Lessons from 21 Years: Lester Olmstead-Rose on Leading Through Uncertainty

 

As firm Partner Lester Olmstead-Rose prepares to retire after more than 21 years with La Piana Consulting, we asked him to reflect on the lessons he has learned from a lifetime of nonprofit leadership and consulting. His insights span strategy, governance, decision-making, and trust, but one message stood out above the rest:

         When uncertainty rises, return to the fundamentals.

In a moment when many nonprofit leaders are navigating funding pressures, policy shifts, and rapid change, Lester believes organizations are best served by focusing on two essentials: a clear strategy and a strong board.

A strong strategy, he argues, is more than a plan. It is a shared understanding of where the organization is headed and the decisions that will guide its path forward. The most effective strategies become “sticky,” understood and embraced by staff, board members, and key stakeholders — the strategy serves as a North Star when conditions become turbulent.

Just as important is a board that functions as a true thought partner. The strongest boards help leaders navigate difficult questions, offer perspective during moments of uncertainty, and share responsibility for advancing the mission. When challenges arise, nonprofit leaders should not have to carry the weight alone.

Throughout a departing conversation with Managing Partner Onuka Ibe, Lester returned repeatedly to the importance of thoughtful decision-making: being clear about what decisions are the ones that must be made first, who is responsible for making decisions, and how organizations can remain flexible without losing sight of their direction.

As he reflected on his career, Lester shared what has kept him inspired for decades: the opportunity to work alongside people committed to making their communities and the world better.

It is a fitting reminder that while uncertainty may be constant, so too is the dedication of nonprofit leaders working every day to create positive change.

 

Retirement Interview with Lester Olmstead-Rose,
in conversation with Onuka Ibe

June 16, 2026
Edited interview transcript

Onuka Ibe: Lester, it’s great to have a chance to talk with you. You are preparing to retire after just over 21 years with La Piana Consulting and a lifetime of work in the nonprofit sector. Given the depth of experience you have brought to the firm and to the sector, I would love to talk about what you have learned and what nonprofit leaders can take from that experience today and into the future.

Lester Olmstead-Rose: That sounds like a fun conversation!

Onuka: One thing on many people’s minds is the current state of uncertainty: economic uncertainty, policy uncertainty, and, in many cases, health and safety uncertainty. Based on your experience, what is your best advice for nonprofit leaders navigating turbulent times?

Lester: It is a good question. These days, I cannot think of a group I am working with that is not feeling high stress. It’s really a difficult time to be in the nonprofit sector. In periods of stress, I think it is important to go back to the fundamentals.

For me, there have always been two basics that matter most. The first is strategy. Many nonprofits have a very strong sense of mission, but they have not necessarily articulated their big-picture strategy: where the organization is headed, how it is prioritizing current or new resources, and what all of its activities add up to over time.

To navigate these times, nonprofits need clarity about their organization-wide strategy and how they are focused within their mission. They also need to make strategic decisions in a way that is “sticky” — understood by staff, board members, and key stakeholders. A great decision that no one understands does not really stick. By sticky, however, I do not mean that a decision can never change. I mean that, for the period when the chosen strategy remains relevant and there is no new information requiring a rethink, the decision holds and serves as a North Star.

Getting to that kind of decision is not always easy. It is relatively easy to describe the steps of a strategy-development process. What is harder, and more important, is first clarifying what decisions matter most: What are we solving for? What decisions do we need to make first? Then it can be hard a portion of the time, not always, to build the information in a way that creates a clear and broadly-supported decision, especially when the choices to be made are difficult.

The second fundamental is to invest time in developing a really strong board. We want a lot from boards: fundraising, subject expertise, meaningful oversight of the executive director, and much more. But the most effective boards I’ve seen function, at their core, as thought partners with the executive director and senior staff.

A strong board is not expected to be all things at all times. The best boards I have seen know enough about the field, nonprofit management, fundraising, and the organization’s particular situation to engage as true thought partners. They can help answer difficult strategic questions, see where staff may be struggling, and problem-solve without acting as punitive overseers. That kind of partnership grounds the organization and means that, when a crisis comes, the executive director is not carrying every decision alone. There is a team ready to move forward together.

