Bossing It: Jeff Dack on the Keys to Genuine Leadership

Jeff Dack is the chief executive officer at Wunderman Thompson Canada, where he is responsible for overseeing the strategic vision, growth, operations and client relations for the agency’s Canadian offices. He leads a team of talented executives across Toronto, Montreal, and Vancouver, with a unique breadth of end-to-end capabilities to help drive growth for the agency’s clients and people, by delivering breakthrough creativity, data and emerging technology to reset customer experiences.

With over 20 years of extensive experience in creative strategy, integrated marketing and business development, Jeff brings a consistent record of delivering profitable growth, a wealth of deep marketing services experience, and a focus on culture that will fuel Wunderman Thompson’s growth across Canada. 

Jeff is based in Toronto where he lives with his wife and flourishing three children.

LBB> What was your first experience of leadership?

Jeff> Babysitting my siblings at 11… which evolved into being a staff member at various summer camps… But in all seriousness, in my career, I have been fortunate to have had great mentors who saw an ability in me to lead others. I have been in some form of leadership in agencies since my mid 20’s. The first experience I had managing other professionals was as an ACD (associate creative director) in a boutique agency in Toronto where I helped guide other creative teams as best I could at the time. 

LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?

Jeff> Having worn many hats in the marketing/advertising/communications/media space and doing so with no real formal training, I have deduced that I am an observational learner. I watch, decipher, and emulate. Simply put; I have learned about leadership by studying others I believe are doing it well. 

But I also believe the most important element is recognising in the moment how a particular leadership style and approach makes you feel. Being able to remember what it was like to be a copywriter just starting out, working for entrepreneurs and witnessing their level of commitment and effort, in contrast to being a marketing executive in a CPG working for a “command and control” style leader, or being fortunate enough to lead a large Canadian agency that is part of a Global matrix and having arm’s length leadership, I have taken “best of” and “worst of” learnings from all of these experiences and tried my best to lead with empathy, enthusiasm, and a love for what we get to do every day. 

The quote I’ve seen bouncing around social media is “Be the senior you needed as a junior” and it’s a beautiful summation of the way I try to lead.

LBB> What experience or moment gave you your biggest lesson in leadership?

Jeff> Once you 'make it' to the grown-up table – which I guess I’ve been sitting at for the better part of the last decade – you learn quickly that while the responsibilities are higher stakes and the scale is much larger, the work is really the same. The learning (for me) is that leading a large agency is the same as leading a small agency. Just a different scale. People are still people, and no matter their title, or experience, or what they do, they want to be motivated, inspired, engaged or they will never buy into a vision. 

LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?

Jeff> Conceptually, I always knew I’d lead a group, but specifically if you had asked me how I’d get here, I couldn’t have answered you. I grew up in the industry believing (as I still do) that if you try hard, produce great work, put your hand up for everything, and do it all with the right attitude, then good things happen. And those good things continue to happen today so I will likely keep doing that.

LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?

Jeff> Today, more than ever – especially after the last year and a half, it’s genuine leadership that is the key. One can absolutely learn certain leadership strategies and techniques (as I have) but if you as a leader are having to put on a façade that isn’t a part of your personality, people aren’t going to buy into your vision. 

Gone are the days of putting on your work clothes, your work face, and playing the role. We’re all behind screens, the great resignation is on, we need to be self-aware, true to our values and just be honest with people. I think the best leaders are those who connect with people in the same way no matter who they are. From my perspective (and feel free to ask those who work with me) I speak with clients the same way I speak with my management and the same way I speak with new team members. I am consistent in approach and that approach is a reflection of my personality. Perhaps cliché, but being yourself, as truthfully as you can be in your role, is key to being a confident leader today. 

LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?

Jeff> There are always parts of the job that I am not “allowed” to share. As a CEO I have certain financial responsibilities and am privy to proprietary intel that at times I wish I could share, but simply can’t. That’s the part that is challenging – when it’s “I can tell you X but can’t tell you Y” even though I am trying to build and maintain trust with team members. 

LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?

Jeff> We have hired a lot of people this year. That is because we have lost a lot of people this year. It’s not unique to our agency, it’s a reality everywhere. But I do feel like I fail every time someone leaves us. It’s not personal, and I never begrudge someone for moving on to another opportunity, I just wonder what we could have done differently to retain that person. We learn, adjust and move on. That “failure” becomes an opportunity. 

LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be transparent as possible in the service of being authentic? Or is there a value in being careful and considered?

Jeff> To frame it another way from my previous answers, I lead a 230 person company from my bedroom these days… if you can’t be open and authentic now, not sure you ever will be.

LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?

Jeff> A mentor of mine once told me “Make sure you have learnt everything you can at a place before you move on.” 

I have been working in marketing services at agencies and client-side jobs since 2000, so I’ll be going into year 22 soon enough. In that time, I have worked at nine different companies with multiple roles. In every job I’ve had a mentor – either someone I sought out, or they found me. Either way, I have incorporated parts of their approach into mine. I am a reflection of those I have worked with, worked for, and worked in the service of.

LBB> It's been a really challenging year - and that's an understatement. How do you cope with the responsibility of leading a team through such difficult waters?

Jeff> Nobody has been through this before and there’s a strange comfort in that. I know that if I lead as I would want to be led, with empathy, inspiration and an insightful gut, fuelled by data, we will be right more often than not. I believe in our team, and I believe in myself. And having been side lined myself a couple of times over the last decade, I know how fleeting it all can be, so I never get too comfortable. Like I mentioned earlier, I continue to put my hand up, try hard, and focus on the work and the clients for whom that work is for. The world is chaotic “out there” but “in here” those are the things I can (sort of) control.

LBB> What are the most useful resources you’ve found to help you along your leadership journey?

Jeff> Nothing too profound here… but read from, listen to, and watch those who do it (whatever your “it” is) better than you and learn from them. Study the greats. Whether it’s a book on the craft of what you do, a podcast about trends, a documentary about an adjacent issue, at Wunderman Thompson we are content creators and as such, big time content consumers. 

Thank you LBB for inviting me to share these thoughts. So many people have helped me along the way, so hopefully there’s a little nugget in here that helps someone else.