Wendy Roberts knows all about the benefits of a co-op. As a student at New Mexico State University, it was how she got her foot in the door at IBM, where she worked on a coveted NASA contract.
Throughout the course of her career, Roberts dealt with many trials and tribulations, from layoffs to reentering the workforce after having a baby. Today, Roberts is the global head of technology education at PayPal. Having kickstarted the company’s technical training program, she’s familiar with hard work. She’s gotten plenty of new projects up and running and learned the ins and outs on how to get employees to embrace change.
How did you start your career?
I did a co-op with IBM in college. It was super cool because NASA was the main contract, and I was working on space-related projects, including the space station and space shuttle. When they offered me a full-time position after graduation, I was psyched to go do that. I was there for about five years.
How did you end up at PayPal?
During that period of time, the Berlin Wall had come down, and a lot of cuts were happening in the defense industry. It affected everything in aerospace and defense, and soon I found myself without a job.
I interviewed at a lot at different places and got an offer from Anderson Consulting (now Accenture), so I took that job and got a big pay increase. The work was amazing and challenging. I ran a support team and moved into business operations. But I traveled a lot and when I had my son, I realized I couldn’t do that anymore.
However, eBay was family-friendly. I started there and then moved to PayPal, where I restarted their entire program for technical training. I grew it from just me and no budget to what it is today. We have a team in India and San Jose, and we support about 5,000 engineers annually.
Have you had any mentors who have meaningfully impacted your career?
Yes, but I had to find them on my own. It was hard for me at the beginning. I sought out people through external training programs. Along the way, I’d meet a person whose point of view resonated with me.
You’ve seen lots of transformations in your time at eBay and PayPal. What have you learned?
No one wants to change, so it’s important to be clear about why it’s good for the company and for individuals. Messaging at the corporate level should be simple. You should be able to express three messages in crisp sentences and communicate them throughout the company. We don’t do that typically in the corporate environment. People underestimate those aspects of change management. If the “What’s in it for me?” isn’t strong enough for people, they’re going to ignore it.
One of your Everwise protégés said that you see management at a much higher level. What do you make of this?
I think sometimes people look at a specific incident. Running a project, for example. Let’s say a person didn’t get something done. That makes me think—why is that behavior happening from a manager’s context? A good manager should set up the right environment for success.
What if you have someone who says their team isn’t valued because no one knows about them? I’d ask them to identify their main stakeholders at the senior management level and then meet with them more throughout the year to gain insight on how the team is delivering against expectations.
What is the long-term impact you see from mentoring others?
I love giving back to people who are dealing with the challenges I’ve dealt with. It’s great to learn from people who are striving, to see how they look at things. It often applies to a situation I’m currently involved in.
Someone I talked to was a new manager and experiencing challenges with her team. It made me think about someone on my own team who had gone through a similar transition, and it gave me better ideas to support that person. It is helpful to hear someone talk about their situation frankly.
What have you learned from your protégés?
I enjoy helping them figure out what is it they actually want. Let’s say they want to have a better executive presence. I might say, “O.K., well how do you know that’s what you need?” Talking through their concerns, I find myself reflecting on my own team, wondering if there’s some similarity.
How have you helped people through challenges?
Once, a new manager was talking to me about the challenges she was facing. I mentioned that she needed to start seeing her role in a new way. We all like our managers because of what they do for us; they help us advance and develop our skills. Friendship from your manager shouldn’t be a priority.
Any advice for someone mentoring for the first time?
Listen intensely. A lot of mentoring is just being a good listener. You often play a detective-discovery role. Figure out what your protégé is trying to do and help them think it through. Ask open-ended questions. If you’ve been in a similar situation and found things that worked, share your ideas in an open way.
You’ve had several different protégés with Everwise. What keeps you coming back?
Everwise creates the space for thought. I have dedicated time with someone. We don’t talk in detail about projects or logical, tactical things. We put all that aside and try and think about what needs to be accomplished at a high level. This is incredibly valuable and powerful for them (and for you) to do this repeatedly, to set aside one day every week where you can reflect strategically on the big picture.