IABC Ottawa’s 2018-2019 season opened with a bang on September 13 as MediaStyle CEO Caitlin Kealey fielded questions in a lively Ask-Me-Anything discussion with chapter President Samantha Rae Ayoub.

Caitlin candidly shared her thoughts on climbing the communications ladder, being a woman at the top, balancing work and home life, and how to succeed in today’s changing communications landscape.

Read on for the five biggest takeaways from the conversation – advice you can apply to your career, no matter what level you’re at.

Confidence will come
Caitlin recalled a great anecdote from Alan Doyle, a fellow Newfoundlander and lead singer of Great Big Sea, whom she met at the Governor General’s Canadian Leadership Conference last year. Alan told Caitlin there’s something better than being the smartest person in the room, and that’s being the most prepared person in the room. Caitlin has found that be true in her career, noting that when you prepare and know what you’re talking about, you will naturally feel more confident.

And if you still don’t feel it? “Fake it ‘til you make it,” Caitlin said. She did a lot of that when she stepped into the CEO role, and found that reading management books, talking to business owners, and asking for feedback helped her through the steep learning curve.

Embrace challenge
Caitlin has helped MediaStyle carve out a specialty working with indigenous organizations and associations, but she admitted to making mistakes on her first project. She stressed the importance of asking questions when you don’t know a particular community or issue well – just be open and transparent.

Her “favourite difficult challenge” was working on the Truth and Reconciliation Commission of Canada, a historic initiative to document the truth of survivors, families, and communities affected by the Indian Residential Schools experience and to educate all Canadians about the widespread trauma that occurred. Through this work, Caitlin discovered the diversity of Canada’s indigenous communities and found her passion in bridging the gap between indigenous and non-indigenous voices.

Be a ‘lazy leader’
One of the AMA questions touched on the concept of the ‘lazy leader’ or laissez-faire leadership. Caitlin agreed she’s very much in that camp and considers delegating one of her finest skills. Knowing when to hand things off and when to check in is essential for people as busy as Caitlin. She even hired a virtual assistant to help her stay organized and handle administrative tasks. “Detail isn’t my strength,” Caitlin declared. “I’m a people person.” Recognize your strengths and weaknesses and play to your strengths – otherwise you’re just wasting time.

Balance when you can
Like most working women with families, Caitlin confessed she struggles with work-life balance. As the daughter of two academics who are “retired but still working,” Caitlin joked she didn’t exactly have the best role models in that department while growing up. Still, she tries to unplug in the summer and enjoy her beloved hobbies – mountain biking and motorcycling – and she looks forward to leaving the office on time when she’s taking care of her three young stepchildren.

Know your power
Caitlin never expected to be a CEO. She initially studied journalism, transitioned to communications, and ended up at MediaStyle almost by accident. She didn’t have a long-term plan, but looking back she knows exactly what she would have done differently in her career: “I wish I had taken myself more seriously.” Caitlin explained she didn’t understand her own ability early on to make change in the world, and she urged audience members to remember the impact each and every one of us is capable of.

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