Manager in his first season says Stevenage have taken a massive risk but the 49-year-old is confident he can turn around the club’s fortunes

The first thing that stands out about Teddy Sheringham as he strides into his office at Stevenage’s training ground is he looks as fit and wiry as ever, even though he turns 50 in April. He offers a firm handshake, flashes a smile and swings his feet on to his neat and tidy desk. He seems at ease, comfortable in his new surroundings. But lingering in the background, behind Sheringham’s easy-going confidence, lies the sense he may not be here for long if he cannot steer Stevenage away from the lower reaches of League Two soon.

Sheringham is a man in a hurry. He has entered management late after spending a few years on the poker circuit. Aside from his spell coaching West Ham United’s strikers last season, he lacks experience and he puffs out his cheeks when he thinks about the opportunity Stevenage’s chairman, Phil Wallace, has given him.

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“It’s a massive risk for him,” Sheringham says. “Hopefully it comes off. One of my family did actually say: ‘why don’t you try and get a job at a higher level? Because if you don’t do it right at Stevenage, where would you go from there?’ You can understand that theory; that if it doesn’t work here, then a Championship team or a League One team’s not going to take me. It was something I thought about. But when I spoke to the chairman and came here and looked around at the building and the pitches, what a fantastic place to learn my trade.”

He knows his name will not win him matches. Sheringham had a wonderful playing career – the club say nothing should be read into him registering as a player this week – and as Stevenage prepare to host Gillingham in the first round of the FA Cup on Saturday afternoon, the mind turns back to him replacing Roy Keane in the ninth minute of the 1999 final and scoring Manchester United’s opener against Newcastle United two minutes later. He scored a rather important equaliser against Bayern Munich on a balmy night in Barcelona four days later.

Yet great players do not necessarily make great managers. Gillingham are managed by Justin Edinburgh, a former team-mate of Sheringham at Tottenham, and are third in League One, while Stevenage are 20th in League Two, five points above the teams in the relegation zone. Play-off semi-finalists last season, they were thrashed 5-1 by Oxford United last weekend, finishing the game with nine men.

Stevenage’s rocky start is the elephant in the room. “That’s the beauty of being involved at this level of the Football League,” Sheringham says. “If I’d have had this start in the Premier League or the Championship, I probably would have lost my job.”

Wallace has a reputation as a sensible owner and when Stevenage made their offer, Sheringham spoke to Sam Allardyce, his manager at West Ham last year. “He knew how sound financially the club was,” Sheringham says. “He knew all about the chairman, he knew all about the set-up. He said it couldn’t be better.”

There is a feeling Stevenage’s players are adjusting to a new style after the departure of Graham Westley, who spent eight of the past 12 years with the club. Stevenage have often started games superbly, only to fade in the second half.

“I’m getting to know the players and individuals,” Sheringham says. “They’re getting to know me. It takes a little while for any new manager to come in, I would presume, let alone a first-time manager who’s not even sure about himself. About what he would and wouldn’t do at certain times, and they’re reacting to that. All right, I’m a big name in football, but a first-time manager.”

He finds he is waking early, his mind racing as he tries to work out his Saturday afternoon strategy, and he has discovered his managers were not wrong to warn him about having to be a psychologist when players are going through tough times. It was said the first yard was in Sheringham’s head when he was playing. That awareness could take him far, but at the moment it can feel like someone has jammed the fast-forward button and he is having to race at breakneck speed to absorb everything about the profession Arsène Wenger has jokingly called hell.

Sheringham may be a novice but he is a young manager only in terms of mileage. His peers have way more hours on the clock. Edinburgh is 45 and he has been managing in the lower leagues for years, growing gradually, building his knowledge at a steady pace. Yet Sheringham argues his fast-tracked route was necessary. He retired when he was 42 and needed to relax away from football. Playing poker allowed him to recharge mentally.

“Some people will have their own team for a couple of years as a youth team or reserve team manager, or they’re an assistant manager,” he says. “If I did all that, it takes me into 56, 57 and then you have a real short shelf life. Coming in now, jumping in two-footed, it’s a massive leap into League Two. I’d never managed anyone before – only myself. Now here I am, managing a football club and managing people. Everyone is under my leadership and it’s a massive change for me.”

Sheringham was lucky to play for some top managers. He benefited from the discipline of George Graham and John Docherty when he was a youngster at Millwall in the 80s. He speaks fondly of Bruce Rioch, Alan Pardew and Glenn Hoddle. He played for Brian Clough at Nottingham Forest, he loved turning out for England under the adventurous Terry Venables at Euro 96 – he won 51 caps – and he saw how Sir Alex Ferguson ruled United.

Facebook Twitter Pinterest Teddy Sheringham is trying to learn froim all the managers he has played under in his new role at Stevenage. Photograph: Tom Jenkins for the Guardian

When he was older, Harry Redknapp’s willingness to let him skip training at Portsmouth was invaluable. “Before I’ve even mentioned it to him, he’s seen it,” he says. “All of a sudden I’m perked up for Saturday and raring to go.”

Sheringham does not want to model himself on his managers but he does find himself unwittingly borrowing some of their techniques at times. Poker, meanwhile, has given him the ability to read people.

“As a poker player you have to study players,” he says. “People’s movements and their psyche, what they’re doing. What do they do when they’re bluffing? What do they do when they’re telling the truth? How do they speak? That’s little things you can take in as a football manager. It’s like: ‘Cheeky fucker, I know you’re lying.’”

He tells a story about how a player might tweak something in training on Tuesday, have a day off on Wednesday and then claim he suffered the injury on Thursday morning, just to avoid having treatment on a rest day. “I did the same as a player,” Sheringham says. “Do you think I’m fucking stupid?”

Who knows what goes on inside someone else’s head? “They might be thinking: ‘This fella’s the bollocks’, or they might be thinking: ‘Who are you kidding, he’s absolute rubbish,’” Sheringham says. “But I don’t know, do I?” The proof will be visible on the pitch in the end.