Bossing It: Why Cynthia Heyd Believes Open Conversation Is Critical
Cynthia is an innovative production leader with more than 30 years experience in the advertising industry working with TV, digital, radio, web content, and experiential projects. She has driven production evolution in management roles at BBDO, Y&R, CBC, and TAXI Canada.
She launched a number of companies after leaving the agency world in response to the ever-changing marketing landscape. Today, she is at the helm of The Deli Production Agency working with agencies and brands to bring ideas to life.
Cynthia is passionate about tackling seemingly impossible projects. Whether embarking into an unknown challenge or a simple ask, her production management and creative problem solving, paired with her talented team of producers and directors, enables her to customise and lead the best team for any project.
Her numerous awards include Cannes, The One Show, The Art Director Annual Awards, and more.
LBB> What was your first experience of leadership?
Cynthia> It wasn’t great to be honest – I was thrown into a role that I wasn’t ready for and I had no experience at all. There was no training, and the expectations were that I would thrive – I didn’t. For me it was too early, and I struggled with the balance of leading a department and wanting to just work on projects. I was also managing those with more experience than I had producing so that was super challenging. I didn’t love it at all! But I learned from that.
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?
Cynthia> That’s a great question as no one trains you to take on this role and even to this day I am learning more! I really found I had to explore this on my own. I took some guidance/learnings from the creative directors I worked for – some I would never want to emulate and others that I thought were gurus – those that made me feel uncomfortable and pushed me were the ones that informed my leadership style the most. I knew I was more quiet than loud and I leaned into that trait. Each experience informs your leadership style.
LBB> What experience or moment gave you your biggest lesson in leadership?
Cynthia> FAILURES! My biggest AHA moment was a bad review and honestly that has informed me moving forward. I was oblivious to how I was doing and thought I was doing great – why else was I promoted? In fact, I wasn’t. It was a gift to be told that I was failing, and I was able to take this and course correct- it also helped me understand the expectations. This has made me better able to deliver bad news as well as trying hard to clearly set expectations for others. Sounds simple but it’s not. I also had an experience early on a huge project where I was micromanaged and felt my credibility was always in question. I knew I didn’t want that for others. I wanted to create room for others to grow and learn without fear.
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?
Cynthia> Well, I am a driven personality and I have always had the next step in my sights. At first that manifested in wanting the bigger projects, the challenges to build skill and reputation. As a producer, I loved being the hub for a project; the translator to make sure everyone was getting what they needed and that the creative was as great as it could be and I loved the role. I also LOVED the business side of creative so my ambitions presented themselves quite early in that I wanted to be part of a team or in a position that grew business as well as delivering great work.
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?
Cynthia> That’s such a great question and my experience shows that a lot is part of who you are BUT training needs to happen. If a person is excelling at their role in doesn’t mean it translates to a leadership role – I really think if this is to happen that person needs to be set up for success but that doesn’t always happen. I stepped outside advertising for a couple of years and worked for CBC. I was fortunate to get some leadership training that was invaluable: business training, leadership skills help, speaker training etc.. There are a lot of areas that could help being exposed to while you are working on projects to better prepare you for leadership such as being involved in the overall business objectives, the financials, and the strategy for the project. As a producer this is often not always offered, and it should be in my opinion.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Cynthia> I have a huge tolerance for allowing others to figure things out themselves and the balance of guiding and not micromanaging is always a challenge. The question of when to step in is tough. Some feel a good leader should step in quickly but I don’t. I need to feel 100% crystal clear on the issue before I act and that can take more time than others see fit.
People management is also challenging – It’s never easy and I always struggled with giving the right amount of time – there is always so much to do when you are in a leadership role and 1:1 meetings or status meetings or regular touchpoints often are the first to fall off. In our industry personality has a great deal to do with success so understanding those dynamics are very important. I try to spend time with staff and encourage them every chance I get even if it’s a quick phone call. They need to feel supported, challenged and valued.
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?
Cynthia> HA ALL THE TIME! It’s important to fail and learn from that. Making mistakes is natural part of learning – the key is to not make them again. Standing behind your goals or the company goals has to feel right. I’ve had experiences where I didn’t agree with the direction and yet didn’t speak up. I have learned that this is so important even if it sends you out the door!
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?
Cynthia> Both I think. There should be a balance, but I really believe that authenticity is important. Your team and your peers need to know who you are. I will say though that taking time to consider responses is important but again staying true to yourself in the response is always the best approach!
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?
Cynthia> Yes I had mentors who were amazing to me. I also sought out mentors from different areas of my work to get a more wholistic view. My head of departments were nurturing, and we had so much fun while I was learning. Fun is important! Pat White, Winnie Alford, Peter Barchou to name a few. And most recently my business partner, Kevin Saffer, who I rely on immensely.
At this stage of my career, I am more in a mentorship position than ever. I love it and have focussed on being a guide for new employees as well as the senior employees. Our business is such a people business so helping those through difficult situations or how to approach a complex problem gives me great career satisfaction.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Cynthia> Open conversation is critical. This is a people first business and having strong relationships is what can help you through difficult times. Treat others as you would like to be treated.
Jumping in if help is needed is also important
Trying to inspire and staying ahead of trends is imperative in our industry as it is always evolving. Having some view to changes can help you navigate them. I also try to find the piece that excites me and talk about that. Honestly if this business wasn’t changing so rapidly it might not be so exciting – even to someone that’s been in it for so long! Sharing my excitement is contagious I hope ☺
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Cynthia> We at THE DELI are always looking at this. We participate in the hire higher initiative and have provided opportunity for young producers and directors to shadow our people. It’s a process of training and providing opportunity so we also try to have conversations with clients about this. Our team is diverse but we can always be better.
LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with increases in remote and hybrid working patterns?
Cynthia> This is important and I’m happy to say that our company culture is all about the people. We want to be kind to our people but firm on expectations. Everyone knows they can approach anyone at our company. We support each other and we LIKE each other- our team goes back along way as many of us have worked together in other roles in other companies. I believe that we collect our tribe as we go through our careers and this is an example of that. We are a family. We work remotely well but love to be together now that we can.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Cynthia> I’ve read a lot – favourite reads include Janet Kestin and Nancy Vonk – Darling you can’t do both, Arlene Dickinson All in, Sheryl Sandberg Lean In: Women, Work, and the Will to Lead, Brene Brown Dare to lead to name a few. I also follow a lot of leaders from different businesses on social as well as LinkedIn.
The other resource is just talking with others in the role. Our industry, while competitive has some amazing men and women and having regular check-ins to chat is great. I always love that.
