The Talent Initiative

I started working in the 1990s, just after the whole “greed is good” era. Back then, a lot of people still believed the myth that the big names were financial masterminds. Then the stories caught up with them. Alan Bond. Christopher Skase. It turned out the legend didn’t match the reality. (Google them kids)

But even after that, there was still a strange certainty about sales. The rules felt simple. You schmoozed your clients. You took them out. Long lunches that turned into nights. Plenty of booze. Plenty of backslapping. I’ve even heard stories of people trying to claim expenses from strip clubs, like it was just part of doing business.

Fast forward to now. I’m running my own business, and someone asked me recently about entertaining clients. It’s a fair question. It’s also one that makes you stop and think.

The old model: entertainment as a shortcut

The old-school approach treated entertainment like a shortcut to trust. If you could get someone out for a big lunch, keep the drinks flowing, and make them feel looked after, you were “doing sales”.

Sometimes it worked. Not because the work was better, but because the relationship was social. The deal happened in the gaps between the conversation.

The problem is, that kind of relationship can be fragile. If the bond is built on alcohol, status, or who can shout the next round, it’s not really a business relationship. It’s a social arrangement.

And when you’re working for yourself, you feel the cost of that model more sharply. Not just the money, but the time, the energy, and the question in the back of your mind.

Do I want a client who only talks to me because we get drunk together?

That’s the question I keep coming back to.

I’ve been lucky to build a strong network over a long time. Most of my best relationships are based on trust, delivery, and straight conversations. They’re not based on who can stay out the latest.

So when someone asks, “Do you entertain clients?” my honest answer is: I’ll catch up for a coffee, a lunch, or a proper conversation any day. But I’m not interested in trying to buy loyalty.

If the only way I can keep a client close is by getting them drunk, that’s not a client relationship. That’s a liability.

What actually builds trust now

The world has changed, and in a lot of ways, for the better.

Today, the best client relationships are built on a few simple things:

• Reliability: doing what you say you’ll do, every time
• Clarity: telling the truth about timelines, market realities, and what’s possible
• Respect: for people’s time, budgets, and internal politics
• Consistency: regular updates, no disappearing act, no surprises
• Outcomes: delivering results that make the client look good internally

None of that requires a boozy lunch.

Entertainment still has a place, but it’s not the point

I’m not anti-social. I’m not saying you should never take a client out. Shared experiences can strengthen relationships.

But the intent matters.

If you’re catching up to celebrate a win, to say thanks, or to deepen a relationship that’s already built on trust, great.

If you’re doing it because you think it’s the only way to get access, or because you’re worried the relationship can’t stand on its own, that’s a red flag.

The solo operator lens

When you work for yourself, you don’t have a corporate expense account to hide behind. Every dollar and every hour has an opportunity cost.

So I’ve started thinking about client entertainment in a simpler way:

• Does this strengthen a relationship that’s already real?
• Does it align with how I want to do business?
• Would I still be happy with this client if there were no lunches involved?

If the answer is yes, I’ll happily make the time.

If the answer is no, I’d rather put that energy into doing great work and building relationships the slow, boring, reliable way.

A better question to ask

Instead of “Should I entertain clients?” I think the better question is:

What kind of relationships do I want to build, and what do I want them to be built on?

Because the clients worth having don’t need to be bought. They need to be supported, challenged when required, and delivered for.

And if that means fewer long lunches and more straight conversations, I’m okay with that.

If you’ve got a view on this, I’d love to hear it. The sales world has changed a lot since the 90s, and I’m genuinely curious what people think still works, and what should stay in the past.