Welcome to The Leader's Playground

Welcome to The Leader’s Playground. I’m so happy to have you here! I hope together we can experiment, fail, and learn fast.

For decades now, I’ve held the belief that life (and work, especially) is one big playground—it’s only when we’re approaching it incorrectly that it doesn’t feel that way. 

That’s why it’s now my personal and professional mission to create measurable playgrounds to disrupt the way people are led and amplify the human in leadership. 

This newsletter will take you along this journey with me, bringing you into the fold—sharing insights from my work with PotentialSquared, offering resources and ideas that inspire me, and creating a conversation to make work more fun. 

Are you with me? 

The Leadership Tales Podcast

It’s finally here. Series 3 of The Leadership Tales podcast will be out next week, on September 20th! 

This first episode features the husband and wife team Jonathan and Melissa Nightingale and their Toronto-based leadership development initiative, Raw Signal Group. Tune in to learn the benefits of working towards tangible goals, improving your leadership techniques and how parenting and management are intrinsically linked. 

With backgrounds in engineering at Mozilla, experience in public relations, and tech start-ups development, Jonathan and Melissa aim to bring pragmatic, focused leadership techniques to bosses, CEOs and MDs in all fields.

What I'm Curious About This Week

If you were having dinner with Cristiano Ronaldo and he refused dessert, would you think twice about that cheesecake slice, too? At a meal not long after Ronaldo joined the team, his Manchester United teammates did just that, and the reasoning piqued my curiosity.  

I recently listened to an old episode of the Journey Further Podcast, in which Professor Damien Hughes shared this story and attributed Ronaldo's magnetic trend-setting talent to him being a “cultural architect.” What’s that mean, though?

Cultural architects are leaders without authority. More precisely, they are simply individuals who hold the sway to shape the culture around them. When they join an organization or team, things change—and change toward that person’s tendencies. 

Specifically, these people exhibit a couple main characteristics: 

1. They are technically very good at their job, and they have likely been around the scene for a while. People listen and pay deference to them.2. They are socially gregarious, and people warm to them easily. 

Cultural architects are a double-edged sword: Because others follow their lead so readily, they can influence a culture very quickly—for the better OR the worse. But the good news is that these individuals can be coached. The vast majority of our behaviors are learned ones, and that’s no less true of these dynamic culture-creators than anyone else. 

My takeaway: If you’re wanting to impact culture on your team (whether it be Manchester United or a 100-member company), look to hire these cultural architects. Be sure to hire the ones who exhibit the traits and behaviors you want to see spread throughout the group, or put a solid effort into coaching them towards that. 

First, I’m really excited about this part of the newsletter—it’s the bit where I get to give you a super-top-secret-sneak-peek at what’s happening over in the P2 Lab. (That’s the part of my company, PotentialSquared, where we get to run wild with crazy ideas for our clients, experimenting to see what might work—and, of course, failing a lot.) 

Okay, here we go. 

THE CHALLENGE: Right now, we’re experimenting with the conversations approach one of our clients utilizes in their practice. Our question is this: How do we simplify leadership conversations to be more impactful, more from the heart, more natural in conversational style?

The beginning and end of every leadership conversation is a breeze, but the middle… Not so much. It’s that middle, meaty part—the part where a good leader has decisions to be made to flow into the right spaces for their team member to achieve breakthrough insights.  Doing that also without either unleashing the ‘Advice Monster’ (as my friend Michael Bungay-Stanier writes about), stepping over the touchline, getting on the pitch and undermining their team member.

We want our coaches to spend the right time in the right places: on the sideline of the field for the majority of the time. But finding that perfect sideline position is trickier than it seems. 

They must pick the right time before the match, at half-time, and post-match to get on the pitch. They must also know when to sit in the stands observing and seeing the big picture. The difficulty is a lot of leaders are being asked to be “player coaches,” and the judgment call of when to get off the pitch and when to step back is a tough one.

So we’re experimenting and learning about how to develop in leaders the ability to judge when it’s the right time to be on the pitch with advice, and when to step back over the touchline and allow the team member to own the situation and decision. The challenge is to know how as a leader we ‘flow’ in a conversation, knowing the right moment to be silent, the right question to ask, the right time to nudge, the right time to show how to do something and the right time to let the team member go forward with their idea even when you see it as likely to fail.

It’s these things that are so tricky to parse out, but which make all the difference when it comes to a successful leadership relationship and conversations . 

We’ll be exploring the edges of leadership conversations and the dynamics of coaching, mentoring, influence, feedback and guiding here in the P2 Lab for the next couple months.

If you have challenges or questions for us to explore next, reply to this email and ask away! We’d love to experiment with you. 

Parting Thoughts...

I hope this first letter found you well and that it has inspired you to challenge the belief that work can’t be fun. I’ll leave you with this quote from one of my favorites, Adam Grant: 

"Strong leaders engage their critics and make themselves stronger. Weak leaders silence their critics and make themselves weaker."

I (do my best to) prioritize humility and collaboration in leadership and aim, always, to be a “practice leader” first. None of us are experts here, so let’s learn together!

If you have anything to share, please don’t hesitate to respond to this email. I would love to chat with you. And if you like what I’m doing and have someone who might enjoy it too, please forward them this email or invite them to subscribe at this link or the button below.

See you in two weeks!

Cheers,Colin

To learn more about my book, Be More Wrong: How Failure Makes You an Outstanding Leader, click here.