Chelsea's president of business Tom Glick initially dismissed a complaint about inappropriate text messages sent by the club's commercial director to a female agent as "not relevant" to his job.
BBC Sport has learned that two weeks after the messages were first brought to the attention of Glick by agent Catalina Kim, he told her the issue was "not interesting" and he had "set it aside".
He said he had not looked in detail at the screenshots of the messages Kim had been sent by Damian Willoughby - just "the headlines".
Only when challenged on his response by Kim did he agree to review the messages again, and an internal review led to the sacking of Willoughby last week.
Chelsea said it escalated the matter "immediately" once the "severity" of the allegations had become apparent.
Kim was involved with British property owner Nick Candy's bid to buy Chelsea in March, through her firm C&P Sports Group.
She was sent the improper messages before Willoughby joined Chelsea earlier in September as one of the first appointments since the takeover by an investment group led by businessman Todd Boehly and Clearlake Capital. His official start date was 5 September.
He previously worked for Chelsea between 2007 and 2010 and more recently had held roles as a vice president at EA Sports and an executive at City Football Group (CFG).
On 3 September, Kim told Glick - who was appointed by Chelsea in July and previously worked with Willoughby at CFG - that she felt "uncomfortable" working alongside Willoughby on a project because she had recently found his manner to be aggressive during a meeting and subsequent phone call, and because of her previous experience with him.
That day she shared screenshots of the inappropriate messages Willoughby had sent her over a two-year period, in which he asked her on more than one occasion if she would "be naughty" and asked her to send photos of herself naked.
There was no response from Glick to Kim's message.
A week later, when Kim had still not heard anything from Glick, she chased up on her complaint.
In a series of messages seen by BBC Sport, Glick blamed his lack of response on him being busy "rescheduling matches and a manager change" and then that he had "come down with Covid".
Kim and Glick spoke on the phone on 18 September, 15 days after Kim had sent the screenshots.
During this phone call, Glick told her he had seen "some of the headlines of the stuff that you sent and I just set it aside" as it was "not something I'm particularly interested in" and "it looks to me like something that is just not interesting or relevant to me in terms of running the business".
He later said: "I set it aside. And so you have now raised it again so I guess we are going to have to deal with it. I will have to go back and look at what you sent. I did not look at the substance of the details."
Later in the phone call he said: "I need to go back and take a look now at what you sent me, which I haven't done yet."
The day after this phone call, on 19 September, Glick texted Kim saying: "I have now read what you sent to me. We are taking this matter very seriously. I will come back to you again shortly following an internal review."
Willoughby was dismissed the following day.
A Chelsea spokesperson said: "Once the severity of the allegations that Catalina Kim raised to Tom Glick had become apparent regarding the conduct of a new hire whilst in previous employment, the matter was immediately escalated for review. An investigation was completed, and the club took decisive action to terminate the individual's employment.
"Mr Glick regrets that he did not initially appreciate the full extent of the allegations. After speaking to Ms Kim, Mr Glick read the evidence in full and appropriate steps were taken resulting in the termination of the individual's employment.
"The club is committed to treating all our stakeholders with dignity and respect and does not tolerate behaviour that falls below the expected standards set by the club. The club has offered safeguarding support to Ms Kim and this offer remains open.
"We take all complaints seriously and have several options for escalation including the club's whistleblowing line, safeguarding team and through our website."