#14 The Inspirational Leader Series: Anna Love

Welcome to the Inspirational Leaders Series, a collection of short interviews with sharp, impactful leaders that I know and respect—because the business world needs more refreshing people like them. 


“I think organizations and leaders often have an imbalanced amount of power—power over, not power with, the individuals that make up the company.”


👋🏼Meet Anna Love, CEO and Co-Founder of Stoked, a global design consultancy focused on humanizing work. She recently made Inc. Magazine’s Female Founders 100, a list of America's most creative and trailblazing leaders. She actively pushes the boundaries of workplace culture and helps organizations innovate and create cultures they are proud of. 


What's a challenge that has turned you into a better leader?

I didn't set out to start a company, and I didn't set out to be a leader. And so, as Stoked evolved over the last 12 years, it evolved naturally, organically, and by nature, unintentionally. I found myself at a place a couple of years ago where things felt unfair to a lot of people. And, you know, fairness has its personality within an organization. 

One of the biggest challenges that I tackled, and I'm most proud of, is attempting to create a work environment where the power dynamic between the individuals that are a part of the organization and the organization itself has balanced power. I think organizations and leaders often have an imbalanced amount of power—power over, not power with, the individuals that make up the company. 

And so balancing that power has required making a lot of changes—changing the way communication happens, changing what is transparent within the organization, and how decisions are made. It creates this sense of self-determination so that individuals have a sense of power over their own lives at work. Work takes such a huge place at the table in our lives. When someone comes into work and doesn't feel self-determination, it is disheartening at best and toxic at worst. And so, for me, that is something that I continue to tackle very actively and am most proud of.


What triggered you? What was the thing that made you decide, "I need to do something about this."? 

What motivated me is I realized that if I believed that Stoked was an organization that should exist for the next 10 years—which is a fair question for anyone to ask to begin with because not all organizations should live on in perpetuity—what is an organizational structure that allows Stoked to have the biggest collective impact in the world? And traditional models for how organizations function and are organized are hierarchical and have a bit of command and control. And I know that if that is the model that we continue to follow and cultivate, we won't maximize our impact, and the team will not be on fire for the work. And so it was a matter of necessity in order to really have Stoked be something that I'm really proud of. If I believed it deserves to exist for 10 years, I had to completely shift how I thought about the way that we functioned and the way that we flocked together as an organization.


What motivates people to do really good work together? 

Equality and trust. And transparency builds trust, I think. It creates shared risk and reward, and that's really motivating. 

And really, I think the more that we can create environments where everyday people get to wake up and choose to be together in that environment versus, “Geez, I signed an employment contract a year ago.”, the better. We're held together by human compulsion versus a contract. When you're creating an environment that's exciting, there's no doubt you're going to make surprising impacts in the world together.


What are you learning so far with this experiment?

It's freaking hard. One of the biggest elements for me was transparency. And making sure that we were transparent in all of the right places, identifying what they are, and what kind of education is needed. So, for example, financials are something we are 100% transparent about, and that includes salaries and bonuses. It takes education, too, when you’re showing company financials or an income statement. Not everyone is familiar with all of the elements. 

Setting up the right rhythms and rituals for the organization to be able to move together in unison while still allowing for that autonomy as an individual was also new to us because we were pretty much like, “We just kind of go with the flow.” And all of a sudden, we're like, “No, there are certain things we need to have a routine around in order to create an environment that works with this shared power.” A lot of companies have values; we call them “Ways of being”. We really needed to get clear on what those ways of being were for us, for each person's job, and measure them all the time, and reflect on them all of the time. We didn't have values as an organization until two or three years ago. So even that was a big shift.


How do you measure whether values are being achieved?

It was important for me to make sure that people were reflecting on the values individually, not as an organization, because it's easy to say, “Oh, the organization isn't doing this.”. It's much more intimate to say, “I'm not doing this.” 

We're a group of a total of about 80 people between fall and part-time with a core team of about 10 folks. And so every month, we do this “Rock, paper, scissors, shoot!” game on video. We ask how many individuals are embodying each of our 6 values right now. It's a personal reflection, not a global reflection, and then we get to have a conversation about the why behind it. It's been a great exercise, giving people an opportunity to reflect on Stoked's values and their own personal values—to make sure that those values align with them. Because if there's a misalignment in those values, then, of course, there's going to be a rub, and something isn't going to work, right? So really being articulate and reflective on the values has been pretty important. 

Sometimes, it's uncomfortable when the values are well articulated. For example, one of ours is that we hold creativity in tension with efficiency. We are a team of incredibly creative people and operations-minded folks. We often have conversations about something that we're designing that is way over budget. And you know, the client lead might say, “But it's what's best for the client.”. Then the operations-minded person might say, “But it's not what makes sense to the budget.”. And so, to be able to use that value and then have a very real conversation about what to do next has been uncomfortable and valuable.


How do you also then avoid groupthink? There are probably times when you need to make a call… 

For me, that has been the harder leadership lesson—deciding where that boundary is between democratic decision-making versus me firmly seeking input, getting information, and then making a decision that I'm going to stand behind with confidence. That took me time to figure out because I was a bit of a reluctant leader. I really wanted to do everything in a democracy because I wanted everyone to be happy. And I wanted them to feel good about the decision. But I think I've realized that a democracy where everything is open for a vote doesn't always feel good. Sometimes one person just needs to put a stake in the ground. 


How do you know when you're getting your leadership, right?

It's a very uncomfortable way of knowing: people bring harder questions to me. And by harder, I mean, people are showing more of themselves. They're being more authentic, real, and vulnerable about what they need, what's not going right, or what they want for themselves. And a lot of times, those conversations are about something I've done that didn't sit well with them. And so I feel like the better I become at leadership, the more difficult conversations I have. I just had one of those conversations right before this call. It's fresh on the mind and it was difficult, but it was also beautiful because it was an opportunity for us to really connect in a meaningful way about something that mattered to them. And they proposed something to me. And it was uncomfortable, and we had to figure out how to navigate this together to get to a place where we both feel good about what's next. That’s also an example of navigating a more balanced power dynamic.


Is there a leadership tool, method, or practice that has had a lot of impact on you?

My first thought is the transparency that we've already talked about, a tool that has transformed our culture in many important ways, creating more trust. 

There’s another tool that feels basic but has been powerful for us. We sat down and clearly articulated our vision: the culture, growth strategy, rhythms, and rituals that we are going to adhere to this year. It allows us to have this picture of the business as a whole and then drill down into specific elements of that business. 

And then, we married that vision with a beautiful story. 

I wrote a story about who Stoked is in five years, with a lot of detail. Like, how does the world see us? And who are our clients? And what is the impact that we're having? And where do people find it? It's a really detailed story of who we are in the future. Having those two things side by side, vision and a story, allows everyone to see where we're going. And we can look back and forth between those two to start to narrow that distance.

There was a bit of an awkward moment when I read the story out loud to the team for the first time. There was this long moment of silence. I'm kind of looking around the room thinking, “Okay, who's gonna talk first?”. And it turns out people were so grateful to have a light—something they could all rally around that is exciting. And then they were able to say, “But what about this part over here? We've been kind of playing in this space; is it not a part of our future?”. So, it was a great conversation. It was inspiring. And then after that, we took turns reading it at future meetings. And so, we returned to it and took ownership of it collectively.