Boards That Govern, Leaders That Lead

 

By Kristen Illes, Principal at Dowling Street 

Consider two people who both care deeply about the same organization.

The first is an executive director, several years into a role at a nonprofit they have loved since their earliest days on staff. They came for the mission. They stayed for the people. But lately a growing portion of their week is consumed not by the work they love, but by the effort of managing a board relationship that was never properly built. Chasing responses. Filling governance gaps. Carrying the weight of a structure that is not pulling its full share. The burnout is quiet, but it is real.

The second is a board member. They said yes because they believed in the cause. They show up, mostly, though life is busy and the expectations were never entirely clear. They want to contribute. They are not always sure how. Sometimes they weigh in on things that probably belong to the staff. Sometimes they hold back when their perspective would actually help. They are doing their best with what they were given, which was not very much.

Neither of them is failing. The partnership is.

This is the dynamic we encounter more than any other in our nonprofit change work at Dowling Street. And in our experience, it is both more common and more solvable than most organizations realize. The solution does not begin with a governance framework or a roles and responsibilities chart. It begins with a question.

Two Rooms, Two Conversations

Early in almost every nonprofit engagement we lead, we ask each member of the leadership team and each board member the same two questions: What are your hopes and dreams for this change initiative? What are your greatest concerns?

We ask separately. The leadership team in one room, the board in another. No comparing notes beforehand. No filtered answers shaped by what people think the other group wants to hear. What surfaces in those two conversations tells us more about an organization's readiness for change than any strategic plan or governance document ever could.

When a board is truly high-functioning, the answers converge. Not because the two groups have coordinated, but because they have actually been paying attention to each other. The hopes build on each other. The concerns, while sometimes different in texture, point in the same direction. There is a shared picture of what the organization is trying to become, and a shared honesty about what stands in the way.

When the answers diverge significantly, that gap tells us something just as important. The board has hopes the leadership team does not know about. The leadership team carries fears it has never named in the boardroom. These two groups are meant to be partners, but they have never actually learned what the other is thinking. It is a governance problem, and we have learned what it takes to solve it.

Why the Lines Get Blurry

At the heart of most board-leadership tension is a boundary question: what belongs to the board, and what belongs to the staff?

Governance is the work of setting strategic direction, ensuring organizational health, holding executive leadership accountable, and stewarding mission over the long term. Operations is the day-to-day execution of that mission -- the work that belongs to the executive director and the leadership team. When those two domains are clear and respected, both groups can do their best work. When they are not, the costs are specific and predictable.

A board that wanders into operational territory -- questioning program decisions, second-guessing staff hires, asking the executive director to justify choices that are theirs to make -- does not just slow things down. It erodes the confidence and authority of the people doing the work. Darryl Young, a governance consultant and experienced nonprofit board member, describes what effective partnership looks like instead: "A good board member and a good executive director say: here's an idea, you don't have to do this, but let me know so I can tune in what I'm giving you as advice."

The inverse is equally damaging. An executive director who withholds the real picture from the board -- who presents polished updates instead of genuine challenges -- denies the board the information it needs to govern well. As Young puts it: "I'd much rather know what keeps them up at night, what challenges they have." The board cannot be a genuine partner to a leadership team that is managing them rather than trusting them.

BoardSource's Leading with Intent research, the most comprehensive study of nonprofit board performance in the country, found that while most board members report understanding their governance role, far fewer feel confident their boards are actually performing it well. Understanding the role and living it are two different things. The gap between them is where organizations lose ground.

The Work Underneath the Work

Here is what we have learned from sitting in those two rooms: the hopes and dreams conversation is not just a diagnostic tool. It is the first act of team development.

When a leadership team spends an hour naming what they most want for the organization and what they are most afraid of, something shifts. Colleagues who have worked alongside each other for years hear things they did not know. The same happens with the board. People who showed up as individuals begin to recognize themselves as part of something shared. And when both groups eventually come together around a common picture of where the organization is headed, they are not starting from scratch relationally. They have already begun the work of becoming teams. We did not design this as a team development intervention. We noticed it kept happening and started building toward it intentionally.

