Take your design org from good to great with these principles from Segment to Twilio — Hareem Mannan

Brett Berson: Thanks so much for joining us for this conversation.

Hareem Mannan: Yeah, I'm excited to be here. Thanks for having me. 

Brett Berson: So we thought a fun place to start might be a Twitter thread of yours, uh, from last year. And, uh, in this, in this read, you sort of outline the idea that the best designers really have three things in common. Uh, the first is that they are amazing product quality ambassadors. The second is they're the glue that connects across product areas.

And the third is that they understand the GTM motion for the product. And so I was hoping you could maybe expand on those three areas and kind of what you've learned about each of them.

Hareem Mannan: Yeah, absolutely. Uh, I remember exactly why and when I wrote that thread, uh, we were just coming off, um, the segment acquisition at the time. And so I, for context, like I worked at segment still work there, but now it's Twilio segment. Um, and we had just been acquired and I remember it was this really great moment of introspection for all of us around, like, how did we get here and what made us special?

And I remember everyone was doing that kind of reflection on their side engineering and product. And then for me, from a design standpoint, I spent a lot of time just like trying to think about like what qualities made designers at segment really, uh, special and, and successful there. Um, so the first one product quality, I like to think about product quality, almost.

A little bit like an iceberg. And I feel like that's an analogy that people use a lot for different things, but in this case, I think, uh, if you think about an iceberg and like the part that's like peaking out of the water is probably the part of the design that you Can see, right? Like the UI or the user interface that people are interacting with is, is like the tip of the iceberg.

And then there's this whole area underneath that is a deeper meaning of what product quality really is. And so that is like how people are interfacing with the product. Are they able to actually accomplish what they came here to do? Are they able to like use the API APIs that they wanted to use, which is a little bit of an untraditional perspective on what designers should be thinking.

But I think the best designers that I had seen at segment really took that like entire iceberg from top to bottom. So whether that was like thinking about the visual design or the product design, or even just like engineering workflows and like made it their problem and made it their problem to not just like focus on in their own work, but also to evangelize and other areas of the product as well.

So almost like instead of just like problem solving, problem hunting as well, when it came to thinking about those areas. So that was the first one, which is just like being an amazing advocate for what a good product experience looks like across the entire stack of product quality.

Brett Berson: Can you give a couple examples of maybe what that looks like or in the last year or two, if you saw a colleague that really exemplified that idea, what, what kind of they were doing.

Hareem Mannan: Yeah, absolutely. I remember there was this period of time, actually. It was a long period of time. Um, sometimes segment gets the feedback that we are a little bit of a black box as in like you send data through segment and then you can't really see what's happening to it. We just like promise you that we're going to send it to all the places that you want to send your data to now, uh, in principle, that sounds like a product problem.

It also sounds a little. Actually it's a lot of an engineering problem, right? Like what's happening to the data as it flows through segment. But I think traditionally it actually is a design problem. And so a couple of designers on our team got together with our researcher and literally mapped out just like the journey of a data point as it goes through segment.

Um, and this is not at all like, uh, something that our customers can see. It's not a traditional interpretation of design, but it was certainly was a key aspect of what it means to invest in product quality, which is to think about the journey of a data point and then figure out what places are important to surface to our customers and our partners as they get a better sense of what is happening under the hood at segment.

And so that was really cool. 

Brett Berson: And so in that example, how do you think about where design picks up and product or product management leaves off or how those two things talk to one another or collaborate around maybe a product area or problem? Like the one you just explained.

Hareem Mannan: Yeah, that's a really great question. And I think one where, um, I have just like really enjoyed where I work because of my answer to that question, which is that. Bit of a gray area. Um, one of my mentors, Vanessa Cho, who's a design partner at Google ventures. Like one of her favorite things to say that, that she ingrained in my head is that good design leaders are indistinguishable from good product leaders.

And that's because the higher that you go in design and the more you start thinking deeply about design problems, you're inevitably overlapping with a lot of quote unquote like product surface area, um, and starting to think a little bit more critically about just like what your customers and the business are trying to accomplish.

And so, um, the key here is just to build a really strong partnership so that it can feel very, uh, fluid between the two. I think, um, in this example, design came with like the map of what this looks like and product picked it up and was like, okay, now let's brainstorm together in thinking about different ways that we can surface this kind of data visibility and observability to, uh, our customers that. 

Brett Berson: So in that example of, you know, you're hearing from customers a pain point, it feels like segments of black box. what is the role of product and designer product and product designers? Like how do you go from, Hey, we think there's a problem and an opportunity to do something better through, in this case, maybe a shipped product, like who, who is owning, what, or how are they working together to solve that customer problem?

Hareem Mannan: yeah. I think honestly, well, first it starts with discovery, right? Better understanding. Like what does black box mean and is all visibility, good visibility. And the reason I even say that is because we learned that that was not the case, that like, there is such a thing as the kind of visibility that feels disempowering to customers when you don't let them action on it versus like, what is good visibility?

And so there's a lot of. Nuance with the prospect of even uncovering what is happening under the hood there. And that's really where that partnership comes into play. Right. And it's not just say product and design partnership. Ideally it's a triad, like you have product design and engineering. So you have somebody who's thinking about like, what is technically feasible to build.

And then, which is the engineering leader. Uh, what does the customer care about, which is the design leader and what does the business need, which is the product leader and all three work together on solving the problem?

But I think each of them having those hats that they wear when they're coming together to ideate and think about what they want to do next really helps clarify who is doing what or who owns, what part of the process as well. 

Brett Berson: And so in one of these meetings that you have with. w what does that sort of look like? How are people contributing or what does it look like for someone in design to contribute in that triad?

Hareem Mannan: Yeah, I think, uh, if we were in office design is standing up writing on the whiteboard, you know, post-its in the hand, the very quintessential view, I think of the designer, but like typically their ownership is like driving clarity to what the problem is in the first place.

And that's typically a partnership between design and product. At that point, once they have a clear picture of what the problem is, they might split off and design tries to come up with some solution ideas, product, uh, approaches it a little bit differently and starts to think about like, what is feasible for the business to address at that period of time.

