Dorothy Dowling is a much-admired and accomplished leader in the hospitality industry. In this episode, she shares her career journey and some of the key factors that contributed to her success. We discuss the lessons she learned along the way. She talks about her personal mantra and the advice that she has given as a mentor. Dorothy also shares her experience as a public company trustee, and how she approaches her work as an entrepreneur of her own life. She shares how she finds strength and resilience in the face of adversity. You wouldn't want to miss her advice to those who have higher career aspirations.
(David) Greetings. I'm David Kong, the founder and principal of DEI Advisors. We are a non-profit organization dedicated to personal empowerment. I am excited and delighted to welcome Dorothy Dowling to our DEI Advisors’ team and to this show. Dorothy is a well-known and respected professional in the hospitality industry. She's won numerous awards and accolades, including Lifetime Achievement Awards from both the Hospitality Sales and Marketing Association International or HSMAI and the NYU National Hospitality Industry Investment Conference. She has been named one of the most powerful CMOs by Forbes and other publications. It is a great honor to Dorothy, join us. Welcome Dorothy.
(Dorothy) Thank you, David. It's a great honor to be here with you as well.
(David) Dorothy, you are a much admired and accomplished icon in our industry. Can we begin with your career journey? Tell us how you progress up the ladder and what are some of the key success factors for you?
(Dorothy) Well, thank you, David. And what I would tell you is that my career trajectory was very deliberate in terms of its planning. You know, I always believe in that old adage of having a plan, working a plan, refining the plan, and reworking the plan. When I came out of graduate school, I had focused in the tourism industry and I wanted to broaden my capability. I worked in government, I worked as an academic, but I will tell you one of the greatest learning journeys was when I was able to be in a consulting practice with Leventhal Horwath in Toronto and really get exposed to a lot of different initiatives. But what I would offer on my career journey, for me, it was always about listening, learning, watching, observing others, and trying to understand where the opportunities were and what I needed to do to get there. . And so every two to three years I made a career switch because if I didn't see the growth opportunities for me, I knew I had to move on to other areas and do that. And I had this most interesting conversation. The person that I grew up with that was my neighbor, where both born within a few months of each other, and he was a very successful investment banker and he was visiting and he said, Dorothy, I would've wanted to dream about this job when I was a kid if I hadn't known it exist. And I think for those of us that grew up, without role models, we didn't know what we didn't know. And so it was always about learning and seeing what those opportunities are and paving the way forward for ourselves. So I found it very interesting when Bruce shared that story with me because it certainly reflected my journey as well.
(David) It is so true. It's continuous learning. We've interviewed a lot of successful leaders and almost all of them talk about their diverse background and how they use that to broaden their horizon and gain different perspectives. And that's why they're so successful. And continuously learning and being curious and finding out how things work is also another trait. And I've seen that in you many times. Let’s talk about the leadership lessons. No doubt. You have learned many lessons along the way.
(Dorothy) Yeah. The first lesson I always say to everyone is, choose your partner wisely. And it has been one of the most defining characteristics of my life. And I say, your partner will define your life. And my husband made so many sacrifices for. In terms of allowing me to really have the career that I dreamed about. So he put his career on the back burner and he became a stay-at-home parent when no one else really did that. And he always was my cheerleader and advocate in terms of supporting us. We made, I think we made eight or nine big geographic moves and our first. I don't know, 18 or 20 years of marriage. He always did it willingly and in a very supportive way. So that's always my first tip is choose your partner wisely. They will define your life. The second tip I always offer people is hire your boss carefully because they define your career. And you know, David, I hired you. I know you always chuckle when I say that, but I think back to the day that you interviewed me and you were clearly going to be a change maker, and I knew about myself that I was also an agent of change. and I wanted to be part of a team that was going to change things. And I know you know Best Western. I remember we did our first focus groups with customers, and I can still see that customer and that focus group that said, you know, Best Western isn't my father's automobile. It's my grandfather's Oldsmobile. And so when I think about the day I hired you, I knew that you were going to be this amazing change maker at Best Western, the legacy that you left and being part of your amazing. , and allowing me to be part of that change with you was something I knew the first day I met you, and it was the reason why I hired you. So I always say, hire your boss carefully. They define your career. And the last tip, that I always offer, it's what we were just talking about, David. It's about the learning journey, and there was a recent Harvard Business Review article about IQ, EQ and CQ. And CQ is the curiosity quotient - Leaders today that are curious and continue to invest in their learning. They are the ones that are defining the change and the success of everything. So I always tell individuals to think about that lifelong learning journey. Invest in yourself and you learn from customers, you learn from peers, and you learn formally and you learn a lot on the job. But it is really having and embracing that opportunity to learn. That will define your career as well. So those are my top three.
