayo-Pearson: It's a much smaller business in the UK, but it carries over a lot of the brand values, the ethos of the bank in the US. And one of the challenges that we used to have is bringing Capital One went through this reinvention, I think mid 2000s, where it really wanted to become a Fintech, right.
Lola Oyelayo-Pearson: Wanted to move from this and it's always been a progressive bank. So it's been very different to your traditional bank. They always use data really well. They always wanted to invest in tech, but then they wanted to transform. So they went all in on scrum and, you know, embedded tech teams and sprint management, and really wanted to kind of adopt this tech first culture.
Lola Oyelayo-Pearson: But one of the challenges they had was now they were hiring people who didn't come from financial degrees, financial backgrounds and so you would bring in somebody who'd kind of graduated from software engineering or from the school of arts to join your design team. And you would want to mobilize them around the mission, but they didn't understand how banks make money.
Lola Oyelayo-Pearson: And so you would often end up in the room where you're discussing a feature. And I remember at one point we were discussing an opportunity around something. We were discussing an opportunity around what became known as the buy now pay later phenomenon, right? So I was at Capital One in the UK ahead of when the UK's biggest player Klarna really kind of hit and we had research behavioral research, not you know, hard facts and statistical data, which is quite key.
Lola Oyelayo-Pearson: And we were kind of making this call that like, hey, we really need to go after this opportunity, but we couldn't price it. And the team that had done that research had basically gone and done interviews and they'd modeled scenarios and they'd built prototypes and they had confidence behaviorally that this thing was going to be a huge thing, but they didn't understand the Capital One is a business basically makes every decision on margin.
Lola Oyelayo-Pearson: And so you have to build the business model first, then you build the customer interaction. And they did not have that foundation. They did not have any of the kind of financial plays and the upside downside planning that was expected before capital one takes a step into a new business area and launches it.
Lola Oyelayo-Pearson: And because of that, Capital One said no. And within a year, Klarna was huge in Europe. And I remember talking to the UK MD at the time when she was the head of marketing. And I was like, this was a really big moment for me personally and why I chose to leave, because I felt like we had misaligned people who didn't understand the business model and didn't understand how to get a decision made.
Lola Oyelayo-Pearson: But they were really passionate about the opportunities and it created this dissatisfaction and it just made for like really negative pushback. And I know some of the design researchers had spent a year on this product. They'd really invested time in it, but this inability to do the business modeling totally removed away the value.
Lola Oyelayo-Pearson: And they just felt. And there's no one person to blame, but I think Capital One kind of reset at the time we reset. And so every new person had to spend like a week understanding card business modeling and like, how do credit cards make money? How do banks make money? What are the ways in which the company considers bets and how do they build risk models?
Lola Oyelayo-Pearson: And then, you know, from a design perspective, we had to think, how do we as designers put behavioral research into database financial modeling so that we don't look like the idiots in the room next time where we're talking about an opportunity. And it was a huge learning curve, but for me also was kind of, yeah, this is not the right environment for me personally.
Lola Oyelayo-Pearson: And I didn't, I didn't want to do everything based on risk management first, but I respected that that's what worked in that organization. And if you didn't align with that, you probably weren't going to be successful there. And I think in any environment, the same thing plays out.
Keith Cowing: And it sounds like a missed opportunity. And then the organization learned from it. And there was some amount of evolution. Mamuna, you've also had a great set of experiences. You have a global perspective. You've learned, lived in many countries, many continents. You've been at places like Shopify and Kickstarter, the U. S. State Department, Bloomberg, government, et cetera.
Keith Cowing: Yeah. Give us an example on the positive side here, something that a leader did well, a behavior that got people to not act out of fear, but act out of optimism and agency and be able to take the right risks.
Mamuna Oladipo: So I wouldn't say that the two were coupled together, but I've worked at environments where the leader, CEO, whomever it is, clearly articulated what it is we were there to do and how they were looking for us or how they were measuring us to be successful.