Onuka: Building on that, what are some of the biggest issues facing the nonprofit sector that you see organizations wrestling with?

Lester: The answer depends a great deal on the organization. La Piana works with policy organizations, service providers, arts organizations, and many others, and each faces a different mix of funding, relevance, strategic, operational, and mission challenges. Across the sector, though, one recurring issue is how an organization stays relevant and well positioned to advance its mission while also being respectful of partners.

That balance matters. Some organizations pride themselves on partnership, but partners may experience them as taking too much credit. Others are seen as true collaborators that make their partners stronger. In turbulent times, how an organization positions itself as part of a broader community of organizations is critical.

For advocacy organizations in particular, the challenge is focus. The status quo can change radically and quickly, and the temptation is to respond to every article, policy proposal, or media storm. But organizations need to be clear about what they will take on, what capacity they actually have, and where partners can lead while they play a supporting role. Those are difficult but essential decisions.

That is where decision-making criteria are useful. I’m proud of projects that have really helped my clients build the muscle to make decisions — day to day, quarter to quarter, and year to year. Having a North Star, a strong and collaborative board, and explicit criteria helps an organization make smart choices and stay as well positioned as possible in turbulent times.

Onuka: What are some of the longer-term issues facing the sector that may not be getting as much attention because of these more immediate pressures?

Lester: One that I keep expecting to break open is the issue of trust in the nonprofit sector. We have seen trust decline across every institution: courts, Congress, the White House, state legislatures, criminal justice systems, media, and even professions such as medicine. As someone at retirement age, I have watched that decline over time, and it has been steady and powerful.

Nonprofits have not experienced that loss of trust to the same extent. People can still name nonprofit organizations they know and say, “They are a great group.” (No one says, “What a great Congress!”) But I worry that changes in the legal and political environment could hit the sector hard, and that nonprofits are not be prepared.

A lot of my concern stems from the Citizens United decision by the Supreme Court and subsequent changes in the legal framework. I am not an expert in this area, but the result has been that nonprofit status can be manipulated to drive political or private agendas by the powerful. Dark money can flow through legal but, in my view, illegitimate nonprofits, and the sources of that money can remain obscure.

That concerns me because, if it explodes publicly, it could tarnish the entire sector. Individual nonprofits can be proactive by being transparent about where their funding comes from, who their major donors are, and how and why they make key decisions. Strong decision-making criteria and clear communication can help inoculate organizations against broader distrust. Fortunately, many nonprofits are already doing this, but that may not be enough to counter a sector-wide scandal.

Another long-term issue is wealth disparity. Nonprofits are increasingly dependent on a relatively small number of mega-donors, foundations, and family foundations rather than being sustained by many medium-sized and smaller donors. The more an organization depends on fewer people, the less independent it can be, and the more power is concentrated among a very small set of funders.

At the same time, younger generations often give in more episodic ways which can be challenging. They see an issue or event, feel compelled to help, and then move on to the next thing. I am not saying that critically because I do see huge numbers of younger people who are deeply engaged in social change. But engaging only when a moment resonates for them creates a real challenge for nonprofits that need reliable annual or monthly financial, volunteer, and community support.

Onuka: Yes, we’ve seen that with volunteers as well. Younger generations are approaching many forms of support differently than prior generations, and the sector is not always as prepared for that shift as it could be. I want to talk about you as a consultant. You have spent more than 21 years at La Piana Consulting working with many organizations, boards, and leaders. What are some of the key lessons you have learned about consulting?

Lester: The first lesson is the importance of shared expectations. I cannot overstate how important it is, when engaging a consultant, to set clear expectations at the outset. I usually feel good about doing that in the proposal phase: listening to a potential client, understanding what they need, and translating that into a strong proposal.

But as soon as an engagement begins, something almost always shifts. I learn more about the organization and its needs, and the organization learns more about itself. Even if we begin with good shared expectations, those expectations may need to change. That is not a problem, it’s actually a good thing, reflective of human nature and organizational nature. What matters is communicating explicitly about the shift and resetting expectations together.

I will be blunt: I find that hard to do. Sometimes I see the shift in my head, or it happens so incrementally that I do not notice how far we’ve moved from the original expectations. That’s why communication and over-communication are so important. I say this to remind myself as much as to offer it as advice.

