Ep. 126 – Casting Workbook President & Chief Marketing Officer, Christopher Ian Bennett

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Being the person behind the scenes requires certain qualities in a person that allow them to put the spotlight on others. Christopher Ian Bennett embodies that role in two important ways. As the President and CMO of Casting Workbook, it is quite literally Christopher’s job definition to put the limelight on people. As second-in-command to the company’s CEO, he provides the necessary support for the chief to focus on the company’s vision. In this episode, Cameron Herold follows Christopher’s journey from Sprint to Vancouver Film School and to his current position in one of the biggest digital casting companies in the world. Christopher also shares how the company was uniquely positioned to pivot during COVID-19; how he manages his time and sets priorities; and how his company attracts talent at reasonable prices.

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With a career that began as a rookie political speechwriter, Christopher Bennett attended Trent University in Canada and developed his love of writing into the public relations and corporate communication space. He worked on several high-profile national political campaigns, including for the Deputy Prime Minister of Canada, the Honorable John Manley. He served several cabinet ministers and US senators before being elected to the Green Party of Canada’s National Council and becoming the leader of the BC Green Party in 2007.

He holds the record for the youngest leader of the Canadian Political Party at just 27 years old. In 2011, Business in Vancouver named him to their annual 40 Under 40 list. Stepping away from politics, he moved to California where he began to build his career in communications, marketing, and public affairs for some of North America’s biggest brands, including Best Buy, 1-800-GOT-JUNK?, Guitar Center, and Sprint. In 2017, Christopher left his adopted home of Los Angeles and moved back to BC. He was named Executive Producer and Creative Head for the Vancouver Film School.

In just three years, he positioned the school to brand new award-winning status globally, including for the first time, Top 25 Global Film Schools, Top Canadian Film School from Variety magazine, Top Canadian Film School and Top 10 Global Film Schools by Hollywood Reporter. Also, #1 Animation & VFX School Globally by Animation Career Review magazine, and #1 Game Design Program in Canada by Princeton Review Journal. In March 2007, Casting Workbook Founder and Owner Susan Fox announced Christopher as the new President and Chief Marketing Officer. Christopher is a good friend of mine and we’ve been friends for many years now.

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Christopher, welcome to the show.

Thank you. I normally do what you do all the time and I read something. You’re the first person to ever interview me and I do a lot of interviews.

What’s weird is I was thinking about it because you are way better at this than I am on both sides of the table. I wasn’t entirely sure where we’re going to go with this, which I never am because you know me well enough. I’ll make it up as we go, but I’ve got some ideas.

It’s a good show and congratulations on over 100 episodes for you. I know a lot of people who watch it. They knew I was in this new job and they would go, “You should watch it.” I go, “I know Cameron.”

Thank you. What’s interesting is there’s some stuff in your bio that wasn’t there, so I’m going to add the rest of the bio. As best as I can recollect from the first time I met you, you walked into a group interview with about seven other candidates at 1-800-GOT-JUNK? It would have been roughly 2002. You walked into the meeting room and sat down at the end of the boardroom table across from me. Over the course of 90 minutes, I learned that you spoke four languages fluently. You had written two speeches for Canadian prime ministers and you played cello in a symphony orchestra. You’d been a pro surfer. You were either on Rock & Roll Jeopardy! or pretending to be or wanted to be. You knew everything about soccer. You read comic books like People Change Their Underwear. You went through many of those. You listen to speeches on political thought for fun. You had managed a bar and at that time, you were 23. Did I miss anything? Was I exaggerating any of that?

I don’t speak four languages. I speak two. I speak conversationally some Hungarian and I’m trying to learn Italian but that doesn’t count. I qualified to get on Rock & Roll Jeopardy! a long time ago, and then they canceled the show before I was able to fly down and do the thing.

What I remember about you is I didn’t believe any of it. When I heard it all, I’m like, “There’s no way that this kid who’s 23 has done all that.” I said I needed proof and you came in five days later with photos of you in magazines and pictures of you in the newspaper playing second cello in London Symphony Orchestra.

I went to the Lester Pearson School for the Performing Arts. I studied cello but I never played in a symphony orchestra.

You proved it all, which was amazing. The other thing I remember was you told me that one of your favorite books was The 7 Habits of Highly Effective People, which I had forgotten in many years. You then told me a year later that you never read the book but you thought I probably would have, so you tossed it into the conversation.

