2.16.22 – The Regroup: What You Should Know About Winning

A look at some of the best content out there from this past week, round up by The Coaches Site founder Aaron Wilbur.

BIG ANNOUNCEMENT coming this week from The Coaches Site.

Watch your inbox!

Otherwise, the Global Skills Showcase is coming up, lots of big coaching moves in the NHL and I think I may have uncovered a couple of gems in this edition of The Regroup.


– Aaron Wilbur, Founder of The Coaches Site




“If (there’s) anything this team needs right now, it’s to have fun. I know when they were pee-wees, they had a lot of fun, so I’m probably the most qualified guy right now.” – Martin St. Louis

When a new GM says the coach he inherited is safe for the balance of the season, I take that with a grain of salt.

But man was I caught off guard when Marty St. Louis was installed behind the bench of the Montreal Canadiens. Part of me likes it. It’s different. It’s fun. It makes the Habs an intriguing team to watch down the stretch in what has otherwise been a dumpster fire of a season.

But another part of me is like – this is the NHL. Coaches pay their dues to earn the opportunity to coach in the league. This felt like an opportunity that was handed to Marty. Like, how was Luke Richardson not considered deserving of this opportunity?!

Time will tell if this is a move that gets Montreal back on track, but I will say that this report on his first practice with the Canadiens, including VIDEOS of the drills he used is worth checking out.




“For me, that started with making sure I was, and making sure that our staff was, seeing things clearly. Once we did that, we spent a lot of time being intentional with our leadership. It was big for us to convey a sense of optimism.” – Jay Woodcroft

I don’t recall ever cheering for the Edmonton Oilers.

I can assure you that I’ll be rooting for them as long as Jay Woodcroft is behind the bench. You never want to see a good coach get let go, however I couldn’t be happier for Jay.

He’s earned this. His coaching career began as the video coach for the Detroit Red Wings in 2005. He worked his way up from there, following Todd McLellan to San Jose and then to Edmonton. He was then named the Head Coach of the Bakersfield Condors, the Oilers AHL affiliate, in 2018. It was his first turn as a Head Coach.

Four years later he’s in charge of the big club.

Ironically, back in September, Jay did a presentation on Dealing with Adversity at our Virtual Hockey Summit. If there is one coach who’s going to walk into the Oilers dressing room and help them see that the glass is half full, it’s Jay Woodcroft.




“A lot of kids, bottom hand, they’re strangling their stick. You know they’re gripping it so tight and they have no movement.” – Swaggy P

Peter Lenes (aka Swaggy P) is a stickhandling specialist.

What do you have to be able to do to call yourself a stickhandling specialist?

Go check out Elev802’s Instagram to find out. The stuff he pulls off is ridiculous. So ridiculous in fact that the NHL invited him to Vegas for the All-Star weekend so they could showcase his skills.

Swaggy P is the co-founder of Elev802 and a coach at heart. He’s also going to be presenting at our upcoming Global Skills Showcase from March 7-11.

He joined me on the Glass and Out podcast recently to discuss his transition from playing to coaching, and how he has grown his brand through social media.




“Are you willing to sprint when the distance is unknown?” – Lewis Caralla

The internet is undefeated.

Every time I think I’ve gone down every possible rabbit hole it reveals more coaching GOLD.

Cue Lewis Caralla, the Head Football Strength & Conditioning Coach at Georgia Tech University. I have no idea how I landed on this tweet, but when I did I became instantly enthralled with Caralla.

You can find more coaching GOLD over at this Twitter account.




“It is the biggest challenge – getting your top players to buy into whatever you’re selling. If you get them on board, then you have a chance to win.” – Mike Sullivan

It wouldn’t be a stretch to suggest that Mike Sullivan is one of the best coaches in hockey. His results speak for themselves and he’s got the Pittsburgh Penguins back in the hunt again this season.

Bostonia magazine is published by Sullivan’s alma mater, Boston University. Back in 2017 they published a profile on Sullivan’s coaching journey.

I thoroughly enjoyed this. It’s a longer read, but takes you through the ups and downs of Sullivan’s career, leading up to the back-to-back Cups in Pittsburgh in 2016 & 2017.




“He’s pale as a ghost, his mouth is dry, he’s like, pacing back and forth, he’s rubbing his head, he’s got his hands on his hips, like everything to let you know how exhausted and exasperated he is.” – Joshua Perry

Joshua Perry and Evan Spencer are two former Ohio State football players. Last year they took part in a podcast series Glory Days: Dreams and Nightmares, recounting their 2014 at Ohio State, in which the program captured the National Championship.

In THIS CLIP, Perry shares how Urban Meyer would react after a loss.

Consider this a lesson in what NOT to do.




“I wake up every morning at 6, 6:15 and there it is; emails and calls from parents, schools, billet families, GMs, whomever. And when I go to bed, 12 at night, that’s when it stops.” – James Richmond

Ask the casual fan what the job of a coach entails and they likely respond with: wear a suit, stand behind a bench, give the occasionally motivational speech…oh ya, and know how to blow a whistle.

Turns out there is bit more to it than that.

James Richmond is both the Head Coach and General Manager of the Mississauga Steelheads. The Steelheads currently hold down first place overall in the OHL standings.

Needless to say, James puts in some long days.

Back in 2017, his first in the dual role, the Toronto Sun shadowed James for a day. HERE is a recap of what a typical day looks like.




“Day by day. There’s no easy road to success. It’s going to be very hard. There’s a lot of things that happen behind the scenes that maybe the whole world doesn’t see, but we know we’re headed in the right direction.” – Zac Taylor

I’m aware the Cincinnati Bengals lost the Super Bowl (what a game!)

Despite that, I still believe that this conversation between Bengals Head Coach Zac Taylor and Super Bowl Champion Tony Dungy reinforces some great lessons. Zac is 38-years-old and in his third season as Head Coach for the Bengals, a team building something special.

One lesson in particular is that he keeps a notebook and refers to it often. He acknowledges that he’s a young coach and has to learn fast. Keeping track of the various decisions he and his staff make, trends he’s observing around the league, and how he manages himself, help him accelerate that learning process.

It’s a discipline we hear great coaches reference time and time again.

How do you keep track of your season? Connect with me on LinkedIn and let me know by sending me a direct message.


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Aaron Wilbur

I’m a husband, father, sports nut and Founder of The Coaches Site. I enjoy cooking, watching live music and hiking the North Shore mountains with my family. My son is a football player, which has turned me into a big football fan. It’s helped me appreciate what hockey parents go through, especially those who have little experience with the sport, when trying to navigate their child up the hockey ladder.

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