Difficult Conversations

On May 10, 2006, Gareth Southgate captained Middlesbrough in the UEFA Cup Final.

On June 7th, 2006, he was announced as Middlesbrough’s new manager.

He didn’t have any coaching experience. He didn’t have a UEFA Pro License. In fact, he didn’t even have a UEFA A license.

And now he’d be in charge of a mid-table Premier League team who’d just made an FA Cup semi final and a European cup final.

It’s quite the origin story.

Despite being a captain throughout his playing career and being quite clear on what he valued as a leader, Southgate found parts of the job especially challenging.

“Here was my problem: I didn’t know what I didn’t know,” Southgate writes in his memoir. He’d played under some of the game’s top coaches like Venables, Eriksson, Keegan, Hoddle, and McClaren, but it turns out Southgate massively over-estimated how much he’d absorbed from observing them.

“From my first day in charge at Middlesbrough, however, it became abundantly clear to me that being a footballer had only exposed me to a fraction of what a manager has to get up to in his working day,” he writes. “The job, it turned out, was multi-disciplinary to a degree that I had barely imagined.”

One area that he writes about in detail is how he struggled with the difficult conversations around selection and deselection.

During his second season in charge, Middlesbrough beat Portsmouth without their suspended captain, George Boateng. Wanting to reward the players for an important victory, Southgate decided to keep his team the same for the next fixture. Despite being club captain, Boateng had lost his spot in the starting lineup.

After consulting his staff, Southgate decided not to address it with Boateng personally, and proceeded to read out the lineup before the final training session. Boateng was fuming. Southgate had created an unnecessary problem, one that would ripple through the squad and affect his personal relationship with Boateng - albeit temporarily. “All because of a conversation I didn’t have,” Southgate writes regretfully.

“I’d always hated having difficult conversations, and I’d always stepped around them when I could. Avoid confrontation, maintain good relations, be the nice guy, stay popular,” he writes. “That had basically been my way of going about things. But that wasn’t going to work, I quickly realized, as a manager. The difficult conversations were now officially on me.”

The Process

The Boateng incident shaped Southgate, and changed how he went about communicating with his players.

“It inspired me to ensure that my communication with players was regular, respectful and thought-through,” he says.

And so, as good coaches do, he made a plan. As Southgate’s career developed and his difficult conversations became more consequential — like leaving England players out of major tournaments — this planning would serve him well.

Part 1: Intent

“Every conversation needs a plan of some sort,” Southgate says. And the first part is to identify what type of conversation you’re having.

• Am I delivering bad news?

• Am I trying to explain a decision?

• Am I trying to make a coaching point to challenge the player?

• Am I trying to make sure a player not in the starting team was motivated and ready to play his part from the bench?

“All of this needed to be carefully considered and strategized in advance,” Southgate says. “I quickly learned that if I turned up for difficult conversations underprepared and without absolute clarity on the conversation’s desired outcome, then I risked coming across as complacent and detached, and was practically bound to make an already bad situation worse.”

Part 2: Message

Once you know what type of difficult conversation you’re having, you can start to script what you’re going to say.

• What do I want to say?

• What do I need to say?

• How is this likely to land?

• How do I want the other person to feel at the end of the meeting?

• What might I need to avoid saying that might cause a bigger issue down the line because I’ve set a precedent or given an explanation that could be used against me?

And as these conversations are never one-way, Southgate would take it another step and began sketching out the dialogue. He writes: “It was so important to me to get it right that I even went as far as writing down the desired flow of the conversation in advance, and mentally rehearsing it in my head, before delivering it to the recipient.”

I’ve not met a coach who doesn’t hate selection and deselection. In is a topic that appears in almost all of the 100+ autobiographies I’ve read for this project. But it being a crappy part of the job doesn’t mean we shouldn’t have a plan and aim to become more skillful at having difficult conversations.

Cody’s Notes

• While this post has focused on selection/deselection, Southgate’s framework is useful for any difficult conversations that appear in the coaching taskscape — of which there are many.

• Having a plan doesn’t mean you’ll even get to have the conversation in the forum that you intend (in-person, for instance). But it’s a good starting point.

• Having a plan doesn’t mean that the conversation is going to go the way you think (a player may lose their cool, for instance), but it’s a good starting point.

• Having a plan doesn’t mean that you’re going to deliver your message in the way that you intend (you may be tired, for instance). But it’s a good starting point.

• One of the key discoveries I’ve made with my craft framework is that coaches need to do a better job at connecting skill to the domain in which that skill plays out. We say things like ‘good communication’ or ‘take risks’ or ‘be brave’ but it’s crucial to understand where those actions are taking place. Am I taking risks with my budget spreadsheet (Organizational Craft) or with my game model (Game Craft). Because the difference matters. What I appreciate about Southgate’s approach to difficult conversations is that it starts to takes this context into account.

• Southgate’s final consideration in Part 2 — where else might this show up or come back to haunt me — is another major discovery from my craft framework. Since all four domains are overlapping and interdependent, you must factor in the impact of your actions on all the other domains, and anticipate the timescale as well. Doing this in advance can help you make smarter decisions.