Macclesfield Town chairman Mike Rance has said sacking Gary Simpson is one of the hardest things he has ever done.
Rance asked Simpson to step down after a 16-game winless run in League Two that leaves the Silkmen only out of the relegation zone on goal difference.
"Gary's and my history with the club are intimately bound together with the events of the last two years," he told BBC Radio Manchester.
"I can tell you this was one of the harder things I've done in my life."
He lead the club to their highest finish in six seasons last year, in a campaign again marred by another death, with midfielder Richard Butcher passing away in January.
He was rewarded with a new two-year contract at the end of last season, but despite an FA Cup run where they drew 2-2 with Premier League side Bolton, the Silkmen have struggled in the league, managing just eight wins.
"When you're doing something like this there is never a right time," Rance added.
"If you talk to people around the club, some people will say we left it too late, some will say it was the right time, some will say we shouldn't have done it at all.
"Gary is a friend and a colleague and I'm pleased to say as we go forward he will remain a friend.
"He's a top guy and he'd done absolutely everything he could possible do for the club and he understands the reasons why we've done what we've done, and I wish him all the best for his future."
With only nine games of the season left, Rance said they expect to have a new manager in place soon.
"All will become clearer later in the day," he stated.
"We've thought this through and we're in control of our own destiny to a certain extent and hopefully we'll go to the Don Valley Stadium as prepared as we can be given the circumstances."