This shows up most often in strategy work. It is relatively easy to describe process steps and stick to them. What is harder is identifying the right questions to answer. Sometimes a client begins with one set of questions, and as we explore them, we discover that answering another, more fundamental question would drive the organization to make better decisions.

Good decision-making is explicit. In the moment, a decision should be firm; you cannot revisit it every second. But over the course of a process, you do need to revisit whether you are solving the right problem and whether the decisions we make in a formal process will serve the organization well with great guidance in making ongoing, day-to-day decisions outside of the process — after we’re gone.

Another lesson is the importance of knowing who makes decisions. Some of the most difficult projects I have worked on were difficult because it was not clear who had the authority to ultimately decide. Expectations should be driven by, and deeply involve, the people who will ultimately decide — but with clear communications about how will ultimately take that input and make a decision. Otherwise, misalignment is almost inevitable.

Onuka: What I hear is the importance, in a strategy development process, of being clear about the decision, while staying open to learning that a different or deeper decision may actually need to be made.

Lester: That is exactly right.

Onuka: When it is unclear who needs to make the decision, what are some ways organizations can unintentionally have the wrong people in the process or in the wrong roles?

Lester: In large organizations especially, day-to-day management of a consulting process may be delegated because the executive director or CEO does not have the bandwidth to manage it. That is perfectly fine. But it is still essential for the consultants to have direct, unfiltered communication with the CEO or executive director.

The chief executive is the linchpin of a nonprofit organization. For strategy work — and even for implementing major strategy — the consultant needs a direct relationship with that person. Without it, everyone ends up playing telephone, and things get lost in translation in both directions. And then, of course, board leadership and staff leadership must be involved, although their roles depend a lot on the culture and practice of each organization.

Onuka: Beyond clarity about decisions and decision-makers, what other advice would you give to clients or prospective clients?

Lester: I would emphasize flexibility. Organizations need a clear strategy, but they also need the ability to adapt. Strategy is not planning. Strategy is the direction you are headed; planning is the zigzagging path that keeps you moving in the right strategic direction while responding to barriers and opportunities along the way.

That is a balancing act. You cannot rethink your strategy every five minutes, but you also should not treat it as sacred. If the world changes or new information shows that the direction is no longer right, you need to step back, reconsider, and adjust.

That balance depends, just like everything else, on good decision-making: clarity about who is involved, who decides, and what criteria guide the decision.

I have done a lot of detailed business planning, and I tell clients when the final plan is done: this plan will be out of date tomorrow. That is okay. The point is to have a strong enough plan and process and understanding of the issues that you can assess and adjust to new information.

Onuka: I like that framing: be clear about where you want to arrive and flexible day to day, so adjustments keep moving you in the right general direction instead of pulling you off course.

Lester: Exactly. No decision an organization makes today has to bind the organization forever. The world changes. If you adjust every day, you will not succeed; if you fail to adjust when you need to, you also will not succeed. The key is to have a longer-term direction and the discipline to adjust when the world changes.

Onuka: What does it take to be a good consultant for nonprofit leaders and boards?

Lester: One of the core things is self-awareness. To be a good consultant, you have to know yourself. Our job is to adapt to clients, understand their culture, and work in ways that work for them. We cannot expect clients to adapt to us.

That does not mean being inauthentic — in fact, it’s quite the opposite. It means knowing how you work best and then flexing in a way that is genuine and useful to the client. That is probably my number-one advice to consultants.

Onuka: Looking back over your engagements, how would you describe the best ones? What characteristics did they share?

Lester: I have been fortunate to have many clients I absolutely loved working with, including a handful where I worked with them over many years, sometimes across leadership transitions. In the best engagements, every time I finished a project, I felt satisfied: not only did I feel like I’d been a catalyst for the organization to learn and grow and improve, but I had also learned and grown.

At their core, those engagements were partnerships. The client treated me as a partner and wanted to work hand in hand to make the best possible decisions about advancing their mission. Trust is essential. Clients do due diligence, choose a consultant, and then the best ones enter the relationship ready to work collaboratively.

That kind of trust only works when the client is open about what they need and willing to work through challenges together. If there is a process issue, I need the client to say so, not as an accusation, but as an invitation to solve the problem together.

