A New Leader’s Tests

90 Days In

I recently had the privilege of sitting in the boardroom as a new CEO, who was only 90 days into the job, presented to her new set of bosses for the first time. It was a masterclass in persuasion, trust-building, and good old-fashioned leadership.

She had accepted the job knowing she was entering a world of pain. This was a large nonprofit, and larger nonprofits tend to come with more stakeholder silos, more competing agendas, and more complicated organizational politics. Trust between the organization’s leadership and several important external stakeholder groups had badly deteriorated.

On her first day, she emailed the board to explain that she would begin her tenure with an external listening tour. I was surprised. Most new leaders begin by looking inward. They meet with employees, assess the culture, study the financials, and learn where the bodies are buried before venturing outside the organization. But you know me. I appreciate an out-of-the-box thinker.

Still, I thought, “Oy vey. Here we go again.” I imagined a parade of grievance sessions in which everyone complained about the previous leader, relitigated old battles, and presented the new CEO with a list of impossible demands. Good luck entering that lion’s den.

Ninety days later, my doubts had completely subsided. In every meeting with an external stakeholder group, she listened carefully and then asked, “What would be a small gesture that I could accomplish in the next 90 days that would help rebuild trust between your organization and mine?”

There is so much wisdom packed into that question. "Small gesture” established that she was not promising to move mountains. She was asking for something specific, achievable, and proportionate to her short time in the role. “Rebuild trust” acknowledged the damage without assigning blame. It also reminded both parties that trust had existed before and could exist again. And “within the next 90 days” created urgency, accountability, and a clear test of whether her words would be followed by action.

The question caught people off guard. They had expected defensiveness, excuses, or grand promises. Instead, they responded with modest, reasonable requests. One group wanted its executive director and board chair invited as complimentary guests to the organization’s spring gala. Another wanted permission to forward the organization’s communications to its own membership so people could remain informed.

These were easy things for the CEO to accomplish. But what she did next was even more brilliant. Even when she almost certainly had the authority to approve a request herself, she responded:

“That certainly sounds reasonable to me. I have a board meeting coming up within the next 90 days, and I am going to run it past them. I promise I will come back to you immediately afterward with an update and, hopefully, good news.”

The Impact of the Right Questions and Responses

That response accomplished several things at once. It gave her a legitimate out if a request proved more complicated than it appeared. It showed respect for the board without diminishing her own authority. It allowed her to return to each stakeholder with evidence that she had followed through. Most importantly, it put the board on notice.

By the time she presented the requests to us, the sale had effectively been made. We were being asked whether we would support our new CEO in making a series of small, visible gestures designed to rebuild relationships that the organization desperately needed.

Would we undermine her 90 days into the job over complimentary gala tickets and permission to forward an email?

Of course not. The requests were approved. The stakeholders got what they had asked for. The CEO demonstrated that she listened, kept her promises, and could get things done. The board became an active participant in rebuilding trust rather than a distant observer of the process.

And she learned something important about us, too.

Not a Tour, a Careful Test

This was not merely a listening tour. It was a carefully designed series of small tests. She was testing whether external stakeholders would respond reasonably when given the opportunity. She was testing whether the board would support her judgment. She was testing whether trust could be rebuilt through actions rather than speeches. 

The best leaders understand that trust is rarely restored through one dramatic act. It is rebuilt through a series of small promises made carefully, fulfilled visibly, and repeated consistently.

She did not ask everyone to trust her. She gave them a reason to.