Um, and so I think it really depends it's on a case by case basis, of course, but that again, like constantly diverging and converging, um, where in, when the situation requires it is, is probably how that would go. I will say, uh, to add to that though, Is one superpower that I've seen designers really lean into is bringing their product and engineering partners along customer calls.

So that they're not the only ones who are steeped in customer context. I think that's a lot of times where teams end up getting a little bit tripped up is when there's only one person who's really wearing the hat of trying to advocate for what the customer needs and the more you're able to democratize that information.

Uh, the more I think in tandem, the team is going towards the same end vision. 

Brett Berson: Great. And before we kind of click over to this, the second category of great designers in, in this first, one of their amazing product quality ambassadors, when, when you talk to, to designer sort of up and coming folks that maybe have a year or two of experience, and they really want to grow in this area, they agree with you.

That it's really important. How do you coach people to develop and grow in, this first big bucket?

Hareem Mannan: Yeah, I think the first, like when you're starting off, especially as an early in career designer. My first goal for you as a designer is to understand what good looks like yourself. So you can't be a product quality ambassador. If, if you don't fully understand what good product quality looks like. So spend a year, two years, three years, five years, however long it takes for you to feel like you are able to, uh, evangelize and really create the kind of product quality that you want to see.

And then the next stage of that is starting to think about how you might influence that in other people. Um, we have like a bunch of endearing terms for that at segment. Like w sometimes I just call it the eye, right? Where you want to give somebody like the ability to see. Design problems wherever they stand and be able to point it out to a designers.

And so, um, being a product quality ambassador means that you're not just evangelizing that within your own product area, but also making sure that other people are also quality ambassadors around juice, that you're kind of building this chorus of like what good looks like in your company that allows you to like, be moving in lockstep with, with a team that agrees that it is important as well. 

Brett Berson: Okay, great. Let, let's go to this second category, um, and you framed it as they are the glue that connects across product areas. So would love you to share more about that.

Hareem Mannan: Yeah. So a lot of times design operates in what's called an embedded model, which is where designers are embedded in specific product teams that have different product charters, um, and what tends to happen. And, uh, in working at segment and then getting acquired by Twilio, you see this time and time again at companies of all sizes is it can be really easy to fall into a pattern of working within a silo of your own product area and not really thinking holistically about the end to end customer experience.

And that's where I think, uh, design can play a really special role. And we're great designers play a really important role is ensuring that there is somebody who is thinking about that horizontal product experience and not just the series of vertical ones. When you think about what makes a good PM successful, it tends to be how well they do in their individual vertical product.

Right. Like how well they're able to drive feature adoption for their specific feature or how well they're able to increase retention based on like the area of the product that they own. But in design, I think because so much of success is measured on how we think about the holistic end to end customer experience.

The very nature of how designers think about the quality of their work has to be more horizontal than vertical. And so great designers I've found really lean into trying to be that.

glue between a bunch of vertical product areas And finding opportunities for people to collaborate and work together to solve these kinds of problems.

Brett Berson: And so similar to sort of the first category, what does that look like in practice? Or what are the habits or what is a person doing if they exemplify this behavior or, or live this sort of characteristic or a value.

Hareem Mannan: Yeah, I think the first thing is, I would say it's on design leaders to create an environment for designers to share their work in such a way where you can see what other people are working on in the first place. Right? Like we can expect designers to be thinking horizontally if they don't know what's happening next door.

So, uh, that's the first piece. But the second piece is once that visibility does exist, there's an element of just like keeping your eyes open for potential areas of overlap. Um, an example is like at segment, we've had several designers think about how data flows through segment. And so like how you might regulate the data that's flowing through segment.

Sometimes that happens early on when you're trying to connect data to segment in the first place. Sometimes that happens towards the tail end where you're. Send data to, and sometimes that happens in the product that we have, that controls data, what I'm describing here, the three places, those are three different teams that are thinking about like the same type of challenge.

And this happens all the time at, at bigger companies as well. And even at, you know, back when this problem existed, like a smaller company, like segment where you have, uh, sometimes three teams that, you know, stumble on a customer problem, it's the same problem. And so how do you think about, um, design being the unifying voice?

And I remember at the time it was designed that highlighted that like, Hey, we're all working on the same thing here. And so how do I get everybody in a room and start to collaborate and think critically and deeply about like, what would be best for the customer in terms of where they should live and how we should solve this problem.

And that starts by recognizing that that was a thing that was happening in the first place.

Brett Berson: And so what are the rituals or touchpoints that allow you to surface these kind of meta problems that exist across the product areas? Because to your point, I, I, I would assume that what normally happens is not, you have, you know, call it five different product teams and everyone's like, I hate everyone else.

I just want to work in my work stream and do my own thing. I think what normally probably happens is like, it's a full-time job to be focused on this one piece of the pie 

Hareem Mannan: totally. 

Brett Berson: an in that you forget the holistic journey that you're talking about, that a customer may take across these product areas. And so is it just sort of a S some sort of meeting that surfaces, this, are there other, company-wide systems or ways in which you operate that.

Increases the chance that there's, um, a stronger emphasis on the end-to-end customer journey versus someone kind of just building their part of the widget.

Hareem Mannan: yeah. That, so, you know, what's interesting is I probably would have answered this question differently. Before we went remote. And like, after we went remote, just given, there was a lot more mechanisms and forums and you found a lot more inherent, just like, it's easy to turn your chair around and share your work when you were in the office together.

And when we first went remote, that was one of the first things that I struggled with in leading this team is suddenly it felt like a vacuum. Like I, you couldn't see what anybody else was doing any more in the ways that we were used to like more organically collaborating within the office or working together, or you would just like ask a designer for feedback just because they were there.

Right. And so it really comes down to creating intentional structures of visibility on your team. And I'll give you an example of how we've done that on my team. The first is that we kick off our week together now as a design team, and this is not necessary at all. Like everyone is working on very, very different things.

But one of the key questions we ask when we kick off our week together, that every designer answers is what problems are you thinking through this week? And the next question. Is what are some areas of potential collaboration with other designers as well. And so when designers fill out this doc every Monday morning, you're you have to like scroll through what other people are doing to understand how you might answer that second question.

