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Up the Board of Directors’ Game: Authentic and Relevant Conversations

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Stephen Bennett writes about the need for authentic and relevant conversations within the Board of Directors and shares a unique exercise Caravanserai Project has been using in its work. This topic is also the focus on the Caravanserai Project September free workshop. To access the event or the recording and materials here.

As organizational leaders navigate a polarized nation heavily impacted by the Covid-19 pandemic, increased awareness of racism, global warming, and economic transitions, the Board of Directors of nonprofit mission-driven enterprises are facing new and unique challenges. Aside from the typical ones related to good governance, there is no question that it is imperative for the Board to be more connected than ever to what the world around us is currently experimenting and have an in-depth understanding of the potential futures about to take shape under our own eyes.

Shifting the Board of Directors’ Dynamic

There is no shortage of articles, blogs, webinars, and workshops on a variety of Board of Directors related topics. But are these conversations and resources actually reflecting the current needs and expectations? Not always. In many cases, the presentation format is different, while the substance stays the same or experiences limited changes.  

At Caravanserai Project alone, we have addressed this particular topic on a number of occasions as part of our monthly free webinars, in articles and ongoing conversations that we are having with some of our partners and beneficiaries. The Board of Directors will be the focus of an upcoming Breakthroughs Masterclass to be offered this fall as well.

Regardless of the angle from which we have approached this topic, we are always prioritizing the need to create a special dynamic within the Board of Directors. Our goal has been to encourage active engagement among its members and provide an environment in which listening to one another is a priority. Since the inception of the Covid-19 pandemic and the shift to online meetings, there is hardly any time left for personal interactions. Exchanges that have allowed Board members to get to know each other at a much deeper level and connect over relevant issues beyond those included in the agenda are absent these days from Board meetings. Yet, it does not mean things have to stay this way.

What the Board of Directors Wants 

Most Board members know what they want: transparency, accountability, being valued and supported, as well as being involved in something greater than oneself. They expect to be appropriately engaged while using one’s skills and knowledge to the benefit of the organization and the common good.  

But serving on the Board it is not only about giving. There is an equal expectation to be exposed to a unique learning experience, an educational journey that is exciting, rewarding and stimulating. And not only related to the sector in which the organization is active. The acumen other Board members bring to the table, their experience in other industries and walks of life, is expected and equally valuable. 

Moreover, we need to be having conversations that are candid about diversity, inclusion, power, role behavior, learning and more, in ways we have never done before. It does not always have to be as part of a Board training, in many cases it is as simple as the members sharing what they have learned and experienced in other contexts.

Increase Communication and Opportunities for Authentic Conversations

Recently, the CEO at the ARCUS Foundation, Annette Lanjouw, led a conversation with the Board about the impact of the Covid 19 pandemic and how it changed our perspective on the organization’s commitments, its engagements and future plans. As a Board, our in-person pre-Covid 19 meetings have always been the perfect balance between the traditional board responsibilities and learning opportunities from the other Board members. This practice used to take place as part of the “official” Board setting or during casual breaks and meetings which has always been included in our Board schedule. While the online Board meetings have been very productive, not spending time with the other fellow Board members has left a gap with which we all have been struggling.     

Annette’s approach was truly eye-opening in many perspectives. It offered us the possibility to reconnect and learn what the others have been thinking about the latest events and how they have perceived issues that impact the organization and us, personally and professionally. Being part of this collective sharing and exchanging process made us realize how important it is to have authentic conversations that go beyond the Board of directors’ agenda. There is no better Board than the one that is thoughtful, informed and visionary. While structure is important, allowing the time to learn from each other (whether in a structured or informal setting) is crucial and to the organization’s benefit as well.

The Big Four Question Game

With Annette’s permission, Caravanserai Project adapted her approach and created four questions to be used as part of a structured conversation with the Board of Directors. The ultimate goal is not to find  the right answer (there isn’t one anyway). The aim is for the Board to be thoughtful about their own professional and personal experiences that in most of the cases differ from one Board member to another and take the time to reflect and share some of the lessons they have learned on a particular topic. 

