Dorothy Dowling: Advice from a Legendary Leader

Last week, trailblazer Dorothy Dowling was honored with the Lifetime Achievement Award at the annual GBTA WINiT Awards 2022, which celebrates the people driving positive change and career mobility for women in the travel industry. Well-deserved recognition for a legendary career.

Michelle (Mick) Lee and Dorothy Dowling at the GBTA WINiT Awards in Manhattan

Dorothy most recently served as CMO for Best Western, where she led the global marketing for 4,700 hotels for 18 years. It wasn't always smooth sailing, Dorothy started as a research analyst and professor who found her passion in marketing in the early 1980s. As Michelle (Mick) Lee said beautifully in her tribute to Dorothy, "She did not allow the stereotypical views that women faced at the time––which often held them down as superficial window dressing entry-level positions. She didn't settle. She proved herself she earned her seat at the table. For the next 30 years, she always brought extra chairs for the women in the room and for her female colleagues or she refused to take a seat herself."

Dorothy proved herself. She earned her seat at the table and for the next 30 years she always brought extra chairs for the women in the room and for her female colleagues or she refused to take a seat herself.

The video is 12 minutes––truly must-see TV––that had us wiping back tears.


We were lucky enough to catch up with Dorothy and ask her for advice and what she is up to next.


What are your top three tips for women on navigating a successful career?


1. Invest in continuous learning. The investment in CQ (your curiosity quotient) keeps you relevant—read, listen, attend conferences, and subscribe to newsletters (sign up for the hertelier newsletter here!). Also, embrace technology as a user so you can connect the dots and understand the micro (how things actually work) so you can connect the dots to the macro.


2. Hire your boss thoughtfully. Fit matters—it defines your career––discretionary effort at work is truly driven by happiness at work which is also driven by your cultural alignment with your organization and your boss.


3. Invest in relationships. Relationships truly are the currency of life—providing learning, growth, and business opportunities that I could never have imagined. Invest 20% of your time in building your network—it provides value to your organization and will fuel your career.


What is a setback you've had in your career and how did you deal with it?

Most people might relate to this setback––"not getting the job"—when I felt I was the most qualified and could contribute the most. It is important to understand that not everyone has the same mindset related to hiring. If you are someone who truly wants to lead and transform business—then you need to find a boss and company that also wants to grow and make a difference. Finding alignment with people and purpose is critical for long-term success.


As one of the first women in a top marketing role, how did you deal with microaggressions and unconscious bias in the workplace?

I finally embraced therapy—it helped me recognize how these behaviors affected me and allowed me to work on a better plan for my future. The recent "Stop Protecting 'Good Guys'," Harvard Business Review article represented parts of my career that I wish I could do over—but instead, I am focused on paying it forward with better self-awareness and understanding how I can be a stronger ally and mentor to others.


Have you ever taken bad advice?

I have had many people weigh in on various parts of my life—but I have always had the good fortune of a remarkable husband and good friends that have allowed me to talk through my ideas and get my thoughts on track.

People often tell you what they think you should do based on who they are—you need to ensure that the recommendation fits with your values, the political capital you want to invest in whatever action is recommended, and the energy you have to deploy. It has taken me a long time to trust fully my own instincts and to listen to others but to always know my true north when it comes to decision-making.

People often tell you what they think you should do based on who they are—you need to ensure that the recommendation fits with your values, the political capital you want to invest in whatever action is recommended, and the energy you have to deploy. It has taken me a long time to trust fully my own instincts and to listen to others but to always know my true north when it comes to decision-making.

My personal brand has always been something I have guarded—even when personal brands weren’t a thing. I don’t want to be associated with folks that drain my energy or compromise my values.

Thank you for all this amazing advice and congratulations again on your recognition from GBTA WINiT. What is next for you?

I love solving business challenges and figuring out how to drive growth and scale. So, I hope to help entrepreneurs solve some of their business challenges through consulting and board work.


I also intend to dedicate myself to paying it forward to others in leadership roles as I am hopeful and determined to support our collective future in shaping inclusion in the workplace. It has economic, health, and social benefits that we all know—it is now a matter of supporting businesses and individuals with plans on how to get there.


Quickfire with Dorothy!


What do you do for self-care?

Self-care for me is a journey. At this point in my career, I am learning to slow down, embrace more personal opportunities, and understand that I am responsible for my mental and physical health. The biggest learning, I have had this year is focusing on being with people who are additive to my well-being and avoiding people that sap my energy. My pets (3 dogs and a cat) and my wonderful husband keep me centered.


What is your my best travel hack ever?

Fly/drive into Canada—Canada is my home—but I now generally fly into a border state and drive over. Really embraced this during COVID and have come to like the driving immigration experience more than the flying one.


What do you always carry with you when you travel?

I like my own products—so even though I try to carry on—I like to bring all my cosmetics. I always carry cash for tips, and I try to bring my kindest self to the travel experience.


What is your favorite footwear for travel?

Dansko clogs or running shoes—glad fashion and comfort have aligned! I also wear compression socks on long flights—they truly make a difference. When I had both my knees replaced several years ago—the doc insisted on compression socks after surgery—and I learned how much of a difference they made to my circulation and overall well-being—so I continue to wear them on all flights of 4 hours or more.


What book are you reading right now?

I always have several on the go—but I love Chip Conley’s "Wisdom at Work". Of course, Lalia Rach’s new book "Managing the Book on You: Rewriting Your Leadership Story," I am sharing with many in my circle. I am a fan of Anese Cavanaugh—and her books on contagious culture and contagious you. Her advice of starting your day with your own IEP—(intentions, energy and presence) plans—is something I am working on consistently adopting


What podcasts are you into?

How I Built This with Guy Raz as I love entrepreneurial case studies and I am a big fan of Brene Brown and her podcast, Unlocking Us.


What is your latest TV show binge?

Again too many to mention—but I love finding Canadian shows that remind me of why I appreciate and love Canadian culture so much. The latest series I binged was Heartland. I lived in Calgary for a few years so the stories on Heartland brought back many happy memories. I also loved the beautiful scenery and the presentation of Canada’s west.