And so many times people have been like, oh, you're working on an onboarding float. So am I you're thinking about upgrades? So am I, you know, you're thinking about this problem, I'm super interested in that my team might be thinking about that. And so that is one example of just like intentionally designing a meeting so that you're able to drive to the outcome of visibility.

So that's one example. The second is like, I would say that first example is a pretty heavyweight example. It's a meeting, you know, people have to get together every Monday morning and share what they're doing. And honestly do a little bit of prep in so far as like fill out the doc before. But it's exhausting to me all the time.

And, you know, I started thinking about like, what are lighter weight ways to create visibility, where we can encourage the sharing of work while not overwhelming people at the meeting. And so a very simple and small example that has done weirdly a lot for us is every Wednesday morning, like clockwork, there's a Slack bot that goes out in our design team channel that asks what's a screenshot or link of something that you're working on this week.

And every week, every designer and researcher shares what it is that they are working on through a link or a screenshot. And it has just been like a really, really great mechanism for visibility, especially in a distributed team, especially in a remote period of time. There's been conversations that are spurred from like, Hey, can I get quick feedback on this thing?

Or I didn't realize you were working on this, but starting to think about like, what are both like very intentional and maybe, um, maybe a little bit more formal mechanisms of visibility, but then also like lightweight and fun ones helps create those avenues for collaboration within a company that feel as organic as it might've felt being in the office and collaborating together. 

Brett Berson: That's incredibly helpful and specific. So thank you for sharing that I I'm interested. Are there other times that you. As a design organization, try to zoom all the way out to better capture sort of the full life cycle of a user, or does it happen in these sort of weekly meetings and sinks where you kind of figure out the rough edges or maybe how things fit together?

Hareem Mannan: no, absolutely. It definitely happens more often as well. I would say, first of all, the way that I like to think about designers stream of work is twofold. It's a, what I'll call a discover stream and a build stream discover is like, what high level questions am I thinking through right now that I'm chipping away at slowly, those might be projects that take weeks or months, and then build, might be like, I'm iterating on this feature right now and working alongside maybe my product manager and engineers on my team to start to figure this out.

Um, The discover questions are the ones where we have more of these like existential conversations about who are we for? Why do customers churn? What does it mean for people to buy this product? Where do people get tripped up in implementation? Why do they get tripped up there and implementation? And so we have these projects that run sometimes weeks, sometimes months to get to clarity on some of these things.

And what's cool is because they're so long. And because they are highlighted in these shared forums, it's really easy for other designers and researchers to jump on the train and be like, I'm actually thinking about that problem too. And so let me jump into that longer discover project and make sure that I'm able to benefit from that context as well.

The last thing that I'll add on that piece is we started doing our research leads, started doing what's called, um, customer insight demos at our company as well, which is a demo that is purely based on research. It's just, what did people learn about what our customers are saying that has helped really guide a lot of these kinds of conversations as well?

Because suddenly you're sharing that context. It's open for all of R and D. So it's, you're sharing that context with engineers and PMs and designers, and a lot of times designers and researchers and PMs presenting, but that context becomes readily available for anyone to action on in environments like that. 

Brett Berson: Let's move on to this third bucket Of what makes a great, uh, designer, which is they understand the GTM motion of the product. Um, and I'm excited to talk about this, this specific characteristic, because I tend to think that commercial orientation is, is sort of one of the most lacking skill sets across product engineering, design, and startups today.

And a lot of people just don't talk about it. And it's also something that I think is a little bit trickier to develop. Um, and so I'm curious when you, when you talk about GTM motion, do you sort of think about it in, in terms of like overall commercial orientation or, or sort of, what does that mean to you?

Hareem Mannan: Yeah. So I guess I'll start a little bit with like where this was born and where I started to realize the importance of this. And I'll caveat this whole thing with, with, um, this is especially important for B2B, SAS designers and product managers in particular, you know, it becomes a little bit less relevant for, um, you know, a designer at door dash to fully understand there's not a different buyer and a user, right.

If I'm ordering my food, I'm also the one paying for it for products that are, you?

know, SAS products that is not the case. Um, and That's where understanding this distinction becomes especially important. I remember when I first joined segment, uh, I joined this team called personas, which is one of segments, flagship products.

And at the time it was. Like five dudes in a sweaty room, trying to figure out this prototype that they had built, that customers were like pulling out of their hands. And so I spent the first six months doing, and I'm making this term up. So bear with me, but like what I'll call bottom of the funnel usability work, which is basically thinking about how people were using.

The product that had already existed. So trying to understand where they were getting stuck, why they weren't implementing it, what was going well, what wasn't if they turned, why they turned a lot of stuff after they had already bought the product and what I was missing. And the big view that was ended up being a huge unlock for me was, you know, the opposite of that, what I'll call top of the funnel usability, which is understanding why people bought us in the first place.

And I remember exactly when that unlock for me first happened. It was when my product manager at the time, Alex, um, was going on a sales trip to New York to go visit some customers. And he asked me to just come along, uh, to just sit in on some customer research. And I ended up accidentally, I think, tagging along a lot of sales calls.

And I still remember the moment when I first heard. Segment personas be pitched, uh, in a sales meeting to a customer. And my mind was absolutely blown. A part of me was like, I can't believe we're pitching it this way. Like, I don't know if what we're building right now fully aligns with the promise that we are making here.

And then I kept thinking about like all the things I would do differently. Had I understood the business outcome that all these customers were driving towards. And because I didn't have that top of the funnel. You know, usability context. I didn't understand to what extent the product should be pivoting to words, the buyer and the user in different ways.

Uh, and I remember as soon as, uh, we, we came back from New York. The first thing that I did with one of our engineers was completely re-imagined the core product experience. Now that I had that context into like why they bought us in the first place. And it sounds abundantly obvious, but again, when you're a designer or product manager, sometimes working knee deep in a feature or a set of features, you're a lot more focused on how it's going.

And maybe for PMs, it's a little different, but like how it's being used than why it was even purchased to begin with, which is a huge mindset shift that I think unlocks a ton for, for designers. Once they do start to understand that.

