Managing through Seasons
On weathering the necessary challenge that comes with growth
There are good seasons and there are bad seasons. One follows the other… I lean into this expecting to go through trials and knowing that those things are blessings.
Tristan Walker, founder & CEO of Walker & Company Brands, shared this perspective during Sprout Social’s 2022 Company Kickoff when asked what he would change if he were to start his career over again.
This frame stuck with me. It led me to reflect on my career, particularly, this most recent chapter as part of Sprout’s Product Design leadership team. At Sprout, we believe in growing passionate, resilient leaders. What this means in practice is precisely what Tristan touched on. Building courage to take on trials as a catalyst for critical growth, creating space to reflect on the learnings that come along the way, and embracing the ups and downs of different seasons that punctuate our careers.
I thought I’d share a few of the lessons that I learned as I navigated some growth seasons of my own over the past few years.
Lesson one — Embrace not knowing
I joined Sprout in October of 2019 as a Senior Manager, tasked with helping establish and grow the people leadership practice for a team of 20-ish designers, most of whom were co-located at our Chicago headquarters. I was ready to embark on a new chapter, having made the tough decision to leave behind a team and product that I had quickly grown to love, in favor of a career opportunity I knew was rare and better aligned with my values and long-term goals.
Despite feeling experienced enough coming off of a few good years of managing small design teams, I quickly realized this would be a new take on the role. For one thing, the way I had practiced management in roles prior was through doing the work. I’d grow others by setting the example — applying deep subject matter expertise in our product and customers’ needs while practicing the craft alongside my teams.
What Sprout required was different in a few ways. I was spanning multiple teams dedicated to different areas of the product. This meant I needed to trade depth of knowledge for breadth. The individual contributors I managed ranged in level from early career to near-Staff, and, in strengths, from front-end development to research to UX. In some cases their skills were out of my wheelhouse and, in others, they had tenured wisdom that I simply could not expect to match. And, despite all of the #SproutLove we get from customers around the simplicity of our UI, turns out that under the hood the product can be sneaky complex (which warrants a kudos to all of the designers that magically transform that complexity to simplicity!)
Cue the panic and confusion. If I wasn’t going to be the expert, who would I be? How would I add value and earn the trust of my teams? I wondered if I was just the wrong fit for Sprout. If I was cut out for this role when it felt so distant from the manager I was before. If I even wanted to take on this new and different set of responsibilities. When I finally shared how I was feeling with my manager and our Sr. Director of Product Design, Boo Fagan, she reframed all of this discomfort — could it be that I was growing?
I had stepped into a role that hadn’t existed before at Sprout. My job wasn’t to have all the answers, but to ask the right questions, learn from others, and figure out how I could shape the future of this role with them.
I had landed in a place where it was safe and even expected to ‘not know,’ as long as I was willing to be curious, persevere, and embrace a learning mindset. This allowed me to lean into more of my authentic self and lead from a place of humility. I began to expose my flaws, openly admit what I didn’t know, and rely on those I led to add context and bring their skills to scenarios where mine were lacking. And, perhaps most importantly, I made a conscious effort to remind others to model the same behavior.
Before long I was acquiring new skills as a people leader, getting my rhythm, and even starting to see the positive impact I was having on others. Self-doubt dissipated and was replaced with passion, purpose and excitement. I found my way back to subject matter expertise, this time by leaning into my experience on product teams to think in terms of people and systems. While I slowly built knowledge on the customer side, I was able to change my craft medium to culture, processes and structures. I found myself more and more invigorated by the challenge of fostering an environment where our talented team of designers could truly do their best work.
Lesson two — Hold intentional space for connection
March 2020 rolled around, and with it came a global pandemic and a truly unprecedented set of new hurdles. On top of all the fears and uncertainties of navigating the day-to-day of our personal lives, the way we worked as we knew it was over.
