I told a rep her problem was being too likable

Have you ever met someone who agreed with everything you said?

Stop and think about it for a second. Maybe a past employee. A friend who thinks every business idea you float is brilliant. Or a contractor who said "yeah, that's our specialty" to every new job you threw at him.

They never push back. Every idea is a good one, every plan is solid, every decision gets agreement. Hell, they may even laugh at all your jokes if they're over the top.

Now think about the last time that person told you one of your ideas was good.

Did you believe them? Like, really believe them?

Of course not. You knew what they were going to say before they even did. Their agreement tells you nothing, and you started discounting a long time ago.

Now flip it around. Think about the person whose opinion you'd actually pay for. A mentor, an advisor, or the one person you call before you do something big.

Is that person’s advice valuable because he tells you you're right about everything?

Chances are, no.

It’s valuable because it isn’t automatic agreement. When that person says a plan is solid, you can take it to the bank — because you've watched him tell you when a plan was garbage, too.

A lot of salespeople have become the first guy to their buyers. And they got there doing something that feels like offering good service, all the while letting it cost them deals.

After all, people buy from people they know, like, and trust. So be the most "likable" person in the room and you'll win the deal, right?

Go back to that person from the top of this email.

Do you like them? Probably, yeah. They're pleasant. Easy to be around. Nothing about them is hard.

Would you leave your wallet on the table with them? Sure. They're not going to steal from you or rip you off. So, you "trust" them in that sense.

Would you make a $500,000 decision based on their recommendation?

Not a chance.

Because there are two completely different things riding on the word trust, and a lot of sellers only build one of them.

The first is character. You won't rip me off, you'll do what you said you'd do, my money is safe with you. That's important, valuable, and necessary.

The second is judgment. Your read on my situation is worth more than my own read on it. And that's the one that moves deals, and being likable does nothing for it.

Your yes-man has all the character trust in the world and zero judgment trust. It's exactly why his opinion is worthless to you.

That's why the traditional take on "know like trust" and "people buy from people they like" is incomplete.

They "know" you if you're talking to them. Check.

They can "like" you inside ten minutes of banter and pleasantries.

But trust? It's earned. Hard to establish, easy to lose.

And you can have the first two without the last.

Most sellers chase likability anyway, and they come by it honestly. They're running a model they picked up somewhere in customer service.

Find out what the customer wants. Give it to him. Be responsive, be flexible, be easy to work with. Do that consistently and you've done your job.

But that's customer service. Sales pays significantly more than customer service, and it isn't because the hours are longer. Earning the kind of trust that leads buyers into taking your recommendation on important decisions is hard.

And I'm not talking about order taking from inbound opportunities and pre-sold referrals.

When somebody shows up knowing exactly what they need, budget approved, and ready to sign? Take the order. That happens.

But it doesn't happen enough to create the kind of growth you're probably looking for (you're here for Repeatable Revenue, right?). And it's not where salespeople earn their keep.

The commission is for this:

I told a seller on my team last week that the most important thing she can do is help people make decisions that are in their best interest.

Do that consistently and you'll close deals. You'll also send away some people you can't help. That's the job of sales.

When I'm watching a prospect make a decision in real time that I know is going to burn him, like sticking with a horrible service provider that's leaving them out to dry, I've got an obligation to correct it.

To challenge it respectfully. To coach him on how that decision will play out. To ask the right questions that lead him to a better outcome.

In other words, I've got an obligation to sell him. I'm literally letting him down if I don't. Because I'm allowing him to make a decision that is going to lead to him being worse off.

It's about as close as sales gets to a fiduciary duty.

Now go back to those four things the commission is for. Every one of them requires the buyer to accept it from you. Nobody takes correction from someone whose judgment they've already learned to discount.

Take an owner deciding between hiring an internal IT person at $50,000 and outsourcing. His plan is to hire the guy and buy support on top of him.

Nobody's walked him through what he's actually buying:

For all intents and purposes, it's a bad decision. And letting him make it without respectfully, and artfully, making him aware of the consequences is wrong. At least in my book.

You actually serve this prospect by selling. You are letting them down if you don't.

But too many sellers are reluctant to come across as "pushy" or "salesy" and end up agreeable rather than helpful.

So they never raise it at all. Not because they don't know the math — plenty of them could recite that entire list in their sleep. They decide somewhere in the moment that pointing it out isn't their place. They take the requirements, thank him for his time, and go build a proposal around a plan they already know is broken.

That's the most common version by a mile.

The next one at least looks like the seller did his job. He raises it. Sort of:

"I mean, you could definitely go that route, a lot of people do. I just, you know, sometimes what we see is it ends up being a little more than folks expect. But either way, we can work with whatever you decide."

Nobody changes a $75,000 decision because of that. The seller got to feel like he raised it. The buyer heard permission to proceed.

And then there's the version where he says it clearly, with conviction, and it still bounces off — because of everything that came before it. If the buyer's already got him filed as the guy who agrees with everything, that breakdown doesn’t carry the credibility and respect to be heard.

Same root cause coming out in three different ways.

And who ends up winning? The prospect doesn't. The seller doesn't. The seller does end up being "liked" as their deal fades and the buyer marches towards six months of frustration and wasted money.

Telling him the truth is what earns the second kind of trust. And it may even cost you a little likability in the short-run.

None of this starts at the proposal or actual close.

I reviewed a call recently where the opener went: we're just trying to make contact and let you know who we are… just kinda chat and see if you might have any questions… see if we might be able to partner on any projects going forward.

Just, kinda, might. Any one of them is nothing. Everybody hedges. But they cluster, the tonality matches, and forty seconds in you've got a grown professional asking permission to exist.

Years ago I worked with a group of subcontractors who lived off work handed down by general contractors. Their whole sales process was calling the GC and asking, "Hey, what have you got? Anything we can help with?"

That question comes from one place. We're beneath you, and we need you to feed us.

Sprinkle in some people-pleasing and a habit of agreeing with everything, and you've lost all the trust it takes to be an advisor who can coach, challenge, and lead buyers into making better decisions when it's in their best interest.

Adios,

Ray

P.S. — Quick gut check on your last three stalled deals. Did you ever tell any of those buyers something they didn't want to hear? If you can't remember doing it, that's probably why they stalled.