Brett Berson: such a great way to bring this idea to life. Going back to what we were talking about a moment ago in this sort of first category. Um, and I think you kind of, you're, you're touching on this as you kind of talked about your, your own own journey in this one specific example, but how do you think other designers can develop this muscle?

Hareem Mannan: Yeah. I mean, I think the first example is, um, you know, sit in on sales calls and, and that is something I wish I did earlier during my time at segment, because I think I would have had this unlock, uh, way sooner. Um, and I think a lot of times designers, again, focus on talking to customers that already exist, not, uh, prospects or customers that could exist.

I think it's also, um, You know, important to do competitive analysis and better understand, not just the feature set of how your competitors are investing in their product, but also how they're framing it, which is not something that product designers tend to think they need to focus on. I think it tends to be more of a brand designer distinction where I'm going to see how maybe the competitor like frames their product, but understanding from a product designer perspective, how your competitors are talking about what it is that they do in the first place can help drive to clarity as well.

On some of the stuff that you feel like you might want to invest in, uh, in your own, in your own product area. And the last piece that I'll say is I, I love to onboard designers with like, you know, we have this concept of just like having a lot of one-on-ones and your first, like few weeks there at a company, um, a lot of times those tend to be R and D focused one-on-ones, but I, I have like a set of go-to-market market people that are like my go-to product feedback, people who are high touch with customers and always like chock full of insights.

That I like to tactically onboard designers with as well, where I'm like your partner for onboarding is a solutions engineer who is thinking about like these problems, but from a completely different angle. And it feels a little out of pocket sometimes for designers who are not used to thinking about the go-to-market motion at all, or who maybe have never worked with the solutions engineer before, but it quickly becomes a one of the most valuable partnerships.

I think that people end up having at a company, 

Brett Berson: Why do you think this specific area is maybe underinvested in or, or at times lacking in the design community?

Hareem Mannan: you know, I'm not entirely sure. I think a part of it might just be, um, you know, design can sometimes be very focused on having a seat at the table within R and D, which can be a little bit. Of a distracting conversation when you can use the insights that are generated from, uh, being a great partner to go to market and marketing and, uh, deeply understanding customer problems to create the seat at the table yourself.

And so I think it's, it's kind of interesting that it's not focused on, cause I do think it's one of the big areas of unlock that starts to really propel designers, ideas and careers forward as they play key roles in unblocking sales deals or understand the exact flow from how somebody buys onboards, uh, implements and then, uh, scales their usage of the product. 

Brett Berson: Something that's kind of been woven through our conversation thus far as is kind of the simple idea that that product designers should be spending a lot of time with customers and, and, and even prospects or folks in your sales, uh, in your sales funnel. And, and I'd be interested. One of my favorite questions is always when, when you're spending time with a customer, how are you using that time?

How is it structured? What are the types of questions you ask? Maybe. Why do you, do you ask them, are there specific things you explore with prospects versus customers that allows you to get the most useful information from that relatively short amount of time?

Hareem Mannan: Yeah, I think a lot of times when we do customer research, it tends to be with a goal. But the thing is because, uh, we were talking to a customer. You never want it to be only about the goal that we have. So if we're trying to understand how somebody had implemented segment, we also want to use that period of time?

to be like, and what would you add if you could, you know, and, and start to more deeply understand just like what a customer wish lists are.

Um, so the way that we tend to approach, uh, these, uh, customer interviews and conversations is obviously starting off at a high level, just understanding the demographic of the customer that we're working with, who they are. Why they bought us. What was interesting to them about segment in the first place, what their team size is, how many people are using segment, what their technical proficiency is.

All of this stuff starts to give us a better understanding of how we can slice and dice the data that we have later on to start to see trends across different types of customers or different types of users. And then we tend to dive into the meat of what it Is that we're trying to understand.

Sometimes it's a lot more free-floating discovery in terms of, we really just want to understand, maybe it's a customer who's turned and we want to understand like, why they've turned. And so we ask some high level questions there Sometimes we're truly testing a specific feature. And so we'll, uh, dive deep into that feature itself and start to talk through, um, how a customer might use it and get their feedback.

But we always close with asking customers my favorite question, which is just, if you had a magic wand, what is one thing that you would change about segment today? And that's my favorite question, because you tend to get like the best kind of answers about either the biggest pain point for customers or a feature that they're dying for you to have.

And it's kind of the magic of having a tool that people rely on that you get really crisp, uh, and opinionated feedback, uh, in those kinds of questions as well.

Brett Berson: Is there anything you do to avoid confirmation bias? I think one of the trickiest things is a lot of times you go into these conversations with an agenda or a story you're telling yourself about your product or customer. And so is there anything you'd do to kind of remain open-minded.

Hareem Mannan: Yeah, absolutely. I mean, first of all, uh, that's The advantage of having a research team? What's interesting is before research existed at segment, uh, everyone was doing customer research. So it was kind of like, why do you need a research team? If everyone is, is talking to customers and it turned out the magic of investing in research at segment wasn't so that people would talk to more customers.

It was to be a funnel for those customer conversations, so that we were able to start to prioritize the right insights to avoid recency bias. And we should build this cause I just heard it and to make sure. That we were asking the right questions to begin with. So it's a little bit of the magic of, of having, um, a research team that is tiny, but mighty here.

Uh, they do a lot in the vein of just also research training for PMs and designers, so that they are able to understand how to ask the right questions. What's cool about our research leader. She also runs that training with people in sales and go to market as well, uh, so that they are able to avoid confirmation bias when they're giving us insights into what they feel like, uh, their customers, uh, need as well.

Um, but I think the key here is something I touched on earlier with. The designer, uh, ultimately having the north star of trying to understand what is best for the customer, whether that means walking away from a project or a future or, or not, it's, um, a lot easier when they're, when they understand that that is the goal that they have and can sometimes be a little bit of where the healthy tension with product and design lives, which is just having two different objectives.

One is to, you know, to, to really think about what the business needs and one really, really focusing on, on what the customer needs. And of course, both ultimately focused on both, but I think just like wearing those lenses really helps, uh, guide that conversation. So it's not biased.

