The Design Leadership Playbook: How to Hire, Onboard & Manage a High-Impact Design Org

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Just about a year ago, in late 2020, Twilio closed on its acquisition of Segment, a customer data platform. For design director Hareem Mannan, the news prompted a powerful moment of introspection. “All sorts of folks on the Segment side really took a step back to reflect on how we got to this achievement and what made each team at the company special,” she says. 

Mannan had joined Segment back in 2018, but quickly climbed the ranks as the company grew — her impressive trajectory includes stints as an individual contributor, design manager, Head of Product Design, and eventually Director of Design and Product in just three years. “I’ve been lucky to always have managers who believed I was more capable than I believed I was,” she says. 

When I first got to Segment, I got the advice that the job will be as big or as small as you make it. I’ve taken that to heart and tried to be a heat map to the biggest problems I could solve in any given moment. 

Amidst this rapid-fire rise, she partnered with folks all over the org chart, from different product areas, career levels and growth stages, giving her a close-up lens on some of the biggest challenges facing high-impact design teams. Along the way, she’s dished out heaps of design advice as an instructor and on her own personal blog for other heat-seeking designers. Plenty of startups focus on hiring standout IC designers but don’t put as much thought into the progression to design manager and director. In this exclusive interview, she ties all the threads together from each step of her career at Segment and delivers tailored advice for each step in a designer’s career path. 

For IC designers earlier in their careers, she articulates the three specific qualities she consistently sees across the highest performers, including one under-appreciated skill not often discussed in design circles. She also draws on her ample experience hiring for growing teams, with tips for job hunters on how to stand out during interviews and the slide you need to include in your portfolio review. 

For design managers and directors, she reflects on the three qualities that stand out amongst the most impactful leaders on her team, particularly their deftness for navigating cross-functional partnerships and boosting trust with their direct reports. She also draws on her own missteps as a first-time manager, and shares why a fear of micromanagement caused some unintentional headaches. Finally, she offers her advice on developing an interview loop that surfaces designer candidates with high signals for her three must-have traits, along with her ultra-tactical guide to onboarding with purpose. Let’s dive in.

Plenty of designers earlier in their career have sketched out their career goals and are eager to be a sponge for pieces of wisdom from higher-ups. But oftentimes, after years of managing later-in-career direct reports, folks higher up on the org chart have begun to lose touch with the unique challenges and opportunities facing individual contributors. Only a couple of years removed from being an IC herself, here’s how Mannan articulates the traits of the best IC designers: 

1. Great designers are product quality ambassadors.

As Mannan puts it, the best designers are amazing advocates for what a good experience looks like across the entire product stack. To further illustrate this point, she leans on what she admits is an overused, but apt analogy. “I like to think about product quality as an iceberg. In this case, the tip of the iceberg that’s peeking out of the water is the part of the design that you can see — the user interface that customers interact with,” says Mannan. 

Dip underneath the surface of the water, and you’ll see the foundation of product quality — beyond pixels and buttons. “Are customers able to actually accomplish what they came here to do? Are they able to use the APIs that they want? The best designers that I’ve seen at Segment really look at that entire iceberg from top to bottom. Whether that’s thinking about the visual design or the product design, or even engineering workflows — they don’t just focus on their own work, but evangelize to other areas of the product as well,” she says. 

Great designers understand the difference between problem-solving and problem-hunting. 

Mannan sketches out an example to further illustrate sizing up the whole iceberg. “There was a period of time when Segment got the feedback that the product was a bit of a black box — you send data through Segment, and you can’t really see what’s happening to it. We just promise you that we’ll send it to all the places that you want to send your data to,” she says. 

Cue the product and engineering folks clamoring to sink their teeth into the problem. “What’s happening to the data as it flows through Segment sounds like a product and engineering problem, but it’s actually a design problem. So a couple of designers on our team got together with our researcher and literally mapped out the journey of a data point as it goes through Segment. It’s not a traditional interpretation of design, and it’s not work that our customers can see,” says Mannan. “But it’s a clear illustration of what it means to invest in product quality — thinking about the journey of a data point and where it’s important to surface to our customers as they get a better sense of what’s happening under the hood at Segment.” 

Mannan doesn’t expect designers earlier in their career to bring a finely-tuned sense of product quality — step one is learning good from great. “You can’t be a product quality ambassador if you don’t fully understand what great product quality looks like. So spend a couple of years learning how to evangelize and create the product quality that you want to see,” she says. 

The next step is bringing other folks along with you. “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 you so that you’re building this chorus of what good looks like in your company,” says Mannan. 

