Passion and Grit

This Wednesdays for Women blog highlights Deb Cupp, corporate vice president, Worldwide Enterprise & Commercial Industries at Microsoft. She offers her perspective on what makes a great leader and shares examples of how her passion and grit has helped her in an industry often dominated by men. In addition, check out her recent LinkedIn article on promoting a healthy team culture, here.

Tell us a little about yourself.

I grew up outside of Philadelphia and still live there with my husband and our dog Penny. I went to the University of Richmond and got a B.S. in Business Administration with concentrations in Marketing and Finance and have my MBA from St. Joseph University. I love to work out and enjoy Orangetheory and yoga. I spend a lot of time on a plane, so I really enjoy my down time when I am at home.

How did you begin your career at Microsoft?

Deb with her work family.

I have been at Microsoft for two years. Prior to joining Microsoft, I was at SAP. Microsoft reached out to me in the past, but I was not ready to make the move. Then, I finally was at a place where I was ready to do something different. I was also inspired by Satya (Nadella’s) leadership. The company was becoming a value-based provider to their customers and I saw the transformation effort that was taking place. The culture and leadership of the company was important to me and I was drawn to their vision, mission and values.

Tell us about your experience at Microsoft over the past two years.

When I started at Microsoft, the first thing that struck me was the underlying approach of ‘do right, do good.’ Essentially, we are using our brand and reach to help the world and I am really drawn to that. Everyone at Microsoft is focused on doing really great work which impacts life and community. People at Microsoft are also generally curious – everyone wants to get to the why behind things. It is also one of the brightest group of people I have worked with in my career.

What are some of the challenges you’ve had to overcome in your career and how did you overcome them?

Prior to SAP, I worked for a company called Standard Register (now Taylor Communications) for 17 years. It was quite a male-dominated industry and it was hard when I first started out. I was the only woman in every meeting I was in. I often felt like I wasn’t smart enough to be in the room and I didn’t have a place to really share my thoughts and ideas. There was a single point in time where I was promoted over my peer group who were all male and all older than me. It was a shock to the system there. I give my then-boss a ton of credit for taking the leap and the risk. I was worried that these guys didn’t think I was capable of leading them, and of  the backlash of them feeling like it should have been their job, but I decided that I was going to hit it head on.

I went one by one to each of them and said, “Let’s try to figure out how we continue to work together and respect each other.” My leadership style has never been one of command and control. I believe strongly in servant leadership. I consider myself part of the team and not one who is leading them. I think that position helped everyone feel like “she’s still one of us” and she will drive the things that we all believe in and isn’t afraid to take risks. All those things combined helped me go for it and continue to do what I think is right for the company, our customers and our people.

What is one big risk that you have taken and how did it work out?

I can recall one at Standard Register. I was 1-2 years into that job, and at that time the company’s sales teams were oriented by geographies and not industries. I started to realize that customers were more interested in sales teams that understand their business and industry deeply. I managed the Northeast territory which spanned from Washington DC to Boston. I had two sales leaders in New York and we essentially split the territory by zip code. I started thinking about breaking the territory up by industry. One of my leaders was deep in Financial Services and the other was deep in Healthcare. I recommended this potential new structure to my sales leadership and suggested piloting it. They were all in – this gave them a chance focus on their areas of passion.

Next, I went to my boss with the idea. It was different than what we have ever done before and I recognized it would create some disruption. Not to mention, it was midyear! I knew it would be on me if it did not work and I would be held accountable. Luckily, it worked out and we moved to this model across the entire company over the next two years. A lot of people said, “you can’t do it” or “it won’t work” or “it’s crazy.” People tend to like status quo but I like to push on things and do what’s right for the customer.

Can you point to a critical moment in your career that really made a difference in your path?

Yes, this role that I just discussed gave me confidence. It helped me realize that no one has all the right answers. We all have a point of view. To me, I feel like a lot of what success is about is execution. You might have a good strategy but if you can’t execute it, it will fail. You have to have both a good strategy that makes business sense but also the ability to execute. I think that is what differentiates me; I’ve always been focused on execution. I continue to push, drive, and learn every day.

What do you wish you knew when you were starting out that you know now?

