From our Agency Intelligence Mastermind session with Tamsen Webster You’re not as good at persuading people as you think. That’s not a shot. It’s math. Tamsen Webster came through our Mastermind recently, and she laid out something most of us never stop to think about: when we try to get someone to change, we are almost always playing the wrong game. For anyone who missed it, Tamsen is a reasoning researcher, messaging strategist, author of Find Your Red Thread, and two years into a doctoral program on how people adopt change. She has spent two decades studying what makes ideas land.  

There are four games you can play. Most of us mix them up.

When you ask someone to adopt a change, you are doing one of four things. Tamsen called them the Four C’s. The problem is, most of us drift between them without realizing it, and that drift is what breaks the conversation.    

1. Compliance

You’re the boss. Or the law is the law. Or the carrier says so. The person does not have a real choice. Don’t dress this up as a conversation. Tell them honestly, give the rationale, and move on. Tamsen’s point on compliance: the biggest mistake is pretending the person has a vote when they don’t. That kills more trust than the order itself.  

2. Convincing

This is where most of us live. Information, pressure, logic, data. Sometimes it works. Usually it feels like brow-beating to the person on the other side. Here’s why. Every human in the room, including the one you’re trying to convince, believes they are a reasonable person. Tamsen takes it one step further: every one of us believes we are more reasonable than the other person. The second you start piling on information to prove your point, the implication to them is “you must not be smart enough to already see this.” They shut down. Not because they disagree. Because they feel insulted.  

3. Coercion

Fear. Psychology. Bait-and-switch. Threats about what happens if they don’t. This is the one that’s going to sting for a lot of agency owners and a lot of sales trainers. Tamsen put the “Challenger Sale” playbook on the table directly. The line “make the pain of the status quo exceed the pain of change” is one a lot of us have used. Tamsen’s position: when you are the one manufacturing that pain, when you are the source of the fear, you are not selling. You are coercing. She’s not soft on it: “I am of the opinion that introducing threat for the purpose of getting someone to act is a coercive act.” Her reasoning has science behind it. When you trip somebody’s fight-or-flight response, the analytical part of their brain shuts down. They are not making a rational decision in that moment. They are making a panic decision in your favor. You got a signature. You didn’t earn a buyer.  

4. Conviction

This is the one you actually want. Conviction is when the other person lands on “this is right” on their own. Not because you overwhelmed them. Not because you scared them. Because the idea made more sense to them than whatever they were doing before. Tamsen is clear: you cannot force conviction. You can only set the conditions for it.  

Why this matters for your agency

Pick any hard conversation on your calendar this month. Onboarding a producer who isn’t hitting numbers. Getting your team to actually use the AI tools you paid for. Telling a client they need a higher limit. Convincing your CSR that routing the renewal to a bot isn’t a demotion. In every one of those conversations, you are picking a game, whether you know it or not. If you’re playing compliance, stop pretending it’s a conversation. If you’re playing convincing, realize that every extra fact you throw on the pile is making the other person feel dumber, not more persuaded. If you’re playing coercion, whether you meant to or not, you are buying short-term action at the cost of long-term trust. Conviction is slower. It is also the only version that lasts.  

What to do about it

Before the next hard conversation, ask yourself:

• Which game am I actually playing?
• Is that the game I want to be playing?
• Am I stacking information to overwhelm them, or setting conditions for them to see this for themselves?
• If they disagree and walk away, is that actually fine? Or do I need a yes so badly that I’m about to drift into coercion?

If you want the science behind why any of this works, Tamsen pointed us at Thinking, Fast and Slow by Daniel Kahneman. Her own book is Find Your Red Thread. If you missed the first post on this session, it covered Tamsen’s Three I’s: the three ways an idea dies in the first five seconds. Pair them together and you’ve got most of her framework. This is what Mastermind is for. Once a month, people like Tamsen, and a room full of agents willing to actually think about their own blind spots. If that sounds like your speed, come find us. Become a Mastermind Member