You called me out on it in an interview and you nailed me. I thought, “I’m never going to get this job.” I remember my father, who is a smart guy, he liked that book, and he would talk about it a lot. I thought, “This is what smart people talk about.” I was 23.

You were young. I remember being told by one of the VPS and one of the directors not to hire you. I went to Brian and I said, “I want to hire this guy.” Brian said, “Would you put your job on it?” I said, “I would stake my career on it.” We were standing out at the front of the junction at Granville Island in Vancouver and I made a good decision.

Maybe with the exception of my dad and possibly Doug Michelman, you’re the most important business mentor and friendship I’ve had in years.

I wasn’t searching for that, but thank you.

I know you weren’t, but I’m surprised I’m finally on your show because I’ve spent my lifetime working. I’m usually the number two for the number two.

Here’s the other thing I’ve always known about you and I’ve been frustrated with. You won’t put your head out into that spotlight other than when you did it for politics. You like to be, for some reason, behind the scenes of the people and make them look good. That is a core trait of a COO, but what is that about you? Why do you do that?

As a speechwriter, it’s not about you, it’s about them. I worked for one of the biggest digital casting service companies in the world. I’m not an actor. You have to want to have a bit of that in you to be the top dog in some cases. I’ve enjoyed being in that number two role and all the years I spent closely beside you learning in the room or with Brian, Marcelo, Doug, or Mike Pratt. Being number two and behind the scenes has afforded me front row seats to some of the best learning I would never have had otherwise.

You dropped some names and a lot of people may not even recognize them. Marcelo was the CEO of Sprint who you reported to and worked directly with constantly. Doug Michelman was the Chief Marketing Officer at Sprint.

Now, he’s CEO of the Sprint and T-Mobile 1Million Project and Mike Pratt was the CEO of Best Buy and Guitar Center.

You were reporting to the CEO of these major brands and stayed in that background. Is that what got you prepared to be a COO now? At Vancouver Film School, you were the second-in-command there too.

I would have happily stayed in that. The political thing was interesting because I got a taste of it for one year and I felt like I had a newfound appreciation for people who have to be at the top and be the CEO. There is a real degree of scrutiny certainly in politics, but you’ve got a lot of employees that I can see now in my new role. I have a great CEO and Founder in Susan Fox and I’m sure we’ll get to her too. She’s incredible. It’s not easy. Maybe there’s a part of me that feels that in these roles, I can be ten times more effective because that one thing that I don’t have to worry about as much is the optics of everyone else. I can just go and do the stuff I know is what will work and I don’t always have to think about the optics. The optics is a big part of that CEO’s responsibility, right?

Casting Workbook: If you use email as a tool for confirmation instead of communication, you can drastically get your inbox to zero much quicker.

You mentioned Susan Fox and Casting Workbook. That’s where you’re the president and chief marketing officer now. What was it that attracted you to that brand? You left a big role as the second-in-command at Vancouver Film School. When you were telling me about it, I thought it was a small business, but it’s huge.

Thirty years of best and largest in the world.

How many thousands of square feet, employees, and students?

About 250,000 square feet of campus downtown, industry-leading facilities from motion and performance capture facilities to sound stages and animation. Everything Hollywood needs is on one campus. It was massive. It was a real playground and a fun job. I was not planning to leave. I probably would have stayed another 3 or 4 years but then I met Susan. I discovered what they were doing at Casting Workbook, which is another company that had been around for many years. They were doing some breakthrough great stuff with technology and software in the digital space for casting, film, and television. She saw something and believed in me. She nudged me and said, “Would you be interested?” Between her, you, and my wife, I thought, “Maybe I might be able to do this.”

I want to go back a step to Vancouver Film School because I thought of something as well. When you left Sprint in that big role that you had and went into Vancouver Film School, did you not get there the first day, first week, or first month and turn around and go, “What am I doing here? This is way bigger than I thought it was going to be,” because I did. I walked in and I was like, “Are you kidding? This place is huge.” Did you have imposter syndrome? Did you feel like that at all?

I always have that. I dropped out of university and I don’t even have a degree of any kind. I always feel that way. Once in a while, I take comfort when I read about somebody who’s been successful that they’ve had it too. I go, “That’s not bad.” I’m always feeling that I don’t belong, but at the same time, I wasn’t afraid. I just thought, “Should I hopefully figure it out?” I hope so.

