5 Talent Leaders Share Their Biggest Work or Career Mistake — and What They Learned From It

If you haven’t made an embarrassing mistake at work or regretted a career move, please raise your hand.

Our guess is that not a single person reading this is raising their hand right now. And if you are, we want to know your secret — you must have superpowers or supernatural abilities.

All to say, we’ve likely all made cringe-worthy mistakes at work, whether it’s accidentally spamming a mailing list of thousands or turning yourself into a potato during a Zoom meeting. And many of us have likely made career choices that were less than ideal, including taking a job that didn’t quite feel right or even staying in a role for a little too long.

But there’s something cathartic in knowing that everyone has made these mistakes and lived to tell their story. It’s in this spirit that we asked five talent leaders:

What’s the biggest mistake you’ve made at work and what did you learn from it?

Below you’ll find their thoughtful — and sometimes playful — answers:

Dr. Terri Horton: Hitting pause on a dream to take a safe and familiar path

“After nearly 20 years in the media industry, I started my management consulting firm,” says Terri, a workforce futurist, LinkedIn Learning instructor, and founder of FuturePath. “I planned for months and was eager to begin the journey.

“Three months in, I was tapped by a recruiter and received an offer from a media giant. It was irresistible, so I accepted. 

“Now I look back and ask myself: ‘What was I thinking?’ It was familiar and it was safe — that’s what I was thinking. It was misaligned, though, with what I envisioned for my future. The cost of accepting was a two-year deferment of my path to consulting. Fortunately, resilience enabled me to not lose sight of who I was to become, so the deferment simply became a curve in the road to the destination and work that made me thrive.”

Crystal Lim-Lange: Panicking when meeting a client for the first (or second?) time

“I once introduced myself to a client,” says Crystal, the CEO and cofounder of Forest Wolf, “only to be told by the client: ‘Oh, we’ve met before.’ 

“At that moment, I panicked and blurted out: ‘Oh, you must have changed your hairstyle!’ The client was bald.

“Since then, I always say ‘So good to see you!’ if I’m not sure whether I’ve met someone before!”

Christopher Lind: Taking an order without asking questions

“My biggest mistake,” remembers Chris, the vice president and chief learning officer at ChenMed, “involved the first time a C-suite leader asked me to build a learning plan. In an attempt to please, I asked a few basic questions about what they thought they needed and ran back to plan with my team. 

“A week later, I sat down across from her, eager to lay it out and receive my pat on the back.

“‘I hate everything about this’ was not the response I expected. 

“That day still sits with me as a stark reminder that simply taking an order and delivering your interpretation of what someone wants is doomed to failure, no matter who’s giving the order. While digging into a problem and identifying a desired outcome won’t always be easy, it’s always worth it.”

Ruth Gotian: Thinking that work is solely a meritocracy

“I mistakenly believed that work was a meritocracy,” says Ruth, the chief learning officer at Weill Cornell Medicine. “If you do good work, people in positions of authority will notice and promote you.  

“What I hadn’t realized was two things: First, it might be convenient for managers if you stay put. If you get promoted, you leave an empty seat and responsibilities, and your boss might need to fill that role in addition to their other duties until your successor is chosen.

“Second, managers are often busy with many other things and may only notice your good work if you bring your successes to their attention. So you need to give them something to brag about when they talk to their boss.”

Al Dea: Not taking the time to listen first

“I was once tasked with building a new training program with a cross-functional team of 10 stakeholders,” recalls Al, a workplace facilitator and founder of Edge of Work. “I wanted to demonstrate ownership, so I put together a strategy and plan for the training without consulting others. 

“I happened to be meeting with another leader when he asked to see what I had built. Unbeknownst to me, after seeing my presentation he forwarded it to other leaders. This became a game of telephone and many of the stakeholders found out about the deck, which caught them by surprise, and they were not happy! 

“The result was an initially angry and frustrated group of stakeholders who had lots of feedback and highlighted some big gaps in the plan. This was a humbling moment, but taught me the importance of first getting input, feedback, and buy-in from others is actually a form of taking ownership.”

Thank you to everyone who responded to our question! To get the latest news and insights from these talent leaders, be sure to follow Dr. Terri Horton, Crystal Lim-Lange, Christopher Lind, Ruth Gotian, and Al Dea on LinkedIn.

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