In the last 18 months, my company has changed its name from the Unreasonable Institute to Uncharted, changed its business model, lost two-thirds of its management team, and nearly ran out of money.
I became CEO when there were only 90 days of financial runway left before we would need to lay off the team.
Eventually, we found solid ground. While previously we had funded startups with social impact, we shifted our strategy to build teams that attack problems like food deserts and urban poverty from multiple angles. After raising almost $1 million of funding for our new vision, we were able to double the size of our team rather than letting people go. But the transition was understandably uncomfortable for everyone.
As humans, we don’t like being in the in-between space of our current reality and our future hopes. We feel exposed and unsettled. My first year as CEO was painful, joyful, uncertain, and invigorating. I made mistakes. I learned. I discovered reserves of resilience I didn’t know existed.
Many growth-stage organizations like ours go through transitions, and I wanted to share what I learned from the experience. To be honest, I am also writing this for myself and our team’s future leaders, so when the next transition comes, we have a reminder of what helped this time.
Timing matters: I quickly learned that the timing of my communication was just as important as the message itself. Though I always strove to be open and honest, sometimes I held back information because I believed that—at that time—it would prevent our team from doing their best work or would cause unnecessary anxiety. Here are two scenarios where I found that timing was especially important:
- New Ideas: As our impact model and business model shifted, I had dozens of conversations with various external partners and supporters. Sometimes I would come back to the team and share multiple new ideas. For a team that was already navigating a substantial transition, these new—and sometimes conflicting—ideas were disorienting. “Wait … are we doing that now?” I learned that a company’s leadership needs to consider the emotional impact of communication. Is a piece of information beneficial to the person receiving it? How might it hinder him or her? The thoughtful consideration of these questions is not at odds with a culture of openness and honesty.
- Difficult news: There was a moment last year when our runway was short and we were considering giving the team options to reduce their weekly hours. I was in the middle of a three-week fundraising trip, and I debated with the management team about whether I should stop fundraising and return home to speak to everyone about the options in person (or if we should wait until my trip was over).I made the decision to pause the fundraising trip and booked a flight home. I knew delivering the news in person was the right thing to do, even though I was afraid to do it.Ultimately I did not have to deliver the news after all. I canceled the meeting a few days later when new funding came in.
Make fewer promises. But make them more specific: I felt a strong desire to encourage our team, help them discover the optimism I had, or maybe just to vocalize optimism, hoping it would boost the feeble hope I had on days when I was afraid. It was tempting to toss around encouraging promises. But ultimately, I lost some of the team’s trust by making promises that we were not able to fulfill. My team later told me there was a sense of, “yeah, the leadership is saying that, but I’ll believe it when I see it.”
In moments of transition, when things are shifting and uncomfortable, a promise seems like the cheapest and easiest form of encouragement and the fastest shortcut back to stability (“Once we get through all this stuff, we will be able to hire again!”). But an empty promise, while tempting for its short-term reward, is ultimately destructive long-term.
Of course the team needs to know that leaders are thinking long-term about what’s next, but a trustworthy leader without the perfect plan is better than an untrustworthy leader with one. I learned that I needed to make my promises grounded, outcome-based, and time-bound.
When you can’t make the promise that you want to make, it’s better to make a more realistic promise: “I don’t know when we will be able to do x,y,z, but I can promise you that in two weeks, during our next check-in, I will give you an update.”
Consistency > Inspiration: In 2017, there was a general, high-level alignment on our team about our new direction. But beyond that high-level alignment, there were specifics that were unclear and needed to be ironed out. Members of the management team had different ideas about how we would address them. This caused confusion and disorientation for the rest of the team.
In times of transition, when things are up in the air, consistency of message from multiple people is more important than instilling one-off inspiration or buy-in. Management should ask itself:
- Is there a consistent message we can communicate to the team right now?
- What is unresolved or undefined, and how can we honestly communicate—with consistency—our progress to resolve and define it?
Listen in one-on-one meetings, and speak when you’re with the whole team: One-on-one meetings with teammates were instrumental in understanding how the team was feeling. It was tempting during these conversations to share progress, the latest inspiring conversation, or something frustrating that recently happened. I learned that these conversations should instead be focused on listening and understanding.
On a retreat earlier this year, the team pointed out that I was sharing information related to strategy, our financial runway, or our upcoming plans inconsistently. I would share it with one person, and then neglect to mention it to someone else.
When it comes to delivering important news to the team, I now either deliver it rapidly in back-to-back one-on-one meetings, so everyone knows the news within a few hours of each other, or simply wait until full-team meetings to communicate it.
Identify and support a cultural leader: During the period in which we had decided to change our name, but had not yet settled on the new name, we felt placeless and faceless, like we were at an in-between stage of identity.
We were fortunate to have a member of our team who lived and breathed our culture and constantly brought us back to those unchanging principles of our organizational identity (and also reminded us to have fun—even surprising us with an unexpected “Waffle Wednesday” waffle bar one morning).
In 2017, I did not have the awareness to charge someone with becoming a cultural ballast to the team, but our teammate did it anyway, perceptively identifying the need. Here are questions that may be helpful when thinking about how to support a cultural leader:
- What cultural practices have we always done that we can continue to do?
- What about our organization is unchanging? How can we create experiences and events for the team to reconnect with those sacred and unchanging parts of our identity?
- What common language can we use that helps ground the team during moments of transition?