Brett Berson: The research training is such a cool idea. Do you happen to know kind of what the modules are? The big ideas that are shared in that curriculum?

Hareem Mannan: Yeah. Uh, she starts off talking about just like, you know, why we do research in the first place. And, and again, that needs a lot less selling at, at places like segment and a lot of different other places. And then she goes into just like, what are, um, good questions to ask and, and like also just a little bit of like teaching what leading questions even are in the first place.

It's kind of interesting. Cause I sat in at a and M sales kickoff, uh, at segment and they basically fundamentally teach you the opposite. Like you want to ask leading questions when you're, you know, going through a sales motion and in research, you basically want to do completely the opposite, which is just find out what's going on with your customer and start to let them really tell you and lead the conversation.

And so it's a little bit of unlearning from that perspective. Uh, when, when salespeople do do take that training of like how to truly, uh, do more listening, uh, than tell them. And I think she also has them, uh, create an interview script of just like how they would approach, um, asking questions to, uh, a specific customer.

And then they kind of go through it together, which is really nice. Cause you get some tactical feedback on, on how you might've approached, um, asking some questions and, and a lot of times that's really great because questions that you don't think are leading are, and it's a great way to start to suss that out. 

Brett Berson: When you think back to some of the last customer conversations you've had over the last months or years, are there some that jump to mind that kind of taught you something unexpected or led you in a really useful direction?

Hareem Mannan: You know, we, we just came off of, of building this new, like suite of futures for our, um, marketing product. And I think it always surprises me how much customers are willing to build alongside you. And the reason I say that is because a lot of times when designers and PMs go into customer conversations, you're kind of trained to go into it, thinking that you're just getting feedback, but you're supposed to have all the answers like going into what this feature set should look like, how it should work, what the product should do in the first place.

But I remember one of the special things about this last, um, set of features that we had built that is shipping soon is, um, we really let customers tell us what they needed. And for me that was like very surprising to have. Uh, just people that were so, um, I think opinionated and willing to build alongside us to that extent.

And it made me think that maybe, maybe I just never did that enough, which is like truly, uh, start from scratch. Like think blank, slate build alongside, uh, our customers. I remember there was this one project, um, that we call a workspace home, which is like, when you log into segment, what your. Homepage dashboard looks like.

And I remember being shocked at how that project went, because the way that that team approached it was when they did customer calls, they basically gave them a blank sheet of paper and were like, tell us what you want to go on here. And customers would just like design their dream dashboard and what they ended up building was basically the average of all those dashboards.

So just like the most common stuff that they had seen in an information hierarchy that made sense. But what was so cool is that wasn't like just customer research. It was really having your customers build the thing that they want for you. And I think that had always been like, whenever I see that happen, I feel like it kind of flips the mental model of how we think customer research is supposed to go on its head.

Brett Berson: I wanted to flip back to some of these characteristics that you described around what kind of great design or grid design leadership looks like. And I was interested in how you translate that to the way in which you recruit designers onto your team and your company. Um, you obviously have built a design team over the last few years, and I assume you've probably interviewed hundreds of designers in the process of building your team.

And so I'd be interested in, in sort of what is your end-to-end process look like and how does that maybe map back to these three big ideas that you shared?

Hareem Mannan: Yeah. so the, you know, we start off with a hiring manager call, um, there, I really like to just get a sense of like how the designer thinks about, um, the work that they have done and how interested they are in the space that is B2B as well. Uh, like I said, it's a very different type of design.

Like somebody who's choosing to spend the next few years designing segment and not like designing a Snapchat is a different kind of designer, right? Because the UI and visual challenges and product challenges that we're talking about here can, can be really tough to onboard to, especially if you are a non technical designer.

So, um, starting to suss out a little bit of that, um, the first interview that I would say really starts to test for a couple of these is the portfolio presentation. That's where designers present work that they've done in previous roles. But the few things that we really pay attention to in that interview are one the extent to which they're talking about, how they collaborate with their partners that they're working with.

So product and engineering, which tells you a little bit about how they think about connecting across product areas as well. And the second. Honestly, just the quality of the work that is presented gives you a good sense of the product quality piece that we were talking about earlier. Right? Cause you can start to get a sense of how deeply they thought about either the problem or the visual design or, um, just like the needs of the business or the needs of the customer based on the case studies that they present.

What's cool is we have PMs and designers and researchers sit in on these portfolio reviews. So we're able to get a pretty calibrated sense across the spectrum of like how well the designer has thought about the product quality piece. What's interesting is. We talked about, like, you know, I really, you know, prefer when designers index on, uh, starting to understand or trying to understand the, the go to market motion.

That's almost an impossible thing to test for. Uh, it tends to be something that I teach when people get here, or I try to push for one when people do arrive at segment, but there is one special interview that we do that helps us gain signal into how Well,

somebody might approach that kind of partnership or any partnership.

And it's called the process in collaboration to interview. It's essentially a researcher and a product manager presenting a problem to the designer. And the goal is for the designer over the course of 45 minutes or an hour. To just walk us through how they would approach tackling that problem. Um, there's no take home.

It's it's all together live. Um, sometimes, you know, in COVID times we use a post-it tool, but we really just have the designer literally mapped through what kind of research questions they'd ask and would they even ask research questions? Like, do they start off by talking to customers and how they would validate what they're working on and you know, how it's going and how they would partner with product and engineering.

And what that does is first of all, it's a very high signal interview for someone's ability to come here and crave that kind of partnership in the first place, which makes designers primed for. Me, pairing them up with, you know, a solutions engineer, an account executive, and being like, go figure out, you know, how people are selling your part of the product.

Um, but yeah, it's, it's a really great interview. And, uh, that output ultimately is not at all like a visual design. It's just a series of steps in terms of like how a designers brain works when it comes to thinking about solving these kinds of problems. 

Brett Berson: Can you think back to someone you hire that you were just blown away through the interview process, maybe in this portfolio review. Or this part of the process, um, the part of the interview process that's around process and collaboration and kind of what, what you saw or what they shared that gave you a lot of conviction in their ability to be a great add to your team.

