While it certainly helped having a father who was a former NFL executive who could bend the ear of coaches when they had openings — make no mistake — Jon Gruden paid his dues as a football coach. A decade before becoming the younguest NFL head coach at the time at age 34, Gruden worked his way up to land the quarterbacks coaching job at Southeast Missouri State University in April of 1988. He wanted to start coaching right away. The only problem was that his $15,000 annual salary didn’t begin until July — so he found a part-time job ripping out carpets that were being replaced in schools for $6 an hour during the hot Mississippi summer.
“Sometimes we had to take chisels and dig the rubber padding off the floor. After a while my hands looked like they were just rotted out. As I ripped through those carpets I kept reminding myself of the only reason I was putting myself through so much abuse…I’d be on my hands and knees, ripping and chiseling, telling myself, Just keep at it, Coach Gruden.” He explained in his 2003 memoir, Do You Love Football?!
It was 1990 when he received the life-changing call from Mike Holmgren at the San Francisco 49ers. His father, Jim, had told Holmgren about Jon’s aspirations to join the staff in San Francisco.
Gruden also credits Dave Razzano, an up and coming scout for the 49ers. Dave warned him that the job probably wouldn’t pay much.
“I will come there for nothing. Tell Coach Holmgren I’ll pay him to take the job,” he stated.
The 49ers were at the peak of their dynasty winning back to back Super Bowls with Joe Montana at the helm. They had the best talent and facilities in football with an owner in Eddie DeBartolo who spared no expense. This was before the NFL implemented a salary cap.
“They had everything in place. It was an offense I always wanted to learn, because of the rythem and formations of the offense — they were on the cutting edge,” Gruden explained to me during our interview.
Gruden’s career has taken many turns, from being an NFL head coach to a seasoned broadcaster, and a coach again. While he always wanted to coach quarterbacks early on, he coached nearly every offensive position over time which helped round out his offensive coaching experience.
“I was coaching tight ends at the University of Pacific with a no back offense, we didn’t even have a tight end,” Gruden said with his signature laugh.
When he arrived in San Francisco, Holmgren asked him if he knew how to work a computer. At that point in his life, Gruden hadn’t turned one before. Now he had one sitting at his desk.
Holmgren told him he was going on vacation for a month and by the time he returned he wanted Gruden to become a computer expert. He also tasked him with transitioning the written playbooks to the computer.
While it wasn’t easy, with a little help from Holmgren’s secratary and some Silicon Valley experts, he figured it out — he adapted. Change has been a constant in his career and I solicited him on how we can build our adaptability muscle.
He was quick to admit that it wasn’t always easy adapting to all the rule changes in the NFL, especially when he returned to the sideline.
“Maybe I’m guilty of keeping the things they way they were. Not in favor of things like moving the extra point back or less padded practices. However — whenever the rules are determined, you can’t worry about all the things you can’t control. When the playing field is set you have to adjust.
Every year they’re going to change. Your schedule is going to change. Your roster is going to change. Hell, the weather is going to change. Adapt or die — be flexible. As hard as it is for me, you have to do everything you can to be flexible and adapt to the circumstances.”
During his tenure in San Francisco, Gruden had a front row seat watching a frustrated Steve Young backing up Joe Montana. He often uses Young as an example with many backup quarterbacks.
“Joe Theisman and Steve Young have gold jackets and they never really started until they were 30. The last thing Steve needed to hear from me was ‘be patient.’”
In fact, Gruden’s father drafted Young to the Bucaneers out of the USFL as the personnel director. New head caoch, Ray Perkins, decided to trade him. Because Jim Gruden knew John McVay, they traded Young to San Francisco.
“Steve didn’t play well in Tampa. When he went to the 49ers he sat there — just like I sat there as the quality control man — and he watched Joe Montana just kicking the sh*t out of everybody. He wanted to play for that offense.”
Bill Walsh believed in Young and the 49ers saw upside in him. Gruden shared a great lesson from the Montana vs Young situation about staying the course.
“He learned how to win in the pocket in San Francisco. Sometimes you have to be careful what you ask for. Have some patience, keep developing your skills and be ready when opportunity knocks.”
