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The power of beginning again: failure’s mighty wakeup call

In leadership (and in life), failure is guaranteed. And when it happens, it’s not especially fun. Each time I’ve been brought face-to-face with the fact that I’ve so completely missed what I set out to do, it feels awful. Failure is never the goal. But it has also, each time, been a gift. 

The success I’ve enjoyed in my life has been built on failure―multiple failures, actually. I’ve realized that alongside its less-than-pleasant features, one of its most consistent qualities is truly beautiful: it has incredible power to become a foundation for future success. Henry Ford said, “Failure is simply an opportunity to begin again, this time more intelligently.” And I say, amen to that, Henry Ford.

This is my story of how I learned that truth. How I used one of my greatest failures to begin again. And how I used that failure to ignite my greatest fire as a leader. 

In January 2013, I joined TSheets, a small startup in Boise, Idaho. I was the company’s 10th employee, and at the time, the only full-time marketer. Soon, though, our team was expanding and revenue was growing. I had found my groove and was fueled by the daily hustle of startup life. My passion was at an all-time high and we were winning.  

About a year into my TSheets journey, Matt Rissell (TSheets owner/CEO and my mentor, coach and friend) recommended that I join Vistage, a professional organization that brings together like-minded executives to challenge one another, practice critical thinking and build leadership excellence. In my first year as a Vistage member, I got the opportunity to hear influential speakers talk about the power of effective leadership. And through these Vistage experiences, I became curious about my own leadership and began to ask the question, “What kind of leader am I?” Little did I know I was at the precipice of an awakening.

My Vistage-inspired curiosity soon turned into action. At my request, a trusted colleague and team member arranged an offsite at a local coffee shop, asking the team two questions: 

What does Jen do well as a leader?

What could Jen do better as a leader?

In small companies like TSheets, you aren’t likely to have a defined process for obtaining feedback. I was flying blind in how to ask for and receive this information, but I did it anyway since I was eager to understand where I stood as a leader. Reflecting on this today, I now know this could have been done better. I have a sincere appreciation for companies like Intuit (who later bought TSheets) that have perfected their feedback process and are committed to helping their employees give and receive feedback. It’s an art—one that I wasn’t familiar with at the time. And when done artlessly, it might have more dramatic consequences. Because when you ask for feedback, you might just get it, and I had failed to ponder if I was ready for that.    

As I sat in my office repeatedly refreshing my email inbox, I felt anxious. Then, it happened. The email I had been waiting for had arrived.

As I began to read it, tears started to well up in my eyes. It seemed that my leadership was creating a mess of monumental proportions. My greatest failure as a leader seemed to be, in fact, my overall leadership. At that very moment I knew I was not the leader I thought I was and certainly was not the leader the team needed me to be. The business was winning but it was in spite of my leadership not because of it. 

I was flooded with total despair. I had let the team down and I was embarrassed because of it. I felt hopeless, lost in my own thoughts and shaming voices. Later that evening, I did the unthinkable. I submitted my resignation as Vice President of Marketing for TSheets and called David Spann, my Vistage chair.  

Three things happened that night. First, Matt Rissell refused my resignation (thank you, Matt!). At one of my most vulnerable moments, he didn’t care only about the feedback or what it suggested about me as a leader. He also cared about me as a human being (the perfect example of true leadership). Second, David Spann shared these powerfully loving words: “If you hear something and it stings, there just might be some truth in it.” As much as it hurt to hear these words, I needed to hear them. And third, I drank a bottle of wine and cried myself to sleep.  

I know what you may be thinking. I overreacted. I put too much emphasis on what others thought of me. I responded out of emotion. Yes, all of these statements would be true. I didn’t know how to receive feedback in a healthy way and certainly did not approach it with the right attitude. However, I got one thing right; I decided that I would take what I learned about myself through this failure and use it to begin the journey of becoming a better leader—one that prioritized trust, vulnerability and transparency. 

