Give, Give, Give. Then Ask.

In my nearly forty years in media, the best salespeople I met never acted like typical salespeople.

They solved problems before getting paid, shared ideas others would have kept private, and made introductions that helped others even if it didn’t benefit them. They gave feedback without being asked (in an additive, not critical way) and always left people better off, whether or not those people became customers.

It took me half my career to realize the irony.

The less they focused on closing deals, the more easily they closed them.

For years, I was one of those people, almost by accident. My phone became a constant source of advice for everyone I’d worked with. Former colleagues reached out for career advice, tips on managing creative teams, guidance on dealing with their bosses, or how to give feedback without upsetting anyone. Producers sent me projects I wasn’t officially working on, always starting with, “Can I just run this by you?” or “Can I pick your brain?” I always said yes.

For a while, I’ll admit, I watched consultants make good money charging for what I gave away as a friend. I saw executives I surreptitiously advised move up the ladder, and I felt envy about both. I’m not bitter, but I can’t pretend I didn’t feel it.

It took me years to see what was really happening, since no one ever talked about the trade. The people who came to me for advice became the executives who later hired me. The producers I helped for free sent me the contracts that built my agency. My advice was my pitch. I was practicing consultative selling before I even knew the term, and it brought me more business than any presentation ever did.

In the end, that envy taught me something more valuable than resentment. It helped me see the system behind generosity, and once you see it, you can use it on purpose.

People don’t buy because you convinced them. They buy because they already trust you, and every helpful thing you do before any money is exchanged builds that trust.

When you make a helpful introduction, spot a pattern quickly because of your experience, give honest feedback on a proposal, offer a free observation, or recommend something that might cost you a deal but helps the other person, you’re doing the same thing each time. You’re making the buyer less uncertain about working with you, because now they know what it’s like. The sale becomes a series of examples, not just a leap of faith.

That’s why the executives who took my calls for years hired me without needing a pitch when they finally had budgets. They didn’t need to evaluate me anymore, they’d already done that over years of free conversations.

When money finally came into the picture, the only thing left to discuss was the scope of work. That’s the unsexy secret, and to be honest, it’s not really a secret. When you finally ask for the business, your prospect shouldn’t be wondering if you’re capable. They should already know.

People often think “give first” means giving everything away, and that misunderstanding can hurt founders. The real point isn’t how much you give, but what you choose to give. ( I get it trust me, I have felt ripped off before too.)

Share proof, but keep your main product.

Proof shows your judgment and usually costs you little. Maybe it’s a quick observation, a helpful introduction, a relevant article, a fast diagnosis, or an honest comment like, “this deck will die in front of your CFO and here’s the slide that kills it.” Proof lets buyers see how you think. The product is what they pay for. The plan, the ongoing advice, an insight or tip they can use, or a bit of coaching after that first observation.

Today, the founders I work with keep showing me new ways to draw this line.

For example, one founder kept sending prospects who weren’t a good fit to a partner agency, then handled the whole transition herself for free. I told her directly, if you’re doing the transition work, you should get the referral fee. The referral was generous, but doing the extra work for free was a loss.

Another founder noticed that his free strategic analysis attracted people who just wanted free advice and never bought anything, so he started charging a small fee for the diagnosis. The tire-kickers disappeared, and serious buyers paid without hesitation. The generosity remained, but now it had a clear boundary.

The best example I saw this year was a studio that took on a pilot project for a big client at a low fee. They used the project to show the client a skill they didn’t even know they needed, coaching a nervous research lead through an important presentation. The demonstration worked. After that, the next project was priced at full value, and we made it clear that the pilot fee was a one-time thing. Generosity opened the door, but discipline decided what happened next.

If you pay attention, the relationship will tell you when it’s time to ask. The questions move on from “Do you think this could work?” to “How would you approach this?” People start sending requests with deadlines, which means they’re relying on you.

When someone comes back a third time with the same problem, it’s clear the free help isn’t enough, and you both know it. If your advice starts getting shared with others in their company, that’s the biggest sign. Your judgment is already at work there. It just isn’t official yet.

When you see those signs, asking for the business feels natural. You’re just saying, “This thing we’ve been doing informally is what I do professionally, and here’s how it works.” No one has ever been upset when I’ve said this, and many have agreed. The friendship usually survives the invoice, much more often than founders expect.

The unspoken trade I relied on during my agency years worked, but it was slow and meant I missed out on some income because I waited too long to ask. Now, I teach the same generous approach, but with a clear ask included. Be generous, but don’t make people guess when it’s time to pay you.

This way of thinking changes everything. Networking turns into making valuable contributions, and those contributions add up. Content becomes a way to give value to many people at once, and every helpful article you share builds trust with people you haven’t even met. Referrals become something you give, not just something you hope for, because the person you refer business to today might help you tomorrow. Even your sales pipeline changes. It becomes a list of relationships at different levels of trust.

The best salespeople don’t try to convince others, they show what they can do. If you’ve been creating value all along, the proposal isn’t when you start selling. It’s just when you explain how to keep doing what you’ve already been doing.

1. Give first.

2. Build trust.

3. Ask for the business when it feels like the natural next step, not right at the start.

The advice here is free. It took me thirty years to learn when to stop giving it away, so I won’t charge you for that lesson either.