Everyone an Entrepreneur: Board and Staff Leading Together Through Uncertainty

Photo credit: Sander Weeteeling via Unsplash.

By Julie Malek and Mark Achler

In Jewish organizations across the country, board and staff are struggling to understand the best way to navigate change and uncertainty together. A group of sector leaders (Leading Edge, JPRO Network, Board Member Institute for Jewish Nonprofits, Jews of Color Initiative, Jewish Social Justice Roundtable, and UpStart) has been sharing weekly insights from the field, including reflections on what they’re hearing from board members. One analysis showed that board members are struggling to see the context within which their organization resides, resulting in an overemphasis on brand preservation rather than execution of mission. While staff might have received significant support and learning during this time, those insights may not be shared with the board, leading to a gap in knowledge and another source of tension. And overall, “there seems to be a lack of recognition that board members also need support in navigating the toll, duration, and complex challenges of this new reality.” 

In this time of unprecedented challenge and volatility, we are operating in an environment similar to that of a startup: significant uncertainty, a rapid pace of change, and the need to constantly adapt to survive. To meet these challenges, it’s critical that board members adopt an entrepreneurial mindset and work closely with staff to successfully drive change. 

As board members of a major Jewish organization, we would like to share some insights from our own experience over the last couple of months. We’ve been serving on boards throughout the Jewish, nonprofit, and corporate worlds for decades, and currently serve on the board of UpStart together. 

We know that board members have a unique vantage point and set of responsibilities, one that is wholly different from staff. All board members make a serious volunteer commitment, giving our time, energy, and financial resources. We have great responsibility in terms of stewarding the organization with limited day-to-day visibility. While these are challenging times for board members, it’s also an incredible opportunity for us to engage in new and different ways of supporting our organizations and their teams. The Board Member Institute for Jewish Nonprofits has done some phenomenal work to begin filling in this gap, and there is certainly more to be done. 

As board members of UpStart, we have the opportunity to see some of the most entrepreneurial ventures in Jewish life firsthand, while working within an organization that embraces an entrepreneurial and growth mindset. This was particularly apparent during our time on the Jewish Innovator Payroll Relief Fund Task Force (JIPRF), which supported Jewish ventures with emergency grants to cover their payroll and keep their workforces whole as they planned for the future. Since then, we’ve been thinking a lot about what it means for board members to lead with an entrepreneurial mindset during moments of great uncertainty, even without operational authority. Below are a few principles we’re trying to abide by:

Engage with a bias towards action. We’ve seen two types of leaders: those who freeze in uncertainty, and those with a bias towards action. This crisis is complex, with a high amount of pressure and no easy answers. Analysis paralysis can take over, or it can be tempting to wait too long for new information before acting. It’s on us as board members to partner with our teams to figure out ways to take the next action, and then the one after that. Together, we can get unstuck and be comfortable with the imperfection of a first try.

The first meeting of the staff and board member-led JIPRF Task Force was a bit chaotic, yet we knew something needed to be done now. We dealt with the messiness and made progress, knowing it was better to do something imperfectly than to do nothing at all. We’re now evaluating that work to improve in the future, another critical step when you lead with a bias towards action.

Challenge assumptions about your audience, what you do, and how you do it. You might have set ideas about what your organization is “allowed” to do, based on what you’ve done in the past. But now’s the time to think creatively about how you might meet or expand your audience, change up what you do, or re-envision your methodology. For example, we’re noticing synagogues across the country that are looking at their audience anew – it’s no longer just the people who can physically enter their doors, but could be anyone with an internet connection. If previously in-person services were the “main draw” for a synagogue, what might be a new way to draw people in, connecting them to Jewish tradition and each other differently? For example, Mishkan Chicago (whose board Mark chairs) is now reaching people in over 22 states and 18 countries who “tune in” and experience their services. Those individuals are starting to identify as an active part of Mishkan’s community. By rethinking assumptions, a synagogue can better meet the evolving needs of an even wider audience.

Maintain a field perspective, not just an organizational perspective. This moment calls for new thinking around how to continue our organizations’ missions with very different (and usually more limited) resources. Be open to new collaborations and formulations of your organization that better serve the mission and the field as a whole, not just your organization’s brand. Serve as an open-minded thought partner when new possibilities come up. Learn more about the field your organization is in so you can better understand the context and options. You may be called on to help evaluate a collaboration or a consolidation, and you’ll want to have a birds-eye view of the field. 

Acknowledge complexity and dualities. The situation is not simple, and there are a lot of tensions at play: urgency versus sustainability, compassion versus practicality, agility versus certainty. We saw this clearly with the applications for the Jewish Innovator Payroll Relief Fund: the tension between ventures with an immediate, urgent need for cash on hand and those that needed funding to remain sustainable in the longer term. We wanted to help everyone but with limited funds and a short timeframe to disburse the money, we couldn’t. And, while we wanted to challenge conventions and think outside the box, we didn’t want to get too far afield from our mission. We can hold these tensions with a “both-and” mindset (instead of “either-or”), realizing that there are no easy answers. It’s in navigating these tensions that some of the most important work can arise, and there the trust and camaraderie between staff and board members can grow stronger. 


This time is full of challenges, but it is also ripe with unique opportunities to shift the way board members relate to their organizations and to each other. It’s a chance to learn how to adopt an entrepreneurial mindset, and to bring these insights into everyday practice that can make your organization more sustainable, and ultimately, more successful. 

Julie Malek and Mark Achler are board members of UpStart, which partners with the Jewish community’s boldest leaders to expand the picture of how Jews find meaning and come together. Julie is an educator with 20+ years of experience, who has served on the boards of a Reconstructionist Jewish community, Colorado I Have A Dream. She is also a member of The Giving Trust, a local giving circle of Jewish women in Denver. Mark is a serial entrepreneur, venture capitalist, and faculty member at Northwestern University Kellogg School of Management.