Welcome to The Inspirational Leaders Series, a collection of short interviews with sharp, impactful leaders I know and respect—because the business world needs more refreshing people like them.
👋🏼 Meet Jason Cyr, Senior Director, Head of Design - Cloud and Network Security at Cisco. I’ve worked with him through the years to help him elevate the skills of designers and adoption of design thinking across Cisco. He’s a down-to-earth, glass-half-full kind of person who cares a lot about creating healthy, vibrant design team culture. And, he’s a great conversationalist, to boot. You’ll see in this interview how attuned he is to what teams need to thrive creatively. Take note!
WHAT DOES LEADERSHIP MEAN TO YOU?
There is a tension in leadership that makes it special. As a leader you need to be accountable while not holding responsibility. This means you need to trust the folks who are responsible (your team). It means when things are successful your team gets credit, and when things go south, you take the heat. It means that for you to be truly successful, your team needs to be successful, and you simply need to be of service to them by doing whatever it takes for them to be successful.
WHAT'S A SONG THAT CAPTURES HOW YOU FEEL ABOUT LEADERSHIP?
There were a few that came to mind, and all are super cheesy lol. As I thought about answering all these questions, a lot of what I realized is (you will start to see this pattern) that I just want to be of service to the people on my team, I am here to do the hard things, to prop them up, to take the heat… etc. So some songs were things like Lean on Me, Whatever it Takes, Count on Me, and You Will Never Walk Alone.
WHAT HAVE YOU LEARNED ABOUT CULTIVATING CREATIVE PROBLEM-SOLVING IN TEAMS?
This is one of my favourite topics and something I have worked with you, Teresa, for years. It’s my passion for sure and I could go on and on about all sorts of things related to design thinking, reframing problems, double diamonds etc… but I think there are three things that I find particularly important.
First and foremost is safety. People need to feel safe enough where they are not self-filtering their ideas, they need to speak up, be ok with saying things that seem silly, and embrace the random ideas of others.
Diversity! Bringing a group of diverse contributors to tackle a problem often leads to magical results especially when they have the safety mentioned above.
Finally, we need constraints. I used to think I needed to create all sorts of space for teams to be creative, but really a little bit of heat is needed for things to really come together. Time pressure, resource pressure, etc, lead to creative ideas and can be some of the most rewarding experiences for creative teams. It can be a little addictive really. Just listen to stories about teams like the cast of SNL who crank out crazy amounts of creativity on a weekly basis…
WHAT DO YOU FIGHT FOR, AS A LEADER?
Building on the above, I fight for the things that let my team be successful. As a design leader this often means making sure design is included at the right time and in the right way. It means insisting my team is treated with respect and can work in an inclusive environment where everyone is seen, heard and allowed to deliver their unique value. It can also mean fighting for ruthless prioritization in times of resource imbalance and often it means not fighting for anything and just saying NO.
WHAT DO YOU HOPE PEOPLE WILL REMEMBER ABOUT YOUR LEADERSHIP?
I try very hard to be honest, selfless, and optimistic/enthusiastic – this is how I try to live my life every day, and I hope I would be remembered for these things.
