In Conversation with Ian Chisholm, Business Yoda and President of Roy Group

With his crack team of advisors at Roy Group, Ian Chisholm is shaping this city's leaders into world-class mentors.

Ian Chrisholm, President and co founder of The Roy Group. Photograph by Jeffrey Bosdet.

Ian Chisholm — Chiz to those who know him — is pretty open about being a bit of a zealot: he sees leadership in everybody. And, after decades of guiding people to bring only their best selves to every single interaction, he’s become one of Western Canada’s most in-demand organizational alchemists, working with government ministries as well as organizations like Fountain Tire, ATB Wealth, West Point Grey Academy, St. Michaels University School and Fraser Academy.

A hardworking farm kid from Saskatchewan, Chisholm entered leadership development in New York City, taking talented inner-city kids through a leadership development program, a job that had grown out of his summer internships with the American Management Association. During his time in the Big Apple, Chisholm helped to expand that initiative to multiple centres across the U.S.

When an opportunity arose to head up an entire centre for international leadership development, he jumped — even though it was on the Isle of Skye. At the age of 27, Chisholm moved to Scotland and took the reins at Columba 1400 Community and International Leadership Centre, pairing tough and trust-broken Glasgow kids with buttoned-up finance executives from Edinburgh. He had them coach each other through a leadership program. By the end of the experiment, the organization had garnered HRH The Princess Royal’s patronage, and Chisholm was named the first Fellow of Columba 1400. The program now runs in three centres in Scotland, one in South Africa and one in Australia.

After Columba 1400, Chisholm knew he had a formula that could change the world. So when he and his wife, Ann-Marie Daniel, arrived in Victoria in 2004, he immediately set to work bringing that formula to life. He called it Roy Group.

Whether it’s with young people or adults, you’ve been focused on leadership development since you reached adulthood. What’s your drive?

I think at the core, all of our work — and my drive — is about the sovereignty of the human spirit. People wanting to be their best and to leverage that into the world. Everything we do is about inviting that potential out. And addressing anything that’s getting in the way of it.    

Roy Group focuses on “small giants” — organizations that want to be great, not big — as well as leaders in education, public service and non-profits. Why these audiences?

They each deliver a high impact on society over the long term. These are the kinds of companies that create meaningful work, meaningful progress and a stronger community. We like to work with … leaders who unfold the kinds of stories that our world needs more and more of. I’m convinced the world needs more small giants because it creates a really high calibre of work, of quality, of creativity, of ownership. I just think it creates a better human life.

How do you help organizations level up?

Through emerging leaders. Organizations who want their game to go to the next level have to invite everyone to start practicing leadership. Regardless of their position, anyone can choose leadership and use their work as a way to become a more masterful leader. We also work with existing leaders in key positions, or as my father-in-law (a former university president) calls them, “The Deans of the University.” This refers to the level of leaders who take the vision from the senior team and translate that vision into what it means day to day. They’re the ones who disproportionately create the culture of the organization. 

What about seasoned leaders?

Seasoned leaders in an organization choose a very special kind of leadership: mentorship. That’s the real leverage. It means learning how to instruct, how to advise, how to coach. So in addition to creating value because of what you do and what you know, mentorship is really about creating value because of who you are. Taking leaders across this threshold is a specialty at Roy Group. It is personal. And delicate. And not easy. But it’s where the magic happens. All of the so-called challenges — recruitment, retention, learning, engagement, performance, succession — just melt away as challenges when leaders become mentors.  

What’s the distinction between leadership and mentorship?

To me, leadership has to involve going beyond getting things done, even big things, and must involve the practice of developing the capacity and the potential of others. If you’re not doing that, what you are doing is not leadership. That makes mentorship a very special form of leadership – one where the connection is selfless and valuable, supporting and challenging, safe and invested. Not all leaders are mentors.     

The Roy Group is in an interesting space. You’re a business, yes, but you provide a service, not widgets.

It’s very much business to business. All of our clients are businesses or organizations. Our job is to make them better at what they do. And that is an indirect thing. I’ve often envied, you know, whisky makers who get to hold it up to the light, and say, ‘I made this.’ We never really get to do that. Our successes are our clients’ successes.

What holds good leaders back from becoming truly great?

That’s the tricky part. It’s different for every person. The greatness is different — and the myriad of things getting in the way of good leadership is different. That makes teams an even more complicated puzzle. Saying that, the one mistake that my colleagues and I often see early on is that leaders underestimate the impact their conduct has on those around them.

And it’s not about being perfect, is it? After all, you’ve helped launch Fuckup Nights in Victoria so that people can share their stories of so-called failure and learn from each other.

In partnership with Jim Hayhurst [CEO of Pretio Interactive], yes. He’s another of these people I’ve learned a lot from. We’ve been through a lot together, beginning with our work on the board of Pearson College where we worked together for seven years. You really get to know someone. Late one night we were talking about how we wanted to do some learning together. I said, “I can’t go to another conference where people talk about how great things are. I want to go to a conference about epic failure.” Jim did some looking around and found Fuckup Nights. We decided that night we would bring it to Victoria.

You spoke at a recent Fuckup night about your experience on Scotland’s Isle of Skye where you almost cratered the organization you worked for with a $650,000 tax bill because you hadn’t done due diligence on the accounting behind your business model.

