How to Know When It's Time to Go
Updated: Sep 5, 2018
Sometime in fall 2017 I made the decision that is was time for Code2040, the successful social enterprise I’d co-founded and run since early 2012, to have a new CEO. I don’t remember the exact date I came to this realization, but I clearly remember the queasy-nervous feeling in my gut when I realized what I was going to do: quit my job and give up my leadership role at the organization I cared most about in the world.
I always knew when I launched Code2040 that I wouldn't be there forever. I didn’t identify with the rockstar social entrepreneurs of the previous generation who spent decades building their organizations, their identity completely intertwined with their companies. I knew I wanted my career to be more eclectic than that. But I felt really committed to Code2040’s mission, impact, and success, and for years I didn’t see how my leaving was compatible with any of those things.
In 2017, that all changed. Since lots of people have asked me what led to my decision to step down as CEO, I thought I’d share my reasoning and the story of why and how I did it.
Really it was a convergence of market forces, organizational needs, professional interests, organizational developments, and personal goals. A perfect storm, if you will. It started with a presidential election…
Trump Reveals Some Truths. To boil a very complex topic down to a very simple observation: when Trump entered office, the climate around racial equity and racial justice in America changed. There was a shift in what was publicly acceptable to say and do, and in what people needed to say and do in response to protect their and others’ basic rights, much less to advocate for equitable treatment. For many of us who hoped Obama in office was proof that we had entered a new phase of race relations in America, it felt like the solid ground we were standing on shifted beneath us. At Code2040 we had built our programs on this idea that diversity and inclusion was the commonly accepted goal, and it became clear that this belief was less widespread than we had thought, even within seemingly-progressive tech.
Diversity Fatigue in Tech. When Code2040 helped to launch the conversation about equity and access in tech, there was a sense that this innovative, solutions-driven industry could make headway where others had failed, and thus there was optimism. In many (though not all) cases this optimism was accompanied by a deep naivete around the level of systems redesign and change management it would take to really balance a workplace. Companies who had excitedly tried diversity quick fixes or inclusion PR moves were tired of the (predictable) lack of sustainable results, and a few years in, as they realized that creating equitable workplaces would take more work and focus than they initially realized, they quietly began to back down and hope, with all the crazy political stuff going on and the way they were leaning into external crises, that no one would notice that their workforce was as white and male as it always had been.
New Strategy Needed. A different climate requires a different strategy. At Code2040 we had created our last strategic plan in spring of 2016. We were riding a wave of impact, growth, and successful fundraising. The media was paying attention to us. We’d gone from trying to convince companies that partnering with Code2040 was worthwhile to having a waitlist of companies who wanted to pay to join our programs. We created an ambitious, expansive strategy to get us through 2020. And we moved aggressively to execute on it.
A year later, in Spring 2017, it was clear that the strategy we had created needed to be revisited to better fit the new market and new climate we were in. Basically it was a great strategy -- based on assumptions that turned out to be flawed. With new information, we had new assumptions to build on top of and we needed a new strategy to match.
One Strategy, One Leader. Here’s where I started to see the beginning of the end of my time at the helm at Code2040. I believe that if you create a strategy, you execute on it and lead people through it. It doesn’t work to create a strategy for someone else. First, you’re likely to (unconsciously) be a little unrealistic if you know you’re not going to be held accountable for meeting the milestones laid out. Second, someone else is not going to understand the nuances of the assumptions and choices that were made in the creation of the strategy, and what seemed clear on paper will be unclear in practice. Third, it will be impossible for that new leader to truly be accountable for the success (or failure) of the organization if she is stuck executing on someone else’s plan.
All this meant that, if I was going to design Code2040’s new strategy, I was going to stick around to execute on it -- a three to five year commitment. So I started to ask myself: Was I the right leader for Code2040 for the next five years? Was Code2040 the right place for me for the next five years?
This was the hardest thing to talk about leading up to the decision, since there is a (well justified) feeling amongst founder/CEOs that you have to be committed to the point of evangelical about the organization in order to successfully lead it, particularly to attract the resources needed for it to thrive. Until the announcement that I was stepping down, publicly I was all in. But privately I had many thoughts that contributed to the decision. This is the first time I’ve written publicly about this part.
That CEO Life. I loved many aspects of being the co-founder and CEO of Code2040. I believed (and believe) deeply in the mission and purpose of the organization. Particularly in a tough climate where many of my law and business school peers felt despondent, I felt so lucky to be getting up every day to do work that was positively impacting the most pressing issues facing our country. I had gotten to work with some of the most inspiring, creative, thoughtful, passionate people I’d encountered over the years. Code2040 had given me a network, a platform, and a brand in a way I’d never anticipated. And I had so much agency over how I spent my days, which was incredibly empowering.
