Leaving a Legacy: Career Advice & Corporate Culture with Former Microsoft EVP & Chief Marketing Officer, Chris Capossela

Since joining Microsoft, I’ve been inspired by incredible leaders in action who have personally impacted me. As an early-in-career who was a part of Chris Capossela’s marketing organization, I must say he was the world’s best CMO because of how he led with such authenticity, passion, and care — resulting in an empowering team culture that achieves world-class excellence.

Today, I am thrilled to share Chris’ extraordinary career and leadership story from new grad to Executive Vice President & Chief Marketing Officer at Microsoft. Besides being inspired, you’ll also find career advice and insights to help you navigate your career path and become an impactful leader in the future!

Making meaningful career changes

Upon joining Microsoft in 1991, Chris never expected to have a 32 year career at a single company. His secret to lasting this long? He never got bored! Microsoft was such a big and interesting company that every new team he joined seemed to feel like a brand new company where he had to start from scratch.

How can you tell when it’s a good time to make a career change?

  1. Try the Sunday Night Test
    • At the end of your weekend, ask yourself what feelings you have about the week ahead. Are you excited or uninspired?
    • Take note of your Sunday Night Test responses over time and observe the upward or downward trend of your feelings towards your current job.
  2. Listen to your intuition
    • You should know when your learning curve is flattening because your work has become too formulaic or boring.
  3. Remember to fulfil your commitment to your manager first.
    • Hiring is expensive and your manager invested in you for your value add.
    • Before you consider moving on, did you give the team what they needed from you?

Job hunting with purpose

Throughout his career, Chris made many non-traditional moves to teams that were completely different from one another. In total, he took on 12 roles across marketing, communications, engineering, sales, and operations — one of them being Bill Gates’ speech assistant!

What should you keep in mind if you’re job hunting?

  1. Develop thick skin and give yourself grace because you will hear more “No’s” than “Yes'” when trying to convince people to take a bet on you. Believe in yourself and remember that not everyone is better than you!
  2. Talk to the people who used to be in the role you’re applying for. Ask them what they would’ve done differently and what skills served them best in the role.
  3. Get good at figuring out what skills you have that are valuable to the team that you’re applying for, even if you’re not the traditional candidate who fits the job description. Be confident and seize the opportunity to reset the hiring manager’s expectations by telling them what value you can offer that is unique.
  4. Cast a wide net and consider 4-5 different opportunities when you’re ready to make a change. This will give you options so that you don’t end up settling. Sometimes, getting really close to leaving a team or company because of a tempting offer may actually reinforce why you want to stay.
  5. Aim for a role that has 1-2 change types (note: taking on a role with too many change types at the same time can be too overwhelming):
    • Change in geography (moving to a new city or country)
    • Change in scope/responsibility (from Individual Contributor to People Manager)
    • Change in product/service offering (from Azure to Power Platform)
    • Change in discipline (e.g. from Communications to Sales)
  6. Think carefully about your aspirations before leaving a company.
    • What 2-3 things do you wish you could do? (e.g. work abroad, join a different product team)
    • Evaluate opportunities in the industry to see if you’re being compensated well, etc.

Leading with care and authenticity

From witnessing the reactions of so many people upon the announcement of Chris’ departure from Microsoft in late 2023, it’s clear that he has made a huge impact on the lives of many people — including myself — over the years. Everyone could see how much time, energy, and resources Chris and his leadership team invested into the people, succeeding in fostering a strong sense of community and loyalty among thousands around the world. Chris credits his empathetic leadership style to past opportunities when he got to see effective leadership-at-scale.

How can you become an impactful leader that drives a positive and empathetic team culture?

  1. Invest lots of time in getting to know the people who work for you.
    • Everyone is different so you should not project your preferences onto the team.
    • Listen and read more than you talk.
  2. Remember that your job is to help your team members grow.
    • Ask how they like to be recognized (e.g. in front of a crowd or 1on1)
    • Ask how they prefer to receive feedback (e.g. email, face-to-face, ad-hoc vs. structured).
  3. Be thoughtful about the team dynamic around team meetings.
    • Who is the meeting really for? Is it for you to get what you need (e.g. roundtable updates), the team to get the help they need on their projects, team building, and/or up skilling?
    • Be considerate about everyone’s time by being intentional with how the meeting agenda is set up.
    • Create space for your team members to build rapport and visibility (e.g. rotating agenda topics with different speakers).
  4. Communications is critical because you need to reach everyone in your organization.
    • Develop a consistent drumbeat of “meta messages” that are echoed in every piece of communication.
    • Dedicate time to interact with different communities (senior leaders, middle managers, everyone)
  5. Put programs in place to address leadership and team culture priorities (e.g. DE&I, career development, talent management)
    • Hire for culture and focus on the people, especially when it comes to recruiting senior leaders.
    • Challenge the systems in place and create a platform for others to have a voice in the community.

Celebrating #ChrisCap

It’s not everyday that you get to meet with such an extraordinary and empathetic world leader like Chris. Below is a poem that I was inspired to write for Chris as a thank you for taking the time to share his advice and insights with us (Fun Fact: I did NOT use any AI help to write this 😇).

Dear ChrisCap
Thank you for
Creating a culture
Where people open the door

Dear ChrisCap
You’re a leader that’s kind
One that has made
MCB a team that truly shines

Dear ChrisCap
Such an inspiration
Who started as a new grad
Now a marketing sensation!

Dear ChrisCap
It’s the end of an era
Many of us will be sad
Walking the halls of One Esterra

Dear ChrisCap
You will be missed
Microsoft will never see
Another leader quite like this!

Dear ChrisCap
Sending you positive vibes
As you start your next chapter
And positively impact many more lives

Thanks for reading!

My personal philosophy is growing 1% everyday through finding inspiration to share with the world. I hope you leave my blog feeling inspired to thrive in your career journey. I’m here to help and support, so please connect and share your feedback and ideas with me on LinkedIn!

You can read more inspiring stories from my Leadership Series here.