Earlier this month I had the pleasure of co-hosting a retreat for senior design leaders, at a beautiful country house hotel in the Cotswolds. The group was comprised of Heads and Directors of Design from a range of well known brands.

Andy Budd
Andy Budd
5th April 2019

Most were from the UK and Europe, although a handful had flown the 10+ hours from North America to join us. They were here to spend the next few days exploring their career journeys, improving their leadership skills, and sharing tactics and advice with their industry peers.

It was clear from the off that these three days were much needed. During the opening circle, people talked candidly and honestly about the pressure they were under, feelings of isolation, and an overwhelming sense of imposter syndrome. They also talked about the guilt they were feeling being away from their families and teams. For many, this was their first chance to spend any meaningful time focussing on themselves and their careers, so they weren’t about the waste the opportunity.

We kicked things off with what I called a Leadership MOT. Essentially a series of exercises intended to understand the individual career paths these leaders had taken to get to where they were today, the highs and lows of that journey, and what this could tell them about their own personal needs. Next, we delved into the topic of leadership styles, plotting their approaches and preferences on a series of charts and graphs, before looking at which areas could be improved upon. We did a similar exercise looking at where they currently spent their effort, and how they’d like that to change over the coming months. We used this information to start filling in a personal design leadership canvas, the second half of which we’d come back to at the end of the three days.

Common challenges setting the agenda

Using Open Space Technology, we pulled out all the key issues the group was experiencing and turned these into a detailed agenda. Topics included the challenges of scaling a team, how to go about measuring and demonstrating the value of design, the best way to structure your design team, tips on building a robust design culture, and approaches for dealing with boards, peers from other departments and organisational silos. We also touched on more challenging subjects like managing difficult staff members, dealing with workplace stress, fears around personal and professional failure, and worries about what comes next.

If you’ve been to a Leading Design Conference before, or happen to be a member of our Slack community, most of these topics will be familiar to you. However, our attendees seemed to find it both helpful and cathartic being able to discuss these topics in a safe space amongst a group of peers. One said of the retreat “It was better than I could have ever imagined and will have a lasting effect both professionally and personally. It was introspective and revelational.”

Topics included the challenges of scaling a team, how to go about measuring and demonstrating the value of design, the best way to structure your design team, tips on building a robust design culture, and approaches for dealing with boards, peers from other departments and organisational silos.

Interspersed between the discussions, we had arranged a number of social events. On one day we got to choose to do a bread making or cocktail making course - an opportunity to get creative and bond with our peers out of the context of our day-to-day roles. The next day we went on a group walk in the Cotswolds countryside. One of our goals for the retreat was to help create a bit of a support network for our attendees, so creating space for people to get to know each other and build lasting bonds was super important.

The merit of a personal leadership plan

While we experimented with a number of different sessions, one of the most popular activities was known–rather cheesily—as a success circle. This involved splitting our design leaders into groups of 4 and giving each person 20 minutes to request help or advice from the other members. Some people asked for help with their recruitment challenges, others delved into the thorny problem of team structure. Some people needed help with a difficult HR issue, while others sought advice on their next career move. The result of this session was that everybody came away with a stack of good ideas for how to solve a knotty challenge that had been bugging them for a while.

As the final afternoon approached, we switched back to our structured activities, asking everybody to fill in the second half of their Design Leadership Canvas. This acted as a helpful way to capture some of the challenges they’d surfaced, the advice they’d been given, and the decisions they’d made. We then set a second activity; to create a personal leadership plan. The plan was broken down into different sections; things you could do to improve your own personal leadership abilities, things you could do to help your team, and things you could to do affect the wider organisations. These sections were divided into three different time horizons; things you could do now, things you could do over the next couple of months, and things you would work towards in the future. We asked everybody to commit to at least three of these as immediate next steps.

design leaders at the leadership retreat

Time for introspection

Even though we were only away for three days it felt like we’d been away for a lot longer. We’d had some pretty intense conversations, and a few tears had been shed along the way. New friendships had formed and we’d bonded as a group. While it would have been too much to ask to solve every problem raised, a good amount of ground had been covered. People left feeling renewed, reinvigorated, and excited for what happens next.

One of the group summarised the experienced best when they said “it has been both a cathartic and delightfully exhausting introspective journey of which I hope to continue and practice with both myself and those of whom I work with.”

Our next leadership retreat takes place on the 16th -20th September, in the forests and mountains of North Norway—the perfect place to escape, recharge and work on your leadership challenges. We’ll be taking applications soon, so follow this link for more details.