… Humility is an important key to leadership. When given the opportunity to be a key decision maker, think back to times in your career when you didn’t feel you could be as influential as you desired to be. You have two paths: One is unleashing some form of “my way or the highway” mentality. The second path is to reflect on how you wish past managers or executive leadership would have engaged you, and aim to be more of an engaged listener than a “boss.” I always aim for the latter. If you think of your colleagues as team members versus direct or indirect reports, the further you and your organization or department will go. Nobody should lead alone.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Kyra Kyles.

Kyra Kyles has spent over 20 years in the media industry, with a consistent emphasis on equity and representation and an impressive track record of expanding young, multicultural audiences and leading sustainable organizational growth. As CEO of YR Media, she has expanded the nearly 30-year-old organization to a new market, Chicago, and continues to work with the YR team to deepen and expand both platforms and supports for majority BIPOC 14-to-24 year old content creators in the Oakland headquarters, the newly established Midwest hub, and across the nation. Prior to joining YR Media, Kyra served as the Field Foundation of Illinois’ inaugural Program Officer of Media and Storytelling, she managed a groundbreaking equity-focused journalism and documentary filmmaking fund, the first of its kind in the organization’s history.

Before joining the Field Foundation, she led both the iconic EBONY and JET brands as Editor-in-Chief and Senior Vice President of Digital Editorial, where she expanded audiences, created new revenue streams, and scaled up operations, including establishing a Los Angeles office and an in-house branded and original content studio. Kyra also worked at the Chicago Tribune for six years, where she was recruited specifically to attract and energize young audiences via its millennial-focused RedEye brand. In addition to achieving this, she increased the Tribune’s multicultural coverage and gained recognition as a digital pioneer, print reporter, blogger, on-air personality, and well-known pundit with her own TV segment, “The Kyles Files” on WGN-TV.

Among her volunteer activities, Kyra served as two-time President of the award-winning National Association of Black Journalists-Chicago where she built a two-way mentorship program connecting students and working members of the media. Kyra is an elected member of the Board of Directors for the Institute for Nonprofit News (INN) and was recently selected as a Fellow for LeaderSpring’s LeadStrong cohort, an initiative focused on elevating and strengthening women leaders of color working for social justice and racial equity within the social sector.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

After 30 years of building a strong, award-winning legacy in the Bay and working with national contributors all over the country, YR Media is expanding to the Midwest, opening a physical hub for learning and multimedia production for the 14-to-24 year olds we serve. This Chicago space, which builds upon a successful virtual hub for editorial we launched two years ago, is a major milestone for YR Media. We’ll offer our unique combination of paid career training; employment; and accompanying supports, including mental health counseling, academic advisement, case management and healthy food. I am grateful for our funders, supporters and my colleagues who made this possible. As a native of the “City of Win” who lived there for most of my life, I know what this resource will mean for the city and the media landscape at large.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

There are many leaders who have really served as my influences and inspiration, including my own sister Kozi Kyles, a bold and incredible marketing entertainment executive; my late father W. Louis Kyles who was a Burger King franchisee; and my mom, Toni Kyles, who was a peerless educator and inspiration to so many generations of students, but I’ll give some examples of inspirational leaders connected to my current role bridging media and philanthropy/nonprofit sectors. The first is early in my career, and that’s Jane Hirt, who co-founded the Tribune RedEye, at the time an experimental start-up within the centuries’ old outlet aimed at attracting and engaging Millennials with a physical newspaper. RedEye, complete with red walls that contrasted with the “blue” decor of the rest of the company, was an oasis of racial and gender diversity, and I always admired the way Jane invited everyone into the conversation, whether it was about what to cover, the artwork we used to illustrate concepts and especially the headlines. The entire team– from page designers to interns to occasionally, folks who just happened to drop by our office– were invited in when we brainstormed headlines and some of the very best ideas came from outside of the editorial team. Jane truly operated with more of a “flat operations” mindset and visibly worked toward building a newsroom that looked like the city it served, though she is non-POC. The other, more recent example, is Angelique Power, President and CEO at Skillman Foundation. True to her name, she leads, or rather guides, with determination but it’s complemented by an openness and an elegance, the opposite of some of the fear- and anxiety-based management that too many so-called leaders fall into. As a brilliant, innovative and creative leader, Angelique– at the time we worked together was the top executive at the Field Foundation of Illinois– launched a portfolio at the Chicago-based foundation that turned media funding on its head by unapologetically seeking to invest in BIPOC media outlets (and leadership) on the city’s South and West sides. This was in response to research results that showed most of that funding was flowing into white-led organizations on the North side and downtown areas despite the concentration of Black and brown audiences and content creators who lived outside of those limited zip codes. I was honored to be the pioneering program officer for this portfolio. She was an excellent leader who never explicitly directed me toward who or what to fund, nor did she respond to people “calling in favors” to override my evaluation of applicants. She asked great questions that helped lead the team to decisions. She hired the right people, stepped back and let them do their jobs but with the proper framing so we were working toward the same goal.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

