THE CONVERSATIONS BEHIND EVERY STRATEGY DECISION
Organizations most often come to us when they're ready to reflect on their community investments — how and where they are giving, whether they should be doing more or less of something, or whether it's time to pilot something new that feels just outside their comfort zone. These are the questions we love. They signal a willingness to look honestly at the work and consider what might need to change.
But strategy decisions with real consequences require real conversations. Different people walk into the room with different visions, different histories with the work, and often a different language for talking about it. One person's "community investment" is another person's "stakeholder engagement" is another person's "brand-building." Before any of it can move forward, those differences have to come into the open.
That's the work we do best. Holding the space where every idea gets a hearing before any of it gets discarded. Saying "why not?" before saying "no." Making sure people don't just feel heard — they actually are. When that happens, strategy stops being something done to a team and becomes something built by one.
Here are four approaches we use to make that possible:
DESIGNING THE CONTAINER BEFORE THE CONTENT
The quality of any strategic conversation depends on the container that holds it. Before any agenda gets built or any decision gets debated, the conditions for real dialogue have to be set: how people will speak, how they'll listen, how disagreement will be handled, and what success in the room actually looks like. Without that container, even the best-prepared meeting can spiral into conflict or polite avoidance.
For a corporate giving team weighing whether to sharpen their focus areas, that might mean naming up front that the goal of the session is to surface perspectives, not make a final decision. For a foundation board discussing a 2.0 version of an existing program, it might mean agreeing that nothing is off the table for discussion, even ideas that feel uncomfortable. These small structural choices change what becomes possible in the conversation.
What works:
Agree in advance on norms for dialogue — time limits, no interruptions, no personal attacks.
Name the goal up front: is it to make a decision, surface perspectives, or simply begin a dialogue?
Recognize that small steps count. Incremental agreements often pave the way for durable shifts over time.
Revisit the rules as needed. What worked in one meeting may need to evolve as dynamics shift.
SURFACING WHAT LIES BENEATH
Progress can stall, or get sidelined entirely, when assumptions go unspoken. Different people often walk into the room with different definitions of what success looks like, how risk should be weighed, or what the program is ultimately for (is "community-led" advisory input or decision-making power?). Taking the time to understand the full spectrum of perspectives — the must-haves, the non-negotiables, and the areas of flexibility — helps avoid unproductive standoffs and gets to the real conversation underneath.
Take a corporate giving team deciding how to define a focus area: should it be broad enough to cover a wide range of community work, or laser-focused on a specific issue, knowing fewer organizations will qualify? Or consider a foundation weighing whether to expand grantmaking to include organizations adjacent to its core focus area, partners that sit in the broader ecosystem but aren't the most direct fit. These are not just programmatic questions. They surface deeper differences about reach, depth, risk, and what the program is ultimately trying to accomplish. Surfacing those differences early through one-on-one conversations before the group convenes, and honest naming of who holds influence over the decision creates space for a more honest dialogue and a stronger eventual answer.
What works:
Ask open-ended questions like: What makes this issue hard for us? Where do you feel compromise is possible? What would success look like in three years?
Identify shared interests and overlaps—no matter how small—that can serve as a foundation for consensus.
Map sources of influence and power clearly, so they can be acknowledged rather than quietly driving outcomes.
Normalize the idea that disagreement doesn’t mean failure; it’s often the starting point of real progress.
RETURNING TO THE WHY
When tensions rise in a strategy conversation, the fastest way through is rarely to argue about tactics. It's to return to the shared purpose underneath them. Funders who navigate internal differences well don't start with "what should we fund?" They start with "what are we hoping to achieve?" Anchoring in shared purpose provides the connective tissue that holds different perspectives together when the conversations gets harder.
This is also where shared language matters most. Words like "innovation," "differentiator," and "impact" can mean very different things to different people, and unspoken differences in how those words are used can shape every downstream decision. A corporate giving team might agree they want to drive innovation, but if one person hears "innovation" as a new pilot in an emerging issue area and another hears it as a full portfolio overhaul, the strategy conversation will be stuck before it starts. Getting clear on what those anchor words actually mean, in plain, accessible language, is often what unlocks the rest of the work.
What works:
Spend intentional time clarifying the “why.” Why this work? Why now? Why us?
Define shared language for the words that matter most.
Test values against real decisions. If a proposed initiative doesn’t line up with the agreed “why,” it’s worth revisiting.
Treat values as living, not static. Reaffirm them periodically to ensure they still resonate as the context shifts.
LEARNING AS A BRIDGE
When a conversation stalls, learning can unlock movement. Bringing in outside voices, like community leaders, issue-area experts, peer funders, often helps reframe debates and surface new options that aren't visible from inside the room. Learning together also creates a shared experience, which builds trust and common language.
This is especially powerful when an organization is considering something that feels just outside its comfort zone. We're currently in a process with exploring how AI and emerging technologies might support a client’s grantmaking, a question with no obvious answer. Rather than try to develop a position internally, the team is interviewing a range of tech-focused organizations and intermediaries to understand what's possible, what's working, and what the real tradeoffs are. The learning itself is helping the team build a shared point of view before any decisions are made.
Structured opportunities for collective learning also demonstrate humility: a willingness to admit that no single funder or board member has all the answers. That shift makes space for new ideas, and often, for unexpected solutions.
What works:
Host retreats or facilitated sessions that combine education with reflection.
Draw on knowledge beyond your usual networks; let impacted communities shape the dialogue.
Use joint learning as a platform for experimentation—piloting a new approach can be a bridge between competing perspectives.
Treat learning as ongoing, not a one-off step. Continuous input strengthens both trust and decision-making.
STRATEGY THAT HOLDS
Strategy decisions rarely fail because of bad analysis. They fail because the conversations that needed to happen didn't, or didn't happen well. The teams that get unstuck are the ones willing to do the harder work of designing the container, surfacing what lies beneath, returning to shared purpose, and learning together.
When that work happens, the decisions that follow tend to hold, and the people who shaped them stay invested in seeing them through.
If this resonates and you're thinking about a fuller strategic refresh, we've written about that process here →.
