December 5, 2025
/
Insights

The Strategy Question Nobody Asks

Britt Hogue
Managing Partner

You have seen it happen: a strategy that looks perfect on paper quietly falls apart in execution. The team has resources, clear goals, and talented people. But projects stall. Communication breaks down. Good people leave.

The diagnosis is always the same: "alignment issues" or "lack of buy-in" or "organizational silos."

But these are not technical problems. They are relational ones.

And the question that could have prevented them, the one that actually determines whether anything moves, is this:

Who needs to be in relationship with you (and each other) for your strategy to succeed?

The Invisible Foundation

Here is what we do when we build strategy: We map stakeholders. We identify decision-makers. We analyze power dynamics. We ask who has resources, who has influence, who needs to approve what.

All of this matters. But it is not enough.

Because the question we rarely ask, the one that actually determines whether anything happens, is this:

Who needs to be in relationship with you (and each other) for your strategy to succeed?

Not just "who needs to be at the table." Not "who are the stakeholders." But who needs to genuinely trust, understand, and be committed to each other for this work to move forward?

This is not about being nice. It is about being realistic.

You can have the perfect plan, the right people, and adequate resources. But if the program director does not trust the executive director's decision-making, if the board chair and the CEO are barely speaking, if your community partners assume you will disappear after the grant ends, your strategy will stall in ways you cannot address with better project management.

What We Get Wrong About Relationships

When I talk about relationships as the foundation of strategy, I watch leaders' eyes glaze over. I can almost hear what they are thinking: Here we go. Another conversation about team building and trust falls.

But that is not what I am talking about.

I am talking about the executive director who spends months developing a new program model without ever asking the frontline staff what is actually getting in their way. When it is time to implement, the staff smile and nod in meetings, then quietly keep doing things the old way because they do not believe leadership understands their reality.

I am talking about the nonprofit that launches a community initiative without building real relationships with the people they claim to serve. They wonder why participation is low and why community members seem resistant, never realizing that showing up with a predetermined plan is the problem.

I am talking about the board and executive team that operate in parallel universes, each frustrated by the other's apparent lack of understanding, neither taking the time to build the kind of relationship where hard truths can be spoken and actually heard.

These are not soft problems. They are strategic failures rooted in relational neglect.

The Research We Ignore

Brené Brown's research on trust shows us something most leaders assume but do not act on: trust is not built through grand gestures or impressive credentials. It is built through small, consistent actions over time, what she calls "marble jar moments."

Every time you follow through on a commitment, that is a marble in the jar. Every time you listen without defensiveness, that is a marble. Every time you admit you do not have the answer, that is a marble.

And every time you make a decision without input from the people it affects, you are taking marbles out.

The problem is that most leaders assume trust exists rather than actively building it. We think that because we hired someone, or partnered with an organization, or have been working together for years, trust is a given.

But trust is not automatic. And when it fractures, when the marble jar gets empty, even the most brilliant strategies quietly unravel.

Projects stall because "communication issues." Initiatives fail because of "lack of buy-in." Partnerships dissolve over "misaligned expectations."

We diagnose these as technical problems. They are relational ones.

The Question That Changes Everything

When we work with organizations at The Collective Good, one of the first things we do is map relationships, not just stakeholders.

We do not ask: "Who needs to approve this?" We ask: "Who needs to trust each other for this to work?"

We do not ask: "Who are the key players?" We ask: "Where are the relationships strong, and where are they frayed or missing entirely?"

This shifts everything.

Suddenly, you are not just checking boxes on stakeholder engagement. You are asking deeper questions:

Does the program team trust that leadership will support them if something goes wrong, or are they managing risk by keeping leadership in the dark?

Do your community partners believe you see them as equals, or do they show up to your meetings because they feel they have to?

Does your board trust your judgment enough to let you lead, or are they micromanaging because they do not believe you will tell them the truth when things are not working?

