Ivan Gazidis loves to talk about process, about journeys, about minutiae, and he was in his element at Emirates Stadium on the day that Unai Emery was unveiled as Arsenal’s new manager.

It was 23 May and the chief executive went into extraordinary detail about how Emery had been chosen to succeed Arsène Wenger. He brought up challenging discussions, long lists, short lists, detailed personal references, outside perspectives and the analysis of “tens of hours of video tape on the three finalists that we eventually narrowed it down to”.

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Gazidis and his recruitment lieutenants, Raúl Sanllehí and Sven Mislintat, would convene for one last powwow. “We spent an entire day discussing among those three [candidates] and, at the end of it, all three of us wrote on a piece of paper – one, two, three – and put them into the middle of the table,” Gazidis said. “And the choices were all one, two, three, the same. Unai was at the top of all of our lists.”

What shone through, as Gazidis spoke in that measured way of his, was the excitement and confidence. Overwhelmingly so. He described himself as “energised” to have Emery at the club.

“We have to work hard, we have to work well together and take this step by step by step,” Gazidis added. “There are so many stories in sport of people who achieve things that were not believed possible at the beginning of the journey because they focused on that process of just getting a little bit better every day.

“I just think that change stimulates the environment and I think it’s going to be very positive. I could not possibly feel better about this appointment. And the feeling that we have between each other – and we’ve spent a lot of time over the last few days together – is that I feel better and better about it by the hour.”

It was in mid-July when the stories first broke about Milan’s interest in hiring Gazidis as their chief executive, although it is now understood that he had told people inside Arsenal a couple of weeks earlier. They were not denied and, on 25 July, Sir Chips Keswick, the chairman, released a statement that acknowledged “the speculation surrounding” Gazidis while adding he had “always been fully committed to taking Arsenal forward”.

Gazidis was confirmed as Milan’s new chief executive on Tuesday. He will leave Arsenal by the end of October and begin work at the Serie A club on 1 December. It took two-and-a-half months for Gazidis to listen to Milan and prevaricate extensively before agreeing to join them, with the saga leading to disgruntlement at Arsenal.

It said much about Gazidis, the contemplator and deep thinker, who considers each decision from every conceivable angle – and takes for ever to do so. But it also shone a light on Arsenal’s weakness at boardroom level. At other clubs Gazidis would have been ordered to make an immediate decision.

The more pertinent time frame was the one between 23 May and the start of July. That was when Gazidis went from Emery project evangelist and participant at “the beginning of the journey” to seeing the end of his role in it. By any reckoning it was a remarkable transformation and raised a clutch of questions, the most obviously relating to the faith he so vociferously proclaimed in Emery and the new structures he had put in place at Arsenal.

Facebook Twitter Pinterest Ivan Gazidis with his successors, head of football Raúl Sanllehí (right) and managing director Vinai Venkatesham. Photograph: Stuart MacFarlane/Arsenal FC via Getty Images

Gazidis was always going to be judged on The Succession, as it became known; the management of Wenger’s easing off the premises and the recalibration of the club thereafter. Gazidis has suggested that with Emery, Sanllehí, Mislintat and others in place, his work was somehow done and it was time for a fresh start. The reality is that his work ought to have been just beginning.

As an aside, a penny for the true thoughts of Emery would be worth the investment. Whenever a person who hires an employee leaves a company, it usually promotes a degree of unease.

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Gazidis has been tempted to Milan by an eye-watering financial package. He was on £2.5m-a-year at Arsenal but the talk at the Emirates has been that he will get the equivalent of £6m-a-year at Milan. Perhaps, it was an offer that he could not refuse. On the other hand, Gazidis is not an extravagant person who needs any further fuel for a spectacular lifestyle. The broader question is whether Gazidis felt he could fulfil his ambitions at Arsenal; could he really help them to the top of the English game?

It was revealed last week that Sheikh Mansour has spent more than £1.3bn directly investing into Manchester City since he took over in 2008 while Manchester United have routinely showed their muscle in the transfer market.

By contrast, Arsenal’s majority shareholder, Stan Kroenke – who is primed to become the sole shareholder – runs a tight ship pegged around a self-sustaining business model. It has come to seem harder than ever for Arsenal to compete, particularly at a time when they are spending a second season in succession in the Europa League. With each season spent outside of the Champions League, it becomes more difficult to re-board the gravy trainand Gazidis knows it. Arsenal finished 37 points behind City last season. The gap yawns like a chasm.

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Gazidis has been at Arsenal for almost 10 years and, during that time, the club have won three FA Cups. Their perennial Champions League qualifications have stopped and it does not feel as though they are in the conversation for the Premier League title.

Gazidis will always be criticised for not standing up to Wenger over the issue of speculating to accumulate on the transfer market (Wenger was against it); for not demanding greater investment from Kroenke and for allowing a sense of drift to take hold.

Milan talked up Gazidis in their press release on Tuesday for building Arsenal into a profitable company, helping double turnover to more than £400m and boosting the club’s following across its digital platforms to in excess of 85 million people.

But it was a strange choice of photograph that Arsenal went for on their website to announce Gazidis’s departure and the internal reshuffle that has seen Sanllehí rebranded as the head of football and Vinai Venkatesham step up from chief commercial officer to managing director.

It showed Venkatesham and Sanllehí seated at a table and Gazidis standing behind them, his hands on their shoulders, as though he had annointed them as his successors – in the style of Fergie with David Moyes. Gazidis, remember, has just resigned in order to join another club. He described himself as “energised” to be going to Milan.