Looking back, I now know I was what Liz Wiseman, author of Multipliers, calls an accidental diminisher. I wasn’t amplifying the team’s capability and momentum; I was draining it. My off-the-charts, well-intended passion was intimidating to others and created the ultimate barrier to connection. I didn’t take the time to relate and didn’t understand what it meant to lead with care and create psychological safety. And most damaging, I didn’t rally the team around a true why or purpose. The worst part was, up until I received the team’s very straightforward feedback, I wasn’t aware that I was showing up this way. I was too busy driving as hard and fast as I could to hit a number.

“Though you cannot go back and make a brand new start, my friend, anyone can start from now and make a brand new end.” – John Maxwell, Developing the Leader Within You

Becoming aware of how I was showing up (or arguably how I was not showing up) as a leader was one of the most pivotal moments of my entire professional career. As ashamed as I felt in that initial realization, I knew what mattered most was how I acted on and responded to the feedback I’d received. I committed to acting the part of the leader I wanted to become and for accountability reasons, I made this commitment to the TSheets leadership team, my Vistage members and most importantly, to the team I had let down.

I knew that if I really wanted to change, to overcome, I could and would. 

I processed my experience with my Vistage group (if you’re a Vistage member, you know how powerful processing can be). I actively sought out coaching from Matt (and other leaders of our executive team) and looked to him to check in with the team regularly. I read books about leadership, transparency and vulnerability. I hired a life coach. I observed and studied leaders around me. I asked for further feedback in my 1:1s with employees and celebrated when they bravely delivered it. I made a habit out of owning up to my mistakes and proactively acknowledging when I could have shown up differently. Every single day was a new opportunity to live into the kind of leader I knew I could be. 

By admitting failure in real time, people began to see me as a growing leader; a leader that worked to deliver her best for herself and her team. The power of saying three powerful words, “I messed up,” fostered an environment where trust and vulnerability could begin to take hold.

Change didn’t happen overnight. But it did come. As I continued to evolve my leadership approach, my focus became first nurturing relationships that are grounded in trust, transparency and vulnerability. I made a conscious choice each day to lead people rather than manage them. 

Fast forward to early 2019. I was in a 1:1 with Rich Preece, my manager and, at the time, Intuit’s Vice President of US Marketing. Per our usual 1:1 flow, I asked Rich if he had any feedback for me. In classic Rich style (a style I’d characterize as his having a heart for coaching), he said, “Jen, you’re a transparent, vulnerable leader. That’s how you show up. You don’t have to say the actual words so much.” Ureka. All I could do was smile. You see, part of my path to becoming a transparent and vulnerable leader involved me speaking the words multiple times each day. I’d often lead with phrases like: “I’d like to be vulnerable for a moment” or “Transparently, I think…” Words are powerful and for me, helped shape how I engaged with others.

My failures as a leader had led me to grow into the leader I wanted to be. 

I will forever be a growing leader. The truth is we all have the same opportunity to evolve―as leaders, employees, spouses, parents, friends and more. No matter where we are on our journey to personal and professional growth, there’s always room to show up differently. I encourage you to actively seek out feedback, invite others to challenge you, be curious about how you show up in the world, and when you have new information—often in the guise of a failure—commit to acting on it. As John Maxwell says in Developing the Leader Within You, “When you’re through changing, you’re through.” And I’m not done just yet. 

I welcome a lifetime of new opportunities to begin again and build ever-stronger foundations for future growth and success.  

One of the best ways to grow is to read. During my journey to becoming a better leader, I read as many books as I could. Here are a few of my favorites (which all helped shaped my view on leadership): 

  1. Multipliers by Liz Wiseman
  2. Dare to Lead by Brené Brown
  3. Rising Strong by Brené Brown 
  4. Daring Greatly by Brené Brown
  5. Trillion Dollar Coach by Eric Schmidt
  6. The Way of the Shepherd by Dr. Kevin Leman
  7. Developing the Leader Within You by John Maxwell
  8. Fierce Conversations by Susan Scott
  9. Lean In by Sheryl Sandberg 
  10. Radical Candor by Kim Scott

I’d also like to give a special shout out to those who took this journey with me (willingly or not!). Thank you for caring about me enough to provide your feedback and to help me understand what you truly wanted to see in your leader. I will be forever in your debt.

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