Coach Gruden helped me realize — that if we pay attention — we can reap the rewards of all the life and career lessons the game of football can teach us.
Arguably the greatest teacher in the history of football was the legendary, Bill Walsh. He cemented the 49ers dynasty in the 1980s with 3 Super Bowl championships. While Walsh retired before Gruden joined the organization, he left a big imprint on him.
“He visisted us at the Bucaneers a couple times. He’s the best football guy I’ve ever been around, period. The most important lesson I learned from Walsh was that the accumulation of knowledge is a powerful thing — so is the accumulation of nothing.”
Gruden explained that to be creative you have to study offenses around you, whether that be in college or places like the Canadian football league. He also shared an invaluable lesson when he spoke to the Buccaneers defense.
“I don’t care how many sacks you have, how many do you have in the fourth-quarter? Can you close the game out with defense? If you don’t have a fourth-quarter pass rush — you don’t have a ass rush,” stated Walsh.
Even if you’re not an NFL coach, transitioning to a leadership role can be difficult. One of the biggest challenges is balancing two things — earning respect and wanting to be liked.
“Respect is most important whether it be in pro football or in business. For that to happen you have to earn their trust. You can’t wing it — you have to prove to them you know what you’re talking about.”
“So earn their trust for them to respect you, and it’s okay for not everyone to like you?” I tried to confirm.
Gruden reflected on a time in the 9th grade at the great college coach, Bobby Knight’s basketball camp. Knight gathered the kids and surveyed by a show of hands how many of them liked their coach.
“How many of you don’t like your coach?” Knight proceeded to asked.
Almost all of the kids raised their hands.
“What makes you think your [expletive] coach likes you?!” Knight said.
“It resonated with me. He told us to do some of the things we don’t like to do so our coach learns to like us,” Gruden explained.
Like Coach Knight, Gruden has also been known for his motivational speeches to his team. After he led the Raiders to their 11th division championships since the AFL-NFL merger in 1970, he delivered a post-game speech for the ages.
“How about those Raiders baby! You’re never going to get this year back, whether you’re an 8-time pro bowler or a no-time pro bowler like me…Can we win a championship? There can be no doubt in your mind.”
Gruden knows how to reach players and what buttons to push. Whether he wanted to make them laugh or cry — he did it in a self-deprecating fashion.
“I tried to be on the cutting edge of creativity.”
He iterated that as a leader, you have to mix up your approach and have a pulse on what your team needs. Also, hiring good coaches is key so the players get to hear a different voice and it provides a platform for other leaders to develop.
“When I was coaching the Buccaneers, we split up the schedule into four segments. For example, I would let Mike Tomlin and Raheem Morris each address the team for four weeks and then critique their approach to help develop their leadership,” Gruden explained.
It was brilliant. Rather than have one voice for 4 months, he’s empowered his leadership team. By doing so, he’s also able to get his leaders to buy-in to the plan as well.
Before Gruden earned the head coaching job for the Oakland Raiders, he went through a grueling, four-day interview with Al Davis. Gruden said it was possibly the four best days of his life and ultimately working with Davis fast-tracked his coaching success.
“You can’t prepare for an interview with Al Davis. He would toss you the chalk and ask you to draw your punt protection. He’d ask you questions he knew you couldn’t answer.
It made you want to go back and study so you knew all the questions. Over the course of time he helped me and gave me a sense of urgency to look at things from a different perspective.”
Coaching the Raiders was his first head coaching job. Looking back, he shared sage advice for any first time leader.
“Stay close to your knowledge base. I was an offensive coordinator in Philidelphia, so I stayed in my role and stayed close to the quarterbacks. I tried to hire a great defensive and special teams staff. Secondly, don’t rush into hiring a staff. Interview people and take your time to find the right people.”
After Gruden left the Buccaneers he spent 9 years in the broadcasting booth. During this time he also hosted his acclaimed Gruden’s QB Camp where he intereviewed and tested quarterbacks entering the NFL Draft. This included gun slingers like Patrick Mahomes, Andew Luck, and Josh Allen.
He’d often ask quarterbacks, “How do you handle pressure?”
