The Smartest People I Know: Meet Penny Wilson

Hello again! Welcome back to The Smartest People I Know, my monthly newsletter sharing rapid-fire wisdom from some of the incredible people I’ve met on my career journey. I’d love to hear what you think in the comments!

Meet Penny Wilson, CMO, Board Member and Advisor

Penny Wilson is a board member and corporate advisor, who has served as CMO at global brands including Hootsuite, Juniper Networks and Macromedia. During our time together at Hootsuite, I was consistently impressed with her passion, drive and thoughtfulness. Today, when I want to bring graciousness and generosity to my own leadership practice, I think “what would Penny do?” It was an honor to connect again recently, and glean some wisdom from one of the smartest people I know. Here are some great insights from Penny on career and more.

The secret to fulfillment in work (and life) is ... For me the biggest secret to fulfillment in work and life is to help others grow. Whether it’s your colleagues, your family, your friends or your community, there is so much satisfaction in seeing others fulfill their potential. 

The best career advice you've ever received? The best career advice I received was from my father, who regularly encouraged me to not be afraid of failure. He always maintained that failure was an integral part of success, and an opportunity to learn.  

The worst career advice you've ever received? The worst career advice also came from my father, when he was trying to help me be more confident with public speaking. He advised me to visualize the audience sitting on the toilet. To this day, it haunts me whenever I step on stage.   

What do you wish you could tell your younger self? Step outside your comfort zone often: it’s the best way for you to grow. Trust your intuition, and move any self doubt aside.  

Is there a quote or memorable saying that you've found to be especially helpful over the years? I am a big Brené Brown fan. I’ve enjoyed her perspective through every book and research initiative she has authored. One quote of hers that sticks with me is, “Courage is contagious. Every time we choose courage, we make everyone around us a little better and the world a little braver.” As a woman with a track record in predominantly male businesses, I clung to having the courage to voice my opinions and the courage to step up to the plate and take action. I strive to give others that same courage. 

Who's the smartest person that you know? My husband is one of the smartest people I know. He has taught me that humor and laughter are critical life medicines. Not that I’m the funniest person around, but it is important to bring laughter into even the toughest situations, as laughter can lighten the mood and help people solve some of the most complex problems.  

Sum up your career/business philosophy in seven words or less! Listen, be brave, be vulnerable, be willing to make mistakes. (Ten words — sorry.)

#OneBigIdea

“Many leaders want to fill the room with what they know but there is so much value in listening first, being curious and then providing feedback.”— Penny Wilson

Huge thank you to Penny for sharing her time and thoughts! Here's what's been keeping me engaged on the leadership front.

What I’ve Been Reading

How a Year of WFH Impacted Work Relationships: Many of us have been working remotely for a year now, and though we’ve all done admirably in figuring out how to get our jobs done from a distance, I’m not surprised at all that it’s taken a toll on our networking, socializing and communication. This story was a great reminder that leaders need to be intentional and proactive about creating opportunities for connection on your team.

5 Ways to Keep Your Company Growing: What I love about this Inc. article is that it’s all about people. No matter what industry you’re in, ultimately all businesses boil down to the strength of their team. Empower your people, hold them accountable and reward your talent, and watch your company grow by leaps and bounds.

Reader Feedback

I’m currently working on an blog post about dealing with “brilliant jerks” — those colleagues who are incredibly bright or talented, but may lack humility or tact. Looking for insight, I recently asked my LinkedIn followers for tried-and-tested strategies to navigate working with this sort of personality type. This comment from David Reichart, a customer success executive, was a stand-out:

I earn the person's trust and then, one-to-one, let them know how they are coming across. This includes a discussion on how it hampers their success and impairs people wanting to engage, collaborate and share with them.

Long term, I always attempt to build a winning team, not a collection of individual superstars. — David Reichart

Thank you for reading. If you found The Smartest People I Know interesting, feel free to subscribe ... or, better yet, share this with the smartest person you know. More to come next month!