When I heard you got it, I didn’t think you belong to them. When I got there and saw you in the role, I was like, “This is his perfect space.” It’s how I felt when you were at Sprint as well. I’m like, “This is absolutely your zone.” When you were moving over to Casting Workbook, I didn’t have any worries about imposter syndrome at all. I was like, “You’ve got this.” What was it that attracted you to Casting Workbook?

I felt that it was a company that was doing this. Who are you going to work for at any time you look at taking that role? You know this better than anyone. Every one of your guests on the show, I’m sure, feels this way. A big part of that decision is the potential or the health of the company, but also talk to me about someone sitting in that number one chair. Who are we going to be working with and reporting to? She’s the most effective CEO that I have ever worked with and I would say she would run circles in terms of her energy and her ability to keep focused and enthusiastic about where we’re going in the mission. She would probably even knock Marcelo out and I didn’t think that guy slept.

I still am not sure that he slept.

He was amazing. She’s the first female CEO I’ve ever reported to and worked for. She’s outstanding and she’s amazing. She’s the best. I mean that.

You do have to develop that yin and yang relationship with the CEO. What does she run in the business? How long have you been in the role now?

Two weeks into the job then COVID hit and the world turned upside down. She retains the founder, owner, and CEO status. In a lot of ways, she is our chief technical officer as well. A lot of the back end and the front side of the technology and the software we’ve created, that transformed the landscape. We were the first to do self-tape mobile apps for the industry and the first to create all this software for casting directors all over the world.

We’re the first to do a virtual casting room. We call VCR software as a response to COVID so that actors don’t even have to go somewhere to audition like they used to. They can do it all virtually like we’re doing through Zoom or their mobile phone and casting directors can do all the things they do. She’s been innovative and progressive that way and has a grasp of technology that I didn’t even see when I was at Sprint. She’s good.

She handles all of that and you don’t go there. What do you manage then?

I manage marketing, message, and operations. She’s trying to leverage my experience over the last several years and different companies helping to systematize the organization more. They’ve been ready for a while for someone to come in and do that. We’re a profitable company and doing well. She left it and handed me something in great shape. One of the things she was never able to get to was when you reach that certain level of growth, systematizing things a little more formally and helping it move out of that small business feeling into and move into a more medium enterprise phase.

With all the stuff that’s on your plate, working with her, and even what you were doing at Vancouver Film School, how do you manage all the different priorities, competing priorities, people, and projects? Do you have any systems or tools that you use to manage your time and priorities?

I was saying that to Kate, my wife, she said, “What are you going to talk about?” I said, “I’m sure Cameron will do the norm.” Most of those things I learned from you, I still top five. You used to go, “Show me. Prove it.” This was something Cameron taught me when I was 23 years old. “Write it on your desk and you check it every day.” It’s the most basic thing. The GS&R, goal setting, and review. You had introduced E-Myth by Michael Gerber, which had a profound effect on me and a lot of us that work for you because we understood that it is those systems that fail, people don’t fail. That carried over.

If you have a good set of goals, review the goals and try to keep them top 3 or top 5. Not much has changed in that respect in years. It was simple and straightforward. That’s how I keep it organized. My phone is my thing but I’m an Outlook guy. That’s mostly how I manage email, etc. My dad taught me something a long time ago that stuck with me and I thought, “This was smart.” He would always say, “Email is not a communication tool, email is a confirmation tool.” If you use email for confirmation and not to communicate, you can drastically get your inbox to zero much quicker. If you make that mental transition, don’t communicate through email, and just confirm information, you’ll be stunned how much less email you have to traffic day to day.

We had a group call with our COO Alliance members and we were talking about using an app called Marco Polo, which is a video chat or video messaging where you just send video messages back and forth to each other, a short 30-second to 60-second video clips. It’s amazing because you get the rest of the picture. When you’re saying something, you see the person smiling when they’re saying it. For me, I can come off as short and acerbic but over a video, I usually come off a little bit better. You got your hat on, you look great and good on video.

I’ve got COVID hair. You don’t want to see it.

What changed then? You were walking into an organization with a vision and a strategy probably in a place that you were excited about, and then a few weeks later, everything got turned upside down. How did that feel? How did you get through that?

We’re still getting through it. Like most companies, you figure out, “Is there some way we can pivot? Do we just have to be patient and wait for this thing out?” Susan and I had a lot of long nights working on that and thinking about that. I felt a lot of pressure to come up with something great and I’m sure a lot of leaders are still doing that and wondering, “In a crisis, could I do this?” I had worked in crises around CEOs and I remember the downturn, I was there for that. Before I started working for you, I remember I worked at a hospitality startup right when 9/11 happened and things crashed. I’ve seen these kinds of things and I’ve watched it, but to go through it, there was no real playbook for this one. In a way, it wasn’t necessarily a crisis. It was like, “What if we change the rules? Tomorrow we say you can’t work together. You have to work apart.”