(David) Well said, I love it. I've known your husband Steve for a long time, and he's a saint. He has given up his career. He's helped your career in so many different ways. You don't have to worry about what's going on at home because of him. He's just such a wonderful man. You're very lucky and likewise, I feel the same way about you. In regards to your comment about hiring your boss wisely, that is something that has stuck with me, but that is so true. Life is too short if you don't enjoy whom you work with or you've got to move on. And CQ, that's exactly what we talked about earlier, being curious and wanting to learn. Those are important traits, wonderful lessons. Thanks very much for sharing that. Now, what's your personal mantra?
(Dorothy) So I think you know this well, David, I've always said that relationships are the currency of life. It was very early in my career and you and I are both introverts. But I went to the sales session. I always tell people because I was someone that just wanted to disappear in that environment, but the woman who was leading the session made everybody stand up in the room and we were doing this chant of, you know, people do business with people they know and like, and we just kept doing it over and over. At the time, I really was embarrassed about being engaged in that kind of activity. But what I learned from her is that that stuck with me forever. and Richard Carib Burn who, was formerly the CEO at ATI and now is a professor at NYU, he has redefined relationships with the current currency of life. He says, “your network is your net worth.” And to me that has been another amazing learn journey because all of the individuals that have invested in me and taught me and mentored me, have really made me into the individual that I am today. So relationships are the currency of life. I had a boss many years ago that told me you should spend 20% of your time in relationship engagement. And I was like, oh my goodness, how do you do that? But it really is the work that you do in the industry. It's a volunteer work that you commit to. It's all of those individuals that you're working together to affect change, maybe across the industry. Those are the individuals that continue to drive your growth and learning. So that is my personal mantra.
(David) I agree with you. Relationship is the currency of life. And I do also agree with you that people do business with whom they like and you have used that very successfully. Now let’s talk about networking. What's your secret to networking? Because you are so well respected and so well connected. You've met so many people and they have become your friends for many, many years. So how do you do that successfully?
(Dorothy) Well for me, David, it's mostly been through the formal opportunities to work in the association space and other voluntary roles. And I've always believed in this opportunity of co-creation for the opportunity to collaborate with others and to make the pie bigger, which I know is one of your personal mantras. It is to not focus on the slice of the pie, but to make the actual pie bigger. But that is really, it's really the opportunities that have been afforded me in terms of a lot of the volunteer industry relationships that have allowed me to develop those opportunities to partner with others. And I will tell you, when I stepped down from Best Western, about six or seven months ago, I was overwhelmed. I didn't know what to expect. I was trying to redefine what my next career journey would be, and I just was overwhelmed. All of the outreach of people who said, “what can I do? How can I work with you? Are there introductions that I can support you with?” Just the mentorship and kindness. I just didn't expect the level of support, and I didn't expect the number of people at different stages in their career path, they just reached out to support me. So to me, that's what it comes back to is that the investments that I made, with some of them I don't even remember, but it was important to them at the time and they wanted to somehow pay it back in terms of helping me in this next stage of my career. I don't know what more to say other than, I've always believed in the Stephen Covey story of relationships are like bank accounts. We make deposits and we make withdrawals. Hopefully, you're never overdrawn in those relationships and that you continue to make more deposits than withdrawals in your life.
(David) I know you and I know you've been kind and thoughtful and generous to so many people. You've got plenty of deposits in that account.
(Dorothy) Thank you, David!