But there were things I didn’t like about the role. The immense pressure, for example - I took every failure and misstep deeply personally. The constant weight on my shoulders of being responsible for 35 paychecks -- even during boom times -- was perennially exhausting. The feeling of being totally alone in the role: when you’re everyone’s boss you have no peers at work, no one with whom you can let your guard down, no one to vent to. And, as the ultimate people manager, the overwhelming focus on guiding others rather than on creating work product myself meant that I never felt I could truly take pride in the organization’s accomplishments as my own, even as I took responsibility for every misstep.
Keeping Options Open. Also, while I knew that racial equity would always be deeply important to me and a lens through which I would view every professional experience moving forward, I didn’t want to build my whole career around workplace diversity and inclusion, and I wasn’t sure if another five years in the role would start to limit others’ view of my potential. Also, I knew I didn’t always want to be a CEO (see above!), and I wanted to be sure to keep my peer collaboration and independent contributor skills fresh -- very hard to do while in the CEO role.
All that led me to realize that I wasn’t prepared to make another five year commitment to Code2040. Which was a big realization. It told me that I needed to start to think about stepping down as CEO.
But of course there are two parts to this decision - the choice itself, and the timing of it. Once I knew I would step down as CEO, it was still months before the leadership transition took place. Two things happened at the organization and one thing happened in my personal life that dictated the timing of the end of my tenure.
A Successor Emerges. I will admit that for the first few years of Code2040’s existence we were light on succession planning. In the earliest phases of the organization, it was too much to even think that far ahead -- we were working on survival. Once we turned the corner from aiming to survive to aiming to thrive, we began to think about how to insulate the organization from the loss of its leadership simply from a risk management standpoint. However, it wasn’t until I’d worked with Karla Monterroso, our VP of Programs, for a year that I realized that I had the chance to think about succession planning not as a way to mitigate risk, but as an opportunity to accelerate impact. I’ll write separately on what it’s like to find your successor, but suffice it to say that by mid-2017, I felt confident that Karla could be an amazing next CEO for Code2040.
Distributed Power in Practice. A lot of organizations say they like to distribute power, minimize hierarchy, etc. In practice, this is really hard to do. But when Code2040 had a set of internal challenges in fall 2017, my leadership was put to the test. I realized that I did not know how to lead from out front to get us through the challenges we were facing, and so I made the choice to try to lead from behind. I sought out several people across the team and asked them to step up to lead us at that moment, with my support -- not because of any authority outlined in their job descriptions, but as teammates committed to the future of the organization. I created space for others I hadn’t directly approached to step up, too. It was amazing. I will write more about this elsewhere, but the bottom line is that it became really clear in fall 2017 that Code2040’s survival, success, and impact were no longer contingent on my leadership, but rather that we had a team of leaders ready to guide the organization based on its needs.
These two things opened the door at the end of 2017 for me to leave the role in the near term.
Bye Bye Bay. Of course there were personal factors as well. I’d been itching to move back to New York for years, and leaving the role would open up that possibility. My husband was ready to leave his job and we worried that if we didn’t coordinate our work departures we’d never get the chance to do the big around the world trip we dreamed of.
Mom OK. Interestingly, becoming a mother in January 2018 was not a factor in the decision in the way most people assume. I’d deliberately attempted to build a culture at Code2040 from day one that was friendly to and welcoming of parents, our second hire had a newborn, we had multiple moms and dads on staff, and at the time my daughter was born, I felt I had the flexibility to be an attentive parent and a committed CEO.
But the birth of my daughter did impact the timing of my resignation. Once it became clear that Karla was the right successor, it also became clear that it did not make sense for her to go from Acting CEO while I was on maternity leave, back to VP Programs when I came back, then to CEO when I stepped down a few weeks later. Effecting the transition while I was out on leave meant that she could have continuity in the role, moving seamlessly from Acting CEO to CEO.
The Actual Departure
As logical and rational and well-reasoned as my decision was, and as confident as I felt that it was the right one, leaving Code2040 was still incredibly bittersweet. I think I was in emotional denial for awhile as we worked out the details. When I came in during my maternity leave to announce to the company that I was stepping down, I cried before I could even open my mouth. Even though I knew that my stepping down was the right thing for the organization and for me, even though I could taste the freedom that awaited me, even though I was filled with joy at the prospect of someone I respected and admired so much taking over the role, I was still sad to leave.
From my last day as CEO in January 2018, I stayed on for six months as an advisor to help Karla acclimate to the role and to ensure that relationships were transferred and knowledge was institutionalized. Then at the end of June, on a Friday around 2pm, I turned in my laptop, hung up my keycard, and walked out of my office as an employee for the last time.
I walked down the street, met up with my husband and baby, ordered a drink, and we started planning our year of adventure. Stay tuned, we’re starting in Rome.