Have confidence and don’t feel like you have to be the smartest person in the room. Every time you walk into a new environment, take over a new business or take over a new role, you probably know the least amount. When I came into Microsoft, I knew less than every person here about Microsoft. I had to think about what are the things that I am bringing that are different, unique, and valuable and anchor myself on those things. Don’t focus on all the stuff you don’t know because that list will be giant. It takes time to learn and get acclimated to a new experience and environment but remember to anchor on your strengths. Everyone should know what they are – but if you don’t – ask your friends.

What’s one leadership lesson you’ve learned and really taken to heart?

Remain incredibly authentic. One thing I noticed throughout my career, especially for people who step into their first management role, they look around and see tendencies or characteristics that they think they have to model or emulate. Often times, it doesn’t work because it is not them. I highly encourage people when I am mentoring to stay true to you and do not try to become somebody else. There are certain tips and ideas that you learn that you might want to absorb, but you have got to retain your own style and personality, even if it feels different than what you have seen in the past.

What advice do you have for young women seeking a career in technology?

Be cautious around who you are getting advice from. It may be unintentional, but I think that sometimes women who are being mentored are getting advice that can be limiting. Make sure whoever you are getting advice from that you have real deep trust in what they are telling you and that you are recognizing the lens from which the advice is coming.

Second, never underestimate yourself. It is important to have confidence in the work that you have done and understand how it applies to what you want to go and do. If you are going to stretch, understand your skills and capabilities and how they apply to what you are trying to stretch for and if you can map that, it will create your own confidence.

And third, don’t be intimidated by having to learn, having less information or less experience than someone else. People often get tunnel-vision and think “this is how we have always done it.” I love fresh eyes and I look for that when I am hiring. I sometimes look for people who haven’t done the exact same job because they come with a different point of view that is incredibly valuable.

Who are some of the leaders you admire?

I lean towards people that I know when I think about people who inspire me. I admire Joe Morgan, who was the CEO of Standard Register when I worked there. He was so far ahead of any other leader I have ever seen when it came to Diversity & Inclusion.  He really pushed people to be different and to think about how they could do things that maybe they didn’t realize they could do. His support of diversity, of women in leadership was incredible. I was really compelled by the way he led. A lot of things he did spoke to me and grounded me early in my career.

I talked about authenticity earlier. Two leaders stand out for me: one that I personally know, one that I admire from afar and would love to meet one day!  The first is Amy Hood, our CFO of Microsoft. She is someone I could just listen to all day long – I learn so much from her every time. She is crazy smart and yet, so down to earth and authentic.

The other person that I think is interesting is Sara Blakely, the founder of Spanx.  She is incredibly authentic. When I see her from afar, see the things she posts on Instagram, or the things that she talks about in interviews, she just seems like somebody who had a unique idea and ran with it and has remained her own person throughout. Leaders like her are inspiring in terms of the way they show up and the things they do.

I am also super inspired by my mom who was a working mom. She was a nurse who worked 11 p.m.-7 a.m. so she would be home when we were kids growing up. Both my parents worked incredibly hard and a lot of what they did helped shape me into the person that I am.

How do you maintain a work/life balance?

Deb and her husband Sam at their favorite home away from home (Outer Banks North Carolina).

My personality style makes this hard! I am very focused on making sure that stuff gets done and have a hard time stopping when that doesn’t happen. It is really driven by customers or the people that work for me. If someone is waiting on me or something isn’t moving forward because of me, I have a hard time stopping because I know that I may be holding things up and that drives me nuts! This is something I am really trying to work on.

However, I am lucky in the sense that I have to ability to sort of flip a switch and shut if off when it’s time…I sleep really well! Exercise is a huge one for me. If I didn’t exercise, I would probably lose my mind. I just started yoga a couple of years ago. It is an incredible hour of time where your mind just shuts off. I also like sitting on the couch with my husband on the weekends binge-watching TV, going shopping with my mom, and hanging out with my nieces. I try to find opportunities where I can take time to stop and reset. This is always going to be a thing that I am not great at and have to continue to work at. I’ve asked my husband to keep me accountable and remind me, and he does a great job of that.

What are three key words you would use to describe yourself?

Authentic, passionate, gritty

What’s one fun (or surprising) fact about you?

I was a Division I field hockey and lacrosse player.