In 2019, Gainsight CEO Nick Mehta said something at a conference that piqued my curiosity: Even though he’d had the same title, CEO, for seven years, he felt that he’d had several different jobs during that timespan.
3 Benefits of Examining Your Role as CEO
- You’re nurturing a growth mindset and setting the stage for your employees to operate with this mindset, too.
- You’re regularly taking stock of what needs to change as your company and the industry around it evolve.
- You’re uncovering missed opportunities for growth and efficiencies.
So, he began periodically questioning whether he was still the right leader for the company. If the answer was no, he began figuring out what he needed to do to become the right leader.
This concept resonated with me. The year before, I had split my one company into three. I remained president of Raw Engineering, our digital consultancy. I sold off one portion of it to a German conglomerate and became the CEO of the new spinoff focused on our headless CMS product, Contentstack, which was gaining traction with enterprise customers.
The result? I went from becoming the CEO of a digital services company to the CEO of a product company and raising a $31.5 million Series A as a rookie fundraiser in 13 months. Those roles require different skill sets, some of which I had a better handle on than others.
How to Fire Yourself
Mehta’s words came at the right time. I decided then that I would start firing and hiring myself. I had to make it a practice to scale my skills as I scaled my company. Here’s how I do it.
Ask Yourself Honest Questions
My leading question is: “Where can I improve?” If you can’t answer that, you’re not looking hard enough or it’s time to challenge yourself with a new role.
Logitech’s former CEO Bracken Darrell rehired himself as an aggressive newcomer. “You're the new guy. The old guy was a bozo. You have no constraints,” he imagined. He was inspired by the Andy Grove Intel leadership team who used this prompt: “If we got kicked out and the board brought in a new CEO, what do you think he would do?" Both companies went on to accomplish great things under the rehired leadership.
If you’re looking for some prompts to drive this process, this list of Extreme Brainstorming Questions could help.
Schedule Your Firing
I fire myself every six months. The speed of business and technology makes this necessary for me. Mehta chooses every 12 months. Consider what the right cadence is for you — factor in your industry and its pace of change, how quickly your company is gaining customers and hiring employees, its business goals, and more.
Get Feedback From Your Team
Don’t fire yourself in a vacuum. Ask your team for an honest assessment of how you’re doing. Sometimes, the view is clearer from the other balcony.
However, as a leader, you must set the tone for this sort of radical candor from the outset. It won’t work if you only encourage feedback when your calendar reminder pops up. That’s why I like to start difficult conversations with: “This is a place and space with no judgment.”
You’re Rehired. What’s Next?
Every time a company reaches a new phase of scale — bootstrapped, $5 million annual recurring revenue (ARR), $100 million ARR, etc. — leadership gets an implicit promotion. I’ve now raised $169 million at Contentstack and lead a global team of nearly 500 people. That’s a lot of promotions since 2019.
Some founders and leaders are better suited for the early stages of a company; others can be in it for the long haul if they commit to growing and learning. I created the EDGE Framework for precisely that reason: to help leaders (including me and my team) assess where they need to grow as they scale. Here are the four dimensions of EDGE leadership.
Envision
A company or team can only grow if the leader has a vision for it. To nail Envision, you need a strategic view of what the company will look like two to three years from now and why. That means fully understanding the business and commercials and keeping a close eye on market trends and tech developments.
As a startup, it’s about figuring out product-market fit, landing your first customer, and making the sales process repeatable. But, as a scaleup, Envision means doing strategic things together with customers inside their organizations and launching new products and features to help them grow.
Envision also means knowing what you want to stand for as a company. Agree on your values early and then model and incentivize the behavior. For example, one of our values is that we are curious trendspotters and brave trendsetters. That hasn’t changed since our startup days, and it’s why we’ve been able to predict where the market is going and move quickly.
Domain Ownership
Every leader must know their expertise and role within the company and own it. But what you own well on Day 1 might be vastly different than on Day 1,095.
Early in Contentstack’s journey, I was in the weeds on the finance side of things such as writing simple budgets and plans. But, over time, I understood that we would be more successful if the CFO and his team took over.
Today, I take a more strategic role with finance, asking the right questions and benchmarking our metrics against the industry. My general rule of thumb across the business is that if I can’t help move the ball forward, I should stay out of the way.
Growth Mindset
Carol Dweck coined this term, which has become our way of working. Her research showed that mindsets can evolve. For instance, say you believe you are and will always be a terrible public speaker. You can improve this ability by embracing challenges and looking at growth versus outcomes.
Leadership teams fall apart when they stop learning and growing. I’m also a big fan of network-based learning, getting close to others who are going through similar challenges or are a few steps ahead of me. Take advantage of organizations that connect leaders to others.
Efficiency in Scale
Stay out of the weeds and focus on serving the highest purpose, considering return on time and finding efficiencies with existing resources. Functional leaders shouldn’t forget to look outside of their departments. This is the only way to handle increased demand without incurring significant costs or sacrificing quality. In this high-pressure economic environment, inefficiencies will come back to haunt you sooner rather than later.
Use this EDGE framework, or another one you find useful, when you are rehiring yourself. When you have an honest assessment, ask yourself: Where should I stand based on my current role, where the company has scaled, or in relation to when I last did this exercise? Then figure out ways to close any gaps.
And never assume you’ve got it all figured out. That’s when stagnancy sets in.
