How I Overcame My Greatest Weakness and Became a CEO

What are the different methods or tools you can use to improve?

There’s lots of things you can do to address your weaknesses. ‍

First: There’s professional counselors and executive coaches. There’s being more open with your manager, or talking to your co-workers. Getting counsel from others (and being open to it) can benefit a lot.‍

Second: You can also dive into best practices. I read a lot of literature on these and many other topics. 

I read a book called “The Growth Mindset” by Carol Dweck that literally changed my career. It’s about this idea of not having a fixed mindset. The book explains that when you’re born, you start with a fixed parameter of ability and skill. Any time something doesn’t go right, you take it so personally that you develop a kind of defensive fascia to protect your ego. And so you don’t collaborate or seek ways to improve yourself, because admitting a flaw means admitting that you failed. 

This is the direct opposite of the growth mindset, which is all about this perpetual journey to improve ourselves. 

I highly recommend this book, and I bought it for many of my colleagues. 

There’s another book I’m reading by Amy Scott called Just Work, which is all about creating safety in the workplace, thinking about inclusion and diversity, and giving people the ability to speak up while feeling safe. 

Above all, you have to have a genuine interest and motivation for improving. You have to be driven to identity and close the gaps you see in yourself. ‍

Third: Practice is another way you can address your weaknesses. Practice makes perfect, right? 

I put myself in uncomfortable situations so that I can adapt and grow and practice and rehearse. 

So what did that mean for me?

In my last company, Boston Consulting Group, I started engaging in more workshops and events. By the time I left five years later, I was actually flying around the country, leading full-day workshops for hundreds of people at major corporations, teach them how to collaborate. 

I started small, with small teams and internal workshops. I continued to push myself and grow in that particular domain. 

Over time, I learned to view myself as a facilitator rather than a presenter (which also helped me overcome my fear of public speaking, btw). 

How can a manager support their employees in identifying and developing their weaknesses?

A couple of things. First, at the foundational level, managers have to be genuinely interested in the development of the employee. I have a lethal allergy to lip service and insincerity. It just kills me. Employees can tell. You’re not fooling anybody. 

Be sincere. Don’t give them corporate jargon and be a true, supportive coach. 

Second is taking a structured approach. Have recurring check-ins with your employee. Put together a plan. Maintain discipline in having those touch points. 

I had a great mentor when I was at BCG, Tony Pelosi. He’s a product leader and cared so much about his coachees. He put together plans for us and was focused and present in all of our conversations. You could tell his motivations were genuine interest in my own growth and development, and not just looking for ways to promote himself or the company. 

This was a sharp comparison to other coaches I had. They gave you the sense that they were doing you a favor by being there. That was not a great experience. 

What about you personally? What are you doing to help others grow?

I run a video series on LinkedIn on how people can build a killer career in Customer Success. We’ve talked to leaders and showcase stories of CSMs as they build their careers. It’s been a great venue for people to share how they overcame their personal challenges, which includes identifying and overcoming their weaknesses.