Questions for the Year Ahead

Originally published on LinkedIn, 12/28/2019

As I look towards 2020, I’m reminded of the questions that were so helpful to me in 2019. 

To be clear, 2019 was a big year for me. 

I lost a job (that I loved)..

To find another job (that I love even more). 

AND my family said yes to an adventure in Japan, where I write this from. 

Some of the choices I made in 2019 were more obvious than others. Luckily, several people asked me the right questions at the right time and helped clarify the path I should choose in the face of a few exciting and different career opportunities. 

As we wrap the year up, I now see how helpful these questions will be in setting goals and making decisions for the years to come.

“Think about the person you aspire to be — what would she do?”

Over lunch, Joanna Curran, one of the best people executives I have worked with, looked at me with a smile in her eyes. I was debating three very different career options before me. She asked, “Think about the people you envy. What do you envy about them? Or in other words, the person you aspire to be, which path would she choose?” 

"What would your 70 year-old self be proud of?"

Alexa von Tobel is exceptional at many things, and asking big, bold questions is definitely one of them. You may have read how she tries to make sure she has no regrets, defined by things she didn’t do. One question she asked me was what decisions my 70 year-old self (or was it 60?) would be proud of. While it’s easy to default to the big picture when thinking about this question, what if we just confined it to the year 2020? What would your 70 year-old self be proud of you for doing this year? Choose, plan and dare accordingly. 

"What if none of these options were on the table?"

Lisa Stone, a world-class mentor despite being busy as a world-class executive, simply asked, “If none of these options were in front of you, is this what you would want? And specifically, is this what you and Paul (my partner) would want?” In a culture of striving (which I am strongly influenced by), this was a transformational question. “If this wasn’t an option, would you want to seek it out?” Deceivingly simple and deceivingly effective. 

"Forget the ‘should’."

Sally Thornton reminded me that interesting, curious people create interesting and meaningful careers. (She is a testament to this!) She had me reimagine my aspirations without any of the ’shoulds’ or expectations. Sure, ‘should’ might help you eat your vegetables or exercise, but it shouldn’t govern your career. What would your to-do list and dream-list look like if it was void of the ’shoulds’?

I’m lucky to be surrounded by many wise colleagues and friends who asked other good questions, and through inspired leadership have honed super-power listening skills (thinking of you Arlyn Davich).

What questions will shape how you spend your time and energy in 2020?