What Happens at Stampede…

Every city has its season.

For Calgary, it’s ten days in July when business meetings are replaced with pancake breakfasts, cowboy hats become acceptable office attire, and people who haven’t worn denim since the previous Stampede suddenly rediscover their inner ranch hand.

Whether you’ve lived here for six months or sixty years, there’s something infectious about Stampede week. It has a way of breaking down barriers. Clients become guests, colleagues become friends, and conversations that would normally take weeks to happen in a boardroom seem to happen naturally over coffee, bacon and a stack of pancakes.

For Riverside Consulting, this year’s Stampede celebration felt particularly special.

The company had doubled in size during the pandemic. Like so many organisations, people had spent months working remotely, seeing one another through the tiny rectangles of Teams meetings. New employees had joined without ever properly meeting their colleagues, relationships had become transactional, and the informal conversations that build culture had all but disappeared.

Now everyone was back together.

Leadership had decided to celebrate by hosting the company’s first Stampede party in several years. The atmosphere was relaxed. There was live music, plenty of food, and more laughter than anyone could remember hearing in the office for quite some time.

As the afternoon wore on, people began drifting away.

Some had family commitments. Others had tickets for the rodeo or evening show. A few were simply exhausted after an early morning breakfast and a full day’s socialising.

Mike wasn’t ready for the day to end.

“Come on,” he said to his team. “It’s Stampede. Let’s keep this going.”

Someone suggested a karaoke bar.

Nobody objected.

Or perhaps more accurately, nobody felt comfortable objecting.

That’s one of the subtle realities of leadership that we rarely acknowledge. Managers don’t always need to give instructions. Sometimes their enthusiasm is enough. When your manager says, “Who’s coming?” declining can feel more difficult than accepting, even when the invitation is technically optional.

Within half an hour they were sitting around a table in a crowded karaoke bar, nursing fresh drinks while strangers butchered everything from Johnny Cash to Bon Jovi.

The atmosphere was exactly what Mike had hoped for.

His team laughed more in those two hours than they had during the previous six months. They swapped stories, teased one another about questionable musical tastes and, for the first time in years, simply enjoyed each other’s company without deadlines, clients or project plans hanging over them.

From that perspective, Mike felt he’d done exactly what a good leader should do.

He’d brought his team together.

Then his song came on.

Nelly’s It’s Getting Hot in Herre.

Mike leapt onto the stage to enthusiastic applause from his team.

At first, it was simply another enthusiastic karaoke performance. A little off-key perhaps, but entertaining nonetheless.

As the chorus arrived, Mike removed his cowboy hat and flung it into the crowd.

People cheered.

Then came the shirt.

The cheers grew louder.

By the final chorus, his jeans had joined the shirt on the stage floor, revealing a pair of cow-print boxer shorts and, painted proudly across his chest, the Riverside Consulting logo.

Mike stood there soaking up the applause, convinced he had become the undisputed hero of Stampede week.

Around the room, several people were filming.

Nobody thought twice about it.

After all, that’s what people do now. Every amusing moment is captured, shared and forgotten almost as quickly as it happens.

Except this one wasn’t.

By Saturday afternoon the video had appeared on Instagram.

By Sunday it had migrated to Facebook and TikTok.

By Monday morning someone had recognised the company logo painted across Mike’s chest and tagged Riverside Consulting.

The comments started appearing underneath.

“Interesting leadership standards.”

“Is this how they entertain clients?”

“Professional image?”

The organisation suddenly found itself associated with a video it had absolutely no control over.

For Mike, Monday morning started much like every other Monday.

Coffee.

Emails.

A quick catch-up with his team.

Then a calendar invitation appeared.

Sometimes team dynamics mean having to have difficult workplace conversations. To find some great tips on how to structure these conversations why not check out this previous blog post 'Use the B.E.E.F Model to Correct Employee Behaviour'

Or check out our online course

Project Review – 10:00 a.m.

Strange title, he thought.

When he walked into the meeting room, Sarah was already there.

She smiled politely, but it wasn’t her usual smile.

The door closed.

There was a pause.

Finally she spoke.

“Mike… I’d like to talk about Friday night.”

Mike leaned back in his chair.

“You mean karaoke?”

