The tough road from Designer to Leader
Some survival tips for making a tough transition easier.

It’s now over three years since I moved from being an individual contributor into a design leadership role. This seemed like an appropriate point to pause, do a little introspection, and share some of the ups and downs of my journey so far.
While this will be a short account of my personal journey into design leadership, I hope the points I’ll cover in this article will resonate with anyone who has recently moved or is about to move into any sort of leadership role.
From contributor to leader
I wanted to start by taking a moment to be vulnerable and admit that my journey so far hasn’t been easy. At times I’ve felt out well out of my depth and wondered whether I’m actually cut out for leadership. At several points early on in my transition, I was genuinely worried whether I could ever live up to the expectations of others and, more importantly, myself.
There have been a number of occasions where I’ve missed being a “real designer,” be that talking on the phone with customers, collaborating with a product team, or tinkering with a detailed layout or interaction. That direct sense of genuinely helping to solve customers’ problems was why I fell in love with product design in the first place. Had I made the right choice moving into leadership? Had I left too many of the things I once loved behind? Would I ever feel confident in this new world?
Yet I was determined to push through the initial inertia, to be open to learning what it would take to be a good leader, and accept that I would inevitably take a few knocks along the way. I needed to experience firsthand what it meant to be a design leader, to develop my own leadership style, and realize that much like being a good parent, leadership is first and foremost about being selfless and investing a significant proportion of your time and effort in the development and wellbeing of others.
Leadership lessons
Reflecting on my experiences to date, it’s fair to say that I’ve had a few stumbles and along the way have learned a few hard lessons. I’ll talk a bit more about each of these in more detail below.
Downing tools of the trade
It’s likely for anyone moving into a design leadership role is that you will have to put down many of the tools you were once familiar with. Be it Sketch, Axure, or a particular set of design methods, the tools and techniques you once used day to day, and to some extent have mastered, are likely to be replaced in favor of developing softer skills like communication, coaching, persuasion, and negotiation (to name but a few).
Over time you can literally feel some of these hard-earned technical skills eroding, moving you farther and farther away from the craft of design itself. Fear and anxiety start to kick in. Perhaps you were well regarded among your peers for these skills, and these very skills helped paved the way for your transition into leadership. Would they now significantly degrade, or worse, be displaced entirely? It was, after all, the mechanical and regular practice of these that once made you a strong practitioner.
Lagging indicators for success
We all want to feel like we are doing good work and that that work is being recognized and valued. For most designers, that sense of fulfillment comes from the feedback loops we’ve established with our teams, stakeholders, and customers. For example, there is nothing quite like seeing a customer genuinely enthused by something you and the team have lovingly designed and built.
However, moving into a leadership role and embracing the types of challenges that come with it fundamentally changes the types of work you are exposed to, and with that the cadence of success. In my experience, initiatives often involve some degree of change management (people and process) and will likely play out over months rather than days. That is something that has required determination, focus, and sometimes just dogged perseverance to come to peace with.
You will need to leave your ego at the door, hire great people, and empower them to rise to the challenges.
People become your primary concern
As mentioned at the beginning of this post, being a good leader (in my opinion) requires that you put others before yourself. However, being selfless extends beyond giving up your time for folks and also includes what you do as a leader to sponsor, stretch, and shield your team and perceptions of your team in the context of your organization. You have an obligation as a leader to genuinely care for the growth and well-being of the folks you’ve hired.
In practice this means you succeed when they succeed. It’s no longer about what you did, your individual contributions to a project or what’s in it for you. Your job now is to stand back a little, to be the advocate for your people and practices, to amplify and credit examples of great work, all while shielding them from some of the inevitable company politics. To do this well you will need to leave your ego at the door, hire great people (some of whom may be more experienced than yourself), and empower them to rise to the challenges.
Trust is key to empowering others
Something I’ve personally struggled with is trust. It’s hard won and easily lost in my case. My natural inclination, therefore, is to hold things close, as I expect a certain level of commitment, quality, and diligence. Delegation for me was hard, and I had a habit of trying to step in too often and too early to make sure things were done to my own standards. But that approach is not scalable, desirable, or even helpful for the team. Of course, sometimes it makes sense and is necessary to be more directive (see Situational Leadership), but I would initially find it hard to adjust my style and bias away from my more directive defaults.
