Every nonprofit CEO has had the conversation: trustees who are not hitting their give-or-get minimums, board members who feel disconnected from the campaign, and a development team that is quietly avoiding the subject.
The problem is almost never the board. It is the infrastructure and the relationships that surround them. After two decades working inside some of the most complex advancement operations in the country, I can tell you with confidence: board giving is a leadership problem, not a board problem.
The relationship comes before the ask
Most development shops treat board engagement as a transactional exercise. They send quarterly updates, invite trustees to events, and then call when it is time to give. That sequence is backwards. The ask is not a moment. It is the outcome of a relationship built over months or years. When boards are not giving, it is almost always because the relationship was never built in the first place.
This is where a Chief Development Officer or Chief of Staff earns their keep. Their job is not to manage the board. It is to create the conditions where board members feel genuinely connected to the mission, proud of the organization's work, and confident that their gift will make a real difference.
Staff behavior shapes board culture
Board members take their cues from staff. If your development team is uncomfortable making asks, your board will sense it. If your CEO avoids the topic of board giving, your trustees will too. The culture of generosity inside your board begins with the culture of candor inside your leadership team.
One of the first things I do when I step into a new engagement is sit down with the CEO and ask a simple question: when did you last have a direct, honest conversation with each trustee about their giving? In most cases, the answer reveals the real problem immediately.
What actually moves the needle
Three things, consistently: individual conversations that connect each board member to the specific impact of their gift; clear and transparent giving expectations communicated at the time of board recruitment, not after; and a CEO who models the behavior by talking openly about the importance of board generosity with their own trustees.
None of this is complicated. But it requires leadership that is willing to have the uncomfortable conversations, and the operational infrastructure to support them.