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The best advice for aspiring leaders? Ask for what you want

Hoping to get to management or the C-Suite one day? This software exec who’s worked for Microsoft and Adobe shares her journey and four top tips.

The best advice for aspiring leaders? Ask for what you want
[Source images: Dmitrii_Guzhanin/iStock; Charles Deluvio/Unsplash]
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Early this year, I accepted the role of chief marketing officer at the content platform software maker Contentful. The company was on a fast growth trajectory fueled by a strong economy. But by the time I started, we were in the midst of a global pandemic and worrisome economic forecast. 

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Six months into my tenure, I still haven’t been into an office. Fortunately, I’ve been able to lean on great advice from past mentors to keep growing as a professional, provide leadership to others, and share with future leaders the lessons that best helped me through the ups and downs of my career.

Build a supportive community

I’ve found that building a supportive community across work colleagues and in my personal life creates the balance I need to be able to handle challenges and accomplish more. I especially encourage women in earlier stages of their career to avoid the myth that you can have it all, and do it all, by yourself. You can’t.

It can be tempting to put all your focus on work, but that approach leaves you off balance. And, for many of us, this is no longer an option. We’re suddenly wearing multiple hats—supporting our children, spouses, parents and others—while working. Children are home around the clock. Plus, the resources that supported us in the past, such as caregivers and other in-home services, are more difficult to access. It is more critical now than ever before to build and lean on your support system, appreciate its limits, and find the right balance.

I’ve worked with my leadership team to model behaviors that encourage balance, and talk openly about what balance looks like. It means that extra effort to deliver on a deadline or major project can be balanced with flexibility and personal time. It also means that we balance the focus on business growth with a focus on the career growth of individuals. And, it means that we provide our employees with the tools and permission to find their right balance.  

Always be ready to pivot

Only when you are in balance can you easily shift and adapt. When I was a young soccer player, there was a lesson we learned no matter the position, competition or game-day strategy: Always be ready to pivot. 

This readiness has served me well. I started my career in the nonprofit sector where I discovered a passion for building new things and leading people. I pivoted towards that goal and went back to school to get my MBA at the Yale School of Management. After graduation, I was intrigued by emerging technologies and again I leaned into my passion and pivoted my career toward the technology sector. 

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This ability to pivot has been critical to successfully navigating leadership challenges. At Contentful, my first task was to radically overhaul the growth plan and marketing budget, in anticipation of a global recession. But within a couple of months, brands realized that digital had become their primary (and often only) connection to customers, so they needed Contentful’s content platform to accelerate digital capabilities. We went back to the plan, and instead of massive cuts, we prepared for major growth. It wasn’t easy to scale up so quickly after winding down. But this flexibility is necessary to adapt to the market, customer demand and new opportunities.

Always be ready to pivot—it’s a lesson business leaders need now more than ever. 

Don’t be afraid to take risks

Early in my career, I recall being fearful of challenging assignments and roles that stretched my abilities. I avoided this risk until eventually, my desire to grow professionally loomed larger than my fear of failure. 

Now, I encourage people to approach risk differently than I did. I suggest they start with small risks, such as volunteering to lead a meeting, give a presentation, take on a stretch assignment, or lead a team initiative. This gradually builds confidence and capability, the muscles most essential for career growth. 

My advice to people who are hesitant to pursue a new role or challenge is to build up your capacity for risk bit by bit. What I eventually learned was that the only real failure was not trying—by avoiding opportunities to fail, we can miss opportunities to take our careers to the next level. 

Speak up for what you want 

I was fortunate to have a boss early in my career who proactively offered me opportunities to grow professionally—I just needed to overcome my fear of risk. But the opportunities you want don’t always show up on their own. 

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For example, at one point I was feeling stuck after being in the same role for a few years. When I finally built up the courage to approach my boss and share my frustration, he told me, “Bridget, you should realize that I am not a ‘mind-reader,’ nor is anyone else that I know.” 

His advice was to “just tell people what you want.” This is a lesson that I took to heart then and put into action ever since. And it’s particularly important for aspiring leaders—you must define what you want and then articulate it. Otherwise, you risk getting stuck and limiting your opportunities for career growth.   

There is not a single path to becoming a successful leader. Aspiring leaders need to be ready to ask for what they want, take risks beyond their comfort zone, pivot when necessary, and build a community that provides the support they need to maintain their balance and thrive. 


Bridget Perry is CMO for content management platform Contentful, and has spent the past 20 years leading marketing at established and early-stage technology companies, including Adobe and Microsoft.