A man who likes to put a timeframe on targets, Sheepshanks' 'five-year plan' as Blues chairman, outlined in 1995, ultimately came to fruition when Ipswich secured promotion to the Premier League in 2000.
After selling the Blues to Marcus Evans in 2009, he went on to oversee the development and opening of the FA's National Football Centre in Burton. And, in 2012, when St George's Park opened, he proclaimed that the long-term target was for the Three Lions to end their long wait for a major trophy by 2026.
England face Norway in a World Cup quarter-final tonight following on from last weekend's spirited victory against Mexico. (Image: PA)
With Thomas Tuchel's men facing Norway in a World Cup quarter-final in Miami tonight (10pm), Sheepshanks said: "The number one mantra of mine is to begin with the end in mind. Because if you don't know where you're going, how are you going to get there?
"I chaired the England sub board until April last year and my last two meetings were with Thomas Tuchel. I gave him the floor say a few words about his approach and what he hoped to achieve. He thanked me and then told everybody, ‘I see my role as very simple. I'm here to put a second star on the shirt’.
"It's so precise, isn't it? And concise. Everybody can get it. It conjures up a picture in your mind of that extra star on the badge. You have to be clear about what you're trying to achieve. And you’ve got to say it in a way that captures the imagination."
The 73-year-old, who is currently undergoing chemotherapy following bowel cancer surgery, has a new book of memoirs out - Man on a Mission: The Agony and the Ecstasy of a Life in Football.
On the subject of England, he continues: "I was very lucky to work with Gareth Southgate, who was kind enough to put a comment on the front of the book. I hold him in enormous esteem and I just want to say that what was achieved under his watch is a very big part of this.
David Sheepshanks has hailed the impact of England manager Thomas Tuchel (right) and his assistant Anthony Barry. (Image: PA)
"But Thomas Tuchel and his coach, Anthony Barry, are a phenomenal double act. Thomas is one of the most successful managers ever, so credit to Mark Bullingham and John McDermott at The FA for getting him.
"Thomas is very driven. He has an infectious passion. He's Germanic, but he's got a lot of Anglophile qualities, I would say. He has an acuity, a sharpness of mind, which I've rarely seen in people in this game.
"Mexico was one of the most exciting England games I've ever seen. Now that we're playing Norway, I think the temptation is everybody's going to say this game will be easy. But they have a certain Mr Haaland and they showed how good they were by knocking out Brazil. Nevertheless, I think we've got a hell of a chance of getting to the final and a hell of a chance of winning it.
"Why shouldn't we win it? I think the Mexico game will have shown the players what they can do in adversity in the most hostile of environments. They will take immense self-belief from that."
David Sheepshanks was a major driving force behind the development of St George's Park. (Image: Nick Potts)
He adds: "Thomas Tuchel has been under the cosh for not taking certain players to America. But I will take a very educated guess that he's chosen his squad on the basis of who is going to interact best over six weeks.
"Yes, it’s very hard on some of those who got left behind - people like Harry Maguire, who have done great things for England - but I’m convinced he chose the ones that he thought would bring the right chemistry.
"It looks like a group that really together and that's so important."
St George's Park became the home for English football in 2012. (Image: PA)
Reflecting on his St George's Park legacy, Sheepshanks adds: “Buildings don't win anything, but SGP was built as a home for England when we didn't have one before. It’s a place where players of different age groups, coaches of all age groups, can come together, learn from each other and create a real catalytic effect on Team England.
"I am really proud of it because we spent three years researching it, me going all over Europe, all over the world, looking at different places with the architect and consulting people. It’s stood the test of time and hopefully will do for more decades to come.
"I'm deeply, deeply proud and loving of St George's Park and everything it stands for."
Man on a Mission: The Agony and the Ecstasy of a Life in Football is available to buy now.