Dundee manager Steven Pressley has reflected on his past managerial mistakes and personal growth during an interview at the club's Gardyne training base.
Pressley, who recently signed a new contract at Dens Park after leading Dundee to an eighth place finish in the Scottish Premiership last season, spoke candidly about his evolution from an aggressive coaching style to building an environment focused on honesty and emotional intelligence.
The manager opened up as his side prepare to face Aberdeen at Pittodrie in the Scottish League Cup on Saturday, having defeated the Dons in league action last week.
Despite losing star players including Cam Congreve and Luke Graham in the summer, Dundee have made an impressive start to the new campaign, easing through their League Cup group and pushing champions Celtic all the way in the league.
Off the pitch, optimism is growing across the City of Discovery as outstanding documents have been submitted to the city council for planning permission for a proposed new stadium at Camperdown Park.
Pressley disclosed that he and his wife will move into their own apartment in Dundee on Sunday, signaling a deepening commitment to the club where 15 different managers have taken charge this century, including multiple spells for Jocky Scott.
"In the times that I'm out and about, there's no doubt there's a greater warmth to me from the people of Dundee," Pressley said. "I'm still not very good at this, but I'm trying to enjoy when you perform well, or you're going through a good period. The bit in me that I struggle with is what's round the corner and that's not a good thing."
Early managerial struggles at Falkirk
Reflecting on his entry into management 17 seasons ago at Falkirk, Pressley recalled carrying a notebook to press conferences and reading pre-prepared statements that alienated senior Scottish managers.
"I had my armour on all the time," Pressley confessed. "I always wanted to pretend I was something I really wasn't."
He explained how his mindset had been shaped by his playing career: "You've got to remember the period that I came through as a player was one where management was very different. It was quite aggressive. As a player, you couldn't show any weakness, especially if you were the captain. I was shaped by that."
Pressley initially served as assistant to Eddie May at Falkirk before taking over as head coach in February 2010. His first act was reading from his notebook to promise that the Bairns would not be relegated from the Scottish Premier League, but the club suffered relegation and failed to secure an immediate return to the top flight.
Scotland coaching role and national team rivalries
Before taking the Falkirk job, Pressley spent 20 months as a coach for the Scotland national team under manager George Burley while winding down his playing contract at Celtic.
That period included the infamous Boozegate incident involving national team players. Pressley admitted that taking the role was a mistake, saying: "It came too soon. It was a bad decision, I think I didn't realise how it would be met."
He noted a stark contrast between current international setups and the club rivalries that divided Scottish squads during his era: "There isn't that resentment, that rivalry that existed during my period, where it was Celtic, Rangers, Hearts and Hibs players. I wouldn't say there was a lot of togetherness between those groups of players. So, it was quite a difficult environment."
Reflecting on combining his playing duties at Celtic with coaching Scotland, Pressley added: "Being a Celtic player and a coach wasn't a very smart move and, in time, I regretted it. For a long period, I wanted to leave the position, but I would like to think of myself as a very loyal guy, and I didn't want to let George down. In hindsight, I probably would have done him a favour by leaving." He eventually departed just before Burley was dismissed.
Coventry City administration and lower league journey
As a player, the former defender captained Heart of Midlothian to Scottish Cup victory and was a founding member of the Riccarton Three alongside team-mates who held an impromptu media conference to oppose owner Vladimir Romanov.
After leaving Falkirk, Pressley was appointed manager of English club Coventry City in 2013, having previously played for the club between spells at Rangers and Dundee United.
Just two weeks after his arrival, Coventry went into administration. The Sky Blues were forced to play home matches in Northampton for 13 months while homeless and suffered consecutive 10-point deductions in League One.
Despite the turmoil, Pressley guided Coventry to survival in the third tier. "I learned a lot during that period," he recalled. "One of the things that I try in my management because of that is to stay in my lane and not get involved in other areas of the club that are not my responsibility."
His time at Coventry ended following an FA Cup defeat to non-league side Worcester City. Pressley then briefly worked as a scout for Southampton before managing Fleetwood Town, Cypriot side Pafos, and Carlisle United.
Player development at Brentford and Dundee appointment
In 2021, Pressley joined Brentford as Head of Individual Development, believing his front-line management career was over. Working alongside head coach Thomas Frank and backroom staff, he supported young first-team players and transitional B team players through match analysis, diet, and gym programmes.
"It probably wasn't the job that I signed up for, for a number of reasons," Pressley explained. "Although I worked with them on the grass, I also had to support them through analysis to make sure their diets were correct, they were doing their gym programme, they were getting the adequate amount of games every season. I was able to create really strong bonds with them because I didn't need to leave them out of the team on a Saturday afternoon."
The role altered his perspective on modern players: "It reminded me of just how challenging it is to be a football player. Everybody thinks life of a football player is a great life. It's not. It's a really difficult life. You're exposed to so many challenges, so much vulnerability, people constantly questioning you as an individual. It made me think a lot about how to manage them and how to support and help them."
After completing a university degree in strategic leadership, Pressley planned to pursue a technical sports director role. However, a telephone call from Dundee technical director Gordon Strachan convinced him to return to management. "If it wasn't Gordon that was here, I wouldn't have come," Pressley admitted.
Cultural shift and stadium progress at Dens Park
Pressley initially caused uproar among Dundee supporters during his unveiling by stating: "if you're looking for a manager with history of winning titles, then I'm not your man".
He stands by that statement today: "What I said was my history didn't suggest that I was a guy to win trophies. But I was only speaking the truth. That's one thing I do pride myself on. It's one of the things that I think is really important with the culture we've tried to create here is that honesty and not pretending to be something that you're not."
He added: "I'm very open about my vulnerabilities and the challenges. I don't hide those things, so when I spoke there I did so as a younger player. The older I've got, and the more educated I've become, the more comfortable speaking like that has become. I don't need to try and pretend I'm somebody I'm not. This is not a lie: my big thing in life is to be a better person every day. It's not about being a better manager, not about being a better coach. Every day I read and I write things in that book because I want to be a better person."
Pressley has fostered a safe environment for his squad: "I want this to be a safe environment, one where our players come in and be themselves. They can bring their personality, they can try things, they can try to be a better player, but feel they'll never be shamed for it or be exposed for it. People are people and they're all vulnerable. You see some people and you think he's a really confident guy. Yeah, he might be on the face of it, but underneath it, unless he's a sociopath, he's got the same vulnerabilities as everyone else."
