Women in Leadership Spotlight on Charlotte Whitmore

What words comes to mind when you think about outstanding women in leadership? Determined, passionate, courageous? If so, you’re in luck as our featured woman today embodies all three characteristics.

Charlotte Whitmore is an Engineering Learning & Development Program Manager based in San Francisco. Armed with a B.A. in Political Science from the University of Pennsylvania, she began her career working in tech at start-ups including Accelo and Prove before moving into enterprise at Atlassian and Roblox.

Charlotte is:

Determined: To bring her full self to work, thereby modeling the type of behaviour she’d like to see from her team as a whole.

Passionate: About creating community, sharing best practices and ensuring all teammates feel welcomed, valued and connected.

Courageous: In sharing her own mental health journey, she is helping to de-stigmatize the issue and build awareness throughout her teams and organizations.

But don’t take our word for it, below hear straight from Charlotte as she discusses challenges she’s faced throughout her career, how she balances work and life responsibilities and when she’s had to #BreakTheBias in her own journey.

What has been the most significant barrier in your career to date?

The main barrier I’ve had was not really knowing what I wanted to do for the first 3-4 years of my professional career. While I don’t believe that 5-year plans are helpful or realistic for anyone who’s just starting out, I just let things happen to me – and while for the most part all of those developments were positive and helped bring me into the career I love today, if I had been more proactive about exploring different types of roles and working styles then I believe I could have found work more rewarding and been more motivated.


Have you ever felt the imposter syndrome, and if so, how did you navigate your way through it?

I definitely have. The vast majority of roles I’ve had to date are jobs that never existed before, even when working for public enterprise companies. While the freedom to develop my own objectives and carve out major aspects of my work has been great, it’s been a struggle for me to need to create my own goals and success metrics without a strong point of view from my leaders.

I’ve worked through that specific issue by spending more time with my stakeholders to dive deeply into their needs and with more seasoned program managers to learn best practices for formulating and structuring clear, measurable objectives that are most relevant to the key outcomes I’m working towards and how to communicate with external partners and stakeholders in ways that they are used to and understand.


What do you think are the three most important characteristics to be an amazing leader in your organization?

These characteristics I believe apply to being an amazing leader in ANY organization:

Be a courageous and clear communicator. Do not be afraid to challenge others, including senior leadership, when you are concerned about a particular decision/direction. Do not be aggressive or overly stubborn in these instances, but make sure that you take the opportunity to clarify exactly what they think the particular decision will achieve, provide the appropriate level of deeper context, and clearly lay out the risks of going in that direction vs another option. Additionally, be transparent yourself! To the degree you’re comfortable, share details about yourself/your work style with your colleagues so you can all communicate well together and understand some of the differences between you to more easily and proactively resolve potential conflicts.

Develop and demonstrate a growth mindset. Actively seek critique on your work as early as possible, and feedback from your collaborators and stakeholders regularly. Do this in group settings when appropriate so others can see you modeling that behavior and hopefully become more comfortable with doing it themselves. Don’t just listen and not take action on what you hear – take the time to truly understand what they are telling you and plan ways you can improve on those areas going forward. And of course, do the same for others!

Don’t be afraid to pivot. Things change at a rapid pace and are only getting faster. It’s quite common that the initial direction and goals of a particular project may need to change during the lifecycle of the work, often due to factors entirely out of your control. If you hold fast to the original decisions, you will not be successful.

How do you balance career, personal life and passions?

I believe in a strong balance across the three, but that that balance looks different to every individual and can change at any time! Personally, I try to make sure that I find ways to connect my work to relevant personal passions (for example, engaging in the clear communication & growth mindset I mentioned above in my personal relationships to build trust and minimize miscommunications.)

My personal life will always come first, and I regularly adjust my approach to my career as necessary to ensure that I am putting myself first while still doing good work that I enjoy. Having some regular activities that I enjoy and make myself feel good are incredibly important – for example stretching, spending time with my dogs, exploring the city, seeing friends frequently.

Engaging in regular self-care is also a huge factor for me; taking care of my skin, going to therapy, staying in touch with my physical and emotional feelings, eating well are all relatively low-impact things to do that have a significant impact on my overall well-being and stability. This is especially important to me as I have a bipolar II diagnosis and will always need to pay more attention to finding ways to regulate my moods than the average person.


What has been your biggest learning when it comes to work-life harmony during the pandemic?

My biggest learning has been how remote work can really help my own work-life balance and allow me to be productive in both areas. I have to focus on setting clear boundaries while enjoying flexibility and creating a regular routine to keep me grounded even though the timing of each element may change day-to-day.

Also, the importance of going outside! Luckily, I have two rescue dogs, so no matter what else may be going on I have to leave my house 2-3 times a day.


What is the role mentorship and sponsorship have played in your career?

A huge role! As I mentioned above, I didn’t have any particular career goals or direction for a long time. One of the major factors that helped me start really thinking about what I’m good at, what opportunities for growth I want, and from there think about the types of work and company culture would best benefit me was discussing these things with my mentors.

I was lucky enough to work directly for multiple co-founders early in my career who were incredibly open and supportive, and as I grew into my program management role I found amazing colleagues from different backgrounds who helped open my eyes to other perspectives. What’s been especially rewarding is that now I am able to mentor others, and supply my own guidance and feedback to my own mentors to help support them.

Most of the people I consider mentors were also great sponsors – challenging me to do more, offering me growth opportunities and supporting me in working on stretch goals, bringing me into conversations with other teams and leaders, help me work towards promotions, and generally assist me in building a positive reputation across the organization.


What advice would you give to your younger self?

Not to be intimidated or hold myself back for fear of failure or not looking like the smartest person in the room. As a high achiever throughout my academic career, the thought of not doing well on any piece or work was always terrifying to me, and that perspective held me back from growing and developing as well as I could have otherwise during the first few years of my professional life.

This is something that I now try to instill in any folks that I mentor, as one of the easiest ways to start having a growth mindset is to see other people you work with, especially more senior and experienced folks, role model that behavior by talking openly about ways they’ve failed and how they’ve learned from going through failure.


In honour of International Women’s Day 2022, has there been a time where you or someone around you has had to #BreakTheBias? What was your biggest learning from this experience?

I can think of quite a few examples of this, but one that comes to mind that’s very personal to me is around de-stigmatizing and being courageous around mental health. I am fortunate to have family and friends who have always been supportive of any mental health journey someone may be on, so when I was first diagnosed with bipolar II I knew I had a great community to rely on. But being open about a diagnosis is one thing in your personal life, and a whole different concern when it comes to the workplace.

While we have made great strides in building more empathy and understanding for the variety of mental health issues anyone might experience and how they can affect their presence/performance at work, stigma and (sometimes unconscious) judgment and even retaliation are still very real concerns. There are many HR departments and managers who aren’t familiar with mental health and simply don’t know how to support someone who is struggling, and the legal requirements for engaging in accommodations.

I was open with my team about my diagnosis from the very beginning, and always let them know when I was in more of a down period so they weren’t surprised by the change in my energy and that I might need more help/direction than usual during those moments.



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