Meet Panelist Lynne Kjolso: Women in Leadership Interview Series

In the leadup to our panel event in partnership with Microsoft Advertising, Growing Your Voice: Empowering Lessons From Women Leaders, we sat down with panelist Lynne Kjolso to learn more about how she came up in their career. Throughout her 12 years at Microsoft, Lynne has worn many hats, her most recent being Vice President of Global Corporate Sales. Lynne values her work in creating a globally diverse team where everyone has space to be their authentic selves while at the same time working with a strong, clear sense of purpose. Read on to learn more about how she’s constantly pushing herself to learn and grow, no matter which stage of her career she is in.

To begin, we would like to dive into your background. What was your early career path like, and what led to you ultimately pursuing a career in marketing?  

At the beginning of my career, I had absolutely no intention to go into marketing, nor to work at a large, multinational corporation.  I was pursuing a PhD in Philosophy and had every intention of pursuing an academic career. But life sometimes throws you curve-balls and when my life took some unexpected turns, I propelled myself into a business career.  I started working for a series of start-up’s in the early Internet days, focused on understanding and improving multi-channel customer experiences. I had my first big break when my client at Expedia asked me to join his team and lead customer experience work for Expedia.com.  Along the way, I became super interested in corporate communications and served as a comms director at both Expedia and AT&T. When I joined Microsoft 12 years ago, I hadn’t the slightest idea what SEM was and actually thought they were hiring me for an editorial position in MSN.  But no, my job was actually reviewing the millions of listings that were being published on LiveSearch.com. While I loved that role, my passion has always been helping customers succeed, so when I got the chance to move into sales management, I leaped at that. My career at Microsoft Advertising has taken me all around the world as we launched our global partnership with Yahoo, and back to the US to build and lead a global sales team focused on Corporate, SMB and channel partners.

Did you have any times in your life where you were inclined to change your career path?

Yes, absolutely.  When you start out in life thinking you want to teach philosophy and end up working for one of the largest corporations in the world, you are bound to self-doubt and have an identity crisis.  I certainly experienced that and sought the help of an executive coach. They helped me see that the things that attracted me to teaching were the same things that attracted me to people management, and that while vastly different contexts, I could play a role in developing talent, helping people to realize their potential, and building healthy cultures.  That journey of exploration really helped me to see new purpose in my work, to get in touch with my core values, and to use those as a touchstone every time I’ve had other moments of self-doubt.

Did you have a significant moment in your life that inspired your passion to pursue your current career?

There was one moment, probably 10 years ago, when I was in a London black cab headed to Heathrow.  I had just finished a business trip with our EMEA-based editorial team, and I realized that the part of my job that I enjoyed the most was trying to figure out how to take processes and tools built in the US and make them truly applicable and useful globally.  That moment inspired my passion to pursue international roles, which ultimately gave me the experience and credibility to secure a global leadership position.

Could you describe what a typical work day looks like for you?

There is no typical day for me, to be honest.  There are heavy internal and external demands on me as a sales leader, I travel extensively across the US and internationally, and there are always curve balls and surprises in this business.  The one thing I try to do every day is take 2 minutes to ground myself in the morning. I walk outside, breathe fresh air, and do a super simple meditation. Those few minutes help me clear my head and get ready for whatever the day is going to throw my way.

How do you make sure that you are always growing and learning in your career?  

On the one hand, I’d say that our industry is constantly evolving and changing, so just keeping up with the industry is in itself learning and growing.  We have a 70/20/10 framework at Microsoft for learning – i.e. 70% of your learning comes on the job, and we pause and reflect 3x per year on recent learnings and growth.  20% is learning from others, and I do that via learning from my peers and team, checking in with mentors 3-4 times per year, and participating in a coaching program. Finally, 10% will come in the classroom – I try to carve out 2-3 days every six months for classroom learning on topics that are either interesting to me or build capabilities that I want to develop.

What was your support system like as your career advanced? Did you have a particular role model? 

I was really blessed to have some strong mentors and role models in my early start-up days, visionary entrepreneurial leaders who loved to question convention and break through the noise with a clear and innovative message.  In the early days of my corporate career, I didn’t necessarily have great role models in leadership but I had good friends who operated as their authentic selves and helped me navigate business problems and relationships in a way that felt authentic and congruent to my values.  As I advanced to Director level, I’ve had the opportunity to work for some brilliant senior leaders who have been radically candid with me and also advocated for me. Mentors – senior, peer and reverse – have also been a great resource.

Do you have any words of wisdom you would impart on your 20-year-old self, given the chance?

You don’t have to remake yourself into a 1980’s stereotype to be a successful leader in business.  I spent way too much time stressing over whether I needed to act like certain leaders whom I observed but did not really want to emulate.  Along the way, I learned that to be successful, I just had to be the best version of myself.

What’s the most impactful advice you’ve ever received?  

One of my first managers told me that it was more important to be effective than to be right.  In all honesty, I have used that advice nearly every day since.

Have you ever feared coming off as pushy or unlikeable when dealing in negotiations in the past (whether it was salary negotiation, client-facing negotiation, or negotiations between your colleagues)?

I have certainly worried and felt some angst about being “pushy.”  But if you read any successful sales methodology, you realize that sales and negotiation is about designing a good conversation, a good value exchange.  Understanding what each person wants from the conversation and doing your homework to anticipate your client or boss’ needs is the key to successful negotiation.

Have you ever purposely held back from sharing your opinion at points in your career from fear of being rejected for being female?  

I don’t think I’ve held back because I was female or one of the only woman in the room.  I do hold back when I’m unsure of my facts or haven’t had a chance to do deep analysis. I’ve also held back when I’ve been uncertain how to steer a conversation successfully.  I’m working on my ability to jump in when not fully ready, because sometimes holding back means you miss the moment – missed your chance to add a valuable insight or shift the tone of unhealthy conversations.  Pushing myself forward when uncertain is a work in progress, but I’ve been surprised at how effective some of these interventions can be.