I spent 4 months convincing the wrong man.

I had constructed what I would call a 'slam dunk' deal. Every single box was ticked. It was just a formality at this point.

Then in two seconds flat the whole deal was struck down, and I was on a damage limitation course.

I had been talking to the head of recruitment about a player I represented. They were looking for a target man striker, and we had a great striker that the head of recruitment loved. He actually couldn't believe that the player would even come to the club, and was overjoyed that the transfer fee and the salary requirements fit their budget. He was referring to my player as the missing piece of the jigsaw. In this game, it's rare you get that level of alignment.

Over the next four months, we went to go and watch the player play together. During that time we negotiated and agreed every element of the deal:

Transfer fee

Salary

Signing bonus

Loyalty bonus

Promotion fee

Release fee

Agent's fee

All the t's were crossed and all the i's were dotted.

And then I got a call that made my stomach drop. The head of recruitment, who had professed to have authority at the club and who I believed, turned out didn't have it at all. In the first conversation with the manager, the manager shut the deal down in two seconds. He didn't like the player nearly as much as the head of recruitment did, and actually had a different target he was going after.

Four months of preparation, down the drain. What made it worse is that I had already told the player about how this deal was going to happen.

That wasn't a mistake in of itself. Your job is to find your player the best deals and to communicate with your player. What I did wrong was not establish the actual level of authority within the club, rather than what the job title on the organisation chart says.

The damage wasn't just the four months. It was the credibility I'd built with my own player over two years, undone in one phone call. That's the secondary cost, and honestly it can be as bad as the financial one.

Telling him was hard. I had to be honest and say that in the end the manager didn't fancy it, so the deal was off. I apologised. I told him that in hindsight I shouldn't have got him excited about it unless it was concrete, and that I normally wouldn't have done that. It just felt like a formality at that point, waiting on the window to open and the two clubs to finalise the fee.

I told him not to worry, that we were at the beginning of the window and we still had time. Luckily I did end up transferring him to a different club later that same window. But it was a huge big speed bump in the journey.

Why this mistake happens

Head of recruitment is often the person who returns your calls. They're accessible and eager to talk. They feel like the decision-maker because they're the one engaging. The real decision-makers are often busier, harder to reach, and deliberately kept at arm's length from the salespeople trying to push their agenda. Inexperienced agents drift toward the person who picks up the phone.

How you fix it

Before you spend serious time at any club, work out who actually signs off on signings. Talk to other agents who've placed players there. Watch the press releases for who is quoted in the transfer announcements. Look at the org chart, but trust the behaviour more than the title.

The bigger principle

This case wasn't a bad negotiation. It was actually a well crafted negotiation, the huge mistake was that it was with the wrong person.

I learned that lesson the hard way in my late twenties, and I've made sure not to repeat it since.

The person who picks up the phone is rarely the person who decides.

If you take one thing into your next negotiation, take that.

A quick story about my course The Sports Business Accelerator before I sign off for the week:

Nick Blain landed the role he wanted in sport four weeks after Cohort #1 ended.

Before that, he'd been doing what most people trying to break into sport are doing right now. Applying. Waiting. Watching the roles go to people with more contacts than him.

He joined The Sports Business Accelerator to do something about it 📈. The sessions are taught from inside the industry. Real deals, real negotiations, the situations they actually happened in. Live Q&As with the Chief Commercial Officer of the Premier League, the world's best sports lawyers, professional athletes. A small group, all working towards the same thing.

4 weeks after the cohort ended, Nick had the job. And so did several others from Cohort #1.