DtG #1: Why leading designers is different from leading other roles

Hey there, and welcome to the first full issue of Designing the Gap! Today, I want to dive into something I’ve thought a lot about: why leading designers isn’t quite like leading anyone else I’ve managed.

I’ve held the title of “manager” or “director” at half a dozen companies. Sometimes these have been “super IC” roles—a team of one with maybe a contractor or two supporting delivery. More often, though, they’ve been people manager roles, responsible for the HR side as well as guiding people through the work. I’ve managed project managers, brand strategists, content strategists, copywriters, and of course, designers (product, brand, and content.)

Over time, I’ve come to recognize that leading designers, whether as a design manager or a senior/staff designer, requires a unique set of skills. Designers are deeply passionate about their craft, thrive on autonomy, and often see their work as a reflection of their professional identity. This makes design leadership uniquely rewarding but also uniquely challenging.

Why is leading designers different?

1. Creativity vs. structure

Designers need creative freedom to do their best work, but they also need structure to stay aligned with business goals. Striking the right balance between autonomy and process is key; too much structure can stifle creativity, while too little can lead to ambiguity and misalignment. As a leader, whether formally or informally, helping designers navigate this balance is crucial.

This can sometimes create friction when working within highly structured teams with rigid processes, like scrum teams. It can feel counterintuitive to encourage creativity within the confines of a fixed two-week sprint, but design is a partner in the product triad, not the lead performer. We need to be accountable to the rest of the team. As a design manager, I’ve found these kinds of boundaries helpful in fostering creativity while also communicating to engineering and product partners that problem-solving in design is often ambiguous and may surface more challenges to tackle.

Our role as design leaders is to create and hold the space needed for designers to thrive, but not so much that they work in an ivory tower.

2. Feedback that works

Traditional performance reviews and direct critique don’t always resonate with designers the way they do with other roles. Good design feedback isn’t just about pointing out what’s wrong and offering a fix; it’s about helping designers refine their thinking and execution in ways that align with both user needs and business priorities. Senior-level designers and managers alike play a role in fostering a strong critique culture that helps designers grow.

During one of my earlier roles at Mailchimp, I was responsible for facilitating critique for the content design team. I had a lot of content design experience coming into the team, so it would’ve been easy for me to provide highly tactical feedback. Sometimes, in fairness, I did. What was more important for me to do, however, was facilitate the experience of giving and receiving feedback. My role was to help the team lead with inquiry, ask provocative questions, and hone their creative problem-solving skills.

Side note: I absolutely love crit for strengthening the feedback muscle within ICs. Crits should be seen as “safe” environments where designers get comfortable giving and receiving feedback as well as a way to improve the quality of the work.

3. The emotions of it all

Unlike more operational, analytical, or technical roles, design is deeply tied to perception, critique, and subjective opinions. Even well-intended feedback can feel personal. Design leaders need to create a culture where critique is constructive, not demoralizing, and where designers feel safe experimenting and iterating. That may even involve acting as a buffer between designer and other product partners, who may not be as deft in providing design feedback.

Another key aspect is helping designers stay attached to the outcomes of their work while remaining relatively unattached to the outputs. Product managers will have design feedback. Engineers will have design feedback. Marketing will have design feedback. You get the point. I’m not saying designers shouldn’t defend their work, but trade-offs and compromise are part of the job.

4. Navigating imposter syndrome

The nature of design work, where there's often no single 'right' answer, can make designers doubt themselves. All designers struggle with confidence, even the experienced ones. Compare this to engineering, where the right answer is often more tangible. A great design leader helps their team build confidence by reinforcing their strengths, giving them the space to grow, and ensuring their contributions are recognized.

At the same time, organizations often hold up "rockstar" designers as the gold standard, showcasing their work as examples of excellence. While this can be great for modeling strong craft and setting a high bar, it can also inadvertently exacerbate imposter syndrome. It’s easy to compare yourself to those shining examples and feel like you’ll never measure up. But even the most celebrated designers make mistakes, iterate constantly, and rely on feedback to improve.

Design leaders need to strike a balance—celebrating great work without creating an unrealistic benchmark. More importantly, those rockstar designers should be seen as mentors, helping to elevate the entire team rather than serving as an unattainable ideal.

5. Helping designers build influence

Great design doesn’t happen in a vacuum; it requires buy-in from stakeholders across product, engineering, and leadership. A key part of leading designers is helping them articulate the value of their work, advocate for design decisions, and build influence beyond their immediate team. Staff designers can model this behavior by mentoring peers, driving alignment, and pushing for design’s role in strategic discussions.

Design leaders, especially directors and above, bear a huge responsibility here: it’s our job to ensure that design’s role and strategic value in the overall product operating model is understood and agreed upon. If this isn’t done, influence will be much harder for ICs to have. At agencies or design-led companies, this need is inherently less important. In product- or engineering-led cultures, however, it’s absolutely critical. Design does not work in service to engineering or product; all three work in service to the company and customer.

Reminders for design leaders (with or without a title)

Wrapping it all up with a lovely little bow: leading designers is about more than execution; it’s about mentorship, influence, and fostering an environment where design thrives.

Here are some tips or reminders that I hope you take away from this post:

• Coach, don’t just direct. Guide designers toward solutions rather than dictating them.

• Foster a strong critique culture. Create an environment where feedback is seen as a tool for improvement, not judgment.

• Encourage collaboration, not competition. Help designers support and learn from each other rather than working in silos.

• Give designers a voice in strategic conversations. Advocate for design’s role in decision-making, whether as a manager or a senior IC.

• Balance creative vision with business impact. Help designers understand how their work contributes to larger company goals.

Bearing these responsibilities in mind can help you support your peers and team effectively, ensuring both creative excellence and good outcomes for the business.

Things I’ve been reading this week:

• Career vs Identity by Nick Cuda, The Unemployer. I worked with Nick a little at Mailchimp, and we both got laid off within a few months of each other. Attaching my personal identity to my career has been something I’ve struggled with for a long time. Nick’s personal account of this struggle, as well as the impact a layoff had on it, is worth a read.

• UX is easy, but we made it complicated by Kike Peña, UX Collective. UX isn’t just undervalued because of external forces—sometimes, we make things harder for ourselves. This piece from UX Collective highlights how over-research, rigid processes, and poor communication can contribute to the disconnect between designers and businesses.

• Design Systems Communities on Bluesky. Like many in the design world, I deleted the artist formerly known as Twitter a while ago. But I’ve missed the conversations and camaraderie that “Design Twitter” had. This list of communities is helpful for folks dipping their toes into Bluesky and looking to join design system conversations.

Thanks for reading the first issue of Designing the Gap. Did it resonate with you? Is there anything you wanted more (or less) of? Please let me know!

Thanks,

Ben