- What stories can we come back to that help situate this transition in a larger context? Are there organizational mythologies that everyone knows that should be resurfaced?
Acknowledge the emotional experience of transition: Our branding agency, Briteweb, had led organizations through rebranding processes before, so it knew to acknowledge the emotion surrounding the experience. Early in the process, the agency led us through an exercise where each of us wrote personalized, confidential thank-you notes to the name “Unreasonable Institute” for what it meant to us. These notes enabled us to honor where we had come from, while also bringing a sense of closure.
In the days before we changed our name, our team gathered to talk through what Unreasonable Institute meant to us, what we wanted to bring with us going forward into Uncharted, what we wanted to leave behind, and how we might consider this organizational transition as a catalyst for our own professional development and growth.
Create new stories and magic: Preserving what is sacred about the existing culture is important, but so is boldly stepping forward into the future with new dynamics, stories, and magic. In The Power of Moments, Chip and Dan Heath recommend “breaking the script” in a way that shifts people out of the comfortable way things have always been. Here are three ways we broke the script:
- Dynamics: On the first workday of 2018, we told the team we were going to re-organize our office and change the desk layout. On the same day, we told the team we wanted to “go on the offensive in 2018.” They cleverly shortened it to the mantra “Be Offensive,” which became part of our daily vocabulary.
- Stories: On the night after we changed our name, we all went out and celebrated with cake, shots of tequila, and a dose of ridiculousness that was unexpected for a Tuesday night. It was an evening that has created multiple moments of joyful reminiscing since.
- Magic: In 2017, our entire team conspired to prank a teammate over the course of nearly two months. The prank was entirely non-essential, overly sophisticated, and delightfully fun (it’s hard to explain—email me if you want to know the play-by-play). We were busy and had more than enough to do, but it was too good of an opportunity to pass up so the entire team got in on it. Sometimes what’s most frivolous is what’s most important, simply because it creates the connective tissue that bonds teams together.
Take the long view: When we were considering the name “Uncharted,” I was most concerned that it was too close to “Unreasonable Institute.” I wanted us to make a substantial step away from our old identity, and this prefix thing was a significant hold-up for me. But now that it’s been over a year, I am stunned by how little that seems to matter.
That’s the perspective of hindsight. But in times of transition, when things feel muddled and disorienting, how do we—as leaders—make decisions that are sober and wise in the long-term? Two approaches helped us to ground our decision-making faculties.
- Take the long view: One of the most helpful questions I asked myself was “What would our successors—the people in our roles 10 years from now—want us to do right now?” That helped me see that 10 years from now, the common prefix “Un” in Uncharted and Unreasonable Institute wouldn’t be a big deal at all. No one would care, and very few would associate the two.
- State your bias: When our management team was making strategic decisions, we first explained to each other how we might be biased or inclined to draw a specific inclusion. Our personal preferences for certain outcomes would come out one way or another, so it was better to acknowledge those at the outset. Doing so allowed other decision-makers to help ensure the bias didn’t overpower sound decision-making and analysis.
We also asked ourselves the question: “What would have to be true for you to change your mind?” Doing so forced us to consider what would make the other position the better option.
Know the difference between wartime and peacetime decisions: Simply acknowledging that 2017 was not “business as usual” helped me get through it. Here are two principles to consider when making decisions during a transition.
- Remind yourself that most decisions are reversible. In his annual letter to shareholders in 2016, Jeff Bezos wrote that most decisions are reversible, so decision-making should be sped up. If it’s the wrong decision, in most cases you can correct it later. The “reversibility” of a decision means a decision-maker should make a decision, but hold it loosely. The key is then to “set a gate” at a future date to re-evaluate the decision.
- What are your non-negotiables? With big decisions, I found it helpful to sort my preferences into “nice-to-haves” and “need-to-haves.” Doing so invoked a necessary pragmatism.
Find an external confidant: Last year was the hardest year of my professional life. There were many days when it felt like I was standing in the gap between who we used to be and who we wanted to be, and that gap somehow was widening, not narrowing.
I’m someone who benefits from externally processing the happenings of my life. It was tempting for me to go to members of the team with my worries (after all, they knew better than anyone else all that was going on), but I sought out an external confidant who was a sounding board and truth-teller for me.
Find lightness and identity outside of work: There were more late nights than I’d like to admit last year, but there were also times when I found lightness outside of work: a weekend with my closest friends from college where we didn’t talk about work at all; an extended camping trip in the Canadian Rockies; and my season-long passion (and ultimate tragic disappointment) in the Colorado Rockies baseball team.
Protecting my ability to see myself as a person altogether bigger than my job title has helped me to put my work—and this year of transition—in context.
Give yourself some grace: It’s tempting to feel like every decision, meeting, and moment is critically important and irreversible. I’m hard on myself, and I expect a level of performance from myself that I don’t expect from anyone else. Looking back at 2017, I could have felt less stress and anxiety if I had just extended a bit more grace to myself throughout the year.
One of our teammates saw my inclination to be unnecessarily self-critical and set a daily task for me to remind myself of something of which I was proud. At the end of each day, I would see that task and try to remind myself that it was okay to be proud of how I spoke in that meeting, approached that conversation, or processed that decision. Over time, I didn’t need the tasks as much, and I slowly began to see that even amidst so much shifting, there were moments I could be proud of the way I showed up.
Banks Benitez is the CEO of Uncharted.