Mamuna Oladipo: So it was that it just trickled down. So they had clarity in the direction we're trying to go. And then their direct reports had clarity and that just kept going down. And there was a lot of, I say education and training, but there was a lot of material available made to individuals to understand and connect at that level at all levels.
Mamuna Oladipo: So we could read what the CEO was reading and what their direct to C level was reading. Ask questions and that environment, you know, you have folks who kind of like questions. Okay. Well, why are we taking this direction? Why are we taking that direction? And people, while they may not have agreed with the direction, they felt heard in that they were able to ask questions.
Mamuna Oladipo: So it was that disagree and commit and people were empowered to take steps, make suggestions. Okay. I see you're looking at this metric. I have some ideas on how we can move it forward. And folks could say yay or nay. And so in that environment, it's almost like it feels two way, even though the CEO said it's setting the tone and say, hey, here's what we're doing. And this is who we're doing it for. This is how we're measuring it and whatnot. Individuals at the bottom still felt that they were having some agency to ask questions, drive direction, influence the roadmap. And so that's important in my opinion, I've worked in places where the CEO did not have conviction and direction.
Mamuna Oladipo: They were not sure how to measure success. And really folks with the bottom were saying,hey, I have all these ideas. You know, let's put this as our metric and every, you know, different teams measuring success and it can get very chaotic. And in that world, you know, you have a CEO growing frustrated stakeholders, board members, et cetera, saying, hey, what's going on?
Mamuna Oladipo: Yeah. And the CEO saying, hey, this team's not efficient, or, you know, when really it starts at the top for that lack of sort of glue. And so in places I've worked that have created that stability, it has been that at the top, there is clarity, there's decisiveness, there is communication, clear communication, but also going from the bottom up, there's opportunity to communicate.
Mamuna Oladipo: I think that's the thing that is missing in a lot of places where. Um, you may just have people top down to say, hey, do this thing. And folks are like, okay, I hope I do this right. You know, the managers are like, hey, just, you know, out of fear as well. Like, hey, just please get this thing done. This is how you're being measured for success.
Mamuna Oladipo: And they may not themselves even know how to direct their direct reports, because they don't feel comfortable asking questions higher up, right? So they're just like, oh, this is what I was told. Okay, why were you told that? Who are we doing it for? I don't know, just do it. You know, and then it starts to trickle down and folks like, I don't know why we're doing this.
Mamuna Oladipo: I'm just doing it. So like, let's see what happens. And after some time, you just get mediocre work. At the higher level, you start asking, why am I getting mediocre work? And as you look down, you start to see your messages watered down. The folks who are communicating the message don't understand your message.
Mamuna Oladipo: They don't understand how they themselves are being measured. But everyone is living in a space of fear because they're afraid to ask that person on top to say, could you pause for a second and clarify?
Keith Cowing: Let's tease out that dichotomy a little bit. Leadership is full of dichotomies. One of them here is clarity and conviction, but also empowering people to ask questions and saying, I have some of the answers, but not all of them.
Keith Cowing: And this is a direction yet, I want everybody to be able to question things because that's one of the key skills in the organization. If you're coaching a team, a leader, whether it's at the CEO level or a new employee that has to be a leader in their own right. How would you coach people to exhibit the behaviors day to day where you can balance conviction, yet encouraging people to ask questions, especially in an environment where maybe they had conviction and then an asteroid hit called COVID.
Keith Cowing: And you had to rethink a bunch of things. And then an asteroid hit and the market was down and the budgets from your customers totally disappeared. And you had to rethink and AI hit, and now you have to rethink. And so you might have conviction. And then all of a sudden I have to figure it out again. So there's these moments where you can feel lost temporarily and you have to find your way again in that moment.
Keith Cowing: How would you coach a team to balance conviction and being open to being questioned?