“Yes.”

He laughed.

“I thought it went pretty well.”

Sarah slid her phone across the table.

The video was already playing.

Mike watched himself singing.

He watched himself removing his shirt.

He watched himself dancing in his boxer shorts.

Then he noticed the comments.

The laughter disappeared.

“I honestly didn’t think it was a big deal,” he said quietly.

“It was after work.”

Sarah nodded.

“I know.”

“It was Stampede.”

“I know.”

“No one got hurt.”

“I know.”

Mike became more animated.

“Everyone wanted to be there.”

“They’re adults.”

“I paid for the drinks myself.”

“Other managers stayed out later than I did.”

“And besides…” he paused before adding, “I thought we encouraged leaders to be authentic.”

Sarah listened.

She didn’t interrupt.

She didn’t argue.

She didn’t tell Mike he was wrong.

Instead, she asked a question.

“What do you think your team learned from Friday night?”

Mike frowned.

“I don’t understand.”

“They weren’t just watching a colleague enjoying himself.”

She paused.

“They were watching their manager.”

The room fell silent.

Sometimes the most powerful moment in a difficult conversation isn’t the explanation.

It’s the realisation.

Sarah wasn’t questioning whether Mike was a good person.

She wasn’t accusing him of deliberately damaging the company’s reputation.

She wasn’t even suggesting managers shouldn’t enjoy themselves.

She was asking him to see the evening through someone else’s eyes.

A junior employee wondering whether saying “no” to karaoke would have been noticed.

A client scrolling through social media.

A prospective employee deciding whether this looked like an organisation they wanted to join.

Leadership is an odd thing.

You spend years earning trust, credibility and influence, often one conversation at a time.

Then one moment of poor judgement can cause people to question all three.

That doesn’t mean leaders should become robotic.

Far from it.

Some of the best leaders I’ve worked with have been funny, approachable and full of personality. They tell stories, laugh at themselves and know how to celebrate success.

The difference is that they never forget that leadership follows them out of the office.

People don’t stop seeing you as a leader because you’ve ordered another drink.

Your title may stay behind on your desk.

Your influence doesn’t.

That’s why conversations like Mike’s matter.

Not because someone sang karaoke.

Not because someone appeared on social media.

Not even because a pair of cow-print boxer shorts unexpectedly became famous.

They matter because leadership is ultimately about judgement.

The difficult conversations we have after these moments are rarely about the event itself.

They’re about expectations.

About influence.

About responsibility.

About understanding that intent and impact are often very different things.

Stampede should absolutely be fun.

Celebrate.

Wear the hat.

Dance.

Sing karaoke if you must.

Just remember that somewhere, someone is still watching—not because they’re looking for perfection, but because they’re looking to understand what leadership really looks like.

And if you’re ever the one who has to begin Monday morning with the words, “I need to f*ing talk to you,” remember this.

The goal isn’t to win the argument.

The goal is to help someone see the situation through a different lens.

That’s when difficult conversations stop feeling like punishment and start becoming opportunities for leadership.

What strategies have you found effective when handling difficult conversations? Share your thoughts in the comments below!

Ready to take your leadership skills further? Explore workshops and resources that simulate real-life workplace conversations using professional improv actors, allowing you to build the confidence you need to tackle tough situations head-on.

For more insights on navigating difficult workplace conversations and enhancing your leadership skills, check out our training program based on our 5 Star Amazon book 'I Need To F***ing Talk To You - The Art Of Navigating Difficult Workplace Conversations'. This program incorporates professional improv artists and forum theatre to provide a dynamic and engaging learning experience.

You can now order copies of our book here.

"Sometimes conversations suck, but you need to have them, and this book lays out how. Russell and Ken have put together and road-tested simple, up-front, and thoughtful approaches to awkward and difficult workplace conversations."

Andrew Phung, CBC's Kim's Convenience

I hope you found this blog useful. As you continue your leadership journey, don't forget that here at Bluegem Learning we are always here to assist you.

If you'd like to hear more from business leaders about handing difficult workplace conversations, check out our podcast here, new episodes bi-weekly ...

Well that's it for this week. I hope you enjoyed the blog and I'll be back soon with more, until then ... be a leader not just a boss!

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