These questions are uncomfortable. They require admitting that relationships might be weaker than you thought. They mean acknowledging that some of your strategic challenges are not about capacity or resources but about trust that was never built or has slowly eroded.

But asking them is the only way to build strategy that does not just look good on paper but actually moves.

Starting With Hope, Not Fear

Here is where most relationship-mapping goes wrong: we start with risk.

Who might resist? Who could block this? Who's going to cause problems?

This framing, while practical, shapes everything that follows. It positions relationships as threats to manage rather than assets to cultivate. It makes us defensive before we've even begun.

What if we started differently?

What if instead of asking "Who might cause problems?" we asked: "Who can help us grow and innovate?"

This is not naive optimism. It is a strategic choice about where to focus your energy.

When you start with solution-focused questions, questions that invite hope and possibility instead of fear and scarcity, you create different relationships. You approach people as collaborators, not obstacles. You are curious about their ideas, not just worried about their objections.

The relationships you build from that foundation are fundamentally different. Stronger. More resilient. More likely to weather the inevitable challenges that come with ambitious work.

The Collectivist Approach

Building strong relationships requires something most leaders find uncomfortable: decentering yourself.

In organizations, we are trained to center certain voices. The executive director. The board chair. The major funders. We build strategy around what they need, what they believe, what they can approve.

But real relationship building requires a collectivist approach, one that intentionally shares power and responsibility across different people and perspectives.

This means:

Listening beyond surface-level needs to understand what truly brings people together and what might be holding them apart. Not just "what do you need from us?" but "what matters most to you in this work, and what has made partnership difficult in the past?"

Creating space for voices that usually go unheard. Not token inclusion, but genuine power sharing where people can shape decisions, not just react to them.

Accepting that building relationships this way takes time. You cannot rush trust. You cannot manufacture authentic connection through a single listening session or a well-facilitated retreat.

This is hard for leaders under pressure. When the board wants results, when the grant deadline is looming, when staff are already stretched thin, slowing down to build relationships feels impossible.

But here is the truth: you are going to spend the time one way or another.

You can spend it upfront, building the trust and relationships that allow strategy to move quickly and smoothly. Or you can spend it later, troubleshooting implementation problems, managing conflict, rebuilding trust after it's broken, wondering why nothing is working despite having all the right pieces in place.

What This Actually Looks Like

A few years ago, we worked with a community development organization that was struggling to implement a new equity initiative. The strategy was thoughtful. The staff were committed. But nothing was moving.

When we started mapping relationships, the issue became clear immediately: the program team and the executive leadership were operating in completely different realities. The program team believed leadership did not understand the community's needs. Leadership believed the program team was resistant to change.

No one was wrong. But no one was in relationship either.

We did not start by refining the strategy. We started by creating space for the program team and leadership to actually talk, not about the initiative, but about what mattered to each of them, what they were worried about, what they hoped for.

Slowly, over weeks not days, trust began to build. Not because anyone changed their position, but because they began to understand each other's reality. The executive director realized the program team was not resistant but scared of losing community trust they had spent years building. The program team realized leadership was not disconnected but under enormous pressure from the board and genuinely trying to figure out how to evolve without losing their core mission.

Once those relationships strengthened, the strategy challenges became solvable. Not easy, but solvable.

Because strategy does not move through structures. It moves through relationships.

The Foundation for Everything That Follows

At The Collective Good, we talk about Humanized Strategy as an approach where every decision, every plan, every action begins and ends with people.

Relationships are where that begins.

Not as a feel-good addition to "real" strategic work. But as the essential foundation that determines whether any of that strategic work will actually succeed.

This is the first principle of Humanized Strategy, and it is the one that makes everything else possible:

Strong relationships are not a byproduct of strategy. They are the essential starting point.

When people feel truly seen, heard, and valued, not as stakeholders to manage but as partners to build with, they show up fully. They bring their best thinking. They take risks. They tell you the truth. They stay when things get hard.

And from that foundation, strategy can take root and grow.