Casting Workbook: There was no real playbook for this crisis.

This was different from a traditional. You can prepare for things like a bomb, an earthquake, death, suicide, or sexual harassment but shutting down the world, every company is like, “What the hell?” That’s just different.

We were uniquely positioned because of the nature of what we do, which is virtual casting.

Did you start the virtual casting at that point?

No. We were doing a self-tape, which was something we introduced years earlier. This idea now that actors could video their audition and phone it in. This was revolutionary because of Casting Workbook, and then a bunch of our competitors followed suit. Now an actor doesn’t have to try to sneak out of their shift at Starbucks and wait around for their audition. They can do it when they can get to it and send it in by the deadline, and the casting director can organize the files and do it. There was no real reason why we couldn’t continue with the exception that Hollywood had shut down production, which is a little bit of a barrier, but otherwise, we felt common.

We shifted to creating content and we went back to the basics, which was, what is it that we stand for? We stand for actors and casting directors and we want to make their lives easier. We shifted to content. We launched a web series dedicated to the working actor, which went huge. We didn’t even think everybody was doing a podcast or whatever. In this one, we focused on what they cared about most. We transitioned to eLearning and things like that. We’re cautiously optimistic. I would not say that it completely saved anybody but our pivot worked anyway.

This is a different question than most COOs have had to deal with. You’re in a marketplace based in Vancouver and you are location-based, correct? Most of your people come to an office normally pre-COVID?

Correct.

You’re in one of the most expensive markets in the world to live like San Francisco or New York, but it’s also expensive for talent here. We’ve got the competition in the technology space. How have you attracted talent at reasonable prices and got them to drive to your offices?

The fact that we have an office, and we still do but we’re just not there, in Olympic Village down by Granville Island. It’s a trendy, sexy area of the city. It’s accessible by public transit. Since Vancouver has the Olympics as you know, transportation from the cities is great, so that has been helpful. It allowed a lot of our employees to work in remote suburbs and get down there quickly. Susan always embraced a culture and I do too, of working from home. We had a lot of flex time. We were a results-driven company before I got there.

One of the reasons I wanted to come in is it fits with my MO, which is results over how much time you’re strapped to a desk. It wasn’t such a terrible thing. It was good for us. That wasn’t the big challenge. The bigger challenge was waiting out Hollywood trying to figure out when they feel they can go back into production. It was a cool company so I don’t think a lot of employees felt too bad about going to that central location.

It is an interesting location. I’d never thought about offices down in the Olympic Village, but it’s better than Yaletown, which was too busy, too crowded, and too 1999 or 2010. You’re in a newer hipper area. I want to talk to you about something that I’ve noticed over the years and I want to know whether it’s a game that you play or whether it’s real. You come off as either an, “I don’t know what I’m doing here. I’m in over my head or this is a difficult thing.” Is that for show or do you feel that? Is it a lack of self-confidence and it’s real and you’re being vulnerable, or is it the way that you mask the fact that you’re overly confident and you don’t want to come off as cocky?

You’re one of the only people uniquely suited to probably ask me that. Most people wouldn’t dare.

I mean it in an interesting way. I will tell people that I did a phone call with you where I was walking into a speaking event and I said that I was hyperventilating and terrified to walk in. I didn’t know what I was going to do or what I was going to talk about. You had to call me off a cliff and say, “Walk up to people and say, ‘How long have you worked with Junior Achievement?’ and it would turn into a conversation.” I’ve had to turn to you because I’ve been scared about things but I’ve seen you and I don’t buy it.

The answer to that is I always suffer from a degree of imposter syndrome. I don’t have any diploma or anything on my wall that makes me feel conditioned to do what I do successfully. I make a decision early on. I’m extremely confident in myself. We all have doubts. My doubts usually last seconds instead of minutes or hours. I feel I don’t have a choice because if doubt lasts more than seconds in your day to day, it can be crippling so I’ve made a decision.

When you don’t know the answer, I’ve built an incredible network of trusted mentors and people that I can turn to and I can be vulnerable with. The answer is I am vulnerable and honest with people that I have known for a long time and a small number of them which includes you, of course, and you know that. Otherwise, to my staff, my team, the people I work with, and to my sons, I try to project indestructibility and invulnerability.

