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Make Them Feel Understood Before You Make Them Feel Wrong

Cliftoncreative.agency

This is Not a Tactic

It is a reframe.

It is also the most important thing I have learned about stakeholder management in fifteen years of content work.

You are trying to make the person in front of you feel genuinely understood — seen, heard, taken seriously as someone with real knowledge and legitimate concerns — and then, from that position of being understood, help them arrive at a conclusion you already know is correct.

This sounds manipulative. It is the opposite of manipulative.

Manipulation is making someone feel understood so you can exploit their trust. What I’m describing is making someone feel understood because they deserve to be, while also discovering that real understanding is also, practically, the most effective path to productive outcomes.

The distinction matters because the internal posture matters. You cannot fake it. We know when we are being handled.

You have to be actually curious why the VP is resistant, what the legal team is worried about, what the founder’s objection is really about underneath the stated objection.

That curiosity is not a technique: It is the thing-in-itself.


Logic Doesn’t Work
the Way You Want It To

Content people and strategists tend to believe if the data is good enough, the argument strong enough, the presentation clear enough, the right outcome will follow. We believe this because we are people who are persuaded by data and argument, and assume other people work the same way.

Senior stakeholders aren’t resisting your content strategy because they have not seen the data, they’re resisting it because the strategy threatens something — a belief, a priority, a past decision, a relationship, a self-image — and the data does not address this threat. It addresses the logic.

Logic persuades the part of a person that processes information. Resistance lives in a different location. Until you address the resistance directly the logic will not land, no matter how strong it is.


The Actual Process

Not the stated objection. The stated objection is not, or almost never, the real one. “I’m not sure about the tone” means something. “This seems like a lot of content” means something.

“I’d like to see more data before we proceed” means something: it is your only job to figure out what.

Sometimes, you can ask directly.

“I want to make sure I understand your concern — is this about the resource commitment, or about whether this approach is the right one for our audience?”

A direct, non-defensive question often produces a direct answer. People want to be understood. They will tell you what is actually going on if you ask in a way that signals you actually, genuinely want to know.

Sometimes you have to infer.

The VP who is resistant to every content initiative has a history with content that produced bad results. The founder who wants to be in every piece is anxious about how their brand is perceived. The legal team that slows everything down is responding to a specific incident you don’t know about.

Understanding the history and context will point you to where the real concern is. This is wisdom for living. Everyone you meet is fighting a battle you know nothing about, and this is true too about content strategy because it is true about everything.

This sounds simple but in fact it requires great discipline. The instinct when you have a strong argument is to lead with it. Resist this instinct. Move like water.

If the CMO is worried about whether content is a good use of the budget, given last year’s performance, address that directly before you present the new strategy.

“I know the previous content program didn’t deliver what we needed. I want to show you what was different about the approach and why I think this one is structured differently — but first I want to make sure I understand what went wrong before, from your perspective.” A sentence that costs you nothing but earns you enormous credibility.

The goal is not to be right, the goal is for the right thing to happen. If the VP arrives at the correct conclusion through a process that felt like their own reasoning, the outcome is better in every way — the decision is more committed, implementation is better supported, the relationship is stronger.

Find the genuine points of overlap between what they care about and what you are proposing. Lead with those. Let them extend the reasoning. Resist the urge to correct or redirect, especially when they are heading somewhere useful.

Ask the questions that help them get there faster.


What This Looks
Like in Practice

Say there is a content strategy that cannot get approved, because the CFO is worried about ROI.

Most people present: here is the content strategy, here is the evidence that it works, here is the projected ROI.

That doesn’t work. This is what works:

“I know content has historically been hard to tie to specific outcomes in this organization. I want to show you a different way to measure it — but before I do, I’d like to understand what signals would be most meaningful to you. What would ‘working’ look like, from your perspective?”

Now you are building a measurement framework together. Now, the CFO is a collaborator and not a skeptic. Now this ROI conversation is happening in language they chose, not language you imposed.

It is the opposite of a trick, it is taking seriously the fact that the CFO’s concern about ROI is legitimate, that their definition of success is the relevant one. It is acknowledging that a content strategy which cannot be evaluated on terms they understand is a content strategy that will not find support.

You can tell this is correct by the way it feels easy, inevitable. This is how it will feel to your stakeholder, too. That is something you did: you created an environment that was safe, and open, and good, and felt easy. And it worked.


The One Thing

Remember this, if nothing else. You are not trying to win. You are trying to get to the right outcome, which requires the people in the room to believe in it.

Believe in them first.

The rest follows. The tactical follow-through — how you actually communicate differently with each stakeholder depending on what they care about and how they process information — is a different skill than the relational one. But it builds on the same foundation.


Jacob Clifton is the principal of Clifton Creative, an editorial strategy consultancy based in Austin, Texas. He spent fourteen years as a flagship staff writer at Television Without Pity and has written for Tor.com, Vulture, BuzzFeed News, and the Austin Chronicle.
For inquiries: jacob@cliftoncreative.agency · Book a discovery call