Trust, however, is key to empowering others and allowing them to work at their full potential. As above, part of a leader’s role is attracting and hiring talented folks who can do great work and help you inspire and grow others. But, how can they do that if you do not trust them with these opportunities?
Design is a function of business
As most designers will profess, it’s very easy to get lost in the craft of design. We can while away countless hours perfecting a workflow or interaction, without a lot of thought given to what impact our efforts will have on the business. Customers will always be our primary concern, but that has to also be in service of moving the company toward its goals. As a leader, it’s your job to bridge these two worlds and drive an approach that often favors pragmatism over perfection.
On the flip side, you’re likely for the first time to be on the front line of arguing and advocating the merits (ROI) of design and why the business should continue to invest and scale. Once oblivious to the world of profit and loss, company strategy, objectives and measures, you’re now on the hook to really understand where design fits in and how it will play a part in the future success of the company. We have to be able to demonstrate how our research and design efforts will contribute to the bigger picture, as opposed to being lost in the purest pursuit of our craft.
Survival tips for new leaders
Having discussed some of my personal learnings along my journey so far, I wanted to share a few of my own survival tips for new design leaders or those who are thinking about moving into a leadership role.
1. Find other outlets through which to explore your creativity
While moving into a leadership role might mean distancing yourself from day-to-day design tasks, it doesn’t preclude you from finding other creative outlets through which to communicate and express your thinking. For me, this took the form of using design tools to visualize concepts like design and development processes, aspects of organizational design, and individuals’ growth and personal development.
2. Apply your design approach/methods to other types of challenges
Many organizations have seen success with applying a design thinking approach to challenges not typically thought about from a design perspective. Wherever possible, it’s been helpful for me to continue to apply this problem-solving mindset to a range of divisional and organizational challenges, ranging from recruitment and hiring to improving sharing and collaboration across teams and divisions.
3. Design vicariously by supporting and challenging your team
While you may not have the opportunity to be hands-on with product work, you still have obligation to get up close and personal with your team’s work. Your job here is to challenge and support your team’s design efforts and foster a community of feedback and collaboration. Being involved with activities like show-and-tells, design walkthroughs, and critiques helps keep you connected to the team, your products, and the quality of the design work.
4. Deconstruct initiatives and set intermediate goals
As above, tackling large initiatives or change management projects can be immensely daunting and create a sense of inertia. Think about how to take something that seems insurmountable and break it down into milestones or intermediate goals. Taking time to regularly reflect on your progress toward these shorter-term goals and recognize some of the achievements along the way can help to keep you focused and motivated.
5. Experiment with delegation — small steps build mutual trust
Trust is mutual and has to be earned on both sides. If, like me, you struggle with the idea of delegation, then start small. Find folks with some experience with a similar task who are proactive and willing to commit, then give them the problem to solve and trust that they will rise to the occasion. Go through this loop a few times and slowly you’ll get more comfortable with the notion of stepping back, intervening less, and seeing the results.
6. Understand what matters to the business
Leverage your design skills to empathize with senior stakeholders. Attempt to understand what’s motivating and troubling them and seek out the opportunities where design can help. In your first few months find someone who “gets it” and can help you traverse business speak and the wider commercial landscape. Start to develop enough of an understanding that you can begin to articulate the value of design in terms that the business recognizes and values.
7. Question the intent and impact of design work
Whenever you or your team starts a piece of work, if it’s not immediately clear, stop to ask how it might support one or more of your product or company objectives. Whether it’s a program of research or an implementation of a solution, check to ensure it can be mapped through to a desired outcome for the business or its customers. We all want to be doing valuable work, and now, more than ever, you have a responsibility to ensure your efforts and those of the team will have the desired impact.
Salvation is out there!
While I’ve learned a great deal over these last few years, I’m still very much on this journey and will no doubt collect plenty more war stories to share with others who decide to follow a similar path. It does, however, give me great comfort to know that I’m not alone and there are many of us out there still trying to figure this stuff out.
Along with the writings of many inspirational design leaders, there are a growing number of communities and events tailored to support design leaders, of all backgrounds and levels of experience. I can personally recommend the fantastic community Andy Budd and the folks over at Clearleft have nurtured, and I’ll be returning again for my third year running to their awesome Leading Design conference.
Originally published in Redgate’s blog, Ingeniously Simple