 I would say the portfolio review can sometimes be almost like science where, you know, you start off talking about the customer problem. Um, I remember a specific designer here, uh, really focused on, um, making sure that we understood every step of what they were working on.

Hareem Mannan: And so even little things like anchoring your presentation on specific steps of the design process. So we're all able to like follow along with exactly where you were along the journey. These things feel really small, but help the team that has probably looked at like, you know, dozens of portfolio presentations, really follow along with your thought process.

There. Another thing I've seen designers do really well is almost anticipating. The, you know, cause you can put in any portfolio presentation and be like, well, they didn't cover X or I didn't get to see why maybe it was a product that never shipped or maybe it was, um, a product that they didn't get to measure the success of.

And there are some key components of a portfolio presentation that you just given the nature of how companies work. You may have not been able to get to that piece. A really great thing that I've seen a few designers on my team.

do in those presentations. Is just like preempt that thought by basically having a slide, talk through all the things you would have done differently or all the things that you wish would have made this an ideal circumstance.

Um, and, and that's just a really sharp take because I think from my perspective, What it shows is like you, you know, to a certain extent, you're beholden to your circumstances, but you get ahead of that by recognizing it and acknowledging where a project might have been limiting, but where under more ideal circumstances you might have approached X, Y, and Z differently.

So I think that is my answer for the portfolio question for the process. One, the goal ultimately is to create. Uh, order from chaos. And so as much as possible while you're where you're able to come with an opinion at instructor on what your design process looks like. So step one, I like to ask, I like to deeply understand the problem.

Here's what I would do. Step two. Here's how I would start to understand what our customers think. Step three, here's how I would prototype something that we could get out quickly and learn from like really starting to outline what each step looks like. I think a lot of times people know the answers to the question, but don't know how to communicate it.

And that's really where they get tripped up. But thinking more about the clarity of what you're trying to present, then getting all of the content out is where I've seen, uh, designers do their best work in those kinds of presentations.

Brett Berson: What about the inverse of this question? what have you learned from the hiring mistakes that you've made or when you got it wrong? Was there a thread that ties the mistakes together, or what have you kind of learned from your own hiring errors?

Hareem Mannan: This is more so mistakes that I've made, not mistakes that I feel candidates have made. 

Brett Berson: Right.

Hareem Mannan: Yeah. I think sometimes, it can be really easy and really expensive as well to basically move every single candidate forward. So there was a period of time when we were hiring where designers on my team were interviewing like five, six times a week.

And that was because I would end a hiring manager call and I'd be like, well, you know, they did well enough. Like I want to see more. And because of the lower bar that early, I ended up just. Really spending a lot of my team's time on interviewing candidates, uh, that were lukewarm or that I was kind of, you know, unsure about, instead of doing a lot more of the due diligence early on myself and making it more of a qualifier type call instead of like an intro call.

Um, and that ended up wasting a ton of time, I think on my end. And I had a really great recruiting partner who like was like cream. We just need to do this differently. And I think starting to think about each interview is just like valuable time that you were not just asking of the candidate, but also asking of your own team helps you set a higher bar for the people that you bring throughout the different stages.

Even if it's early, it's still time that's being spent from your team, um, to, to interview those candidates. And so that's definitely, I think a mistake that I had made, uh, in the past that was Easy to rectify, but for some reason, just like did not occur to me at the time. It felt like I was just progressing candidates forward.

And that feels like an easy and, and find thing to do, but with like very real effects. 

Brett Berson: I want to flip over and talk about a related concept, we talked about what sort of, uh, the, these characteristics of great designers or, or, or some of the characteristics of, of great design leaders. We haven't talked as much about what makes an exceptional design manager and I'd be interested.

What, what are those things for you You have a really high potential designer that you think could be a great design manager. Um, what are you sort of seeing in those raw ingredients? And then maybe the inverse of that is when you think about folks you've worked with, or your own journey, what are the very best design managers doing that is maybe different than an average design manager?

Hareem Mannan: Yeah. To answer the first question on just like if I was looking at a high potential designer and they had certain qualities that for me, from my perspective, made them like an ideal or prime candidate to be a design manager. The first things that I think I would see are. Really a focus on bettering the team, even if it's not your responsibility in some ways.

So for instance, being like, Hey, our design critique process is broken. Let me fix it. Um, you know, I think we could run this meeting a little bit better. Here's an idea, and it doesn't have to be necessarily you doing the work, but you starting to identify and take ownership of, um, operational or cultural or people, processes shows to me that you were thinking about your role as multiplicative, instead of as just like, how can I focus on what I'm doing right now?

And that's, to me, a signal of being multiplicative is starting to think about how can I create a better environment for everybody? Um, not just for myself. I think another is expanding your scope of influence. So it's outside of just, uh, again, just designers. Cause I think a lot of times when we talk about, um, what somebody would be, if they were to be a good design manager?

or transition to design manage.

We talk a lot about design and then we talk a lot about designers, but what we don't talk about is design managers spend a lot of their time, uh, with cross-functional leaders and being able to build that kind of trust with your cross-functional peers early on and, uh, influence projects and people And pro like, how is a team better because you were on it, whether there were designers or not on that team or whether it was a designer or not, that is better off because you were, there is how I like to think about just like high signal, uh, people who are thinking about just like creating, just like making things better.

I would say is just the thesis of what I would say is like the highest signal, uh, for me, for somebody transitioning to design management,

Brett Berson: And does that also that, that sort of second point get into the, the idea that that leaders really understand the company and business and all the nuance that exists outside of their. And so if, that sort of something you're interested in a great place to start is by getting outside of your swim lane.

Hareem Mannan: Yeah, absolutely. I mean, you said it better than I could, and I think that's exactly right. And It's interesting, right. Because what I said makes good designers is thinking horizontally about product experiences. It, that would mean that also what makes great design managers is thinking horizontally about an organization and starting to build those bridges.

It's, it's the same motions, but just like a different layer to the, or a different altitude that you're operating out of. And I think once you start to internalize. The horizontal nature of your role of really being that glue and starting to build bridges for designers and PMs and et cetera, to collaborate and be better because of you is where that huge unlock is.