Using this model, we provided pro-bono facilitation to four mission-driven organizations in Southern California from various sectors. We first “tested” this approach on the Caravanserai Project Board and ourselves saw the value in having this conversation. 

This exercise is not an additional item to the already packed agendas Boards usually have. It actually offers a break from the “business as usual” approach. Our role was limited to facilitating the conversation and we did not try to change ideas, influence the participants, or offer our opinions on a specific issue. We wanted to make sure that things progress as the conversation continues and everyone gets to share. We also wanted to strike a balance between the participants so all those present engage and share their opinions. In some cases, the Executive Director was a silent observer. In others, they were not present as the Board wanted an even more open conversation.

Over a period of 2 hours, the maximum time dedicated for this meeting, there was not a dull moment. Like in any conversation, some tend to take over, others to hide. We made sure that rules were in place, and everyone was familiar with them. We also shared the questions in advance so the participants had time to reflect and think about their own experiences. This created a unique opportunity for board engagement, authentic conversations and a thoughtful and timely reflection on the moment in which we find ourselves as Boards and organizations.

Four Questions for A Different Board Engagement Dynamic

The four questions we have used as part of our work with these Boards were specific and reflected a particular moment of the year 2021. They can always be adjusted depending on the goal of the exercise, time and the audience. Here are our four questions.

1. What is at stake, now? Do the imperatives facing your organization look different now than a year or 18 months ago? How? 

Guiding questions: What do you think are the most significant headwinds that we are facing now? Do you see climate change, conservation, or racism differently now than you did a year ago? Are there implications for our work? Is there something that you worry might take us by surprise in the coming year?

2. What is the opportunity? 

Guiding questions: What might the U.S., state, or regional government do now both domestically and unilaterally to affect our work? What will be decided during the next four years that will affect our partners and mission long-term? Are there engagements we should be forging at this particular time? Do you see an opportunity window closing or opening on the work that you or your organization is pursuing? 

3. What is the role of your organization and philanthropy?

Guiding questions: Do you think differently about our role now than a year ago? What are your observations about the way that Philanthropy has responded, adapted to unanticipated crises? Do you see any learnings for your organization?

4. What lessons have you learned or seen this year in your personal and professional work that it would be useful for us to know and consider? 

Guiding questions: 2021 and what will be 2022 are seismic in their impact on every industry, every economy. Some of these impacts will be long lasting. What might be in our blind spot in terms of permanent change for mission driven organizations?


Some of the Boards with whom we worked decided to write short reports to document the ideas shared and, eventually, incorporate them one way or another in the organization’s approach and future work. Others left the 2-hour conversation surprised by what they have learned and with the declared intention to continue as a group exploring some more challenging topics.

 Although some of the contributions might have been uncomfortable for the rest of the group while others demonstrated an in-depth and thoughtful soul-searching process, the conclusion was unanimous: these structured and intentional conversations are a must as part of the Board of Directors engagement.   

One of the major impacts of Covid 19 and the isolation and separation it caused is the absence of the richness and interactive opportunities of in-person meetings. It can be very helpful for organizations and boards to be very deliberate in creating more communication opportunities where we listen to each other and create agendas and safe environments for authentic conversations.  We invite you to try this conversation with your own board.



Stephen Bennett is Co-Founder and Board chair of Caravanserai Project. Along his professional career in the for profit and nonprofit sector, Stephen has served as Executive Director as well as Board member and chair for profit and nonprofit ventures. Currently, he serves on The California Endowment Board of Directors where he chairs the Finance and Investment Committee, the Arcus Foundation where he serves as Treasurer and Save the Chimps chairing the Audit committee.



This blog was made possible in part by the generous support provided by the Wells Fargo Open for Business Fund. Caravanserai Project is the recipient of a Wells Fargo Open for Business Fund award aiming to provide programs and services that support small business viability through growth, expansion, innovation, and increased productivity. Read more about this award.

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