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One might assume that the departure of a long-time director and the arrival of their successor could be an awkward or even adversarial process. But as former Church Mutual Insurance Company S.I. director Marsha Lindsay and current director Jessica Saperstein demonstrate, that handoff can instead become a rich opportunity for shared learning and continuity.
Lindsay served for more than two decades on Church Mutual’s board and was deeply invested in its mission and leadership. “I was quite passionate about the company’s mission and quite vested in its success,” says Lindsay. As the company completed a succession plan, she wanted to ensure the board retained her perspective on marketing and brand strategy — skills she had long championed. “They wanted to continue having someone on the board with the kind of skills and sensibilities I brought,” says Lindsay. The search yielded a standout candidate in Saperstein, whose background combined communications and customer-focused management. “Like others, I thought Jessica was a real gem, and her background quite admirable,” says Lindsay.
For Saperstein, joining Church Mutual was both a professional milestone and an opportunity to apply her expertise in a well-run organization. “I really felt like as I learned more about the board and about what Marsha had brought to the table, this was really a place where I could make my mark,” says Saperstein. “I was very familiar with being on the other side of board service, but becoming a board member was very different.” Saperstein credits both the board’s structured onboarding and her overlapping term with Lindsay for helping her integrate quickly. “We overlapped for several board meetings, which was great — to be able to sit side by side with Marsha, listen, learn and start to contribute.”
Lindsay agrees that shared meeting time was invaluable. “As well organized as any orientation can be outside of the board situation, when something comes up and without being rude to just whisper to each other, this is what that’s about,” says Lindsay. “It just sped up her orientation and my feeling like she now is in the loop on this and I can sort of let go.”
Both directors also discovered the process was not just about mentoring. It was reciprocal. “It is so important to listen and observe when you are new to a board,” says Saperstein. “I learned a lot from Marsha on being an effective board member. She has a wonderful way of getting to the crux of issues, asking questions in a way that advances the progress and the conversation.”
At the same time, Lindsay says she benefited from what she calls “intelligent naïveté.” “When someone very smart, like Jessica, comes to a new situation, she will ask questions that might seem naive, but are actually really smart,” says Lindsay. “She started asking some questions that I was mortified I could not address.” That fresh perspective prompted Lindsay to reexamine assumptions and helped the board itself think differently. “She was contributing greatly to the organization just by raising a great question,” says Lindsay.
Lindsay continues. “The role of a good director is to ask questions that make people think — to probe,” says Lindsay. For her, effective questioning is about clarity and critical thinking. “The best way for board members to ask questions productively is to ask the kinds of questions that get whoever is presenting to think in a way they maybe had not yet thought about something.” She offers examples directors can use: “What is the problem we’re trying to solve? What’s the essential challenge we must really address to stay viable or competitive? What is the metric of resolution?”
Saperstein echoes those principles and adds her own insights from her management experience. “I favor the kinds of questions that help us understand what is going to drive to execution and outcomes,” says Saperstein. “Sometimes it’s not until you get into that boardroom that it becomes very clear to the leadership team that ‘Well, we have this great strategy, we have these great ideas, but we’re stuck.’” Her goal as a director, she says, is to help management connect strategy to action. “Getting to the crux of how you convert good strategies and ideas to execution is really important.”
For Saperstein, the transition from management to governance also requires a mindset shift. “Our role as board members is to guide,” says Saperstein. “Not asking questions that are simply quizzing them on data or asking for data that isn’t germane to the oversight role.” She likens it to a personal transformation in her own life. “I’m the mother of three kids and my youngest had just gone off to college,” she says. “It’s a very similar kind of role that you’re in as a board member to the role you’re in as a parent of adult children — you’re there to guide them, to support them, to catch them if they’re falling, but you’re not there to do it for them.”
Together, Lindsay and Saperstein show that a board transition can be more than a routine succession. It can be a partnership that strengthens the board and deepens its collective insight.