Lola Oyelayo-Pearson: So many thoughts on that one. You know, I think our caveat, what's the largest team I've ever led is probably 200 odd people. So this is not like multi thousand multinational advice. But I think the thing for me that I have observed, worked for me as somebody participating in an organization that had to make decisions in difficult or pivot in difficult times, and certainly that I try and apply to my leadership style is to just state very clearly where you're at. Here's what I know for sure. Here's why I feel confident that this path we're going to go down is a path that we should go down.
Lola Oyelayo-Pearson: Here's the stuff that's unknown. And this is what we're going to try and use as a measurement to help us correct. Um, and I'll tell a story about something that I ended up using as a tool a few years back. So in the same agency, we're doing a digital transformation project for this not-for-profit, which was a super interesting world, like not for profit that was cash rich in the music industry.
Lola Oyelayo-Pearson: So they don't lack funds to invest and they don't need to just make profit. So this creates a very weird business context. But they had to digitally transform. So we're talking about pre-streaming era. everything is changing around them and they need to serve their mandate really well. And one of the things that we had to develop was this you know, they were looking at things like OKRs and ways of communicating.
Lola Oyelayo-Pearson: How do we go towards this digital era and like help people understand what they're doing? And we ended up dumping them and developing something called GRIP. Right. And it was, what numbers do we need to see grow? What numbers do we need to see reduce? Recognizing that there's a tension between these. So we can't be profit seeking while we're making massive investments.
Lola Oyelayo-Pearson: We can't be cost cutting massively when we're shifting the shape of the organization. What improvements need to exist in the culture? So the things like, you know, team norms, process norms, productivity, and then what potential that we invest in it on the assumption that it's If we have to do digital transformation now, we should never digitally transform again.
Lola Oyelayo-Pearson: And this kind of GRIP view of like metrics, it ended up working really well because at the senior level, you could set five to 10 things across those four categories that really matter to you. And then you could hand it over to department heads and they could take those five to 10 and then interpret them still inside the GRIP.
Lola Oyelayo-Pearson: And they could say, well, my version of helping to grow that number is probably focusing on these three things that are in my control. And as much as it was like a painful exercise and everyone was like, where did you read this? Is there a book? Can I go to do an online course? Do you have a YouTube was like, we just made it up in a workshop last week, so we're going to work it out.
Lola Oyelayo-Pearson: It did still allow for that clarity of we care about these things at the top. And as Mamuna was saying, each department then being able to say, okay, well, this is how I'm going to contribute to that. And I think from a leadership perspective, putting something out there that people could understand how it worked, as imperfect as it was in many ways, and make clear decisions, it really makes a massive difference.
Lola Oyelayo-Pearson: And so I always try and be exactly the same. GRIP doesn't work in every environment, just like OKRs don't work in every environment. But as long as people know how your decisions were made and what assumptions you have and how they can ladder up into that. You're probably helping them to feel safe in decision making.
Lola Oyelayo-Pearson: And then failure becomes a collective thing. It's like, well, we didn't have the information we now have. And so we need to change path. And I think one of the misses, if I can, you know, not that I'm controversial on purpose, one of the misses in the post-pandemic era that I think a lot of tech companies did is...
Lola Oyelayo-Pearson: We were in this weird grow for growth sake period where it felt like if you weren't growing and hiring, you were doing something wrong. But I feel like if you'd asked a lot of leaders, what were you hiring for? They didn't have the work, they didn't understand the value of growing their workforce.
Lola Oyelayo-Pearson: And so their metric was misaligned. And what we've now seen is a correction, but we're also seeing the converse. It's like, why are you doing layoffs? Well, the market really likes them, but I'm not sure if I need to do them. But if I don't do them, it's not seen very well. So again, you're kind of missing this clarity of what am I actually measuring for my company? And I think as a leader, if you're going to stand up and say, we're doing layoffs because we cannot afford this amount of staff and we've got to reset our business model, no, one's going to resent you for it. If you're doing layoffs because you hired people, cause you didn't really know what you were hiring them for and now you've got to fix that. Cause it's you've got a communication tax on your company. Everyone's going to be like, do I trust the next decision you're going to make? Cause wasn't that obvious before you did it? You know? So I think that clarity. Is the leadership quality that I think I'm looking for personally.