This matters because becoming a high-performing team does not happen automatically. It requires time, honest conversation, and shared experience. Most boards skip that process entirely, moving straight to governance tasks without ever building the relational foundation that makes governance possible. When that foundation is missing, the burden shifts to the executive director, who ends up managing the board rather than partnering with it. The mission pays the price.

It is worth holding both sides of this with empathy. Board members are volunteers. They said yes out of genuine commitment, often without a clear picture of what they were agreeing to. Leadership team members in nonprofits tend to operate well above a standard job description because the mission asks it of them. Neither group is looking for more friction. Both groups deserve a relationship that makes the work feel worth it.

Young is direct about what executive directors can do to build that relationship: "You don't have to do a long-winded report, but that social high-touch thing is something that goes a long way." The executive directors who build the strongest board relationships stay in touch between meetings -- a forwarded article, a quick note, a message that says: I am wrestling with this, have you seen it before? Those small gestures signal to a volunteer that their presence matters. That is how trust is built, and trust is what makes honest governance possible.

On the board side, Young is equally clear: "Zoom has so ruined board cohesion and it's a tangible thing." His recommendation is specific: every two years, take the board out of its comfort zone for an immersive in-person experience where members come to know each other as people, not just as names in a meeting invite. "When I'm talking to someone, if I know them, I can read what they're saying. If you only know a person over Zoom and you never really see them, you don't have a relationship with that."

What Intentional Partnership Looks Like

The organizations that do this well do not wait for a crisis to invest in the board-leadership relationship. They build specific practices into their rhythm.

They are explicit about what they ask of board members before anyone says yes -- not a general invitation, but a specific conversation about what the role actually requires. We need someone who will review our financials monthly and flag risk. We need someone who can open three doors a year in the philanthropic community. When expectations are named clearly upfront, a board member can commit honestly or decline before anyone's time is wasted. The frustration we see most often comes not from bad board members, but from good people who were never told what good looked like.

They invest in the board chair. Young describes the chair role as one of the most underestimated responsibilities in the sector: "So often people want to be board chair, and I don't think they really realize the amount of work that's necessary to do it right." A strong chair holds members accountable, has early conversations when someone is disengaging, and gives board members permission to step off gracefully when the time has come. That conversation is not a failure. It is how the board stays functional.

And they protect the communication boundary between board and staff. When board members bypass the executive director to reach staff directly, the damage is rarely visible in the moment but accumulates over time -- mixed messages, eroded authority, confused staff. Young calls this one of the most toxic dynamics he has observed. The fix is a simple norm established early: substantive board-staff communication goes through the executive director, not because information needs to be controlled, but because the partnership only functions when both parties know what the other knows.

The Partnership Is Never Finished

The work of building a strong board-leadership partnership does not end when the strategic plan is complete. Boards change. Executive directors turn over. New tensions emerge. The relationship has to be tended, or it erodes.

The organizations that sustain the strongest governance treat alignment not as an achievement but as a practice. They return to the questions. They check in on the relationship, not just the work. They build in time, at least annually, to ask honestly: are we still in this together, do we understand each other's hopes, are we naming the concerns before they become crises?

The Bridgespan Group's research on what separates functional boards from extraordinary ones points to exactly this: the willingness to do the relational work that most organizations deprioritize. That work does not require a new governance framework. It requires two groups of people who care about the same mission to decide, deliberately, to invest in knowing each other.

The most important thing a nonprofit can do before beginning any strategic work is to find out what its board and leadership team are actually hoping for, and actually afraid of. What those two conversations reveal changes everything that comes after.

Sources:

Does your board know what keeps your executive director up at night? Does your executive director know what your board members are most hoping for? If the answer to either question is no, that is the most important conversation your organization is not having.

 
Sana KhanNonprofit Leadership, Board Leadership, Nonprofit Strategy, Organizational AlignmentComment