A few years into my tenure as CEP’s president, when I was in my mid-30s, I made a confession to our board of directors in executive session. It was a big one.
“I don’t really know what I am doing,” I said, explaining that the organization was growing quickly and that I’d never been in charge of an organization before — much less one that had grown in a few years from a few staff to perhaps 10 at the time.
That really got their attention. By about a half-hour after the meeting ended, one of our board member’s executive assistants had reached out to schedule a one-on-one for the next day.
The board member, who was the CEO of a significant global management consulting firm, sat in the hotel bar in Cambridge where he took many of his meetings. “Don’t say something like that to your board again,” he advised me, sternly. “You want us to have confidence in you, don’t you?”
“Yes, of course,” I stammered, struggling to explain that I was just trying to be open and honest.
“Also, I am getting you a coach from our firm,” the board member told me.
I started to protest that we couldn’t afford that when he added, “pro bono.”
I met with that coach every other week for 90 minutes for the next year-plus. His counsel and support were invaluable — a gift. I came to understand that what I had experienced as a sense of overwhelm, or even inadequacy, was actually just part of a process of growth. I realized that, although I had felt like I was a fraud who was faking leadership, everyone feels that way at times.
Over the years that followed, I gained more confidence. But I’ll be honest, the past few years have brought me back more than once to that earlier version of myself. The mayhem of our times and the challenges facing nonprofits (and admittedly we at CEP don’t have anything like the level of challenge we have documented for many organizations, but then it hasn’t been easy for anyone) have led me to reconsider some of what I thought I knew about leading and managing. This has made me question, at times, how I could have been so wrong about important things.
But, then again, maybe there is something to be gained in reflecting on, and sharing, those lessons learned — so let me highlight realizations I have had, courtesy of this challenging context.
Planning too early. For years, I had seen planning as an unalloyed virtue. CEP engaged in comprehensive strategic planning processes, informed by stakeholders and grounded in data. Annual workplans, derived from the strategic plan, laid out our major activities — team by team.
I am not here to tell you planning isn’t helpful, but rather that I was sometimes blind to its downsides. I have learned that making decisions too early — about what you will do or how you will do it — can have real costs.
Especially in the current volatile and rapidly changing context, planning things out too far in advance often leads to rework. We could all learn something from the “Last Responsible Moment” movement championed by people like software developer and entrepreneur (and now philanthropist and CEP friend) Jeff Atwood. He argues in this influential 2006 essay that “decisions made too early … are hugely risky.”
Atwood points out that “early decisions often result in work that has to be thrown away. Even worse, those early decisions can have crippling and unavoidable consequences for the entire future of the project.”
I think this applies far more broadly than software development, but that perspective is not always an easy sell. I find that it’s become even harder for people to avoid the temptation to try to plan early as the world around us has grown more chaotic. The prevalent uncertainty, and bad news, make the seeming certainty of a detailed workplan all the more alluring, offering a sense of control in a time when so much feels out of control.
I feel it, too. At CEP, we have always disdained self-created crises that result from procrastination, and I stand by that as a virtue of our work culture. But at times, my colleagues and I have tipped too far in the other direction, making decisions only to realize, months later, that we should have waited for more information to decide — because we now have to rework our plans. Like most things in life, it’s a balance: starting something too late, too close to when it needs to be completed, can be hugely problematic, but so too can starting something too early.
I’ve found it helpful to name this tension, directly, and to ask, “Do we really need to make a decision now, or start planning this now?” I have started proposing a specific date that we’ll revisit whether to start worrying about something if I think no good can come from worrying about it now. At the very least, we can decide that.
Doing too many things at once. Like most organizations, we typically have a lot of concurrent projects going on, and, depending on their role, an individual staff member might be involved in several — or more. As long as workloads remained manageable, I have tended to think of multiple, concurrent projects as in many ways a positive: multiple projects offer variety for individuals; downtime and idle capacity are reduced (in theory at least) because when something is slow on one project, you can focus on another; and, in grant-funded areas like our research initiatives, more efforts mean a wider menu of potentially fundable projects at one time.
In recent years, however, and especially as our digital context (from email to Slack to AI) has led to more and more difficulty creating opportunities for focused work, I have come to see the challenges of too many overlapping projects: they can simultaneously decrease quality and efficiency while increasing burnout. Cal Newport’s work, including his 2016 book “Deep Work” and his 2024 book “Slow Productivity,” has challenged my assumptions and helped me understand the costs of “context switching” between projects. Newport advises us to “do fewer things,” “work at a natural pace,” and “obsess over quality.”
Over the years, as we have learned these lessons more deeply, we have, for example, reduced the number of concurrent research projects we’re undertaking at any one time — improving turnaround time and relevance at a time when our audience is seeking data that is as close to real time as possible.
We have work to do still to improve in this area, but we are increasingly pushing for fewer, shorter-duration projects and less overlap. I have always been a fan of focus but, even still, projects proliferate in organizations, and it takes conscious effort to beat back that tendency.
Communicating like I did before (and thinking that would work). If there is one thing I always thought I was pretty good at, it was internal communication: keeping our staff well informed and aligned. We are uncommonly transparent. We have always shared our board materials, for example, with our full staff, and we create opportunities for staff to ask whatever questions are on their minds. We also get feedback regularly — including through an annual staff survey and a 360 process in which any staff member can give feedback about me that goes to the board committee that’s responsible for my performance review.
It’s these very feedback processes that made me realize, in 2024, that what I was doing wasn’t working well enough anymore. As the organization had grown in size and complexity, it was no longer reasonable to assume, for example, that people would want to raise their questions in a staff meeting of 60 people. Our shift to hybrid work had reduced the frequency of spontaneous interactions between me and other staff, and this had been further exacerbated by the growth in numbers of our staff working in our San Francisco office (I am based in Cambridge). Yet I had not shifted my approach to communicating. As a result, at least some staff felt more disconnected from me, and from the decisions made by our leadership team.
So I decided to experiment with new approaches. I now write a monthly message to our staff, typically ranging from 1,000 to 2,000 words, discussing what’s going on at the organization and what I am hearing in my external interactions; I host a monthly open meeting on Zoom to discuss the “changing context” in which we’re working; and I have, in various ways, tried to find more opportunities to check in with staff at all levels in the organization in one-on-one conversations. I have realized (later than I should have) that my approach to internal communication needs to constantly evolve, responding to shifts in how we are working and the needs of our staff today.
Those are just three of many, many things I have learned in the past few years. They are, perhaps, not revelations to those who will read this post; we all have different stuff to work on, after all.
But the biggest lesson of all for me is that, though it may have been a mistake to say it out loud to my board, no one in a leadership role ever really has it all figured out. The moment we think we do is probably the very moment it’s clear that we’ve lost touch or are no longer effective.
So, put another way, and please don’t tell the CEP board, I am still not sure I really know what I am doing, especially given the chaos and unpredictability of the current context. But that not knowing keeps me curious, learning, and reflecting on and seeking to address my weaknesses as a leader — and maybe that’s not entirely a bad thing.
Phil Buchanan is president of the Center for Effective Philanthropy, author of “Giving Done Right: Effective Philanthropy and Making Every Dollar Count,” and host of the Giving Done Right podcast which will start its sixth season in September.