Lola Oyelayo-Pearson: And I try and aspire to, you can make good and bad decisions, but as long as it's really clear why, and you've got a way of helping people contribute to that, you're probably doing it more right than wrong, but you're always going to be wrong somewhere, you know,
Keith Cowing: I love how you call out leaders being really clear on this is what we know, and this is what we have conviction in, and this is what we don't know, which accomplishes a few things.
Keith Cowing: One is trust. You generate trust when you show people what you know and what you don't know. Another one is it helps people put energy into the right things. Things where everybody in your team, they have a lot of context and they're there because they're intelligent and they're hardworking, but they don't know where to put their energy if you don't tell them.
Keith Cowing: And a lot of people have had bad experiences where they questioned something that leadership had conviction in and they just told them to go away and shut up. And that experience leads them to not want to contribute in other areas. But if the senior leadership says, we don't know this, we need your help, then you can take your energy and you can apply it in a good way versus just bottling it up.
Keith Cowing: And that can be really productive and create a facilitation of healthy tension on the team. And if you have no tension, you're not going to get anywhere. If you have unhealthy tension, it'll get toxic. Somewhere in the middle is this healthy tension. What have you seen leaders do to facilitate healthy tension and debate on the team?
Keith Cowing: I think we've lost some of the intellectual debate that came a little bit more naturally in a room that doesn't quite come as smoothly on Zoom. And I think it's incredibly important, but it takes hard work to facilitate. What are you seeing people do well right now that our listeners can learn from?
Mamuna Oladipo: So COVID hit and everyone went remote and then we made a bunch of changes. There are layoffs. You know, there's a lot of, there's a lot just happening all at one time and folks were uncertain. They were nervous. And, you know, I as leader was saying, okay, I want to pull the group together.
Mamuna Oladipo: I want to capture their feedback. I want to understand how I could improve. What are the things that leadership can be doing to better just lead, manage the group of individuals we have on earth to keep them engaged, interested, feeling secure in their roles. And I remember getting into a room, and I was like, okay, you know, here's where we are, like, trying to take Lola's approach there, but I, like, had not done this before, and it was remote, so it was kind of awkward for me because it was the first time, and I was asking folks for feedback, and people were just mad.
Mamuna Oladipo: Like, they were just like, why are we doing layoffs? What does this mean? It's COVID times, you know, like, don't you have feelings? And just like a lot of, just a lot of emotion. And I didn't understand at the time how to ask the right questions to, like, I didn't know why I was asking the questions. I think I just wanted to get people in a room to like create a release valve.
Mamuna Oladipo: And in reality, if I were to do it again, I likely would have gone in with intention to say, okay, first, here's where we are. Same thing I was saying, here's what we know. Here's where we took the steps we took. You know, there are, you know, three areas of investment potentially that we want to go down.
Mamuna Oladipo: You know, I want to get from you all, you know, how you feel we could better approach these areas. Like you want to be able to bring people's voices together. Like you want them to feel heard, but you want to make sure you direct that energy in the right directions. So how can our whole conversation be useful for everyone?
Mamuna Oladipo: So I don't want them to just be like, hey, this place, you know, whatever it is, but like, okay, I'm frustrated, but you know, I'm frustrated because I feel like I have this idea. And here's what I would have done. Like, okay, great. Or that into what we're looking for, we're looking to move into a new direction.
Mamuna Oladipo: If we're looking to pivot, you know, what are you all seeing? You all are doing the work hands on. You're doing the research. Like, let's all use our collective energy and put it towards, you know, bettering the company. And I think having people feel like they have an outlet for frustration, but a, a like an impactful voice is important and helping them form that impact I think is the important thing.
