Wining and dining prospects has always felt a bit cringe to me.
It might be my introverted nature (yes, salespeople can be introverts), but I don't think buyers want to spend two hours being wined and dined by someone with an ulterior motive, while everyone around the table politely pretends otherwise.
The salesperson thinks they're building a relationship.
But your buyer knows they're trying to build a deal.
A dinner becomes uncomfortable when the seller assumes that paying the bill buys them access, attention or affection.
That doesn't mean I don't value more human contact, where everyone can drop their guard a little.
I just have a very specific strategy for it.
I call it Three Dinners.
Each dinner happens at a different point in the sales process. Each has a different guest list and a completely different purpose.
The first dinner belongs to their peers
Early in the relationship, I'll create a dinner for the buyer to meet people like them.
Their peers. Other senior people from their industry. People wrestling with similar problems, operating in similar environments and making similarly difficult decisions.
I set the stage, shut the fuck up, let them hang out with their peers, and quietly pay the bill at the end.
I want them to remember having a great night, not to be able to recite back the top 5 reasons they should work with me because I was pitching them all night.
I might be in the room as the host. I might run a roundtable or keep the conversation moving. But I'm not supposed to be the most interesting person at the table.
If I am, I've got it wrong.
Before I've asked the buyer for anything, I've done something useful for them.
The second dinner signals seriousness
The second dinner comes deeper into the sales process.
By this point, the opportunity is real. The buyer is investing time in us, involving more people and deciding whether they're prepared to stake some of their own credibility on the relationship.
Now the guest list changes.
I bring my founder or senior execs to the table.
In an enterprise sale, every customer should matter enough to get the attention of the people at the top.
Bringing our top brass to the table makes that visible. It says: you're important. We care about your success. If you need us, the senior people won't be hard to find.
That matters in an enterprise sale.
Buyers aren't only assessing whether your product works. They're deciding whether they trust the people they may need when something goes wrong.
Keep the title theatre out of it. This should be a genuine conversation between senior people who understand the responsibility that comes with the decision.
The buyer should leave feeling valued, appreciated and confident that the relationship has support at the highest level.
The third dinner is earned
The third dinner happens after the contract is signed.
This one is about me and the buyer, because at that point I've genuinely earned their trust.
By the time the contract is signed, we've probably spent several months together.
Making the time to sit down with them isn't an attempt to influence. It's an opportunity to show some gratitude for the journey we've been on together.
We've sat through workshops, answered difficult questions, disagreed over terms, solved problems and occasionally tested each other's patience.
There's some scar tissue, and goodwill. And I want to focus on the goodwill as we begin the delivery.
The buyer no longer has to wonder whether every question I ask is a sales technique designed to move them into the next CRM stage.
I've earned the right to become what I call a professional friend.
That doesn't mean the commercial relationship disappears. It means there's enough trust behind it for us to spend time together without pretending there isn't a relationship at all.
I can thank them properly. We can talk honestly about how things are going. I can continue showing my appreciation for something we've both spent months building.
Their signature hasn't bought that dinner.
The outcome we both worked for has.
If you're using dinner to try to create trust, you've got the sequence backwards.
The first two dinners earn you the third.