I remember one long-term client where I produced a document that really did not land well. The team told me it wasn’t right and some members of team leadership even felt disparaged. That had not been my intention, of course, and because we trusted each other, they could tell me directly. We sat down, revised the work plan, made adaptations, and ended with a strong result. I have no doubt that each person on that team today would speak highly of the process, the process outcome, and of working with me. Those are the kinds of engagements I love.

Onuka: In those moments, you become part of the team rather than simply an external vendor or contractor.

Lester: Yes, that’s so well said. Even if I am only part of the team for six months.

Onuka: What do you think you will miss most about consulting?

Lester: Two things. First, I will miss being able to step into a great organization’s substantive and meaningful challenge, help unstick a moment in time, and then see them move forward. That is a big part of why I became a consultant.

Second, I will miss engaging with so many people who are doing such a great job, in their own specific ways, to make the world better. In these times, I feel, like others, a lot of underlying unhappiness about where the country is headed. Working with nonprofits has been soothing because I get to contribute, even in a small way, to people and organizations working so hard and so successfully to make a corner of the world better — sometimes with amazing local successes, sometimes with huge national ramifications. What a gift!

Onuka: What are you most proud of in terms of your contributions and your time at La Piana?

Lester: One thing is having been part of developing some of the firm’s intellectual capital and ways of thinking. I joined early enough to be in the middle of an organization that was still being formed, and it was exciting to help shape ideas that became central to how we work, including Real-Time Strategic Planning and our Dare2 Succeed business planning methodology.

Another thing happened early on. I made a significant mistake on a project, and David La Piana did not come to me angry. He came to me and said, “This is what the client raised. Let’s talk about it. What happened, and how do we get to the other side?” I had the opportunity to work through a challenge, learn about myself, and grow as a consultant, and I was supported in doing that. It’s now twenty-one years later, so obviously we successfully got through that moment — and that’s how I want to work with clients and colleagues every time. It’s easier said than done!

Finally, over the last five or ten years, I think I’ve played a grounding role in the firm. I moved from being the new guy to being the center of institutional memory, helping hold together certain kinds of practice and culture, training new consultants, moving into leadership, and supporting colleagues. It has been really satisfying to play that role and also to see it shift as new leaders step in, take that fantastic base, and make it something new and better.

Onuka: If you had not been with La Piana, what do you think you would have been doing over the last 21 years?

Lester: I do not know — maybe I would have been a travel guide! Before consulting, I was a nonprofit manager, and I liked it, so the easy answer is that I might have gone back to that. But I do not think it would have used my skills in the best way.

I became a nonprofit consultant because I had the opportunity in mid-career to stop and ask, “What is the job I should have?” It did not take long to realize that consulting was the right thing for me. It connected with what I am good at, what I know, and how I can contribute. I was fortunate to have that choice.

Onuka: It sounds like you found the right place.

Lester: I did. I had no other job in mind and no plan B. When I reached mid-career it was clear that this was the right job for me, and La Piana was the right firm for me. That has always been the case.

Onuka: Last question: what comes next?

Lester: Anyone who has worked with me knows I love to travel, so I have to say that first. But before I really get there, I am thinking of retirement as a ramp-down: I have open projects to finish and will continue consulting through La Piana on a few things for a while. But to celebrate my formal retirement, my partner and I are going to New York City for about ten days. We love being there — walking, exploring, and seeing many, many, many shows!

So I expect a lot of travel. I also expect to read more — which may not sound so exciting, but it is for me! And then I always feel like a cliché, but as I age I find myself spending more and more time with friends, especially those I’ve known for decades. Definitely more of that!

Does that sound kind of peaceful? That’s the intent! And not too much political doomscrolling and social media!

Oh, and, of course, I want to clean the house!

Onuka: That sounds well deserved. Thank you for everything you have done for La Piana and for the many organizational leaders you have helped make important decisions and, as you say, who are able to make the world a better place because of the way you and La Piana have been able to support them. Thank you, too, for this conversation and for sharing how you see the work and the world.

Lester: Thank you, Onuka. For me it’s really exciting to see you and others step into firm leadership and expert consulting. It’s an amazing team — the firm has a great future, and I can’t wait to see where that future goes