Mamuna Oladipo: So asking very direct is not the word, but asking the right questions is going to help people understand how you are looking for them to use their voice in the company.
Lola Oyelayo-Pearson: And I think that emotional safety is foundational to having tension work in your favor versus against it, because, you know, again, for me, one of the things that I always value is, I think it's so important to disagree.
Lola Oyelayo-Pearson: It's so important that you can say, I see what's happening, but I actually, I have a concern. I have a question. I see a risk. I don't agree. And then to be able to have a genuine discussion about it. And then to be able to arbitrate so that either you've added input that somebody can be like, you know what, we're going to add a mitigation for that.
Lola Oyelayo-Pearson: Or you're going to disagree and commit, but you know, you feel heard. And there is somebody we both used to work with. He encapsulated the framing. He gave it a phrase, really effective phrase that I now use in my role, which is this concept of clean escalations. Right. Sometimes you're not going to agree that this is the right way forward.
Lola Oyelayo-Pearson: You're going to, you know, whether it's in a product team, you're all kind of arguing the bit about this, but that, or this happened and we've got delays or this is going to impact this and it's going to reduce the amount of revenue. And there are so many things and you just need one decision that allows you to move forward and being able to tap into the concept of a clean escalation.
Lola Oyelayo-Pearson: It's not your fault. It's not my fault. We are not going to lose our jobs because of this, but we do need to escalate. In order to make a clear decision that we can move forward with and that clean escalation, that concept allows you to say, you can do it without personalizing it. You can do it without being overly emotional.
Lola Oyelayo-Pearson: It is okay to be passionate because you clearly have to go and escalate. You've decided that this requires an intervention, but it still allows us to say, whatever the decision is, we escalated well, so we can move forward. Well, and I think allowing The emotional safety that exists as an undercurrent to be supporting the concept of construction tension in an organization that's like the holy grail of anywhere anyone wants to work so I can come in.
Lola Oyelayo-Pearson: I can do my job. Well, I can disagree. I sometimes will disagree and commit. I sometimes will advocate very strongly for what I believe and I don't necessarily fall into this trap of being made to seem aggressive or angry or upset or emotional because everyone does it because it's nurtured as a good way to do our jobs.
Lola Oyelayo-Pearson: I think that's what we're all aspiring for. And ultimately the companies that do that well, I think are probably navigating this particular timeframe with less trauma and less like swings. Like, today we do this, tomorrow we do that, and blah, blah, blah, it's like, no, you're they're much clearer on their, like, how they go from one step and put one foot in front of the other.
Keith Cowing: What have you found if you're coaching a leader of a team to have them exhibit the behaviors that empower the team and make them feel this way versus having the fear what specific behaviors would you be encouraging this leader to exhibit every day every week?
Mamuna Oladipo: Empathy.
Keith Cowing: And how would they do that? So it's empathy it can show somebody how to behave but how would they demonstrate that empathy?
Mamuna Oladipo: I mean, honestly, I think it's putting yourself back at the beginning of your career or early on in your career when you're just trying to get your first steps in, you're trying like you want to be impactful. You want to be heard. You want to move up, you know, whatever that means for you. And so it's like, okay, as a leader you know, that the person you're speaking with, the person that you're guiding wants those things.
Mamuna Oladipo: And some folks like withhold that because they just don't care. Or whatever it is, right? So you just want to say, okay, as a leader, tap into those things, because those are motivators. If you can get a person who feels they are heard, listened to they have space for development, they are going to give you whatever they can.
Mamuna Oladipo: And that's how you really engage an employee. And so that's what I would really just like, you know, that's what I would start with if I was coaching a leader.
Lola Oyelayo-Pearson: Yeah. I think I would build on that. You know, if you're a leader in a small organization, small team, small communication tax, then just invest the time in connecting with your team.