2. Great designers are the glue across product areas.

Across companies of all different sizes, Mannan sees one particular problem crop up again and again. “Oftentimes design operates in what’s called an embedded model, with designers sitting on specific product teams that have different charters. And it can be easy to fall into a pattern of working within a silo of your own product area without thinking holistically about the end-to-end customer experience,” she says. “That’s where design can play a really special role in ensuring that there’s someone thinking about the horizontal product experience, not just a series of vertical ones.” 

Here, she points to one of the biggest differences between design and its product counterparts. “When you think about what makes a good product manager successful, it tends to be how well they do in their individual vertical product — driving feature adoption or increasing retention. But in design, success is often measured by how we think about the holistic end-to-end customer experience. The best designers I’ve found really lean into trying to be that glue between vertical product areas, finding opportunities for folks to collaborate to solve those horizontal problems,” says Mannan. 

The key here is for design leaders to create an environment for designers to continuously share their work with one another. “Even on a smaller team like Segment, we can have three different teams stumble on the same customer problem — how can design serve as that unifying voice?” she says.

We can’t expect designers to be thinking horizontally if they don’t know what’s happening next door. 

Mannan admits that this visibility into the end-to-end customer journey has become trickier in the shift to remote work. “It used to be a lot easier to turn your chair around and share your work. When we first went remote, that was one of the first things I struggled with in leading the team — it felt like everyone was operating in a vacuum. We couldn’t rely on organic collaboration and needed to create intentional structures of visibility on the team,” she says. 

Her team relies on two separate touchpoints that cover what Mannan calls the two streams of design work: discover and build. “The discover stream is about the high-level existential questions you’re turning over — like ‘Why do customers churn? What does it mean for people to buy this product? Where do they get tripped up in implementation?’ These projects can take weeks or months,” she says. “Whereas build is iterating on a specific feature alongside a project manager and engineers.”

To sync on the discover side of the coin, every Monday morning each designer on Mannan’s team fills out a doc posing two questions: 

What problems are you thinking through this week?

What are areas of potential collaboration with other designers? 

“It’s all about intentionally designing a meeting to drive visibility. You scroll through the doc and you realize that someone else has also been thinking about onboarding flows,” she says. 

Tactical tip: In addition to a weekly formal sync every Monday, plenty of design leaders will want to borrow her lightweight idea for the build portion: “A very simple and small example with an outsized impact was creating a Slackbot that pings the design channel every Wednesday morning asking every designer and researcher for a screenshot or link to something that you’re working on that week. It’s been an incredible mechanism for visibility in a distributed team,” says Mannan. “So many conversations are spurred Wednesday morning, like asking for quick feedback on a project or folks realizing they’re working on similar problems.”

Don’t just rely on formal mechanisms for visibility — look for lightweight opportunities that boost collaboration. 

3. Great designers understand the go-to-market motion. 

As Mannan puts it, this third pillar is the most underrated in design circles, particularly for B2B SaaS designers. “Understanding the GTM becomes a bit less relevant for a designer at DoorDash, for example, because there’s not a different buyer and a user. If I’m ordering my food, I’m also the one paying for it. But for SaaS products that’s not the case — and that’s where understanding the distinction between the buyer and the user becomes especially important,” she says.  

The gravity of this third trait more clearly crystallized for Mannan when she first joined Segment. “I initially joined this team called ‘Personas,’ which is one of Segment’s flagship products. At the time it was like five sweaty dudes in a room, trying to figure out this prototype they had built,” she says. The first six months she spent doing what she calls bottom-of-the-funnel usability work. “Basically thinking about how people were using the product that had already existed — where they were getting stuck, why they weren’t implementing it, what was going well, why they churned, all questions prompted after they bought the product. What I was missing was top-of-the-funnel usability — why people bought us in the first place,” says Mannan.

That unlock came a bit by accident. “My product manager at the time invited me to go on a sales trip to New York and sit in on some research visits with existing customers. During that trip, I ended up accidentally tagging along on a lot of sales calls with prospects. I still remember the first moment when I heard Segment Personas be pitched in a sales meeting — my mind was absolutely blown,” she says. 

“A part of me was like, ‘I can’t believe we’re pitching it this way. I don’t know if what we’re building fully aligns with the promise that we’re making here.’ I kept thinking about all of the things I would do differently had I understood the business outcome that all these customers were driving towards,” says Mannan. 

Her first order of business after returning from New York was to sit down with an engineer and completely re-imagine the core product experience. “I now had the context into why they bought us in the first place. It sounds abundantly obvious, but when you’re a designer you’re often knee-deep in a set of features rather than zooming out to why it was purchased to begin with,” says Mannan. 

