Early in My Career with Anna Milner

This is the first in a series of articles about people in leadership roles at Cengage and how they carved their path to leadership.

I chatted with Anna Milner, former Director of Content Development at Cengage, in her DC_Imagesoffice one afternoon. Her career at WebAssign started eight years ago when she joined the company as a Project Manager. When WebAssign adopted Agile Methodology, Anna transitioned to Scrum Master and then to Manager of Application Development, where she managed software developers. After three years in tech, Anna went on to become the Director of Content Development, a position she retained even after WebAssign was acquired by Cengage.

Anna surely dispels the myth that leaders are born, not made. After changing majors three times in college and finally earning a degree in English Literature, she had no idea what career path to take. She ended up teaching English at St. David’s, a private school in Raleigh—something she thoroughly enjoyed. Anna later worked as a librarian and then was a stay-at-home mom for a few years. When she was ready to go back to work, a project manager position at a startup company fell into her lap. She had no experience in business or computers and simply threw herself into the job and gave it her best shot.

“If someone had told me when I was back in college that I would be working in software development, I would have laughed,” says Anna.

I asked Anna a few questions about her career journey and here’s what she had to say.

From teaching to managing content, how did you get to where you are today?

Have you read Sheryl Sandberg’s book Lean In? She describes career growth as a jungle gym and not a vertical ascent. I followed that pattern and moved in whichever direction made sense to me at that time and it took me to where I wanted to be. I just did the next best thing that made sense.

What made you decide to go into a leadership role?

It wasn’t a conscious plan. I was interested in working with people, solving problems, and building organizations.

When did you first realize you were a leader?

I don’t know. I played sports a lot and usually ended up being team captain. Actually, I’m comfortable leading or following. If no one else steps up then I take the lead. I think it’s part of who I am.

What do you think are the qualities that make a good leader?

The ability to have hard conversations, which includes reviewing someone’s performance, calling out bad ideas in meetings, or resolving conflicts. It is important for leaders to be service minded. They also need to be able to collaborate well and do more together. Leaders need to be able to draw boundaries and say no when appropriate. Casting vision is another important leadership skill. It is basically having an idea of where we are going and what we want to be as a company, team or department.

If you were to honestly evaluate yourself, which of those qualities do you need to work on?

I would have to say casting vision and dealing with conflicts. By nature, I avoid conflicts and I’m working to change that.

What obstacles did you face on the path to leadership and how did you overcome them?

To be taken seriously as a woman in tech is challenging. I was not recognized by some higher-ups for what I had accomplished.

Juggling a career and kids is hard. To achieve a work-life balance I’ve had to let go of some responsibilities in order to have time for others.

What are you really passionate about?

I’m passionate about investing in people. I think people are the most important part of a business. Products and technologies come and go, but people are what make a business or company successful. I also think management excellence is important and by that I mean how can we be the best managers and have a positive impact on people’s lives?

Do you have any advice for folks who want to go into management?

Don’t go into it because you want a fatter paycheck or want to climb the corporate ladder. Do it if what you love matches the job description. If you are not comfortable having tough conversations or giving feedback, then this is not the job for you. Although it is only one aspect of the job, you are not going to be happy if you have a hard time giving constructive feedback.

Start building skills right where you are by learning how to have hard conversations and volunteering to lead. You will grow and you will be noticed by others.

During my time at Cengage-WebAssign, I’ve seen that Anna walks her talk and truly believes in investing in people. Her door is always open and she is always interested in what you have to say. She also made it clear that management is not for those who are timid at heart. You have to have tough conversations and resolve conflicts from time to time. I also learned from her to be open to opportunities that show up in your life, because you never know where it could lead you! 

(Right before publication Anna Milner left Cengage to pursue other opportunities. She will be missed.)

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