#6

I want to introduce the first "company" you keep that may not be a positive experience at first, but if you stay engaged, they help bring you to a much more authentic place. Let me introduce you to the Skeptic.

The Unexpected Resistance

It was almost six months into a major organizational identity project, and I was getting the feeling things were starting to unravel. Not dramatically. Quietly. The way permanent damage usually happens.

Our strategy was solid, the Board had approved direction and the executive team had signed off on budget. We'd done everything right.

Then we started hearing whispers.

Someone on the senior leadership team had concerns. Not in meetings—in meetings, everyone nodded along, asked good questions, seemed supportive. But afterward, it was the hallway conversations and email chains we weren't copied on that had doubt spreading.

At first it felt like nervousness, then more direct questioning, then it was outright rejection.

How New Ideas Die

We had a quote we used when we first started Cause+Affect:

"Growth requires change which requires things to be different than they are."

Seems obvious, but it's amazing how often a client says, "We want things to be better, but please, don't change anything." Of course, they never say that directly, but it's implied by decisions—or lack of them.

Change is hard, and when you're asking people to believe in something that doesn't exist yet, you're asking them to embrace that things will be different than they are. One skeptical voice, especially from someone respected on the team, can cascade through an organization faster than a dozen supportive ones.

Doubt spreads more easily than confidence because doubt requires no proof — it just requires possibility. What if this doesn't work? What if we waste the money? What if this makes things worse?

We'd spent months building support for this initiative. We were about to watch it collapse because we hadn't understood one person's concerns.

Getting to the Root

The stated objections kept shifting — timing, strategy, process. Classic skepticism pattern. The surface concerns weren't the real concern.

Finally, after weeks, she said what she'd been thinking:

"We're asking donors to increase their giving during a recession. Unemployment is high. People are struggling. And we want to spend money on brand engagement? What message does that send? It looks frivolous."

There it was.

She wasn't skeptical of the strategy. She was worried about how others would see it. In her mind, the community — donors, board members, partner organizations — would look at this spend and conclude the foundation was focused on itself at precisely the moment it should be focused outward. That perception, she believed, would undermine everything the campaign was trying to accomplish.

It was a legitimate concern. But it was also, we believed, a misreading of what the work actually was.

The Shift

Foundations don't exist to stay quiet when times are hard. The foundation leaning into engagement was the mission in action, not a distraction from it.

But we also heard what she was protecting. The concern about perception was real. If a trusted insider had concerns, outside audiences would likely follow. So we made it unambiguous. The storytelling series featured community organizations, not foundation programs. The tools and frameworks they created were freely available to any nonprofit.

The message became: look at what's possible when we work together.

And once she saw it clearly — that this was the foundation doing exactly what foundations should do, especially during hard times — her skepticism dissolved on its own.

When Questions turn into Answers

A few months into the campaign, someone suggested including her in the video series. She initially resisted — but eventually agreed when they framed it as speaking on behalf of the sector's needs rather than the foundation's role.

She was extraordinary on camera. Passionate, articulate, completely authentic. She talked about why the work mattered, why the sector needed support, why collaboration was essential. She became one of the most powerful voices in the entire campaign.

The skeptic had become a champion.

When someone who initially questioned an initiative becomes its strongest voice, people pay attention in ways they don't when Champions have been enthusiastic from the start.

The Pattern We Keep Seeing

This has happened dozens of times across twenty years of client work. A project has momentum, a respected voice raises concerns, doubt spreads faster than enthusiasm, everything stalls.

The organizations that navigate this well do something counterintuitive: they stop trying to convince and instead focus on understanding the concern.

When you are in persuasion mode, Skeptics dig in. They sense you're trying to overcome their resistance rather than understand it, and they become obstacles to your predetermined solution instead of partners in solving the actual problem.

Skeptics are early warning systems. They flag problems before they become crises. They represent the silent concerns of the broader community—these are the people feeling the same doubts but not willing to say so out loud.

Your Champions will give you enthusiasm.

Your Allies will provide the implementation strength.

But your Skeptics will give you integrity.

You need all of them.

In my next newsletter, we'll look at what happens when an objection isn't about confusion but about conviction—and how to push bold ideas forward when some people will just never come along.

—Steven

P.S. Next time someone raises concerns that feel like resistance, try asking "What are you protecting?" instead of "Why don't you agree?" Different question, different conversation.