Leslie Miley possesses an extremely impressive career history, leading engineering teams at Slack, Google, Twitter, and Apple. In addition to leading these tech giants, Leslie also served as the very first Chief Technology Officer to the Obama Foundation. 

Listen to this episode (or read the transcript below) to learn about the importance of culture, and how learning about the culture of those you work with aids in cultivating strong relationships. 

1 Who was your favorite or most memorable boss throughout your career?

One of my favorite bosses was my very first boss that I had in tech. We were running a program where we were distributing antivirus applications to fortune 500 companies and I was in charge of the entire program at only 21 years old. During the program, I made a massive mistake and accidentally infected about 250 of the fortune 500 companies with a virus and the CEO of the company literally came to me and fired me on the spot. 

My boss’s boss came in and essentially saved my job. He told the CEO that I was young and new and I was moving really quickly and explained that it’s not about the mistakes we make but rather about how we react to them. He let the CEO know that I acted on the mistake as soon as I discovered it and he remains my favorite boss to this day because he advocated for me very early on in his career. He allowed me to explore the world of tech and learn a lot along the way. It was also a really big leadership lesson for me. 

2 When did you first start to lead a team and what were some mistakes that you may have made early on? 

One major mistake that I think back on is not having the patience and tolerance that I have today and also not having a clear understanding in terms of what people are experiencing. Another thing would be not respecting the different views of large teams of people that I was managing and putting people in uncomfortable positions that they may not have been prepared for. You have to know your audience and also be respectful and considerate and make sure you’re always living up to your own values and principles. 

3 Do you have any tips for people who are managing different people from different cultures? 

I’m a very big proponent of taking the time to learn about where people are from a personal, geographical, and geopolitical standpoint. When you’re a leader, you have to make a point of learning about everyone’s cultures because you need to learn how to effectively lead them and it also helps you develop some form of common ground. 

4 How do you recognize certain cultural norms? 

I think it’s all about doing your research and being open to learning as much as you can about whichever culture you’re working with. I was managing a team in India and we were talking about how to work together and how to make the relationship work and something I found out was that everyone who worked with us when I was with Apple went through a training program on Americans, and American culture and the United States and that really opened my eyes and I realized that I needed to start doing the same thing.

5 What can companies trying to create a sense of diversity do differently? 

One of the main problems is that these companies are performative or what one of my friends refers to as “diversity theatre” which essentially means trying to exude a positive story without putting in the work that needs to be done to create an inclusive workplace. You have to have a shared understanding of what systemic racism and discrimination is so everyone understands that the systems and structures that they may benefit from may negatively impact someone else. In addition to fixing the system, you also have to repair the damage that was done and that’s what a lot of companies and organizations don’t fundamentally understand. 

6 What are some things that companies or organizations could do? 

Is the issue systemic? Yes, and the next question is what can you do about it? I think what you can do immediately is fix the compensation problem and factor in how these barriers have impacted people’s careers so we can help accelerate them and level the playing field. It’s important that everybody understands and agrees so it can be made up from a compensation standpoint. Another thing that can be done is providing resources to get coaching. Repairing the damage means rebuilding trust because there is a distinct lack of trust with African Americans in tech when it comes to organizations following through on what they say. 

7 What are some of the lessons you learned from going to different types of communities? 

Venture For America was founded by Presidential Candidate Andrew Yang and he is all about learning about people and going into their communities and doing work in those communities and building within them to create something from nothing and that’s what community organizing or community building is all about. Those goals can be political or not and they allow you to learn to understand or respect people who don’t share the same views and accomplish something with someone who doesn’t share the same views with you and I believe that’s extremely important. 

Birmingham, Chattanooga, Nashville, Memphis, Detroit, Columbus, Cleveland, and Pittsburgh were all places that I never thought I’d spend any time at and I met people from so many different backgrounds that had so many different political affiliations who were all about building up their communities. 

I can’t stress enough how important it is to get out of your bubble and talk to other people and listen to their perspectives. Sometimes it’s more important to listen than to talk and you can always try to build something with someone that isn’t like you and see where it goes. 

8 What are some things that you would recommend for people who are looking to get out of their bubble? 

It’s all about recognizing what your bubble is and getting out of that bubble without having to have an argument. You have to talk to people to understand why they might make a certain choice and we should all keep a bit of space to understand other people’s perspectives. You also have to know when to cut the bait and cut your losses because some people may not be worth your time because they may not be willing to open their minds and recognize that they may be racists or close-minded or you may be so far apart that you can’t cross the bridge. 

9 What leadership lessons did you learn From President Obama during your time at the Obama Foundation? 

There’s also a lot of bias on my part because he is a president who looks like me and the power of that is amazing and I’m bringing that up because we all know that people of color do suffer from imposter syndrome and President Obama actually helped with that. I realized that I was in a room with only 8 people and I was sitting next to President Obama and then I realized that I was sitting next to the President of The United States who also happened to be an African American and it really made me feel like I belonged. I did the work and I got my own seat at the table, nobody gave it to me and that really helped me eliminate my imposter syndrome. 

From a leadership perspective, something that I was amazed to see was how inclusive he was. It was shocking for me to watch him go around the room and pull people into the conversation that may have been struggling and he did it in a way that made you feel like your input was wanted and appreciated and he always listened intently. 

10 Do you have any advice for leaders or managers who are working towards becoming better at their craft? 

One thing is to be inclusive and to figure out how to promote and uplift the people in your organization who have traditionally been left behind or marginalized and make sure they can be the best that they can be. I really think that having a deep understanding as a leader and building your empathy and being able to empathize for what people experience is what’s going to make you a next level leader.