Brett Berson: It's also why I think there's just tremendous returns to curiosity, 

you know, I think, and, and a lot of great designers are, are locally curious in the sense that they might be curious about their craft or their customer, but they often don't apply that curiosity to sort of what the director of sales is, is, is up to, or this new pricing project, or why are we creating this new, why are we moving up market versus doing horizontal expansion?

And when you find those people that are curious and they go ask a zillion questions, there they're often a force to be reckoned with. And they're often in, in, in, in short supply. 

Um, and so it's an amazing way to differentiate yourself. I was talking to an engineer recently who was like questioning, you know, should I go learn a new language or development?

And my thought is, go learn about all the other parts of the business. Uh, before you go and learn, learn a new language.

Hareem Mannan: Yeah. The best engineering leader I work with is exactly that we joke that he there's nothing, that he doesn't make his problem, whether it is pricing and packaging or how a design was perceived or, you know, uh, how a product doc was written or what the vision for a product area that is not his, uh, w is focused on, um, it, that doesn't just apply to design leaders.

I think it's what really makes great leaders overall. You're spot on.

Brett Berson: Yeah. Like simplifying it. You just make things better. 

Hareem Mannan: Yeah, exactly. 

Brett Berson: So on that point, you know, you touched on this a little bit in terms of what you look for in high potential talent. Maybe you can build a little bit more on when you, when you think about the folks on your team who exemplify exceptional design management. And I think you're sort of getting at this a little bit in terms of what we talked about, but are you able to sort of put a finer point on, like, what are the behaviors or, or, or what is the play on the field, uh, in that role?

Hareem Mannan: Yeah, I think the first is like just a really high trust environment is key. And that takes a lot of different forms. Right? One is like, I shouldn't feel like I'm being micromanaged, but another is like, you should feel like you can go to that person and give them feedback on something you wish was going better.

Or like have like, you should be able to feel like you could cry to them and be like, I don't feel like I understand what's going on and it's safe for you. And it's an environment for you to be able to do that. I think like the, One of the big things that I look for is like, Just being a talent magnet to a certain extent as well, where it's like, people just really enjoy and want to work with you.

And an example is like one of the design managers who works under me crazy, like we had a group product manager of one of our biggest product areas that was like a very fun and exciting product area. She recently decided that she wanted to be a designer, which is a very untraditional shift as well from group PM to design.

And she was so excited to learn that the role would be under one of the design managers that I work with crazy. And the reason is because of like his impeccable, like reputation and ability to really focus on and unlock the highest potential and the designers that. Works with, and I think the ability to attract talent, not just externally, they don't know you, but also internally where you've created a reputation where product leaders are excited to work, not with you, but under you, I think is just like a different level and dimension of, of starting to be able to, you know, have that environment really walk the walk as well as talk the talk.

And I think the last piece that, you know, I've seen a lot of discourse about, you know, work is not intended to be a place where people like make friends or have fun kind of thing lately of just like, you should be able to like log on, do your work and sign off. But there's certainly something to be said about managers who make your job more joyful because they are there and it's like tied to retention.

And it's really great for productivity. Like all the business stuff is there too outside of just like the human nature inclination to make work like fun and interesting and a warm place to. And I think that's the third quality that I would say makes for really exceptional design managers is like really that warmth in welcoming people in, in, uh, making them feel included.

Like they have a place there and making it a joyful place to work. Uh, I think is, is the third and slightly underrated in my mind. Quality as well.

Brett Berson: One of the things you just mentioned is sort of this topic of, of micromanagement and not being a micromanager. And I'm, I'm, I'm fascinated with the topic of micromanagement, because I think there's, there's sort of a very delicate line in the sense that, that when a lot of people talk about micromanagement, it, it is a bad thing.

And it's very disempowering at the same time. I think a lot of great managers and leaders. Um, both are exceptionally detail oriented and often can go up and down the stack and in whatever vertical you're talking about, and many of the worst leaders are the ones that, that can't get into the details or don't understand what's going on.

And so, you know, the finance example would be, you know, you can ask a world-class CFO, some arcane question on tab 72 of the model, and they could explain what's going on there. And so that's kind of an in one bucket. The other one is that I think oftentimes great leadership or management is about setting the standard and holding the standard of excellence for the team or the company.

Hareem Mannan: Yeah. 

Brett Berson: and those two things can, can, can easily get into sort of micromanagement territory, or maybe can be confused with micromanagement. And I'm curious if maybe you agree with that if you have any reflections on it, because I do think that, uh, emerges is, is people are so concerned about micromanaging or disempowering, their team that they, that they're, that they lose connectivity to the work and the work product and the details of what's going on.

And that can often be just as dangerous or damaging as, as kind of command and control micromanagement.

Hareem Mannan: Yeah.

You know, that's such a great point because if I had to reflect on the biggest place where I felt like I had failed as a manager, when I was starting out was actually. Because of a paralyzing fear of micro-managing. Cause I like read all this stuff about how you shouldn't micromanage. And when I first became a manager was so allergic to the concept that I ended up under managing, which ended up being like to the detriment of the person I was managing.

And so it's interesting, right? Because I think like I'm sure that that happens more places than just me, right. Where people are like really don't want to micromanage and as a result, end up not managing enough. And I think that there is when you take a step back and you think about like how your success is measured as a manager outside of the.

And their happiness and like quality of life is also their quality of work. And when you start to think about like what it takes to produce that quality of work, sometimes it's like micro managing in the traditional sense that we'll need to get you to a higher quality of work at some point. But I think there are actually more creative ways to tackle that.

And I'll give you an example. So like, if a designer is not doing work, that is at the visual quality that I expect, micro-managing might be every one-on-one me pulling up like the, uh, design and, and working with them and giving them my opinion on what I feel like should, and shouldn't exist there. And a lot of people will do this.

It's not really my style to like really do that. And nor it is, I think my design manager's style, but creating instead mechanisms. For peer accountability or gates for quality, like start to solve that problem in a more creative ways. So you don't have to be a micromanager to produce high quality output.

Instead you can create tools and mechanisms in your team that allow for that kind of quality bar so that you are still able to ship high quality work as a manager, without having your hands in. Everything for design that often looks like having a really tight design critique, cadence, which is every week you show your work.