For our fast-growing people leadership team, this meant getting back to basics. What did people need right now from their jobs? I found myself reorienting around Todd Henry’s stability and challenge matrix, from his book Herding Tigers. He says that in order to thrive, creative people need a combination of stability and challenge.
In times of crisis, not only does challenge dramatically increase, but stability goes out the window. We knew that our team needed an anchor — something that felt in control when the world was spiraling into chaos. The values-driven culture of Sprout has always been core to who we are, and for Product Design, the way this culture manifests is through our community-centered practice. We needed to rebuild the sense of community we had in-office for the realities of a remote-first world. We needed to give people space to experience all of these challenges, together.
We began to brainstorm against the following:
- How might we create the organic moments of connection that gave us small but necessary reprieves from our days?
- How might we ensure we continue to check in on one another, even if it couldn’t be informally over a lunch or coffee break in the cafe?
- How might we continue to foster a sense of play, even if we couldn’t jam together at the whiteboard IRL?
The ‘remote constraint’ allowed us to be more intentional about how we connected. We experimented, failed, and some great ideas were born. We evolved our new hire welcome lunches to a virtual Miro session where we all participated in ice breakers, allowing us to both get to know new team members and deepen our relationships with old ones. We extended our monthly team-wide ritual to make space for intentional play, from fun design warm-up activities to dreaming together about the future. We broadened our hiring pool and were able to add new, diverse voices to our team. We normalized holding space to check in on each other at the start of meetings instead of jumping straight into the work. We celebrated creating healthy boundaries between work and life with the introduction of company-wide R&R days. A remarkably tough time proved to create a lot of good.
And of course, our dedication to building a great product didn’t stop. The human-centric approach to our people carries over into our product, ensuring we stayed focused on delivering impact for our customers. Turns out the investments we made in taking care of each other made us better at how we approached our work.
Lesson three — Ask for what you need
This brings me to what has been the most formative milestone for me personally. In October 2020, I became a mom to my beautiful son, Caleb. The experiences of being a first-time parent oscillated fast from immeasurable joy to wild overwhelming challenge and back again.
And it came with a new reality. I was a different person with different priorities. When it came time to return from my maternity leave, I was part ready, part heartbroken. While I was incredibly grateful to know I was returning to a place where I could embrace the new version of me and bring my full self to work, I also knew bringing myself to work required trading off precious time with my son.
This meant I needed to get laser-focused on how to make my work as purposeful as I possibly could. I needed to find balance and make the most of my time so I could show up to the best of my abilities in both aspects of my life.
And lucky for me, Sprout is a place that acknowledges that not every individual’s career needs to follow the same path. We fit roles to people, not people to roles. After plenty of introspection, I knew I wanted to shift my focus to be further in service of the team that had given me a safe space to grow. My passion continued to be around setting them up to do their best work, and doing it in a way that not only maintained my new boundaries but also worked to give designers time back, too.
With the support of design leadership, I shifted into a new role establishing our Product Design Enablement Practice. I feel an immense amount of privilege to be given this opportunity to focus fully on equipping designers with what they need to thrive. There’s a long road of learning ahead, but this step has helped me recognize how far I have come. I’m now able to have the courage to step into the unknown, acknowledge the fear in doing so, and continue to push through and act in spite of it.
I’m proud to be part of a Design program that actively fosters growth through our individual and collective seasons of change. That aims to strike the right balance between stability, support, and challenge. That values openness and humility. That understands the power of caring personally. And that empowers individuals to shape their own paths. I’m proud to work somewhere that encourages the self-reflection and courage needed to lean into the discomfort that comes with all the highs and lows. What I’ve learned here has shaped me into the kind of leader who can support and cultivate this same growth in others.
As I reflect again on Tristan’s remarks, the biggest lesson I’ve taken away has been in adjusting my expectations. Trials will happen. Expect them. Or better yet, run towards them. Because what’s waiting for you on the other side tends to be well worth it.
