Steve Bruce sometimes looks back at his younger self and cringes. If the memories of playing centre-half for Manchester United rightly remain a source of immense pride, the recollections of his first, rather awkward managerial steps provoke embarrassment.

Hull City's manager was in his late 30s when he took the helm at Bramall Lane for a season in the division now known as the Championship. As he prepares to face Sheffield United in Sunday's FA Cup semi-final at Wembley, Bruce has been examining the past through a 53-year-old's eyes.

"When I was younger I was a nightmare," he said. "I let people down. I resigned from Sheffield United because things were promised to me that weren't forthcoming. I let people down when I was younger, certainly in management. Simon Jordan comes rushing back to me."

Jordan was the owner of Crystal Palace to whom Bruce tendered his resignation after a mere matter of weeks in charge at Selhurst Park to defect to Birmingham City. In three volatile years between 1998 and 2001 he managed Sheffield United, Huddersfield Town, Wigan Athletic and Palace before finding stability at Birmingham and, later, Wigan again.

"I was a little bit headstrong; when you're younger, you want to take on the world," Bruce said. "At first you try to prove yourself to be the boss.

"I don't think I lose my temper as often as I used to now but, back then, I needed someone with grey hair, with experience, to help me, to tell me certain things didn't matter, didn't make a difference. Today I'm the one with grey hair but I was going through a power battle at Sheffield United in the days when I didn't even know what a power battle was. I got upset when things were not like it said on the tin."

It did not help that, during his year in South Yorkshire Bruce worked under several different chief executives. "I don't think I was a control freak. I just couldn't get my head around things. When I joined Sheffield United I was told I had £5m to spend, then when I went to see the chief executive he told me if I didn't raise £350,000 no one was getting paid.

"I think I had six chief execs in one year. They were difficult times but I'll be eternally grateful to them because the one thing it did was give me a chance in management. It put me on a learning curve, very quickly."

Bruce added a quirky episode to Sheffield United's history when he famously marched his players off the pitch during an FA Cup fifth-round tie against Arsenal at Highbury. United had kicked the ball out of play to allow treatment to an injured player but rather than return the ball to them Kanu, making his debut, passed to Marc Overmars who scored the "winner".

An outraged Bruce led United off for six minutes. "I'd only been managing six months. I was nearly arrested. A police officer came in and said: 'If you don't take the team back out on the pitch, you'll end up in the nick.'" Arsène Wenger offered Hull a re-match, also at Highbury, which once again was won 2-1 by Arsenal.

Fifteen years on Hull's Cup run allied to the virtual certainty of Premier League survival has prompted fans to produce Bruce face masks. "I just hope the kids aren't frightened by these masks," he said. "I don't mind, though – at my last club [Sunderland] they threw darts at me."

Now he is daring to dream of the route into the Europa League which an FA Cup final against Arsenal would almost certainly guarantee. "We'll all go on easyJet," he said. "It shows you how far the club's come. Europe would be a hurdle for a club like ours but it would be quite remarkable. Hull in Europe would be terrific. Of course we'd enjoy it."

Winning the FA Cup would be even better. "I've been fortunate enough to win the FA Cup as a player but it's taken me 15 years as a manager to get to a semi-final. But we've got to get there and win the thing. Until you do it's not an achievement. If you don't win, Wembley's a horrible place."