Too often designers focus on talking to customers that already exist, not prospects or customers that could exist.

Along those same lines, she encourages designers across the org chart to keep an eye on the competition. “It’s important to do competitive analysis and better understand not just how your competitors are investing in their product, but also how they’re framing it,” she says. “Brand designers often think about how competitors frame their product, but it’s critical clarity for the product designer perspective as well.” 

Mannan sets the tone with all new designers who join her team to help them develop that GTM muscle. “In the first few weeks of onboarding you’ll have plenty of R&D focused 1:1s, but I also like to onboard designers with a set of GTM folks who are high-touch with customers and chock full of insights. I’ll partner new designers up for onboarding with a solutions engineer, which can feel out of pocket for designers who are not used to thinking about the GTM motion or haven’t worked with a solutions engineer before. But it quickly becomes one of the most valuable partnerships that designers have at the company because they have a different angle on some of the same types of problems,” she says.  

Hareem Mannan, Senior Director of Product, Enablement & Design, Twilio

Just over a year after joining Segment as an individual contributor designer, Mannan was promoted to design manager. It was a steep learning curve, shifting from a regular cadence of delivering tangible design assets — Figma files, wireframes, usability test results, and user interview notes — to a calendar jam-packed full of meetings. Now, as a manager-of-managers, she’s taking on the work of empowering other managers in her org to build the team infrastructure that allows designers to thrive and produce high-quality work. Here’s how she articulates the traits of great design managers:

1. Great design leaders run towards problems. 

“The first things that I like to see from a prime design manager candidate are folks who are really focused on bettering the team, even if it’s not your responsibility. Whether that’s saying, ‘Hey, our design critique process is broken — let me fix it.’ Or, ‘I think we could run this meeting a bit better — here’s an idea.’ It’s about identifying and taking ownership of operational or cultural processes,” says Mannan. “Great manager candidates signal that they are multiplicative, instead of focusing on their individual output. They understand that work is not something that you are owed, but something you create. When there are so many customer problems to help solve, how are you driving clarity and influencing the product roadmap?” 

She also looks for folks who build bridges cross-functionally. “We talk a lot about design and then we talk a lot about designers, but what we don’t often talk about is that design managers spend a lot of their time with cross-functional leaders. You need to build trust with your cross-functional peers early on and influence projects. How is a team better because you were on it, whether there were designers or not on that team?” says Mannan.

If designers are interested in moving into management, a great place to start is by getting outside of their swim lane.

2. Great design leaders consider the org horizontally.

And while great designs apply a horizontal lens to the product suite, standout design managers think horizontally about an organization. “It’s a huge unlock once you start to internalize the horizontal nature of your role — being that glue and building bridges for designers and PMs etc, to collaborate,” says Mannan. A leading indicator that you’ve got a prime candidate to move into a management role? Curiosity. “A lot of great designers might be locally curious about their craft or their customer, but they often don’t apply that curiosity to what the Director of Sales is up to, or a new pricing project, or why are we moving upmarket versus horizontal expansion? When you find those people that are curious and they ask a zillion questions, they’re often a force to be reckoned with,” she says.

3. Great design leaders build high-trust environments. 

As a designer, feedback and critique is a part of the job description, so design managers must take extra care to build a high-trust environment. “I see that applied in a few different contexts. One is that designers shouldn’t feel like they’re being micromanaged, but another is that designers should trust that they can go to that manager and give them feedback on something they wish was going better. Or designers should be able to feel like they could cry to their manager — and it’s safe for you and it’s an environment for you to be able to do that,” says Mannan. 

A leading indicator of a high-trust manager? Being a talent magnet. “We had a group product manager of one of our biggest products and she recently decided that she wanted to be a designer, which is a very untraditional career shift. She was so excited to learn that the role would be under one particular design manager because he had an impeccable reputation for unlocking the highest potential on his team,” says Mannan. “The ability to attract talent, not just externally, but also internally where you’ve created a reputation where product leaders are excited to work not just with you, but under you.”

Mannan points to performance management as fertile ground for flexing those high-trust muscles. “If there’s a performance problem with a designer, it’s really important that I’m honest with how I’m showing up or how my design managers are showing up for that person. Are we creating an environment for that person to be productive and inspired?” she says. 

She also points to a couple of key questions that must be answered before opening up a conversation about performance. “You’ve got to start with your own self-evaluation as a manager. Is there a lot of team churn or thrash? Has it been really distracting at work lately? Have we switched up the projects four times? And do we have unrealistic expectations of the person in the first place? For more junior designers, what great looks like is just doing exactly what your PM and engineering partner need you to do. You can be a lot more reactive to the work that is coming down the pipe,” says Mannan. 