Iron Man. That makes a lot of sense. It lasts seconds. You open up, you question it and you’re curious, but then you move on quickly, whereas I stew on it for years.

I moved past it. You have to.

You are one of the strongest leaders and one of the strongest performers I’ve ever met. I remember doing a reference check on you with the CEO of Hcareers, that hospitality group that you work with. Mark Hamilton, was his name and I called him up.

That was more than many years ago. How do you remember that?

I had to put my career on the fact that I was hiring you. I did seven reference checks on you and you stood at my desk. I called Mark Hamilton and I said, “I’m calling about Christopher Ian Bennett.” He said, “You’ve got my best guy.”

Is that what he said?

That’s what he said.

Casting Workbook: At the end of the day, someone’s true intentions as a leader matter more. If you can identify and align with those in a leader, the personality stuff works itself out.

He was Scottish.

Everyone probably feels like they lost their best guy when you’ve moved to the next brand.

That’s incredibly kind of you to say.

Where do you struggle as a COO now? What are you working on? We all struggle. Everybody has their parts that we’re working on that are getting better. Even a pro athlete like Beckham, who is one of your favorites, had a coach. He’s always working on his game. Where are you working on your game?

As you know I even reached out to you. I was exploring, and I have for a while been on a lot of first dates with executive coaches. I wasn’t quite finding the thing that I was looking for in that respect. I’ve been trying to do a lot of professional development. Once you’re in that mid-level executive director and VP level, you go to a lot of conferences and workshops that the company pays for. They’re okay, you do okay and you read a lot of books, you get to the C-Suite and you’re like, “I need to go to that next level.” I thought an executive coach could be effective. We had them at a few companies. I worked with our HR and a few of them over the years when I was at Best Buy.

I was at a leadership level where you had one assigned to you from the company. Mike Pratt believed in that and it was something that was important to him and for all his team below him. At the Guitar Center in the US, we had that too, but I’ve always felt they worked for the company and they didn’t necessarily work for me. I felt like often there was a lot of, “Why do you think you’re doing that? What do you think is the reason?” “I don’t like the guy.” I don’t like that.

The Socratic method.

If I want a coach, I want a coach to bench me and say, “Your jump shot is terrible right now. You’re dragging your elbow and your follow-through,” or whatever. I can take it. I was looking for someone who wasn’t afraid to critique me and on a lot of these first dates, they were trying to woo me and I didn’t want that. I wanted somebody to tell me you have a whole lot to learn. I wasn’t able to find them. I explored form groups and things like that. I wanted a couple of those dates, but the challenge was there were a lot of experienced people sharing their expertise. I didn’t feel I was in a position to give some guy advice on his company as well. Certainly not yet. It didn’t go anywhere. The real answer is, I’m not doing enough and it’s the number one thing on my mind now.

I would disagree that you don’t have and you shouldn’t be giving people advice. You should be sharing experiences in similar situations and let them draw advice from that. You have in this case and I can see you learning, which is an old joke of ours. As a COO, you want to be giving other COOs your experience and share. Let them draw from what they can and by the way, you’re not looking for a coach or looking for a mentor. You don’t want someone to use the Socratic method and ask you a lot of questions to get you to figure it out. You want somebody who’s been there that can give you the shortcuts and the cheat sheets and can show you where you’re already making errors.

I am a copycat. I am a combination of years of working with Mike Pratt, Marcelo, Doug Michelman, and you. I copy and it works. I’m looking for someone that will give me close access so I can learn. I know how to ask this question and get myself in situations to learn. I know where I’m not strong and finance being one of those areas. That is the challenge. I don’t have a good mentor at the moment that is accessible and available to me easily in this role.

You met my mentor years ago, Gregg Johnson, who was being groomed as a second in command at Starbucks. Greg mentored me for eighteen months. I would do a call with him every month and an in-person meeting every quarter. I would go down to the Starbucks’ head office for one quarter and he’d come up to the 1-800-GOT-JUNK? office. We’d alternate and he was somebody who’d been in the path that I was going in and I wanted him to keep teaching me. He didn’t ask me many questions. He would take a look at what I was working on and he would show me how to do it faster, better, and simpler. That might be where you are as well.

Frank Palmer is someone I lean on a lot creatively in a certain way I have to wear my CMO hat. I love Frank. He’s an iconic guy to learn from. He’s making his own second act in his creative career, which is exciting. In that respect, I’m learning and trying.