(David) It's nice to be able to leverage that and to have so many people extend their thoughtful kindness. That's very nice. Now, you have mentored and coached a lot of people in your career. What are some of the advice that you have shared with them?,
(Dorothy) There's a couple things that I always talk about, David. One of the joys for me was always a commercial understanding of trying to understand how people make money, and I do think financial literacy and understanding how to put numbers on the scoreboard is what I advise everyone, and particularly women, because a lot of women do not get the P&L opportunities early enough in their career to really understand how to really drive profitability and growth. So I always tell individuals that’s the number one thing. And I know many of us, when we were in school, I remember taking accounting and some of these other courses, I painfully remember some of them because they were not natural things for me. But understanding that financial capability and how you really support that owner mindset in terms of their profitability is critically important. And I remember again, early in my career, I was living in Calgary at the time and I had an owner share with me this story about the breakfast plate, he talked about the bacon and the egg. He said, “The pig was committed, the chicken was involved.” And I know that's a story that's told often, but he always talked about the owner mindset - they were the pig, they were committed. They had made a huge investment in an asset and they needed to ensure that they drove that profitability factor. So understanding that and making sure you understand the commitment level that some of the asset managers have, and being a good steward of capital and driving profitability. To me that is job one. The second area that I often encourage people to do is making sure you are really involved in knowing yourself. And that is a lifelong journey. But I think when you understand your hot buttons and you understand your strengths and you understand others, that helps you in terms of being a better leader. And David, you have done many things for me over the years, but I’ll never forget how you shared with me early on about appreciating people's strengths and giving them their own latitude to do things in their own way, because we often have a different way of doing things. But if someone is truly competent in their space, you have to allow them to do it in their own way. So to me, knowing your self-awareness, and some of us want to exert more control in certain areas, but knowing when you're working with others that you have to appreciate yourself and you also have to appreciate them. And then the last one is really about this network understanding and that it really truly is your net worth and the kinds of deposits that you make in people's bank accounts in terms of the referral side of what they do for you, and then how they support your growth is something that many of us don't fully appreciate. Another lesson that you shared with me many times was to be aware of that informal network. Because if you are overdrawn with someone, sometimes that phone call happens when you least expect it. You might be looking for a job or an opportunity, and sometimes that person may not be as complimentary as you would've liked, so being fully aware of your net worth with your network, and making sure that you're always doing the right thing for me are the lessons that I offer to others that I think have been very important in my career.
(David) Well said. I think there are a couple memorable lines in there. I really like that Chicken and bacon analogy. The network being your net worth is also a very memorable line. I appreciate your sharing that. Thank you. Now, Dorothy, you are a trustee for a public company. Tell us about that Experience.
(Dorothy) Yeah, sometimes I still pinch myself about that, David, because it was a very lengthy process in terms of the selection of becoming a public trustee, and I went through a pretty significant journey. They did wanna bring someone in with digital competency and marketing and understanding the customer side of the experience. But I invested a tremendous amount of effort in preparing myself for the process, because I knew I was up against a lot of very well recognized and skilled individuals. So I listened to investor calls. I read annual reports. I visited multiple stores of the Cubesmart group, and I also went and visited a lot of their competitors because I wanted to be prepared. So part of it was just the elongated process of the selection and the due diligence that was executed in terms of really choosing someone to join their board. But there's a few things that I would offer back to you. This was the very first time I sat in a business environment where there was more than one woman in the room of significant capability. And I will tell you, David, I know I've shared with you over the years, there have been times when I've been in meetings where there's been 30 men and I've been the only woman, and I felt sometimes the oxygen was sucked out of the room because just asserting yourself and offering a point of view sometimes takes a lot of courage. But for me, being in a boardroom with two other very accomplished women, it just allowed the oxygen to flow into that room and for us to participate at a different level. The second thing that I gained through the public trustee experience was just the incredible. that became part of my network because all the individuals sitting around that board are incredibly accomplished investors or real estate individuals, and the executive team at Cubesmart was second to none in terms of their core competencies. So I guess what I would sum up - one was just this experience of being with other high powered women and how that allowed me to become myself in a different way and offer my point of view in a much more comfortable environment. But the second was continuing to be in an environment of such accomplished people that it really continues to elevate me in terms of being on top of my game to be a continuous learner, to be very well prepared at meetings and to continue to seek out advice as I go down that learning journey. The other areas that I would offer to listeners is that if they're really interested in pursuing public trustee roles, National Association of Corporate Directors is the advice that I give to everyone because it has become the gold standard and it offers tremendous resources in terms of learning for individuals to build their credentials and understanding of what the role really demands. So I hope that gives you some insight into what it has meant for me, how it's still continues to offer me so much in terms of personal rewards, but also I think continues to fulfill me in terms of my learning and innovation desires that I have personally.
