It’s Okay Not to Know: Interview with Former Microsoft Executive Jane Boulware
I recently went one-on-one with former Microsoft executive Jane Boulware. Jane is the author of the new book Worthy: From Cornfields to Corner Office of Microsoft.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Jane: Truth is, I was born with no expectations of being or doing anything other than what was done by my mom and her mom before that - get married, have babies, and stay on the good side of the church and the law, in that order. Born the fourth of five kids in a one-bedroom house, I came from multi-generational blue-collar, hard-working folks who didn’t go to college. I didn’t know about life outside of Carroll, Iowa, because I never saw, experienced, or talked about it growing up. I didn’t know what we didn’t have because the families I knew were in the same boat. We had, found, or created what we needed. My mom was brilliant at making the old like new again…even bread bags had nine lives, becoming socks in the winter to keep your feet warm and dry in boots that leaked… until the bags were woven into rugs. My dad was clever and could make something out of nothing. And did. I learned to see and appreciate the things that people/others discard or consider useless. I learned intelligence comes from experience, not a college degree. I also learned all people are worthy and deserve recognition and a seat at the table, regardless of their title, bank balance, or pedigree…and that we all need a hand to get ahead.
Lucky for me, a gnarly old nun helped me secure a $320 college scholarship to a future I didn’t know existed. I left for college before my folks knew I was gone, selling my dad’s used carpeting and mom’s prayers to pay my way. I was penniless and married at 21 years old, I had an MBA at 24, first saw the ocean at 25, led marketing for Kimberly-Clark Latin America at 31, was a mom of two sons by 35, a millionaire and one of the top Microsoft executives at 40. By 52, I had launched and led three major ventures, navigated the US's largest merger, and left a trail of influential leaders in my wake.
Along the way from cornfield to the corner office, I’ve been hit on, spit on, shot at, yelled at, a zero, and a hero. I’ve been called a bulldog, a bitch, and brilliant all on the same day. And all along the way, I’ve been dismissed and underestimated by many, often myself. But each time I did something someone thought I shouldn’t, couldn’t, or wouldn’t do, every time I did a difficult thing I never imagined, I began to imagine myself differently. I learned it’s okay to admit you don’t know, that being afraid just means you are stretching and growing outside your comfort zone and that failure means something didn’t succeed yet…it doesn’t mean I am a failure. And I learned to begin again. And again. And again. Because the difference between those who do and those who don’t succeed is the word “yet”. Above all, I learned I am worthy as I am. No one can give me worth or take my worth from me. I didn’t become it, lose it with failure, or get more with success. That knowledge helped me get out of my own way, to build upon my strengths, and recognize/develop the strengths of others around me to make amazing things happen.
Adam: In your experience, what are the key steps to growing and scaling your business?
Jane: Ideally, start with a meaningfully differentiated product or service, then….
1. Be clear what success looks like; ensure you know how to measure, track, and manage progress.
2. Hire people who supplement your strengths and develop them to be more successful than they thought they could or would be.
3. Create individual and team success metrics so all are aligned and have clear yet mutually accretive accountability.
4. Remove the barriers to your team’s success, including yourself. Get them the resources and take the bullets so they can take the hill.
5. Reward and celebrate success often and meaningfully. Welcome, recognize, and appreciate the contribution of all, regardless of title.
Adam: What is your best advice on building, leading, and managing teams?
Jane:
Be level agnostic – success isn’t built by people with pedigree, it’s built by people with a track record of having overcome obstacles, who have the drive and ability to keep going until mutual success is achieved.
Hire better than you are. Top performers hire top performers; medium performers hire low performers so they look better in comparison. Become good at assessing people based on their ability, aptitude, and attitude.
Assess for:
Aptitude- put people in roles aligned to their natural capability.
Ability – train and develop skills and talents of individuals.
Attitude – a can-do attitude trumps aptitude and ability. A bad attitude is a cancer that must be eliminated fully and quickly, or it will kill a team/business.
