Featured Member: Leslie Grandy

Time and again, we’ve watched our members parlay a vast and varied array of skills into entirely new careers. Their continued ability to reinvent themselves and seize new opportunities for professional—and personal—growth is nothing short of astonishing, even to us—and this is what we do! Leslie Grandy exemplifies this kind of magic, which is why we chose her for this month’s featured member. Her interview is compelling to us not only because of her accomplishments, which are impressive, indeed, but also for its wise and clear articulation of how to follow in her footsteps, and walking right out of one brilliant career trajectory into another.
Tell us your work story : Who are you and what do you do?
I am a seasoned digital transformation leader with over 15 years experience, and I am especially adept in building high performing global teams that convert physical businesses into savvy digital enterprises. I have over 18 years of executive experience in large public companies like Apple, T-Mobile, Discovery Networks and most recently at Best Buy, where as part of the Renew Blue transformation, I co-founded and grew the company’s first remote technology office to over 125 people and scaled my overall team to 265 people on two continents. While I enjoy working within established enterprises to launch new products or lines of business, I am equally passionate about the opportunity to develop and scale small businesses.
What is the hardest challenge you’ve faced, work-wise?
The hardest challenge I’ve faced was opening up a technology office for a 35 year old Minnesota-based brick-and-mortar retailer in Seattle, the birthplace of Amazon. Attracting qualified talent, building a Seattle-friendly, diverse culture as part of an old school Fortune 100 midwestern business two time zones away challenged all of my leadership skills. I had to understand what rules I could break to make the office competitive and successful, while also having to stay within the corporate lines for operational support. As a woman leader of engineers, designers and product managers, I had to show both empathy and backbone to stand up for what we needed to do our jobs in the world where we were out of sight, and I couldn’t let us fall off the radar. Sometimes it felt as if I had to change everything from the way our internal network needed to enable my remote team to accomplish their work, to how we were perceived as a stodgy old retailer in this high tech community we were sourcing from. And I had to do that while enabling us to achieve – and actually exceed – an aggressive revenue forecast each year.
If you could change one thing about how your given field operates, particularly with regards to women, what would it be and why?
Diversity in hiring takes effort. I believe there are many times where my colleagues do not operate with a growth mindset, but rather tend to operate with confirmation bias about their potential women colleagues. The tendency to do this results in their hiring more of the same, and looking for reasons not to take a flyer on a woman who can do the job but perhaps in a different way, even if it could be just as useful or better than their male counterpart’s performance. The fear and the discomfort of working in a new way can prevent people for being open to what different style or perspective a woman may bring to the situation.
What advice do you have for other women looking to make a career change but who are afraid or lack confidence? How is it on the other side?
I worked for 13 years in the TV/Film industry before switching into technology product management, after pursuing my MBA. I started over from the bottom in tech as an intern, and I was ready to be scrappy, with a strong work ethic and and openness to learn. What I knew about my strengths I leaned heavily into during the internship – showing my problem solving skills, trustworthiness, integrity and commitment. Those became the pillars I built my new career on. What I didn’t know about my job, I set about learning and showed my willingness to take coaching and feedback to fit into the corporate environment that was completely antithetical to my on-set film industry experience. My advice is this: know what your strongest soft skills are, and how they are applicable to your new career. Find out what you don’t yet know about your new career, and make a visible effort to develop yourself in those ways, whether it’s taking a coding class or going to meet-ups. Be willing to start over without ego, and show your potential to learn and grow. (I did a talk at CodeFellows recently on this topic called “Using your Career Strengths to Start Over”. https://www.youtube.com/watch?v=F88cJN15xA4 )
Do you have any advice on how to craft a winning pitch?
To make a pitch resonate with a potential client, I always use specific, measurable examples of what I have done previously to illustrate my understanding of and experience in the domain. I believe data always helps someone make a better decision. I also feel it’s important to tailor a pitch to the business and brand in order to show you’ve done your homework and are clear on why you can add value to their team.
What is the best piece of professional advice you’ve ever received? 
Bring solutions, not problems. You own the problem when you identify a solution, and you are more likely to fix it when focused in this way, than you are if you choose to waste time placing blame.
How do you negotiate the balance between life and work when you’re the one setting the boundaries?
It’s always helpful to love your work to make this balance viable. My family knows that when I am happy at work, I am happy at home, and vice versa. So they are a huge part of supporting me in both places. I manage the boundaries fluidly, looking at circumstances discretely to assess the need for unusual working hours, travel and presence. I weigh those requirements against my capacity to succeed with what else my life might demand from me and my family. At different points in time, my reaction to those requirements has been varied. And, I suspect it will continue to be as well.
If you could tell your younger self one thing about what this professional journey would be like, what would you tell her? 
Don’t over plan. Technology – and life – bring new opportunities in unexpected places and it’s important to be open to the possibility that something awaits you that you couldn’t have imagined previously.
How do you make work work for you?
Work works for me best when it is challenging me not merely to use my expertise but to also learn and grow. I think without the chance to learn and grow in my work, it becomes merely a job, and could then be just as well be any job. My life’s work has to include improving and growing myself, and in that process I am better equipped to improve the lives of others, whether they be team members or customers.
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