(David) Thanks for sharing that experience and that advice. I appreciate it and I think our audience will find it very useful, but let's talk about the comment that you made earlier about being uncomfortable because you were the only woman in a room of 30 men. Do you ever get that imposter syndrome? I'm gonna sidetrack for just a moment because I had a conversation with a very accomplished white man yesterday, and he said that despite the fact that he has a lot of experience, he never finished university. He was called a testify one time and he felt inadequate because he didn't have his university degree and he felt the imposter syndrome. So it's not something that's only unique to women or to people of color. It's something that a lot of people experience. They just feel like they're not adequate and they're not comfortable in that setting. What's your advice when someone has that feeling?
(Dorothy) Well, in some ways I think it's healthy, David, because I do think we all feel that way. And that's why I said sometimes I pinch myself when I'm in that boardroom with such accomplished people that, you know, to be considered a peer among them is, just really an honor. But I do think that for all of us, it is about that journey and continuing to fuel our souls and be comfortable about the kind of learnings that we bring to the table, but I also think humility is a good thing. I think a lot of the executives that I had experienced early in my career suffered from a lot of hubris, and I do think that puts you out of touch with individuals that can really contribute and that you can continue to learn from. And that's where I think reverse mentorship and just understanding some of the gaps that we all have in our life and being honest about them. I think that the imposter syndrome, I don't know if it's a bad thing. I think it's about understanding that we're still a work in progress.
(David) Yes, I've actually heard that you can use it to your advantage and to your point, remind yourself to be humble and to be respectful and to be well prepared. All those are really good things, and the opposite of that is having hubris and being arrogant or complacent. Those are not good qualities. Thanks for sharing that perspective. Let's talk about work life harmony. It must not have been easy for you. You have a child who’s grown up now. Nevertheless, you went through a long period of time when you have to raise him and take care of the family and the demands of your work. What was it like and how did you balance this work like harmony?
(Dorothy) Well, I like the framing that you've chosen David, in terms of work-life harmony, because I think that is much more reflective of the world that we live in. And I would tell you early on my observations, when I was looking at people that were successful, I did recognize that women had to do much more lifting to be able to penetrate opportunities - so putting your head down, working hard. and also putting work first was really what was required. I had people early in my life that said you had to be like a man to succeed. And I knew I couldn't do that. But you remained silent about a lot of things in your life. I can remember being in meetings and at six o'clock knowing, okay, childcare, I gotta pick up my son and it's $5 for every minute that you'd pay overtime. But when I was at that point in my career, you never even said those kinds of things. You just said, okay, well 6:30, I guess it's gonna be $150 when I go and get my son. But, I don't know that there is a right or a wrong way. David, this was something I had to accept about myself is that we made a decision as a family. My husband became the primary caregiver for both my son and myself, and he made tremendous sacrifices to do that. But I had to accept that I would make different investments with my son. What it meant often is that I would take the red eye back to hopefully be back in time for whatever it was, a hockey game or a function at school. I was always very thoughtful, as I said earlier, about choosing my bosses wisely so that some of that flexibility that I needed to be able to partake in at least some small portion of my son's life was there. But the trade-off that I've had to make over time is that I hope I have paved a different path forward for my son, that he's going to be a very different individual and be very supportive of his partner whenever he makes that decision, and that he's going to demonstrate a different level of commitment in terms of child rearing and whatever responsibilities are around the house to his partner. So that is what I hope my legacy will be with him.
(David) I'm sure your son appreciates all the sacrifices and hardships that you endured, and you are right - There's no right or wrong, but you always did your best. Yeah. And look at him . He's just such a wonderful man now. You've done a great job, Dorothy.
(Dorothy) Thank you. You know, David, there's lots of memories that I have because our house was always a center of all the boys wanting to hang out because. Steven wasn't a traditional homemaker. He had fun with them. He was a dad that piled everybody in the van and took them to McDonald's for lunch and, the play center. So it was a different experience and the boys liked hanging out at our house because they liked being with Steve.
(David) Yes, Steven is such a wonderful man. Well, we’re all older and wiser now. Is there any advice that you would give to your younger.