She leans on her scientific background (before pursuing design, she was a biology student and conducted Alzheimer’s research) to guide her perspective on performance. “Before a formal performance conversation takes place, there should have been several 1:1s that have articulated the problem and tried to diagnose it. In science, you isolate the variable and repeat the experiment. Before you understand if there’s a performance challenge, try to isolate the variables that might be complicating it. Maybe the designer is getting tripped up on a particularly thorny project, or it’s a tougher PM to work with,” says Mannan.

Don’t let a fear of micromanagement stop you from helping your reports grow.

When she first agreed to take on a managerial role, like plenty of first-time managers, Mannan piled a fresh stack of books on her nightstand. “I read everything I could get my hands on, and over and over again folks talked about not being a micromanager. I was so allergic to micromanaging that I ended up under-managing, which was probably the biggest place I failed early on — to the detriment of my direct report,” she says.

When people really fear micromanaging, as a result, they often end up not managing enough. 

To thread the needle between micro- and under-managing, Mannan unpacks a few of the structures she’s implemented at Segment — particularly when someone on her team is struggling. “If a designer is not doing work that is at the visual quality that I expect, micro-managing might look like this: Every 1:1 I pull up the design, give them my in-depth opinion and critique. That’s not really my style. Instead, I prefer to create mechanisms for peer accountability or gates for quality,” she says. “You can create tools and mechanisms in your team that allow for that quality bar so that you are still able to ship high-quality work as a manager, without having your hands in everything.” 

That meant shoring up her team’s design critique process, with a predictable weekly cadence. “One of the first things I did to scale critique was implementing design office hours with design leads. I never want folks to say they didn’t have an opportunity to get feedback on a piece of work. When I felt like the work of a direct report was not of the quality I expect, instead of using my 1:1 time critiquing, I would ask them to go to office hours that week. Sometimes I’d chat with the person that was leading the office hours and let them know the challenges I was seeing and where I’d like to see improvement, without dictating exactly how to get to that end result.” 

She also made it a priority to add more social touchpoints across the team, which goes hand in hand with scaling opportunities for critique. “Every design team right now is growing — 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 that feedback,” she says.

Now, every other week, the Segment design team has “Design Hangout,” with the goal to get folks more comfortable with each other. It may not sound like design-specific advice, but Mannan sees an outsized impact. “I’d say that Design Hangout and 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 even know were friendly with each other are meeting and sharing their work. As a leader, it’s your responsibility to create that environment,” says Mannan. 

You can’t expect critique sessions or office hours to work unless you create forums for folks to connect with each other socially, so they’re comfortable with using those forums to begin with.

Like nearly any interview process, Mannan’s hiring loop starts with a call between the hiring manager and the candidate. Her primary goal with this initial touchpoint? To make sure the candidate’s career goals align with the work Segment produces. “I want to get a sense of how the designer thinks about the work that they’ve done and how interested they are in B2B. Somebody who’s choosing to spend the next few years designing Segment and not designing the next Snapchat is a different kind of designer. The UI, visual and product challenges that we’re tackling can be tough to onboard onto, especially if you’re a nontechnical designer,” she says. 

Hiring managers: Be mindful of the strain on your team’s time.

A word of caution here — be very careful about your passthrough rate during this phase. “It can be easy to basically move every single candidate forward. There was a period of time where designers on my team were interviewing 5-6 times a week. I would end a hiring manager call and say, ‘You know, they did well enough — I want to see more.’ It’s an expensive mistake I made early on,” says Mannan. “I spent so much of my team’s time interviewing candidates I was lukewarm about, instead of shouldering that due diligence early on — treating it as a qualifier call instead of an intro call.”

The aha moment came when she got some tough love. “I had a great recruiting partner who finally said to me, ‘Hareem, think of each interview as valuable time that you’re asking not just of the candidate, but also of your own team.’ Progressing candidates through feels like an easy and fine thing to do, but can have some real negative effects,” says Mannan. 

Candidates: Every portfolio presentation should include these two elements.

Next comes the portfolio review, where designers present work from previous roles. “We’re primarily testing for two things here: Of course, the quality of the work. As the candidate explains the projects they chose to highlight, you can start to get a sense of how deeply they thought about the problem, the visual design, and the needs of the business,” says Mannan. 

Circling back to one of Mannan’s top three designer traits, she’s also looking for folks who will collaborate outside their swim lane. “We pay attention to the extent to which they talk about the partners they teamed up with on the project, particularly product and engineering,” she says. Drawing on her experience as a panelist across dozens of portfolio reviews, she shares a few tips for design candidates prepping their presentations. 