I have very few regrets, but one of the leadership lessons I learned the most from was when I accepted a role of high accountability for a project that, in retrospect, did not offer enough guardrails and resources from the onset. I was charged with launching a product, but we had minimal financial resources to do it and there were hard and fast parameters already in place created by parties who would not be part of the ultimate rollout. Though I am proud of the work the team and I did, we were under extreme duress and pressure with no margins to push back due to an aggressive timeline that had been determined before I even accepted the job. If I had it to do over again, I would have been insistent we needed more time, more money and cushion, particularly for my colleagues. What could have been an exhilarating experience was needlessly stressful. As a Black woman leader, you sometimes feel you have to accept and triumph over every challenge no matter how punishing the conditions or insurmountable the odds. Newsflash: You definitely don’t and should not make a habit of “rising” to such challenges because you do so at the expense of your own wellbeing and others’.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

I have never believed in “bosses,” folks who sat around and barked orders while they were golfing or online shopping for a new yacht. I can’t imagine taunting employees with the loss of their jobs over small slights or being callous and complacent about the challenges team members face at every level of an organization. That’s somewhat of a caricature but I see media headlines in real-time where bosses are doing just that and being lauded for “toughness” and “certainty,” meanwhile they are making reckless decisions (Elon Musk, I’m looking at you.) True leaders are true teammates, not asking anyone to do anything they themselves aren’t willing to do or demeaning others simply because of their so-called level within an organization. No one is a perfect leader, but I aim to be fair, engaged, willing to listen and quick to admit if there is an error and turning it around in enough time to ensure that the teams I work with are not negatively impacted by individual ego.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

Tons of meetings to establish accountability or forced brainstorming sessions. First of all, we must acknowledge that not everyone has the capacity or ability to blurt out gems of thought under those conditions, and you may lose valuable input by making this the main means of engaging teams. Throughout my career, I have inherited standing and recurring meetings from previous leaders and wondered: “Why are we doing this?” Earlier in my career, I would keep them going in case something would be lost if I just hit “no” on an invitation or canceled a series. Now, I’m happy to leverage technology and techniques that can get the best out of my colleagues without them having to engage in performative participation.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

Prioritizing listening to the experts instead of relishing a role as a “boss.” It is a privilege to be in a position to build up a team and bring on experts who complement your knowledge base. I’m always puzzled by those who want to be surrounded by yes-folks who could nod and “mmm hmmm” an organization into complacency or failure.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

In business, just as is the case with nature, evolution is key to surviving and thriving. There are so many clear examples of a business model going extinct due to inertia. The organizations that prevail are willing to question their playbook, tweak it and even toss it when it no longer suits their model or the moment. Think about the shift from video rental to streaming, and now even streaming has to rethink its approach. It can be challenging to let go when you think you have a “winning” strategy and you’ve built systems around that approach, but if you fall behind, even for what feels like a moment, you look up and you’ve been surpassed by your peers.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

Humility is an important key to leadership. When given the opportunity to be a key decision maker, think back to times in your career when you didn’t feel you could be as influential as you desired to be. You have two paths: One is unleashing some form of “my way or the highway” mentality. The second path is to reflect on how you wish past managers or executive leadership would have engaged you, and aim to be more of an engaged listener than a “boss.” I always aim for the latter. If you think of your colleagues as team members versus direct or indirect reports, the further you and your organization or department will go. Nobody should lead alone.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

Resilience, innovative thinking, humility, a collaborative nature, and excellent listening skills.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

I try very hard not to deem any day a “bad” day because that declaration can become a self-fulfilling prophecy. In fact, I try to inject humor into everything I do. There was one morning when I nearly dropped a coffee cup, couldn’t get Zoom to function and then tripped over a computer cord. I went back into my room, closed the door and then came back out anew for what I later told one of my colleagues was a hard reset. When you face setbacks, don’t throw the whole day away. Reset and resume.

What is the legacy you aspire to leave as a leader?

I would like my legacy to be that I centered diversity, equity and inclusion in every organization or initiative that I touched.

How can our readers connect with you to continue the conversation?

They are welcome to connect with me on LinkedIn, and all other social media platforms via @thekylesfiles, as well as our organizational site of yrmedia.org.

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!