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One of the most difficult things to do as an assistant coach is to confront the head coach about something you see happening in the program you disagree with or that you don't like. This can be something that lingers in your head for weeks or months. You might lose sleep. You might become bitter.
I've coached 16 years of high school football and was a head coach for eight. In my eight years as an assistant, there were times I felt like I need to approach the head coach about something I saw happening in the program. Some were on-field issues, while others concerned off-the-field issues. There were some great conversations when my assistants approached me about something happening in the program.
This confrontation can go a number of different ways depending on the humility of the head coach, and the approach of the assistant.
If the immediate success or failure of your team is at risk because of what you're seeing and or hearing, approach the head coach.
For instance, during my first year as a head coach, two assistants I'd coached with on the varsity staff for the two previous seasons approached me together. They told me that I changed too much, I was trying too hard to be authoritative and thought that I was "losing the locker room." They were absolutely right. I met with a few kids the next day; these were kids I had coached the last two seasons. They echoed the same sentiments that my trusted assistants did. This was Week Two of the season. Luckily, these assistants confronted me on this issue. There was still a whole lot of football to play. As the head coach, I had to change my ways. So, I did.
I appreciated the way my assistants approached me. I could tell that this had been weighing on them, and they had discussed the approach to use. This wasn't an off-the-cuff thing they brought to me. I knew it was very important to the success/failure of our team that year.

Listening to assistants is crucial not for just players, but for the head coach.
File photo by Ralph Rath
I also appreciated that they came with solutions. They didn't just come with a problem for me to address, but they had some ways that I could take a step back as an authority figure, ways that I could relax a bit and be more personable with the kids.
I appreciated they had specific, concrete examples of what they were seeing and hearing. This made the issue real for me. Yes, I was defensive at first. But as they pointed out specific times where I had made errors as the leader, it drove home their point about the negative effects it was having on our team.
If you need to approach your head coach with an issue, make sure that it is something that really needs to be dealt with, especially in-season. Head coaches have so much on their plate, a lot that assistants simply will never see. Don't approach the head coach about a non-essential issue during the season. Ask a few people whom you trust, people who are not in your program, and see what they think. Getting outside advice will help you determine if it's an issue that needs to be dealt with during the season, or can it be held until the offseason.
For instance, I had an assistant coach from a program in the Midwest reach out to me last season on Twitter for my advice regarding an issue in his program. He thought the head coach did an awful job of building leadership. It was midway through the season when he reached out to me; he saw the negative effects of failing to build up leaders.
His ideas were great, but too late to make happen in the middle of the season. I told him that his ideas were valid, that what he was seeing did need to be addressed. But that these deep issues could not be fixed in the remaining five weeks of the season. I told him to hold off, and bring this up with the coach in the offseason. He agreed with me, and ended up having a great conversation with his coach.
Chris Fore is a veteran Head Football Coach and Athletic Director from Southern California. He consults coaches and programs nationwide through his business Eight Laces Consulting.