That was a bad day. On Skye, there were so many fuckups. I was 27 years old in a small rural community. Thank goodness I had a board that had faith in me, and that allowed me to make mistakes and recover from them. There were financial mistakes and personnel mistakes and strategic mistakes, and at the end of the day you just learn from those fuckups and still make it happen. In terms of viability as an idea — to start a leadership centre for young people from tough realities at the north end of the Isle of Skye, five hours from the nearest city — it was a total long shot. Even with all those fuckups I made, which were numerous and which we publicly got hammered for, me and my team were able to make that thing happen.

Tell me what you’re up to with VIATEC’s Orca Pod.

VIATEC has its finger on the pulse of the potential of this city. VIATEC’s CEO Dan Gunn and COO Rob Bennett have curated a group of 40 (soon to be 65) senior-level leaders — no-nonsense, highly effective community-minded leaders — to work with Roy Group. We’re really honoured to be asked to be a partner in something so visionary and impactful. We’ve had some great discussions and experiments with VIATEC focused on developing the kinds of leaders in Victoria’s tech sector who can build toward what VIATEC believes is possible here.

And what is possible here?

In a world where many organizations can choose where they want to be, Victoria has a distinct advantage. We have the opportunity to fill this city to the brim with creative, effective and talented people who raise their families here and make us better. As a city, you can’t lose if you do that well.  

People like to grumble about the public service. What do you say to them, after having worked with so many of its talented leaders?

People who grumble often don’t understand the public service. I know I didn’t before moving to Victoria. Our attention gets drawn to the “elected circus” — think Trump. I understand the grumbling about that! But true public service is a very potent case study of leadership — think [of U.S. special counsel Robert] Mueller. They tackle long-term, wicked issues. They’re asked to work in a way that is very consultative and collaborative across ministries and functions. They’re asked never to fail publicly — an impossible request. They’re asked to be incredibly careful with public money. When the bottom falls out of society, we all turn to the public service to find a way forward. 

You say listening is important for leaders to do. But we’re all in a rush. Listening takes time. And people whine. How does a leader handle that?

We have a fundamental principle at Roy Group: “The way you choose to conduct yourself creates an atmosphere inside others.” That’s what leadership has always been and it’s what it will always be. Conduct is kind of an old-fashioned word … but it’s where everything inside a person meets the rest of the world. To master yourself, and to become a master of storymaking, you’re going to have to master the way you conduct yourself. Listening is just a form of conduct. It sends a message to people around you that you believe they are intelligent and thoughtful and capable. Real leaders want the people around them to feel this way.  

You’re an inspiration to so many leaders. Where do you draw your wisdom and influences from?

I had the chance to be coached by some of the U.K.’s most incredible coaches, people I really consider mentors. Being 27 years old and reporting to a very capable board really evolved me, supplemented by working with people I will consider mentors for the rest of my life. I’ve had a chance to meet extremely skilled people and learn why and how they do what they do. That’s how I learn the most.

What one book would you most recommend for leaders to read?

Small Giants by Bo Burlingham. I knew immediately those were the kinds of clients I wanted to have, and that’s the kind of company I wanted to be.

What was your first job?

In addition to being a farm kid from Saskatchewan (I don’t remember not having jobs that needed to be done), I was the janitor at my dad’s accounting office. Every Friday after school, I would sweep and wash all the floors and clean the bathrooms. I knew that it was not pretend work; I really needed to own it. If I didn’t, I heard about it. I’m grateful in retrospect for being responsible for a real thing.  

If you hadn’t ended up doing this, what would you be doing?

Well, I didn’t get into med school, so … the initial dream was to be an actor, making stories come to life. Pretty much the same vocation as the one I’ve answered!

You talk a lot about “story.” Why is it so vital to developing leadership?

Because that’s the only thing that leaders ever leave behind. Bakers bake bread; leaders create stories. So if you’re responsible for unfolding stories in the world, you have to understand the architecture of story. You have to understand the importance of character and of being a character in the lives of other people. You have to have a strange appetite for adversity, because without that, the stories are not that engaging, and characters don’t become deep friends. You have to recognize when it’s time for a new chapter. 

Where does your gift for story come from?

My apprenticeship into leadership came in the form of posts inside nonprofits and social enterprises. In these sectors, story is key. If you can’t capture people’s imaginations with a story about practical ways that the world can be better, you’re done. 

What inspires you?

People whose conduct changes the story or whose phrases stir people for the better. In my iTunes, I have a lot of speeches from people like Churchill and Mandela and Kennedy. People who used phrases to stir people. The poetry of that inspires me.

What are you quite hopeless at?

Finance. I couldn’t create a spreadsheet or an accurate financial report if my life depended on it.

Finally, I hear you’re working on a script?

I’m working with a great screenwriter named Marcus Gautesen (This Means War) to create a six-season series. Great characters. Deep flaws. Epic situations. Mythical significance. It’s about the last 20 years of human existence before AI (with no malice) comes to the very logical decision to remove human beings from all major decision-making for the planet. It’s been a wonderful way to find out what is actually happening in the world.

This article is from the December/January 2019 issue of Douglas.