Where do you think that you’ve grown the most in terms of working with the two CEOs, the CEO of Vancouver Film School, and Susan, the CEO of Casting Workbook? Where have you grown and adapted to work with those kinds of leaders?

I would say probably less at Vancouver Film School because the owner there was hands-off. James Griffin is a wonderful man and a brilliant man. He did a great job of letting his leaders do what they do. I would say I grew the most in my time, from Mike Pratt right across to Doug Michelman from Sprint, who I think of sometimes as a second dad and he’s a tough guy. He taught me where Mike would have allowed me to be close to him. He was a great guy to study and learn from and had gentle patience about him and wisdom. Doug had an instinct, an impulse, and a temperament that demanded results and demanded that you keep up with him, and some people couldn’t do it. I learned that I’m way stronger than I thought I was.

Personalities don’t matter. Results matter and someone’s true intentions as a leader matter more. If you can identify and align with those in a leader, the personality stuff works itself out. Sometimes you’re going to like each other and sometimes not. He was a challenging guy. I’m trying to say that in a nice way. He goes, “What do you mean?” I love him. I joke that he’s like a dad to me too, in that way but he demanded things and I grew a lot from him because if I didn’t, he would have fired me.

I’ll put some color on that as well. People may not realize that Sprint at that time, was the 82nd largest company in the United States. You’re talking about a guy who is making approximately $2.5 million a year in salary. They were in a turnaround to try to sell the company to T-Mobile moment under a fierce CEO who had been brought in by SoftBank to turn the place around. These guys weren’t messing around. You were working with a team of at times probably seeming disasters and corporate people but these were serious executives with serious skills that were under a lot of pressure to get things done. It must have raised your game.

It was a brand war between T-Mobile. You’ve got Claure, Ray, and Legere before they merged. Every day was Coke and Pepsi. I was on the frontlines of this battle and Doug was an incredible commander. You had to keep up with him and he would tell you when he was not happy. I would go home most days, and I would know what I had done wrong because he’s not afraid to voice that. I ended up liking that. I ended up thriving under that. I never had that before.

You manage somewhere in the middle the way you lead, and he was like, “Here’s what’s wrong with this. Go fix it.” I grew the most because of my personality type, I do well under that. When I bought the time he got me ready. By the time I get to Susan, she’s not like that. She’s collaborative and extremely open to new ideas. She’s who I try to aspire to be now. She could be talked out of something. There’s a real humility to the way she leads, but I wouldn’t have been able to be effective that way unless I had Doug first.

What can you teach us about working at that C-level of a major corporate environment and dealing with politics? You were working fast in that place and you were in a division that had to move fast. You’ve got the ear of everybody there. How did you navigate all the politics that most people get caught up in?

I felt that in my years with Best Buy and with Guitar Center in LA, politics was something where it was my job to make my case for my department and make it stronger than the other leader in that department. Everything I think about at the time was about, “I’ve got to make a better case. I’ve got to win the ear and the competence of the CEO.” After I left Sprint, I realized more than ever before the importance of relationships and how everyone is battling something.

I mean this genuinely. Incredible things happen when you understand that the guy over in IT, in digital customer service, or HR is genuinely and truly aligned with the same objective you are. If you’re partners and you figure out what’s driving them, or what they’re battling, you have way more in common with them. I ended up finding and learning about that more at Sprint. I felt every one of us was staying up late and working these 15, 16, 17-hour days because we all wanted the same thing. It was awesome. I don’t know if I’ll ever have another job like that but it was a good learning place.

You’re right that everybody is trying to battle through something that they’re working with. Everyone is also battling with some personal issues as well. They’re struggling at home, with their family, spouse, kids, or with themselves. We’ve got to be empathetic to the human struggle that our team goes through as well.

Casting Workbook: If more business leaders went into politics, our government would be far superior than it is today.

How much of that do you give up? I always feel like I’m not supposed to let them know what I’m battling but I’m supposed to figure out what they’re battling by doing that and learning when I can be a bit more vulnerable and when I’m overthinking. The trick is I don’t know.

You can be vulnerable with your weaknesses, but not necessarily with your fears. You can’t necessarily tell them you’re scared. This is not about your company but I’m making up an example but you can’t say, “I’m worried that the company is going to go bankrupt.” That one you’ve got to keep with the CFO and the CEO behind the scenes.

They don’t like that when you say that.

