On January 1, 2023, Scott Kaufman’s term as chair of the board of Leading Edge came to an end. And quite a term it was. A mere month before the pandemic began, we sat down with Scott for an entrance interview. Now, as he passes the baton to Daryl Messinger (read her entrance interview here), we asked Scott to reflect on what he’s learned and observed.

What Leading Edge achievements are you proudest of having seen happen in your term as board chair at Leading Edge? 

While I could provide half a dozen answers here, including the smooth integration with the Boardified team, two achievements rise to the top of my list. First, how adaptive and nimble Leading Edge was in the early days of the pandemic as far as building successful new programs and resources to address the rapidly changing situation. And I don’t mean fast “for a nonprofit,” I mean fast for any business. The other achievement that stands out is that during a pandemic, which for Leading Edge was almost exclusively a remote working environment, we were able to triple the size of our professional team while not sacrificing, and maybe even improving, our organizational culture. I think this was a result of many things. Most importantly, our team hired extremely well, in terms of both talent and character. Great people, when empowered, build a great culture. 

A board chair often works more closely with the president & CEO than the other board members do. What, if anything, have you learned about Leading Edge President & CEO Gali Cooks from this close partnership that you didn't know before becoming chair?

While I was already a big fan of Gali, working closely with her during such a challenging period only increased my admiration for her leadership. Her ability to deliver excellence was evident from the beginning, but her steadiness in dealing with the constant change of the moment and her compassion for our people during these difficult times only deepened my appreciation of her as a leader and a person. I was especially impressed with her growth in terms of embracing the inherent risks of rapid and frequent innovation, which perfectionists often struggle to do.  

Did you learn anything about yourself or about leadership from this experience of helming the Leading Edge board for three years?

I have had two big takeaways from this experience which I think have significantly improved my leadership performance. First, I became far more conscious about not “giving my feelings the keys to the car’.” As a board chair, I wasn’t in the trenches. Thus, I was able to maintain a certain emotional distance from the work; sort of a “view from the bleachers” perspective. I am now far better at recognizing, both in others and in myself, when feelings like ego or insecurity are creeping into decision-making. The answer isn’t “don’t have feelings;” we don’t get a vote there. Rather, it is to recognize when feelings are trying to “grab the wheel” and then get them an Uber.

The other key learning is that Leading Edge, or anywhere I play a leadership role, would benefit if I were to become far more practiced at having productive difficult conversations as soon as the need arose. As a pleaser, this was not something I always jumped in to do. Armed with the clout of the “chair of the board” title, I made a conscious decision to lean in far more often to take on these conversations as needed, and this has made me a better board chair and a far better CEO in my day jobs. 

Succeeding you in the board chair role is Daryl Messinger. What skills and qualities have you observed in Daryl that you feel will most help her succeed as chair?

Daryl brings a depth and breadth of skills to this role matched only by commitment to our mission. Her analytical skills are elite and she has tremendous leadership experience from many local and national Jewish organizations. She has an exemplary work ethic, and she does all this with a big heart. A significant upgrade for sure! 

What advice, if any, do you have for Daryl about this particular role at this particular organization?

Leverage our amazing board. “Jewish is a team sport” is a truth that is evident in most of our greatest moments as a people, going back millennia. My Leading Edge experience has only reinforced this conviction. While we certainly have a great professional leader, our secret sauce is the depth of talent on our professional team and how they each are put in positions to shine. The same is true with our board, and while I am proud of the role I played as chair, the pandemic limited the kind of gatherings where we could have really leveraged the exceptional talent of our board members to support our team and drive our work even further. 

What do you come away from your term as chair still curious, uncertain, or wondering about, related to Leading Edge and our work?

By industry standards, a relatively small amount of our team’s bandwidth goes towards engagement of stakeholders just for engagement’s sake. This allows us to have the bandwidth to deliver excellence as both a professional services provider and a think tank in service of our field. My concern is, as we grow, will we be able to avoid the trap of spending too much time and resources engaging, promoting, and selling, and not enough in driving excellence across our ecosystem?  

Do you have any other reflections you want to share?

I never would have imagined that at dinner in Miami, my friend and founder of Leading Edge Rachel Monroe would lead me on such a profoundly meaningful and enjoyable leadership journey. That evening, while discussing an upcoming conference we were co-chairing, Rachel asked me to take a look at a strategic plan for this new project that would soon launch. The next day, I shared many thoughts about talent and culture, and then got roped into joining a small group to name and brand this new organization.   

I am so grateful to the professional team, current and past board members, and the generous and forward-thinking philanthropists who provide our fuel, who have given me the honor of serving Leading Edge—an organization that lives its values every day. This has truly been one of the pleasures of my life, as I cannot imagine a more fulfilling volunteer role.