It made me wonder, how did Gruden coach his own players to handle pressure? How can all of us do a better job of handling pressure?
“It’s easy to me to say ‘Don’t feel pressure, apply the pressure.’ You have to prepare yourself for these pressure moments instead of waiting for these critical moments on game day. Let’s have a period of fourth and six yards to go. Practice crunch time situations. To have the confidence to perform in a pressure packed situation, you have to have done intense preparation.”
Gruden said one of the best players who handled adversity was his eventual starting quarterback and future NFL MVP, Rich Gannon.
Gannon stepped in for an injured Elvis Grbac and led the Chiefs to a six-game winning streak. However, when the playoffs began Marty Schottenheimer decided to start Grbac and they lost at home scoring only 10 points against the Denver Broncos.
The Chiefs never gave the keys to the kingdom to Gannon and when free agency hit, Oakland was the last place on his mind because the Chiefs and Raiders had a long-standing rivalry.
Suddenly, he received a call from his agent telling him to get on a plane to Oakland. Who picked him up from the airport? Jon Gruden.
They had dinner at a restuarant and went back to Gruden’s office to talk football over a beer. Even though they were trained to dislike one another, they hit it off.
“We were cut from the same cloth. We were like the perfect match at the time for what the Raiders needed.”
At the end of their meeting, Gruden said “We’re either going to succeed together or fail together, but we’re going to do it together.”
Over the next few years the duo turned the Raiders into a Super Bowl contender. Eventually, Gruden recruited the legendary Jerry Rice from across the bay to play alongside future Hall of Fame player, Tim Brown — and they both caught for over 1,000 yards.
The Raiders were fireing on all cylinders. When I asked Gannon about what type of leader Coach Gruden was, he simply said:
“He was consistent, a great communicator, and a really good listener who valued feedback. He respected the people he worked with and he clearly communicated the message and the plan each week. He was very detailed because he helped build the plan. He also helped install it, teach it, and coach it. From a leadership perspective I cherished that because he had a vested interest not only in the results — but getting there.”
Gannon also described his attention as uncanny. For example, if a receiver was supposed to run a 10-yard out and they over ran it to 12-yards, Gruden could see that in real-time. Most coaches wouldn’t notice it until they watched the practice tape.
“Why is attention to detail so important?” I solicited Gruden.
“Time is the one thing we don’t have enough of. We’re not allowed to meet or practice as long, so you better be listening carefully. We can’t miss any assignments because if you have one mental lapse the play is dead. The wide receiver cuts his route short, the quarterback takes the wrong drop, it’s over. I was obsessed with the attention to detail and I learned that from Bill Walsh and Mike Holmgren.”
The throughline of our conversation has been about resilience and building mental toughness.
“You can be as physically strong and talented as anybody in the world, but if you don’t have mental toughness — you aren’t going to win a championship and you are not going to be a great success.”
He says the best leaders weave in examples of mental toughness on a daily baisis — they practice it.
“A lot of people would say ‘Take a dive into adversity,’ and we would say ‘Thrive in adversity.’”
In my own experience, I’ve found one of the hardest skills to improve is self-awareness. In Gruden’s QB Camp, he interviewed countless young quarterbacks. He’d often show them bad plays or interceptions they threw and promt them for feedback. As a viewer, you could read their body language as some were defensive while others leaned in to the constructive feedback without ego.
“Your teammates are watching you when you’re the quarterback. If you’re slouched over or not totally invested they’ll pick up on that.”
At the same time — how do players move on to the next play after they make a mistake? Do they ruminate on the bad plays, should they just forget about it?
“You can’t come unglued when you make a mistake. Every interception or bad play has a story. Why did we do that? Let’s learn from it and move on.”
Bill Walsh’s advice came full circle — the accumulation of knowledge is a powerful thing — and if you want to build a championship mindset you have to be a lifelong learner. You have to be open to new ideas. You need to test yourself by putting youself at the edge of your comfort zone both mentally and physically.
Doing these things will help develop resilience that you can bank on and experience you fan draw from in critical moments. One snap at a time, Coach Gruden would say. Let’s try to string a few good snaps together, whether that be in football or in life.
Click here to watch the full interview with Coach Gruden on YouTube