Create a culture of respect and mutual success that is clear, recognized and rewarded
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Jane: AI and its radical impact and implication for new aptitudes, abilities, and attitudes. AI will redefine who, what, and how work gets done, impacting every sector and function. Leadership and trust will become more important than ever before.
Adam: What do you believe are the defining qualities of an effective leader?
Jane: Communication skills, humility, curiosity, a growth mindset, courage, and the ability to attract/retain talent.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Jane: Be curious and ask questions, admit and learn from mistakes, and surround yourself with people who are better than you at what they do. Ask for and be a mentor – it will change your perspective and enable you to grow in ways you didn’t think possible. For example, I mentored an employee when she left Microsoft to start her own company. I provided business acumen and encouragement. She in turn, supported me in writing my book, Worthy. Weeks before it’s launch, we confessed that she hated the cover artwork…and in my inbox the next day, she sent a new cover design she’d created. It was much better and is now the cover for my book. Another person I’d been mentoring became my mentor when she began teaching me how to leverage social media. Mentoring is a give-take experience where the mentor becomes the mentee and vice versa. Remembering we all have something to teach and learn enables continuous learning and a growth mindset. Both are critical leadership skills to take us and our business to the next level.
Adam: What do you hope readers take away from your new book?
Jane: You are worthy as you are; do not let circumstances, fear, or others define who you are or what you can become. Failure can be learned from and overcome and happens when you are learning or trying something new. Fear is okay; it occurs when we are uncomfortable because we are stretching ourselves - the good stuff in life happens when we’re afraid but act anyway. So don’t try to be fearless; try to fear less. I shared my journey in Worthy to the executive offices of Microsoft in relatable stories that are funny, vulnerable, and scathingly honest because I didn’t see any books that talk about overcoming the circumstances and people (including ourselves) that limit us. People see my title and “accomplishments” and think there is something unique about me, that I have the “secret sauce” to success. There isn’t and I don’t. By openly sharing my struggles, successes, and shortfalls, I want others to know that they aren’t alone, they aren’t imposters, and they too can overcome expectations, failure, and fear. I want people to rethink what is possible and to claim their worth.
Adam: What is the best lesson you’ve learned over the course of your career?
Jane: It’s okay not to know. In my career, I was often surrounded by people who knew more, were better at their jobs, than I was. It was a constant battle to keep my ego at bay, to remind myself to listen and then force myself to shut up so I could learn. Donning the false mask of bravado that said “I’m invincible” had been as much a part of my morning routine as brushing my teeth and combing my hair. But I didn’t want to fake it; I wanted to be real and honest. Lacking the courage or confidence to remove the mask completely, I learned slowly but surely to remove the mask to reveal the real Jane, bit by bit. Without exception, every person I shared my vulnerability with, each person I asked for help, graciously did so without reservation. If they judged and found me lacking, I didn’t see it. As I got to know my teams and they me, my focus shifted from what I was and wasn’t to what they were. Unconcerned about being the best or the smartest left space for me to recognize, appreciate, and develop the best in them.
Over time, I stopped trying to hide, stopped making myself smaller or bigger, which enabled me to open myself up to the issues and needs of my team, partners, and customers. I didn’t have all the answers and came to realize it was better to listen and admit to others what I didn’t know, giving myself permission to say, “I don’t know” and to ask for help… and get out of the way of those who know more. I try to live by the saying “Together we can do what we can never do alone.” I don’t need to have all the answers; I just needed the courage to seek the answers from others, for others. Only Ego expects to know all despite asking nothing.
Adam: Is there anything else you would like to share?
Jane: I am giving 100% of the proceeds from the sale of Worthy to the Boys & Girls Clubs of America’s Youth of the Year scholarships to give club kids an opportunity to a life most don’t know exists. I hope you will join me in paying forward what you have learned and earned throughout your career and life.
Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.
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