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Women Of The C-Suite: “Know what you’re not good at” With Udemy SVP Cara Brennan Allamano & Akemi Sue Fisher

Know what you’re not good at. I see a lot of people who try to fit themselves into a role they “should” succeed at. It rarely works in the long term. I’ve been in HR positions where the requirements of the role weren’t what I could deliver at a level I’m comfortable with. In those […]



Know what you’re not good at. I see a lot of people who try to fit themselves into a role they “should” succeed at. It rarely works in the long term. I’ve been in HR positions where the requirements of the role weren’t what I could deliver at a level I’m comfortable with. In those situations, I’ve had to get real about it and move on. Being honest with yourself about what you can’t do well is critical. Ask colleagues how they would rate you in your role, and if they don’t think you’re performing at a high level, ask them what they think you’d be better off doing. You have to be prepared to hear some hard truths, and you may be surprised at the answers. Either way, the information could put you on the path toward something that will be your best work.


I had the distinct pleasure to interview Cara Brennan Allamano, the SVP, Human Resources at Udemy.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I was working at Franklin Templeton when I realized I was much more interested in what was happening with my friends in recruiting/HR than my immediate work. When the company moved from its offices in Carmel where I was living, I decided my next job would be in HR.

Can you share the most interesting story that happened to you since you began leading your company?

This is both personal and professional. I’d wanted to work at a company that was making a real difference, and I knew Udemy was changing lives around the world, but after I started working here, my husband and I started getting really curious about taking courses at home ourselves. That’s when I realized how great it was for us, too! We’ve since stopped watching TV after the kids go to bed and, instead, pick a course and learn together. I’ve gotten tons of insight into really interesting topics, from home construction to how to save on my taxes to how to be a better mom.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I have a really bad sense of direction and was late to most of my meetings in the first few weeks because I was wandering around looking for the rooms!

What do you think makes your company stand out? Can you share a story?

We’re lucky to be in an industry that infuses meaning and purpose into everyone’s job. When your mission is to connect people who want to learn with people who want to teach, you’re truly doing something to make the world a better place virtually every day, something not a lot of other companies can say. The people who work at Udemy are smart, passionate, and committed to our mission, while also being supportive and respectful of each other. It’s a really special culture. One of the stories that really captures the difference Udemy is making is about a Syrian refugee in Germany, who took several courses on Udemy and landed the job of his dreams as a software engineer. Our impact isn’t just an abstraction; it’s very real.

Are you working on any exciting new projects now? How do you think that will help people?

Most of my team’s work is internal. We support Udemy employees as a single group that encompasses recruiting, learning and development, human resources, and facilities. Right now, we are working on a project to unify the employee experience across all of these areas — to map out what the lifecycle should look like and ensure we’re optimizing in all the right places. It will take time, but our goal is to continue to maintain Udemy’s status as a Best Place to Work, a designation we’ve earned four times. In fact, we came in first place for 2018.

What advice would you give to other female leaders to help their team to thrive?

Be authentic. This was a company value at Pinterest when I worked there, and I loved it. Now, we are in a transition period where women are gaining seats at the table while also eschewing the traditionally male-gendered behaviors that used to be a requisite to get there. We need women who are comfortable being themselves and are demonstrating how “feminine” behaviors and styles can be equally helpful in leadership. If you are able to be yourself, it sends a message to your team that their authenticity is valued too. I’ve found that retention starts when people feel truly respected for who they are, no matter their gender.

What advice would you give to other female leaders about the best way to manage a large team?

See above 🙂 Ask that people bring their best selves to the table and work to help others do their best work as well. For large teams, this attitude of goodwill and communal effort can eliminate a lot of friction, and when you’re driving hard toward big goals, it can mean the difference between success and failure.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My father was a pediatrician. He loved what he did and helped a ton of people. I grew up in a small town in Kentucky and went to school with two people who were named after him because he’d saved their lives. I saw what rewarding work looked like and have held myself to the same standard of doing work I believe in and that I feel is helping people.

How have you used your success to bring goodness to the world?