It is critiqued by these people. You have to show your work and then take the criticism and then take the work and iterate on it and show us how you've evolved the work because. Sometimes it looks like I, uh, one of the first things I did to scale critique was, um, implementing design office hours with like design leads so that there was never a mechanism where people couldn't say like they didn't have an opportunity to get feedback on something.

And so a lot of times after we instituted office hours, when I felt like, you know, this work is not at the quality that I want it to be. Instead of using my one-on-one time, because it's different coming from a manager like demanding or pointing at that quality of work that you want to see. Instead of me spending my time with the person doing that, I would ask them to go to office hours that week and sometimes chat with the person that was going to be doing the office hours and be like, Hey, I'd love to see these things improved in this design.

I'm not going to tell you how to get there. Like you YouTube we'll figure it out. And that's like, almost always worked out for me, which is creating structures that incentivize high quality work instead of micromanaging to get there. If that makes sense.

Brett Berson: I think that's a, that's a great way of, uh, of framing it. And it, you sort of shared a couple of these rituals in terms of design office hours. I was, I was interested. Are there other, are there other rituals or things, um, that you do in the way in which you run your design team that you think maybe are a bit unique or different, or you have a different approach to, to whatever that thing might be?

Hareem Mannan: Yeah. So we do the design office hours. I mentioned the slack bot that we do, where people are able to like tactically, see the work that is done there. This last one's a little unconventional in terms of like an operational thing that I'm proud of that indirectly, but I think is important contributes to, um, you know, making the rest of this successful.

And that is like, you know, every design team right now, frankly, is, is growing. It's a really hot market out there and people are onboarding in droves to new companies. It is really hard to give or get critical feedback when you don't know the person who is delivering. And so like clockwork, I, we have this thing called design hangout, which is like every designer gets together and we all just like do something as a team.

And the goal there is to just try to get people more comfortable with each other, because I've found that expecting things like critique and office hours to work never will, if you don't create forums for people to connect with each other outside of that, so that they're comfortable enough to use those forums to begin with.

Right. And so that doesn't feel like a tactical, you know, productive design tip. But I would, if I had to hedge my bets, I'd say that design hangout and like us, you know, doing something fun together as a team every other week, Has done more for design quality than even design critique itself. Because now I find that designers, I didn't know, knew each other, our meeting because they enjoyed hanging out and, you know, we'll, one-on-one share their work and then start to get better at their craft because of it.

And it's all about creating that kind of environment where people feel like they are comfortable in doing so. And as a leader, it's kind of your responsibility to create that environment to begin with. 

Brett Berson: Flipping back in, in our last few minutes and talking about rituals and process a little while ago, we left off on, on sort of how you run the interview process. And I wanted to sort of close that loop by talking about once you, um, once you hire someone, what have you learned about what great onboarding looks like specifically for design talent?

Hareem Mannan: Yeah. What's interesting is like, I have changed my mind on this as again, we've gone remote because I think great onboarding looks different when you are a designer joining a technical complex company remotely. And for us, it's changed twofold in so far as you're not just getting to know segment. Now we got acquired.

So you're getting to know basically two companies at once. So I would say some of my big learnings after, after seeing a lot of, of that unfold live is first of all, giving people the time to learn the way that they need to. Um, there was a designer recently, two designers onboarded around the same time.

One of them. I spent the first, like two weeks creating a comprehensive map of how people onboarded to the product with all the areas that she felt like she would improve. She was also a growth designer. So this was well in her product area, but it really just like helped her understand the product by her creating that artifact of like how people move through the product for herself.

And it ended up being this like incredibly powerful deliverable. That's still powering a lot of her team's projects today. And That's how she learns. Like she likes to create visuals of, of user flows and diagrams that highlight that work. Uh, another designer recently onboarded, she ended up creating a.

Just like this long doc of who's who in the company. And like with an extensive list of like, almost imagine doing user research at a company and she, she just started doing user research into each person. How did you get here? Why did you join? What teams are you on? Have you worked on, what are the biggest problems you're facing right now?

And basically went person to person over the course of a few weeks, really deeply understanding a bunch of people. And she was a more senior designer, which is why she probably felt like she needed to spend more time investing cross-functionally than investing in a specific product area. So that's a little bit of how people have like customize the onboarding.

What we've done on our side is first of all, try to create like onboarding sessions. so you're like fully introduced to the entire company, uh, at your own cadence there's recordings for every single team and who they are and how they work and what they work on, that people, um, worked through and sometimes watch.

The second is we do a pretty comprehensive onboarding doc in terms of here's what your first 30, 60, 90 days look like with clear and measurable, like goals and expectations. You shouldn't meet maybe everyone, your first 30 days. Like there are some people that you can start to trickle down and meet later.

But the last piece is, is my favorite. And we had done a we'd realized that we had done a lot of the operational rigor to get people onboarded into the concept of what is segment, the product of what a segment, the people of who are the people at segment. But there was an element of 

Like the warmth aspect that was missing there that we used to kind of be able to do a little bit more intentionally when we were in person. So We started this series called "Dear new designer," where every designer on our team wrote, and is writing, cause we're onboarding new people every week, a letter to the new designer joining, not by name, but like "Dear new designer," titling it that way, basically sharing things that they wish that they did, or they knew when they were onboarding.

And it's been just like a really powerful onboarding tool, a complete hit with every single person who's joined because people are able to really take that, take the onboarding doc that we've made and then kind of decide how they want to approach onboarding based on their role, who they are and how they like to learn.

So that there's room for people like the first woman had talked about, who made a whole map of the onboarding flow and room for the second woman who like created basically a whole list of user interview questions for people that she wanted to talk to and how she wanted to get to know people internally.

Brett Berson: That's so cool. And there was that great, uh, medium post that you put out that, that captured this. And we'll be sure to link that in the, uh, in the show notes.

 Well, thank you so much for this fun and wine ranging conversation. We don't get too. A lot of design ideas. And so it was fun to get to unpack a lot of yours, uh, in this session. So thank you so much. 

Hareem Mannan: Yeah, thank you. I appreciate it.