Lola Oyelayo-Pearson: Like, you know, the larger your company gets in the bigger your teams, the more one to ones become inefficient, but if you've got a right size team, one to ones done really effectively or group meetings, team meetings regularly, where you talk about what are we working on? Why are we doing it?
Lola Oyelayo-Pearson: Make your decisions transparent, invite people into product reviews who aren't working on that product, but they can see how you're making decisions and asking questions about someone else's work. So they get to know how you apply your judgment, they get to know what matters to you, and they get to understand what you're thinking about on a daily basis, but also in a small environment, you're accessible in a large environment. I remember when I joined Shopify, I was due to work in the office and the pandemic, the office locked down the Thursday before the Monday when I joined. So I started leading a new team in a new country, completely remotely working from a tiny house.
Lola Oyelayo-Pearson: But very quickly I started recording videos because it was a very large company. And so every week my team could expect a ridiculous 20 minute video from me, sometimes wearing a headscarf, no makeup, on my phone, on the couch Sunday night, but they didn't know me and I wanted them to get to know me. And there were so many that I had to do a one to many.
Lola Oyelayo-Pearson: And so these videos became a way of sharing what I cared about, what I was asking questions on, what I felt mattered, my observations on what had happened the previous week. And eventually we didn't need them anymore. But I think that concept that as a leader, you need to be accessible, your decision frameworks need to be accessible and the way in which you respond to queries and questions need to be accessible.
Lola Oyelayo-Pearson: Whatever that looks like in your organization at different sizes, that's what you invest in. And as long as that foundation exists. People believe you and they trust you and they come to you with their ideas, they come to you with their challenges and your behavior by being accessible becomes a role model for how to actually engage around product work or people work in the team.
Lola Oyelayo-Pearson: And again, it's something I look for when I'm looking at an organization is like, do we have a battalion person who hides behind 10 chiefs of staff and like is never available and only does perfect comms? Or do you have somebody who feels available and is clearly part of the team and is constantly talking to the team?
Lola Oyelayo-Pearson: And the difference between those two is is a massive decision vector for me personally.
Keith Cowing: I love how on that you got a two things. One is sharing yourself and one is sharing your reasoning where it's incredible how powerful it is as a leader when you share why you're doing things and how frequently people don't just because it takes time.
Keith Cowing: And it's easy to assume that everybody has the context because as a leader, you have so much context. And a lot of times the people on the ground don't. And when you go out of your way to communicate that we have this natural instinct to fear the worst. And if somebody doesn't explain why you just assume the worst, and I don't know why, but it's a very consistent part of our evolutionary minds and leaders that say, well, this is exactly why we're thinking this and why we're making this decision that resonates and then it leads to trust. And when I first took on a key leadership role in one company, the founder told me you need to communicate and communicate and communicate until you think it's about enough and then double that.
Keith Cowing: And that's probably about right. And it was absolutely true. And you learn this over time. And Mamuna you had something to share.
Mamuna Oladipo: I just want to say really quickly, I like applaud what Lola said there, because you know, one of the, one of the great things I think about, like having a well oiled machine or a ship that's running efficiently is that everyone knows what to expect as to the quality of work becomes, you know, raised just naturally, because before you get into a room, people know, okay, these are the types of questions they're going to ask me. This is the structure, like, whatever it is, they know what to expect. They know what you care about. They know how to present the information. And so that just takes a lot of the questioning in their day to day out of, you know, the normal and they can run faster, which is great.
Lola Oyelayo-Pearson: And we do not like the, sorry, I was just that the popular, this is my decision, the kind of the the example being set by some very famous tech leaders at the moment that, you know, it's kind of my way or the highway I think is so toxic because there are a lot of really successful companies that have run for years.
Lola Oyelayo-Pearson: On a much more accessible leadership model that they, that is way more effective. And I think as a role model for people developing their leadership skills, you don't want to pay attention to that, like the enroll thing. It really, most of the time doesn't work.
