How I Overcame My Greatest Weakness and Became a CEO

Josh Schachter
CEO

Interview Highlights:

  • Weaknesses are always a work in progress
  • When you fail, be open to the idea that you’re not perfect and embrace the opportunity to improve
  • Managers have to be genuinely interested in helping employees overcome their weaknesses

Can you please introduce yourself and what you do?

I’m Josh Schachter, the founder and CEO of Update.ai. Update.ai is the latest solution platform in customer success. We help detect the key moments of truth - the key customer signals in teams’ conversations with customers - and help CS teams scale value delivery and actions from those conversations. This results in less frustrated CSMs. 

I’m the CEO of a startup now, so my role is more of general management. But I spent the first 15 years of my career building myself up as a product manager. 

What is your greatest weakness and how did you discover it?

A bit of background first:

I love building things. I love building products. It’s fun and it’s challenging. What I came to realize in my career was that as a PM, you’re in the middle of a lot of conversations and key decision making. It’s not dissimilar at all from being a Customer Success professional. 

You’re interfacing with all of these groups, and what you're trying to do is carry influence in making key decisions. I’m talking about situations where we bring the team together to collaborate on ideas. This involves a lot of facilitating, socializing ideas, and presenting concepts to large crowds. 

The social aspect is what tripped me up: the presentations, the social influence, the collaboration. I was terrified by public speaking, too. At a certain point, I realized that my Achilles heel was going to keep me locked at a more junior level, so I needed to solve that if I was going to get anywhere. 

How did you overcome that weakness?

The correct answer is that it’s always a work in progress. If someone ever says that it’s not, then that person is full of it. <laugh>

That’s the whole spirit of “progress,” right? It’s never fully complete. 

For me, it was encountering certain situations in my career and recognizing that I needed to work on addressing my shortcomings. I can remember it, even today. 

I was in a startup that had just been acquired by Intuit. We were having a challenging year for our particular product. Google had just released the Panda update, and it was crushing us at the time. We saw a 20% drop in traffic over two weeks, and it kept dropping.

So we hit the panic button and had to brainstorm how we would get out of this. So I led a workshop of options, ideas, and theories that we could try. I was at the whiteboard. I was the only one at the whiteboard. I was even the only one standing up. My whole team is sitting down and there I am, writing out ideas and then having the team vote on it when I’m done. 

Afterwards, I got some really blunt feedback from my team. They said, “Josh, it was clear you were just gonna go with that one idea that you really wanted at the end. You took us through the motions, but you didn’t actually try to collaborate or generate thinking from the rest of the group.”

That hit me hard, and it stuck with me.

When you’re young, you may not be as self-aware. But when these different situations pop up, you need to be open and willing enough to take the learnings. You need to reflect, internalize and understand that this is an Achilles heel that you need to fix.

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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. 

About 
UpdateAI

You focus on the people stuff. UpdateAI sweats the small stuff. Great customer relationships take A LOT of meetings. Your day becomes a solid block of calls and emails full of tasks, questions, and problems to tackle, with more cropping up on every call. But hey, it’s 2021. That’s what tech is for. Recover the time, attention, and energy needed to build and develop invaluable customer relationships. Champion Development through UpdateAI is how growth-oriented CS teams turn relationships into revenue.

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