I recently went one on one with Orlando Ashford, former president of Holland America Line. Orlando is also the author of How Did You Get That Job?: 8 Principles To Accelerate Your Career and Soar In Corporate America.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

My career has really played out in three phases: 1) Functioning primarily as a consultant, 2) Functioning as a human resources leader, and 3) Functioning as an operations/P&L leader. The one thing that has been consistent in my career is that people have seen things in me that told them I could do big things, oftentimes before I’ve seen them in myself. I’ve been offered many stretch opportunities over the years and I’ve been willing to take some of those risks. One of the things I’ve been good at is assessing the risk and reward in any situation, looking at the worst case scenario if I took the risk and deciding whether or not I could live with it. And then deciding I could live with it and taking the risk. 

One of those opportunities was moving my family to Istanbul, Turkey, to lead Human Resources for Eurasia and Africa for Coca Cola. I oversaw countries from Moscow to Cape Town, managing about 90 countries from a Human Resources perspective.

Another big opportunity was being asked to serve as the head of HR for Marsh & McLennan Companies, a large Fortune 220 company, at the age of 39. 

And a third big opportunity was when I was given the chance to run Holland America Line, which at the time was a 140-year-old cruise line (the 2nd oldest cruise line in the world), and I took it over having never even been on a cruise. 

I go into some of these stories in a lot more detail in my book, “How Did You Get That Job? Eight Principals to Accelerate Your Career and Soar in Corporate America,” which was released in October of this year. 

Adam: In your experience, what are the key steps to growing and scaling your business? 

Orlando: One of the keys steps to growing and scaling any business, is developing an understanding and connection with your guests/customers, and an understanding and connection with your employees. When I took over Holland America Line in 2014, the business had been flat to negative in growth the prior seven years. The first thing we did was engage in a deep dive understanding with our current guests and with our aspirational guests. Once we felt like we had that understanding, we made adjustments to the product to speak to those guests, and we were able to attract more people and spending to the brand. At the same time, we looked at our most important customer-facing employees: our crew. We worked hard to improve their living arrangements, pay, meals, free time, and how well we were communicating with them, and we were able to improve employee engagement by eight points it the first two years. When we applied those two approaches together, it resulted in significant growth to the company. 

Adam: What do you believe are the defining qualities of an effective leader? 

Orlando: I believe in the concept of collective intelligence, the idea that teams outperform individuals, and diverse teams outperform homogeneous teams. And the way to get the most from people, no matter what geographies or industries I’ve been in, has been to create an environment of collective intelligence with those around me where people feel safe to show up as their authentic selves.

I also believe in being a truly engaged listener and creating an environment where team members feel safe to share ideas to make the business better, come to an agreement on those ideas, and to move forward with an integrated execution of those ideas as a team. 

It’s also important to have fun. On my teams, we try to have a lot of fun.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level? 

Orlando: We should all be permanent students and learn from both good bosses and bad bosses. We’ve all had each—leaders that we’ve admired, appreciated and revered; and leaders we didn’t care much for. But in both scenarios, there are things to observe and learn that can added to our own personal leadership toolkits. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Orlando: My three best tips would really apply to anyone, professionally or personally:

1. It’s important to develop your own personal board of directors. These are the people who you tap into for guidance and advice as you make decisions professionally or personally. 

2. Be oriented in a way where you pay attention to the wants, needs and agenda of those around you, because if you can understand those around you, it makes it easier to partner with or influence them as you need to. Many people believe influence comes from place of posture and strength. I believe the ability to influence actually comes from understanding the other person, where they are coming from and what is important to them. 

3. Have a point of view. The only way to truly influence others, to give advice and win the hearts and mind of others is to have a point of view of your own. It doesn’t mean you will always agree with others or even be aligned with them, but you have to stand for something. My Mother used to say, “If you don’t stand for something, you’ll fall for anything.” I believe she was right about that.  

Adam: What is your best advice on building, leading and managing teams? 

Orlando: My best advice on building, leading and managing teams is to create an environment where people can show up as their best selves. As I said before, I believe collective intelligence. But collective intelligence only works if you create the environment where that team feels comfortable and safe to communicate freely, and allows you to tap into their collective intelligence. 

Adam: What are your best tips on the topics of sales, marketing and branding? 

Orlando: The key in thinking about sales, marketing and branding is the concept of culture and storytelling. Each of these is about building the truths about your product or service and then developing the stories around those truths that resonate with customers. Your stories are about your culture and your culture is about behaviors. How do you want the experience you provide to be felt by your customers? How will employees execute and deliver that story? And what behaviors describe how people will engage with your brand? Define all of that and then explain it with the sales, marketing and branding messaging.  

Adam: What are your key takeaways from your recent book? How can anyone better navigate their careers? 

Orlando: In the book I discuss eight principles for navigating success, but I’ll just highlight a selection of them here. 

1. Envisioning. You have to have a clear picture of where you want to go in order to get there. This vision may change over time, but it’s important to have a personal roadmap in mind. As Yogi Berra once said, “If you don’t know where you’re going, you’ll end up somewhere else.” 

2. Delivering results. If you can’t draw a clear line between the work you do and its impact on the business, you are in the wrong role to achieve promotion and success. The rest doesn’t matter if you don’t get things done and deliver results.

3. Being purposeful about your career community. Having a team of resources you can tap into for ideas, advice, and counsel becomes increasingly important over the course of your career.

4. Being purposeful about your brand. When your name comes up for promotion or job consideration, what do people say? What’s your reputation? You can influence what people say by investing in your personal brand.

5. Leaning into your differences. We spend a lot of time clashing in the world today, and I think we should get comfortable leaning into our differences and the things that make us unique, powerful and differentiated. 

Adam: What is the single best piece of advice you have ever received? 

Orlando: The best advice I’ve received several times over the course of my career is to go for it. 

I’ve been presented stretch assignments and opportunities, whether it was moving from Chicago to New York City, or moving from Atlanta to Istanbul, or going from consumer products to risk and insurance, or leading a cruise line having never even been on a cruise ship. All were stretch assignments and there were reasons to say no, but the advice I was given was to go for it. And once I looked at the worst case scenarios, I decided that all were worth the risk in order to be a better leader and executive. So, my advice is to others would also be to go for it.