Mamuna Oladipo: Well, it's good to pay attention to it because you know what not to do.
Lola Oyelayo-Pearson: What not to do. Yeah.
Keith Cowing: Final question for each of you. We've talked a bunch about how people feel on the team and whether it's fear and uncertainty, or if you're giving them conviction and energy and optimism and a sense of agency and how much that changes the outcomes for a company, whether you're a big company that's moving slow or a small company that just has to find its way again.
Keith Cowing: The two of you have a podcast called Lost in Tech. I think you can read a lot into that. From a naming perspective, people will, at some point in their career, feel lost. Organizations will, at some point in their evolution, feel lost. And the question is, how do you find your way and how do you come out of that?
Keith Cowing: And how do you do it with the right leadership? And so the question for each of you is, if you're an individual feeling lost, what advice do you have? And if you're an organization feeling lost, what advice do you have?
Mamuna Oladipo: Yeah. I mean, it's kind of, it's probably one in the same, but as the individual, I would just make sure you understand who you are and what motivates you at the core, you know, it sucks to be a job that you dislike or that misaligns with your values.
Mamuna Oladipo: And so having clarity, just like if you were going out to date, like having clarity on who you are, what your values are, what's important to you is important. So, you know, what to select, who to choose. So then on the other side is an organization. The recommendation would be for you to understand who you are, what your values are, what types of folks can thrive in your environment. So when you are hiring, you hire fairly, you know who you can select to be impactful within your organization.
Lola Oyelayo-Pearson: Yeah. I think individually my advice is a bit more maybe on the spiritual side, but like go towards what really brings out the best in your skillset. I think some people might be like, I don't know what my skills are. Start with what you're interested in. Start with the content that you find yourself able to spend the most time with.
Lola Oyelayo-Pearson: We are fortunate enough that you can get jobs, especially in tech with, you know, less experience, but a lot of initiative, right? If you've applied yourself to learning something and acquiring knowledge because you're really passionate about it, there will be an opportunity for you as long as you're honest with yourself and going towards that.
Lola Oyelayo-Pearson: Faking the funk on something that you don't really enjoy. I think there's a limited amount of time that's going to buy you and certainly resting on your academic credentials only, also don't get you that far because there's a lot of us with all the degrees in the world and that's not enough to get the right job.
Lola Oyelayo-Pearson: So really moving towards what motivates you and brings out the best in you. I think if you're lost in tech as an organization right now, you need to go back to your fundamentals, know why you exist, know how you make sure people get paid and the lights stay on, and really understand how you move one foot in front of the other in order to maintain the right balance in those two things.
Lola Oyelayo-Pearson: Everything else is probably a waste of your time. The 0 percent interest rate era is gone. So you're not going to be the next Uber. You know, and there are a lot, a lot of questions that an investor or shareholder or an employee will ask of you these days. That means it's really hard to fake it. If you're one of these like resting investing managers as well, it's like you actually need to show up and do your job.
Lola Oyelayo-Pearson: So like as a, as an organization right now, if you're lost, it's time for fundamentals. And I think really think about. Why you're doing what you're doing because it's going to be what matters long term.
Keith Cowing: ...And then share that, repeatedly.
Lola Oyelayo-Pearson: And then share that, yes. Please tell us all.
Keith Cowing: What a great note to wrap on. Mamuna, Lola, It's been a fantastic conversation. thank you and thank you so much for sharing your expertise and your knowledge.
Lola Oyelayo-Pearson: Been a pleasure. Thank you.
Mamuna Oladipo: Thank you.
Chris Wofford: Thanks for listening to Cornell Keynotes. Check out the episode notes for more information on the product and tech leadership summit that takes place this September at Cornell tech in New York City, and be sure to check out Mamuna and Lola on the podcast Lost in Tech. Thank you again, friends, and subscribe to stay in touch.