The importance of being Elvis: Dundee boss Steven Pressley opens up on his weaknesses and mistakes as he finally finds comfort in the dugout

In a meeting room inside Dundee’s Gardyne training base, Steven Pressley is recalling his past self with a grimace.

Our conversation has taken us back to his press conferences in his first managerial posting with Falkirk 17 seasons ago.

Pressley’s shtick back then was to read pre-prepared statements from a notebook he carried around.

His bold proclamations were manna from heaven for the members of the fourth estate. Not so much for senior members of the Scottish managerial fraternity who just couldn’t take to this new kid on the block.

‘I had my armour on all the time,’ he now confesses. ‘I always wanted to pretend I was something I really wasn’t.

‘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.’

As skipper of Hearts, Pressley lifted the Scottish Cup and was a founder member of the Riccarton Three, who stood up to the madness of Vladimir Romanov by holding an impromptu media conference.

He always seemed destined to remain in the game once his boots were on a peg. Yet his first role as a coach for Scotland manager George Burley while his Celtic playing contract wound down proved a lesson in the need to look before you leap.

‘It came too soon,’ he admitted of the20-month period which encompassed the infamous Boozegate episode. ‘It was a bad decision, I think I didn’t realise how it would be met.

‘Do you know what’s interesting about this? I see this in the English national team just now, as well as the Scottish, and there seems to be a much better feeling around the squads now.

‘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.

‘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.’

Pressley jumped just before Burley was pushed, first assisting Eddie May at Falkirk then taking over in February 2010.

Pressley admits it was ‘a bad decision’ to join George Burley’s Scotland coaching team

His first act was to read from that notebook and emphatically tell the world that the Bairns would not be relegated. But they were. And there was to be no fast-track return to the top flight either.

Yet he still did enough to catch the eye of Coventry City, who he played for in between turning out for Rangers and Dundee United.

It was to prove the ultimate hospital pass. Two weeks after being appointed in 2013, the Sky Blues went into administration.

Despite the club being homeless for 13 months — they played in Northampton — and suffering successive 10-point penalties, Pressley kept them in League One.

‘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.’

It ended after a humbling in the FA Cup by non-league Worcester. Pressley worked briefly as a scout for Southampton before unremarkable spells in charge of Fleetwood Town, Cypriot side Pafos and Carlisle United.

When he moved to Brentford in 2021 to take up a role as Head of Individual Development, it was assumed that his managing days were at an end. He certainly believed so.

‘It probably wasn’t the job that I signed up for, for a number of reasons,’ he explained. ‘But I worked a lot with the young players within the first team group, and then the transitional players from the B team to the first team.

‘So, I worked closely with all the coaches and with Thomas (Frank), but my main job was to support and help develop the young players in all aspects of their development.

‘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.

Pressley suffered relegation from the top flight during his time in charge at Falkirk

‘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.

‘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.’

It was not intended as a sabbatical from management. Although he was always set on leaving Brentford a year ago, Pressley didn’t go seeking another position in the dug-out.

You could well understand his reluctance to alter his course. Given that 15 men had already been Dundee’s manager this century (including a second and third spell for Jocky Scott), Dens Park has hardly been a model of stability.

‘I genuinely wasn’t really seeking a head coach’s role,’ he explained. ‘I’d just finished my degree at the university around strategic leadership and I was more probably drawn to the technical sport director’s role.

‘Gordon (Strachan, Dundee’s technical director) phoned me about this position. If it wasn’t Gordon that was here, I wouldn’t have come.’

You probably could have named your price on him still being in situ at Christmas after his opening gambit.

All that stuff about ‘if you’re looking for a manager with history of winning titles, then I’m not your man’, had the Dark Blues supporters in uproar.

He managed Carlisle United before becoming Head of Individual Development at Brentford

Pressley regrets plenty of statements that he read from his little book back in that day. But not that one.

‘What I said was my history didn’t suggest that I was a guy to win trophies,’ he stressed. ‘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.

‘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.’

Without question, though, he is a better manager than the one that first burst onto the Scottish scene. Aside from his tactical knowledge, there’s an emotional intelligence to him which players evidently relate to.

‘I want this to be a safe environment, one where our players come in and be themselves,’ he explained. ‘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.’

Pressley has won over many of his doubters at Dundee after getting off to a shaky start

He hasn’t yet lifted a trophy, but he has won the battle for hearts and minds in the City of Discovery. Shaped by experience, he’s shown himself to be a manager of real substance.

Dundee safely finished eighth last season. Despite losing a raft of star players including Cam Congreve and Luke Graham, they’ve started this campaign impressively, easing through the League Cup group, pushing Celtic all the way and taking Aberdeen to the cleaners last week. The football is both eye-catching and effective.

As they prepare to face the Dons again today at Pittodrie in the cup, there’s a sense of optimism around the club.

With the outstanding documents submitted to the city council, approval for planning permission for the new stadium at Camperdown Park may finally be just around the corner.

While it remains to be seen if Pressley is around to witness that historic switching, moving into his own apartment with his wife in the city on Sunday feels significant.

‘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,’ he 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.’