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Navigating Challenging Conversations: Getting on The Same Page to Strengthen the Impact of Your Family’s Philanthropy

We are in a time and place where more families and family foundations are reflecting on their role in society and examining how their philanthropic presence can or should be growing, adapting and evolving to better address societal changes.  As part of this process, families and family foundations are grappling with complex issues and facing some challenging questions, including:

  • How can our family uncover a common vision and align on philanthropic motivation and the “why” of philanthropy?
  • How can our family foundation engage the next generation(s), especially given varying levels of interest, and experience in philanthropy, as well as varied approaches to grantmaking?
  • How will our governance structures and procedures need to adapt to allow for shared decision-making processes?
  • How do we create an inclusive process that engages both family and non-family members?
  • What will it look like for our foundation to embrace participatory grantmaking?
  • Is our foundation ready to incorporate internal and external practices that include an equity lens? What does that mean for the various stakeholders, including family members across generations?

Answering these questions in an honest and productive way always requires holding open, candid, and often challenging, conversations.  These are the type of conversations where sensitivities, generational and/or ideological differences, leadership dynamics, entrenched ways of working and apprehension around change may be present. Tensions and emotions often run high, and compromise is almost always necessary.  To be successful in these conversations, it is critical for the individuals involved to share core beliefs, values and opinions and be open to hearing the same from others. While discussing these matters can be quite challenging, it is often what helps families and foundations move forward in setting a direction or achieving their goals.

At TCC Group, we work with families and foundations of all shapes and sizes and are often called upon to help facilitate these conversations, which require a unique set of skills and techniques to ensure that conversations remain respectful, thoughtful, and most of all, productive.

Clients often come to us because they feel that they are at an impasse.  They typically fall into two categories: 1) they are pushing through what feels important to a small set of stakeholders without consensus or input; or 2) they are avoiding facing challenging decisions altogether and continuing to work in the same, often unproductive way.  In our experience, an open and honest dialogue about what matters  is what is necessary to help them move forward. We help carve out a balanced, neutral space – one where everyone brings their desires and opinions to the table with the goal of achieving a small step forward or even possibly, a great change. While there may be no “secret sauce” to navigating challenging conversations, there are certainly some key elements that can help move to a successful and satisfying conclusion.

Agree on the Rules of Engagement and a Shared Goal

The first and most critical step is to align on what the invested parties or individuals want to achieve – this can be as straightforward as agreeing to simply discuss a challenging issue with an open mind and willingness to hear and listen to other points of view or to commit to a model of shared decision-making in the future.  Our preference is to allow for a dynamic and iterative process that is anchored on mutually agreed upon rules of engagement.  We focus on respect, empathy and patience as key tenets that establish a safe, productive, and collaborative environment.


Create rules of engagement together; common ones include agreeing on time limits for people to speak, not speaking over another, avoiding personal attacks, and a commitment to open dialogue and active listening.

Encouraging a larger commitment to the process itself is critical in ways: 1) it acknowledges that change is incremental and that small steps should be seen as wins as they create a pathway for reaching mutually desirable outcomes, and 2) its recognizes that shared decision-making requires mutual trust, and that building trust takes time.


There are no shortcuts when it comes to holding open and honest conversations. There may be temptation to hasten the process, to skip over having to dig into challenging topics or pretend they don’t exist. In our experience, the investment of time is critical to long term success. 

Understand the Playing Field

To begin any challenging conversation, we must first understand the extent of the barriers or pain points and find those open spaces where there may be points of consensus or agreement.  To do this we begin by asking key questions to better understand the various viewpoints, ideally in one-on-one interviews to protect anonymity, and to free people up to reflect and speak honestly. There are almost always differing opinions about the “right” course of action and there are almost always power dynamics in play – who holds it, who wants it and how it might be shared, expanded or transformed. This work of mapping the playing field is also where you can plant the seed of compromise and find those areas where you think there may be some potential give and take.

As we talk to each of the key stakeholders about what makes the conversation challenging or difficult, we also listen for the areas of intersection and shared interests and points of agreement to map a shared path forward. The goal is to find common ground to reduce tension and build rapport to focus on finding a solution that works for everyone.


Ask open-ended, thought-provoking questions:  What makes this conversation hard? What is contributing to the tension? What are your must haves in this process? What are those places where you can keep an open mind?  What are the nooks and crannies where you envision change? What are your non-negotiables?

Identify Shared Values

We know that uncovering shared values lends itself to building understanding, empathy, trust, and cooperation between individuals who have different points of view or beliefs; ultimately it can help to lay the groundwork for working together towards a common goal. Establishing a collective vision or values provides the framework to help align families, foundations, or board members to a common purpose.

To uncover shared values, it is helpful to start with the “why” of the enterprise. Why are you on this journey? In the case of family philanthropy, why has the family chosen to create a family foundation? How would we like to be remembered? What values guide me? What are the most important values we share? For other organizations or foundations experiencing change, the questions are similar.  What are the core values that drive our work? What is guiding our desire for change? What are we trying to affect in the world? Spending time to uncover motivations can help create a shared answer to “why are we doing this?” that can then serve to bridge varying points of view.

Learn Together

A commitment to learning together helps interested parties continue to build rapport and provides a platform to create a shared language and common understanding of the goal they are trying to reach.  A significant way to promote open dialogue and maintain forward momentum in conversations is to tap into outside knowledge and expertise. Often, discussions or decision-making processes may run into barriers that can be addressed by seeking additional information from outside the foundation; additional inputs and feedback might come from impacted communities, other funders, issue area experts or grantees. This is especially critical if a foundation is exploring a strategic shift, a refinement of a focus area or a new way of operating in the community.  As much as possible, we work to structure an engagement that provides a holistic review of knowledge and experience outside a foundation’s immediate circle to better support decision-making efforts.


Find time for and commit to shared learning. This could be a retreat that offers safe, neutral space and time to deepen understanding – of philanthropy, of a subject area, and of each other.  

At the core of challenging conversations are deeply held beliefs and points of view; honesty, flexibility and compromise are essential elements to achieve success. TCC Group approaches these conversations by leading with empathy, curiosity and sensitivity, and encourages families to hold these same principles close as they move forward in their process. The process is iterative by nature – families or foundations grappling with differences will likely encounter other difficult conversations in the future. Having done the work to arrive at a productive conclusion, we codify the steps and methods as a tool that lays the groundwork and supports the process the next time a family or foundation faces a challenging conversation.

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