You’re allowed to say, “I suck at financials and I don’t know how to read a balance sheet but I’ve got a good finance team that can so I focus on this stuff.” “Susan is great at technology and I’m not.” You’re allowed to say that. Do you still tell them that you don’t like vegetables?

I eat like a teenager. It’s terrible. Thank God, my wife makes a veggie shake in the morning, but my diet is cheeseburgers and cinnamon toast crunch.

You’re also in great shape. Maybe it will catch up with you. You’re lucky. It’s amazing still what you’ve done at such a young age. It still pisses me off. You’ve done so much work. Did you learn from being in that politics role and do you carry any of those lessons into your role as a COO now?

How you execute a campaign is to win over your district or your writing. To win over a demographic is exactly the same construct as designing a message to keep your customers or to attract new customers. It’s the same stuff and that’s why I ended up going into communications and marketing from there because the parallels were so much. From a leadership perspective, I think of my opinion now. If more business leaders went into politics, our state of government and our state of effective government would be far superior than it is now.

No matter what we think, we elect people in a popularity contest, who we like and we don’t stop and go, “Aside from showing up and voting on important legislation, what does this person need to do to be effective in representing me in Washington, Canada, Ottawa, or wherever?” Business people get that. The C-Suite understands quarter by quarter, year by year, what are we trying to do and how are we getting there? We don’t get a lot of exposure to that publicly. That’s still a bit of a mystifying area that people don’t understand. I’m talking Canadian politics right now and I don’t want to get too political. Trudeau, whatever you think of him, he’s a likable guy. I don’t think he’s a total idiot or anything like that. At the same time, he’s not qualified to do that job yet.

At least he’s likable. Talk about US politics, we’ve got somebody who’s not likable and isn’t qualified as well. I don’t want to get into politics either. Here’s something I want to ask you from politics that occurred to me. You are one of the most talented writers and communicators. I’ve seen you in stages. I’ve seen the work that you’ve written. You’ve done a copy for me. We worked together for years. I’ve seen the work that you’ve done with Sprint. You’re good at that. What are the tips that CEOs and COOs can use on communicating when they’re doing things like a State of the Union with their company or town hall meetings when they’re listening or in written communication? Can you give us some cheat sheets on how they can be better? Where do they classically screw up?

Three things. If you have a pen or pencil, write these down. Number one, clear message. Number two, clear messenger. Number three, clear message pathway. A clear message is pretty obvious. Clear messenger is where a lot of people stumble. They think that they are supposed to go, “I’m giving the speech. I’m writing this email to my customers. I’m standing up in front of my employees. I’m the messenger.” That’s rarely the case. Three, a clear message pathway is, what vehicle are you choosing to deliver that message?

If you go back to point number two, most of the time, your voice should be from the perspective of your audience. You need to speak from a place of identification with who you are trying to convince or deliver a clear message to. You should always speak from the perspective of your customer. You can’t say, “We understand our customers. We love our customers. We’re going to look after them and give them the best service and satisfaction they’ve ever had in their life.” You can’t do that. You can’t say it. You have to demonstrate that by understanding their position. In essence, clear messenger means how well do you know your audience? Have you figured out the way in your voice to project that?

Pathway, sometimes, where can you do a speech or a talk? There are many great ways to do that now like social media, email, a venue, a public event, a staff meeting, or a phone call. You have to entertain. How do I want to deliver this message the most effectively? Those three things right there come from politics. If you put those things on the board first and then start to break down from there, you’ll have the tenets of a great talk.

I remember when I was coaching Marcelo at Sprint and also his second in command, Jaime Jones, for about eighteen months. I was pushing Marcelo a number of times to do some video messages to the company into the team. I said, “You come across so much better with energy and passion than you do over in writing.”

Jaime was an amazing guy.

I wanted Marcelo to do it. Jaime did it with his team too. I was trying to get Marcelo to do it as well. You said something about the messenger. You feel like I’m supposed to be the one but that’s not always the case. What did you mean by that? Is it that if you’re the CEO, sometimes you can get someone else to speak for you?

The audience carries your message.

The messenger isn’t the person delivering it, it’s the people that are hearing it and that are then taking it as the messenger.

If it’s delivered clearly, it is your audience who becomes the messenger. They become the mailman that will deliver that to even more of your audience. When you understand that you are not the messenger and your audience is, you have to speak in a way that they feel like they identify with it and it connects with them. They will walk out of the room and it won’t have gone over the head and going, “So what?” They’ll talk about it. They’ll evangelize it for you. They will become the messenger.

