On Persuasion Trees

2025.11.16

CXXVI

[Finding The Root; Starting With Revenue; A Recursive Tree; Show, Don't Tell; Charlatans & Word Salad; Say It Again and Again]

Thesis: The more simple & explicit you are in your arguments, the more persuasive you will be.

[Finding The Root]

It’s way easier to convince someone of something by explicitly going back to the root of the issue, the core of what you're trying to convince them of.

For my startup BirdDog, this means that I say we help increase revenue at least 3 times per sales call.

This sounds like a "no shit" statement… but really, it's simplicity is deceptive.

For starters, you yourself need to possess enough clarity to actually know what you're trying to convince the other person of in the first place.

And even if you know that core reason, it's shockingly easy to get caught up in other technical details and features. This is especially the case for founders who built their own product and know everything about it.

While you yourself might understand the root of the issue very well, restating what you think is obvious almost never actually hurts and almost always helps. In a lot of cases, restating the obvious can win the argument or the sale.

[Starting With Revenue]

We have changed a lot of things in the BirdDog sales process, but one of the most critical things that I credit for getting my win rate from ~10% to over 30% is starting each call by explicitly stating our value prop.

Within the first 3 minutes, I will have said that an investment in BirdDog leads to revenue for the sales team by increasing qualification rates, shortening the sales cycle, focusing on accounts with high contract values, and increasing close rates.

That's a hell of a claim. It seems really obvious to me--that's our core value prop, of course it is!

But saying it is so important because it tells the other person that I am trying to convince them of something they actually care about: increasing revenue.

It also starting to reveal the structure of the rest of the argument... I didn't just say we'll increase revenue with "magic." Rather, I set the tone for the conversation by making it clear what levers we pull.

The rest of the conversation now has an obvious goal: convince the other person that we improve these stats to convince them that we increase revenue. Revenue is the anchor, the root we can keep going back to.

[A Recursive Tree]

A useful way to model a persuasive statement is as a what and how:

1. What is the outcome?

2. How will you get there?

Go back to the BirdDog pitch:

The what is increasing revenue.

The how is by improving the listed stats.

Now, they know that I'm not vaguely trying to convince them that BirdDog will increase revenue; rather, we've shown the trunk of a tree that we will be examining with them.

Why do I say it’s a tree? Well, since each of the hows are also themselves whats, we can give them more hows, too, and you can start to think of them as the branches of the tree:

• BirdDog increases qualification rates (the how that became a what) by finding the accounts with relevant executive initiatives or investments that your sellers can use to book meetings and attach your product too (new how)."

• "BirdDog decreases sales cycle (a how that became a what) by..."

We don't have to stop there, either. BirdDog finding accounts with relevant executive initiatives or investments is itself another what that, below it, has another How. That how also might have some what's. In this way, we get a tree:

Navigating up and down this tree, you have all of the information you need to justify your core "what". Everything else you say is supporting evidence for the root of your tree.

By starting at the root, by the time you’re explaining a feature or a very fine technical point, you can follow the tree to trace it back up to the root.

We show you which companies went out of business -> your reps spend less time list cleaning -> your reps spend more time focusing on real companies -> qualifications go up -> revenue increases

This helps descope the argument to very fine points. We both know we’re not arguing about more qualifications leading to more revenue. Rather, we can hone in on where the debate or doubt might be.

And, we have a damn good reason to do so, because we both want you to have more revenue.

[Show, Don't Tell]

Every sub claims is stronger if you can substantiate it with a story

There is a phrase in writing and acting and many creative endeavors called "Show, don't tell." In short, rather than explicitly stating something, you give an example of it or tell a story to make it real.

Unlike creative endeavors, I think you should show AND tell, but the showing part is truly important, too.

If we say that BirdDog increases contract value by identifying low hanging expansion opportunities in the middle of a sales cycle, you'll believe me a lot more if I tell you an actual story of one of our clients where this happened.

Since we’re empathetic and emotional creatures, picturing someone else's journey as similar to ours makes an argument a lot more convincing.

Think about if you were selling someone a sports car. You maybe know that some where in the tree of justification is the claim that "Buying this sports car will make you feel cool because other people will want to be you." You could say that, and you probably should, but you can make it a lot more persuasive if you add in a story:

You could also start to paint a picture and simulate experience:

Either way, once you know what the branches are, you can bring them to life with anecdotes. And, since the root is clear, the stories lead back to that, too.

[Charlatans & Word Salad]

The opposite of clear communication is unclear communication, best known as word salad. Understanding word salad can help re affirm the importance of not only having a what and the how, but making each of them crystal clear and as simple as possible.

Take this claim, partly made up, partly inspired by a real start up:

Now, this claim is utter bullshit! But hey, at least it has a decent structure:

• What: reach AGI faster

• How: by leveraging thermodynamic blah blah blah…

The how is buzzword soup with nothing real underneath. Since it has a lot of big words, though, and a smart person is saying it, there is a decent chance that more people fall for it than should. (this is your friendly reminder that not being able to understand something like this is more often a red flag for the speaker than it is a demerit for the listener)

The first part, the what, is actually worse, though. The issue is that AGI itself is a terribly amorphous term... what does it actually mean? There are dozens of definitions, and most of them are themselves vague. Likely, if you were to ask this person for a definition of agi, they would give you something as meaningless as the rest of the statement and hope that your eyes glaze over in awe of their intelligence.

A lot of people who can make significant decisions are constantly on guard for this sort of nonsense. The more clear and direct and explicit you are about the what, the final outcome, the easier you make it for them to separate you from a charlatan.

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[Say It Again and Again]

Being exceedingly explicit about the root of your claims and arguments might seem overkill at first, but it sets the stage for the rest of the conversation and makes the goal very obvious.

It also helps you isolate the argument to the parts that the other person actually disagrees on, rather than having these massive, unwieldy claims with a bunch of missing steps.

Further substantiating those claims with stories and anecdotes will help make it real for them.

And, all in all, being clear and explicit will make it easier for people to separate you from a quack.

While I applied this to my startup, you can apply it to yours or your product or really any time you’re trying to convince someone of something.

Clarity is king.

Live Deeply,