Don’t skip over the steps: “I remember one candidate really focused on making sure the portfolio panelists understood every step of the design process the candidate used. Anchor your presentation on specific steps so we’re able to follow along with exactly where you were along the journey — what were the deliverables? Who were your collaborators? What key results were you trying to drive? It seems small, but it helps the team that has probably sat through dozens of portfolio presentations follow along with your thought process. Don’t expect us to read your mind.” 

Anticipate the “buts”: “Given the nature of how companies work, you might be presenting on something that never shipped, or you didn’t measure the success the way you’d want to — all sorts of different variables. Great portfolio presentations anticipate those ‘Well, you didn’t cover X’ or ‘I didn’t get to see Y’ rebuttals from the panelists. I suggest a slide that talks through all of the things you would have done differently. You’re beholden to your circumstances, but you can get ahead of that by recognizing and acknowledging where a project might have been limited and where you might have approached X, Y and Z differently under more ideal circumstances.”  

Hiring Managers: Loop in your cross-functional partners.

The third key piece of Mannan’s interview loop probes for what she sees as the most underrated designer quality — understanding the GTM motion. “I’ll admit it’s almost impossible to test for and tends to be something that I teach when folks onboard at Segment. But there is one special interview we do, called the process and collaboration interview, which helps us gain signal into how someone might approach those GTM partnerships,” she says. 

Typically it begins with a researcher and a product manager presenting a problem to the design candidate. “The goal is that over the course of 45 minutes the designer walks us through how they would approach that particular problem. There’s no take-home aspect, we use a virtual post-it tool now in COVID times. We ask the designer to map through each step in their journey. Do they start by talking to customers? How do they validate what they’re working on? What kind of research questions do they ask? Would they even ask research questions? How would they partner with product and engineering?” she says. 

The most promising interviewees, according to Mannan, are able to create order from chaos. “I want folks to have an opinionated structure on what their design process looks like. ‘Step one, 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 produce quickly and learn from,’” she says. “A lot of folks aren’t able to articulate those steps, and that’s where they get tripped up. The folks that can present with clarity are often the folks that are best primed to be paired up with a solutions engineer or an account executive.” 

Lightweight ideas for making onboarding productive and fun.

Reflecting on the last couple of years adding new folks to her design teams, Mannan admits that the onboarding ramp has gotten steeper. “Onboarding for us has changed twofold — one, joining a technically complex company remotely has shifted the ways in which we can deliver great onboarding. Two, with the acquisition, you’re not just getting to know Segment, you’re also getting to know Twilio,” says Mannan.  

To smooth the path, each team records onboarding sessions that share who they are, how they work, what they work on, which new folks can watch during their onboarding period. Mannan’s also a big believer in comprehensive 30, 60, 90 onboarding docs with clear and measurable goals and expectations. 

But one of her biggest lessons in onboarding is that it’s important to give folks the space to direct their own learning. She sketches out a recent example of watching two designers onboard in tandem. “One of them was a growth designer who spent the first two weeks creating a comprehensive map of how customers onboarded to the product, with all the areas that she felt she could improve. It was incredibly beneficial for her to create that visual artifact to better understand the product and the user flows — it’s still a deliverable that’s powering her team’s projects today,” says Mannan. 

That onboarding path is contrasted with another newer designer: “She ended up creating a long doc of who’s who in the company, essentially doing a lightweight version of user research into different folks at Segment. ‘How did you get here? Why did you join? What teams are you on? What are the biggest problems you’re facing right now?’ As a more senior designer, it made sense for her to spend that time investing in cross-functional relationships, rather than investing in a specific product area,” she says. 

Tactical tip: The final piece of onboarding at Segment is a recent addition to the flow, but quickly became Mannan’s favorite. “We’d realized that we had been doing a good job operationally of getting folks onboarding to the product of what Segment is and who are the people at the company. But the warmth aspect was missing once we shifted to remote,” she says. “We started a series called ‘Dear New Designer,’ where every designer on our team writes a letter to the new designer joining, sharing what they wish they did or wish they knew when they were onboarding.”

It’s a tactical tip that goes hand in hand with her choose-your-own-adventure onboarding style. “It’s a complete hit with every single person who’s joined because people are able to take that onboarding doc that’s chock full of ideas and then decide how they want to approach onboarding based on their role, who they are, and how they like to learn,” says Mannan. 

This article is a lightly-edited summary of Hareem Mannan’s appearance on our podcast “In Depth.” If you haven’t listened to our show yet, be sure to check it out here.

Photography by Bonnie Rae Mills

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