Bossing It: The Power of Empathy with Kit Winter

Kit Winter brings a holistic understanding of the needs of brands and artists in the creative music process to provide creative musical solutions for branded content to her role as executive producer at Squeak E. Clean Studios. 

With over 20 years of experience in the advertising industry across the agency and post production sides, Winter has returned to her roots in music after previously serving as Executive Producer at Human Music. She is known for her strong leadership background and deep understanding of the creative process making her an asset to the team. 

Coming from a family with an advertising background, Winter was inspired early on to pursue the industry. She studied marketing at the University of Richmond and landed her first gig at BBDO New York where she worked as an Account Supervisor and Manager for top brands including Gillette, Oral-B and Lowe’s. After five years, she stepped into a VP, Account Director role at Arnold New York, managing the agency’s Hershey’s account. Combining a lifetime passion for music with nearly a decade of experience in advertising, she made the move to the music side of the industry as Executive Producer at Human, where she oversaw the planning, development and execution of music in advertising for operations. Soon she transitioned back to the agency side at Hogarth Worldwide, serving as the Director of Client Services and leading the team of people responsible for managing global productions across key clients such as Nestle, Volvo, Bayer, Galderma, Bank of America, Rolex and Johnson & Johnson.

LBB> What was your first experience of leadership? 

Kit> From a technical standpoint, in high school I was on the student council, so that was my first leadership role. I actually minored in leadership in college as it was something I was always curious about and interested in. 

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? 

Kit> By constantly watching everyone around me in any form of a leadership position, I think that’s really the main way you learn how you want to be and definitely how you don’t want to be. Reading about it as well, educating myself on what makes a good leader was immensely helpful. Also having my own successes and failures was huge in shaping my journey, lots of trial and error for sure.

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

Kit> I was fortunate to go to a week-long, offsite leadership retreat that WPP provides for client leaders across their agencies. It was by far the most profound experience in understanding interpersonal communication and how important that is to building relationships and developing who you are as a leader. 

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? 

Kit> It’s a mix of both I think. Empathy is a huge part of being a good leader, being able to put yourself in someone else’s situation and see it from their perspective, and that doesn’t come naturally to everyone. The further along you get, the more you realize good leadership takes a lot of time, attention and practice. It’s very intentional. I guess that’s kind of the crux of what it is; to be a good leader you have to intentionally be trying to be a good leader. Good leaders make it look so natural, but like any talent they are honing it and preparing when their audience isn’t around. We only see the performance they want us to see.  Being a leader isn’t about being the smartest or most experienced person in the room, it is the person with the ability to lift up everyone up and orchestrate whatever is needed for the team to achieve the collective goal: to motivate, direct, inspire everyone so the team as a whole is greater than the individual parts. 

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

Kit> Right now two things are constantly on my mind: how to lead a team remotely and how to avoid letting personal life affect too much how I show up each day. As a mom, some days I show up to my morning call with the team and I’m so tired, stressed, or overwhelmed. I was struggling with that right after returning to work from maternity leave and I had a leadership coach wisely explain that as a leader, the energy I show up with every day has the power to set the mood for everyone else. So back then, I’d have to go into the restroom before entering my team’s area and shake-off the hard morning with a newborn and come in with a smile and good energy. That is not at all to say it's about hiding the reality of life and what we go through, it's just knowing when to let that out and knowing when it's more important your team starts the day with positive and motivating energy. In regards to leading a team remotely, I try to initiate more 1:1 time with team members to check in and then when we are all together trying to be as present as possible. 

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? 

Kit> 100%. I had a really hard moment in my career where upper management handled something very poorly with my department when I was on vacation and I didn’t do my best to quickly address it/support the team as it unfolded. We are all human and are going to make mistakes, what’s important is that you own it and talk about it to your team. They need to know you can be self-critical and are still learning and growing yourself. In that instance that’s what I did, I called a department meeting to recognize the situation was handled poorly. Relationships with your team are no different than personal relationships: Recognizing and Repairing are foundational to healthy relationships regardless if they are personal or professional.

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? 

Kit> Being caring, considerate and curious are the three things I think are important in leadership. A good leader knows every situation is unique and needs an intentful approach based on the desired outcome. Similar to being a parent, someone younger in their career may not quite know what is best for them in the moment and has to trust those that are ahead of them or privy to more information to them. Sometimes openness is required and sometimes you have to protect your team more.

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?

Kit> I’ve been lucky to have great bosses over the years that I learned so much from in all aspects of leadership. Some were great culture leaders, others were incredibly talented with clients. I just tried to take as much as I could from each of them, but have not had one single mentor. I was a mentor with Advertising Women of New York and really enjoyed the time with my mentee. It was a great way to put all my knowledge of the industry to use in terms of how to navigate asking for a raise, a tricky boss situation, etc.

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

Kit> It weighs on me for sure, much more than the work or clients. What we do is we talk about it, to recognize what is happening in the world and weighing on all of us, even if it is a difficult or uncomfortable subject. For people to know it’s okay to be mentally and emotionally exhausted or struggling and know they are not alone and open the lines of communication.

LBB> This year has seen the industry confronted with its lack of action/progress on diversity and inclusion. As a leader how have you dealt with this?

Kit> There will never be an end to what needs to be learned and understood and then applied in the area of diversity and inclusion. Both personally and professionally it is an on-going journey of constantly seeking out different perspectives and seeing things through a different lens. Learning how my place of privilege has the ability to impact someone else and the importance to use my voice in a leadership position to speak up for those that can’t.  And a lot of that comes with the territory of making mistakes and knowing that is all part of the journey. The best of intentions can still fall flat or be wrong and that is okay. It’s the only way to learn. The biggest thing is knowing it’s on me to do the learning and seek it out, not on the diverse members of my team to do the educating. 

But in the end, it’s about being intentful. Intentful in your hiring. Intentful in how you work with your team and in your communication. It has to constantly be top of mind.

LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with staff working remotely in 2020? 

Kit> Company culture is everything in a creative industry, where your people are inherently your product that you offer to clients. The culture you create, which comes from the top down, is a huge factor in creative output. And by culture I don’t mean office amenities, benefits, or perks: but how management treats their employees and ensures they feel respected, cared for, empowered and most of all preventing burnout. 

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

Kit> Constantly learning from others and different perspectives on leading and always a healthy dose of self criticism. There are so many leaders and voices on social media that are able to feed tidbits of useful info each day that have really helped me craft my leadership approach.