(Dorothy) I thought long and hard about this, David, it's just about smelling the flowers a little bit more. I do think that the intensity and my drive in terms of my career and where I wanted to go, that sometimes I invested so much time in work that, in retrospect, I, the advice that I would give to myself is that I could have given up a few of those things and taken. Time to enjoy things a little bit more, but quite honestly, a lot of other things I wouldn't change because of the interdependency of our life in terms of how some of those roadmaps are. We just never know. I often think back to when I was in my early twenties, my dad was really sick and I had gotten a really big scholarship to go to the US to a university. , but he was dying. And I chose not to take that. And I went back to the University of Waterloo to do my graduate degree because it was close enough to be there for both my parents. And, I step back and I say, okay, that was a decision I made to support them because they had done so much for me. But on the other hand, I never would've met my husband if that choice hadn't been made. So I do believe there's a master plan for. and I just think we have to be kinder to ourselves and perhaps give ourselves a little more space to enjoy life, because as you get older, you certainly see that the journey isn't forever, and we better make the most of the time we have here.
(David) I like that. I think we all need to be kinder to ourselves. Sometimes we are our own worst critic, and that's just not right. We need to be kinder to ourselves and give ourselves a little space. Well said. Thank you. Now, I know we've all encountered hardships and setbacks and disappointments in our lives. How do you find strength and resilience in the face of such?
(Dorothy) I think about the dynamic nature of the travel business and there have been so many ups and downs. We've all been laid off during our careers. We've had to deal with sometimes very difficult situations in terms of financial environments and the companies that we were working with. But what I have always found is that this relationship network that I have had has been the key to really allowing me to be a resilient person. Because having other peers that are going through similar circumstances, they boost you when you need it. They also give your ass a kick sometimes when you need to be kicked. And don't take yourself so seriously. And I've had lots of people that have tuned me up over time that have helped me in terms of understanding that it really isn't as challenging or as difficult is what I might be seeing. And so, getting laid off isn’t the worst thing that can happen. And sometimes those doors close and another one opens. And I've always had this remarkable group of individuals that have always kept me balanced and, have helped me find the strength that I needed in those difficult times you included. So I think about Covid. I think it was the worst that any of us. But you know, I still think about, and I know you and I went through a lot of those layoffs at the same time, but there is a woman that I clearly remember when I had to make the call and she just said, Dorothy, lay me off and not one of my teammates because she needs medical care. She's pregnant and she needs that medical support. And she said, I have other resources to keep myself going through this time. And that to me is where that peer network, I have just seen it shown to me so many, many times about how we all support each other. We lift each other up. and sometimes we give ourselves those kicks that we need to, power through whatever adversity might be in front of us.
(David) Yes. Sometimes when we face those hardships, we see humanity at its best, and it's so uplifting and heartwarming. I do remember when we were going through that very uncertain period when covid was declared a pandemic, everyone was so scared, but I found solace in knowing that I have the best team in the industry, and I could lean on them. It’s to your point about being able to lean on your network when there's a crisis. It is really important to have that. All right, we're coming to the end of our show. Is there one last piece of advice that you'd like to share with us before you go?
(Dorothy) I'm reading this remarkable book right now that talks about life as a portfolio, and it has really spoken to me, David, because it uses a metaphor of an investment portfolio and your life portfolio. It talks about it being mostly post 50, but the author of book is really trying to characterize everyone in terms of thinking about your life as a portfolio and having lots of ways to fuel your purpose and passion. And to me that was a remarkable way of framing our life because we all have these pieces of our life. But if we think about a portfolio and having short-term and medium-term and long-term investments that we make and thinking about our career journey and our life journey in that way, I think it helps all of us reevaluate some of the decisions we make in our personal life as well as our professional life. It has really grounded me as I think about this third chapter of my life, because to me it is about paying it forward and giving back to so many that have given to. And that is that passion and purpose of really trying to pay it forward through others, because we can't go back and give it back to the people that did so much for us. But hopefully we can create a legacy in others in the future.
(David) I love that! Absolutely love that! Thank you for sharing that. We're at the end of our show and I thank Dorothy Dowling for being with us today. I am very excited to welcome her to the DEI Advisors team. And for our audience, if you enjoyed this show, I hope you will join us on our website, DEI Advisors.org. We hope to see you there. Thank you very much.
(Dorothy) Thank you, David. Thank you for your mentorship through my journey.
(David) Thank you!