I read an interesting book about that called Trends. It talked about how women communicate ten times more than men do. If you’ve got a message to deliver, deliver it to the female audience because they’re going to multiply it much faster than any of the males that you share it with. If you have any points to speak to, speak to the females in the group. Women don’t stop talking in a good way. If you and I stayed at a hotel and then Kate and my girlfriend, Ashley, stayed in a hotel and we stayed at the best hotel in the world, you and I probably wouldn’t tell anybody. They would be talking about how great that place was for years. If you’re the hotel trying to get a message across, you want to deliver it to the female audience and speak to them because they’re the ones that, as the messenger, are going to multiply it much more than you and I walking out of the room or even going to do.

I don’t think that’s untrue but I have seen a lot of males who, whether they’re happy with something or they’re not happy, can vocalize it. One thing I have observed and this is true, I’ve read it and I have observed it. Women, when they are in a room, will seek to identify who they might already know or who they can connect with or have something in common within their network or otherwise. Men, when they walk into a room, will often try to determine who’s the most important person in the room. Their perspective and how they will then receive information are different. That’s tricky. In a lot of ways, that means you have two messengers if you break it into that the gender-based, which good messengers need to do.

Christopher, final question. If we were to go back to when you were 21 and you wanted to give yourself some advice, if you were going to listen to yourself, what word of advice would you give yourself as a 21-year-old that now you know to be true but you wish you’d known at 21?

I write in a journal or I keep a log every year of the things that I’ve learned along the way. I do reflect on this fairly often. Usually, it’s a week or a month behind me. I would probably say, “You don’t need nearly as much sleep as you think. You need way more sleep than you think.” I don’t mean to contradict those two things. When I was young, I have under-appreciated how important my mental state was and how it directly attributed to how creative, effective, or how great I can be in problem-solving related to my diet and my sleep. I would probably advise myself to take that a bit more seriously. Maybe I could have been on your show a couple of years earlier. I don’t know.

I’ll tell you one. When I was a kid, I could never ask a girl out. I always had a crush on the girl and I could never take the step. You took the step and asked out the girl and have ended up with an amazing life partner, Kate. I don’t think I’ve ever said this in 110 episodes of the guests I’ve interviewed but she found an amazing partner as well. I’m happy for both of you.

Thank you. That means so much to me. If you ever get a chance to marry up and someone way better, grab it. My granddad always said, “Get the girl, grab the money, and run.”

You both did, in this case. Christopher Bennett, the President and Chief Marketing Officer for Casting Workbook. Thank you so much for being with us on the Second in Command podcast.

I love you. Thank you. I’m honored. This is my first interview where someone interviewed me. I appreciate it.

Bye, everybody. Thank you.

Important Links:

• Christopher Bennett
• Casting Workbook
• 1-800-GOT-JUNK?
• The 7 Habits of Highly Effective People
• 1Million Project
• Guitar Center
• Vancouver Film School
• E-Myth
• Marco Polo
• Marcelo Claure – LinkedIn

About Christopher Ian Bennett

With a career that began as a rookie political speechwriter, Bennett attended Trent University and developed his love of writing into the Public Relations and Corporate Communications space.  He worked several high profile national political campaigns including for the Deputy Prime Minister of Canada, The Hon. John Manley, and served several cabinet ministers and US Senators before being elected to the Green Party of Canada’s National Council and becoming the Leader of the BC Green Party, in 2007.  (He holds the record for the youngest leader of a Canadian Political Party at just 27 years old). In 2011, Business In Vancouver Magazine named him to their annual “40 Under 40 List”.

Stepping away from politics, he moved to California where he began to build his career in Communications, Marketing and Public Affairs for some of North America’s biggest brands, including Best Buy, 1-800-GOT-JUNK?, Guitar Center, and Sprint. 

In 2017, Bennett left his adopted home of Los Angeles, and moved back to BC. He was named Executive Producer and Creative Head for the Vancouver Film School, and in just 3 short years, he positioned the school to brand new award-winning status globally, including for the first time: “Top 25 Global Film Schools” & “Top Canadian Film School” from Variety Magazine, “Top Canadian Film School” & “Top 10 Global Film Schools” by Hollywood Reporter, “#1 Animation & VFX School Globally” by Animation Career Review Magazine, “#1 Game Design Program in Canada” by Princeton Review Journal. 

In March 2020, Casting Workbook Founder and Owner Susan Fox announced Christopher as their new President and Chief Marketing Officer.