Udemy’s mission is to improve lives through learning. Virtually everything we do here has the ultimate effect of helping people around the world gain access to learning opportunities, so they can reach their goals, both professionally and personally. In my role, I feel privileged to be developing the workforce that can fulfill our mission more effectively and to support them along the way.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

A) Don’t limit yourself. I started working at both Pinterest and Planet when I was five-months pregnant. Both times, I didn’t believe anyone would want to hire a woman who was about to have a baby — and I was clearly pregnant at all those interviews! Fortunately, I was wrong; both CEOs had total confidence in me. As a result, I had a great time building out the people functions at both companies, knowing they really valued women and families and were showing their commitment in tangible ways.

B) Know what you’re good at. I had two jobs in my early 20’s before I landed in HR. Prior to that career pivot, I was on track to be a bond trader, which involved a lot of analysis and spreadsheets and was very different from what I knew I inherently enjoyed doing. I got advice from lots of people, many of whom said I was crazy to give up a strong career path in finance. I was pretty good at it, but I knew I couldn’t reach my full potential doing it if my heart wasn’t in it. It took a little courage, but I quit that job and headed into HR. It was the best decision of my life. I’m so much more successful on my current career path than I ever would have been had I stayed in finance because it’s a better fit for my strengths. When people seek out my advice about how to manage their career, I always ask first, “What do you like doing? What part of your job are you good at that are also satisfying and motivating to you?” If you’re in a role where you’re not leveraging your strengths, quit. The sooner the better. Otherwise, you will be forced to change paths later anyway, and you’ll wish you moved earlier.

C) Know what you’re not good at. I see a lot of people who try to fit themselves into a role they “should” succeed at. It rarely works in the long term. I’ve been in HR positions where the requirements of the role weren’t what I could deliver at a level I’m comfortable with. In those situations, I’ve had to get real about it and move on. Being honest with yourself about what you can’t do well is critical. Ask colleagues how they would rate you in your role, and if they don’t think you’re performing at a high level, ask them what they think you’d be better off doing. You have to be prepared to hear some hard truths, and you may be surprised at the answers. Either way, the information could put you on the path toward something that will be your best work.

D) Know what you need to know. When I started in HR, I realized that the people I respected most in the function knew employment law inside and out. It’s a huge value-add to have an HR leader who has a strong foundation in the “rules” of employment so you can build a great culture on top of that. I bought the encyclopaedic “California Labor Law Digest” and read it cover to cover. This was not exciting content, to say the least, and people thought I was crazy, but I’ve been able to move faster because I don’t need attorneys to review all of the People Team’s plans. I can partner better with them and others because I’m knowledgeable myself.

E) Get a hobby. The best employees I’ve seen are those who bring a lot of different insights to their roles. Most often this comes from something they’re engaged in outside their professional domain. I’ve had Olympic divers become amazing salespeople, surfers excel as attorneys, and HR people who love to garden. They learn skills and habits in their hobbies that are positively reflected in their day jobs. Plus, it’s just a great way to bring more balance and resilience into your life. My personal hobby is world history; I read a ton and watch programs and travel to places of historical note. Learning about real-life stories that are full of success, failure and everything in between helps me develop empathy and a clearer view of the diversity of human experience. I use this everyday in my work.

You are a person of great influence. If you could inspire a movement that would bring t\e most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

One of the members of our team came up with the idea to build a community for older professionals called TechOver40. In the tech world, I believe this group is often marginalized and underappreciated for their contributions. Many younger workers assume innovation and energy only come from youth, but I’ve seen plenty of examples of the opposite. Depth and breadth of experience can play a powerful role in building and growing an organization. Through our TechOver40 initiative, we’re going to share stories of older workers and their impact on team success. Stay tuned…

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I’m a big believer in action — pushing forward with optimism until or unless you need to change course. In college I came across the Epictetus quote, “First say to yourself what you will be; then do what you have to do.” I have it posted on my wall to remind me to get going!

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I’ve been reading the work of Cambridge professor, brilliant historian, and Twitter maven Mary Beard. Hey, Mary Beard! I’m a big nerd when it comes to history. SPQR: A History of Ancient Rome was my travel book this summer, and I also love your point of view in Women & Power: A Manifesto.

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