5 Habits I Had To Abandon As CEO As My Startup Scaled

If you’re not careful, what helped get your company off the ground may prevent it from reaching new heights.

5 Habits I Had To Abandon As CEO As My Startup Scaled
[Photo: Dave Blahlentino via Unsplash]

Of all the challenges I’ve faced as the head of a startup, learning how to let go of things while growing fast has been one of the toughest. In the early stages, every founder is a master of all trades–there’s no other way to get off the ground. But as your company scales, it’s important to let go of some of those responsibilities.


This is something startup CEOs and founders hear all the time, but “Just delegate!” is a far cry from practical advice. So here’s a look at the five key activities I’ve had to learn how to let go of, and what it took for me to relinquish control.

1. Constant Problem-Solving

Before I founded my mobile analytics company, Leanplum, I was an engineer at Google. Like most people with a technical background, when someone tells me about a problem, my mind immediately starts racing to solve it. But as a CEO, I’ve learned, you can’t solve every problem.

Today, I’ve gotten better at encouraging shared leadership. I listen, ask questions, and coach others to arrive at the solution themselves. Making this shift in thinking wasn’t easy, and there’s always the risk that someone will fail. But empowering your team members to think independently and giving them the tools to make their own decisions (with a little advice from me here and there) lets them do their jobs so I can do mine.

2. Being The Go-To Knowledge Source

I used to host weekly one-on-ones with each member of our executive staff. This meant keeping track of everyone’s needs and understanding how I could connect with each person. For instance, if the head of customer success mentioned they needed someone to write a case study, I would track down marketing to make that happen. But acting as the sole source of knowledge got more and more time-consuming, and as we grew, I had less and less time to spare.

I didn’t realize it until later, but before changing course, I was hoarding institutional knowledge. Now, we have a biweekly roundtable where the entire executive staff meets to share highs and lows, and to brainstorm together. In lieu of top-down mentoring, we created team mentoring. This way I’m no longer the center of all the company’s happenings, but I rest easy with more confidence in my team’s abilities.

3. Setting Qualitative Goals

When we were at 20 people, I understood the health of the company and could pinpoint exactly what caused something to go wrong. But as we grew to 100 employees, that was no longer possible. I needed an objective way to understand performance, and that meant abandoning certain qualitative goals.


These days, each quarter, employees create measurable, quantitative goals. A content marketer doesn’t just write blog posts, for instance, they write blog posts on X number of external content sites to increase referral traffic by Y percent. A customer success manager doesn’t just keep clients happy by executing a mobile strategy. They assist clients with X number of use cases to help them hit their KPIs, thus keeping our churn rate below Y percent.

This shift toward quantifiable outcomes took getting used to, but as the company grew, it helped us hold every employee accountable for their goals and progress. So if we ever fall short, we don’t have to dig into how it happened.

4. Keeping My Finger On Company’s Pulse

I fondly remember the time when I could meet with every employee on a monthly basis, whether they were an intern or an executive. Then that turned into every six months. Now, I randomly pick an employee to meet with once a week, to get a sampling of employees’ happiness and job satisfaction within the company.

Some CEOs prefer to have an open-door policy every Friday, for instance, where anyone can walk in and ask questions. That’s great, too. We picked the “at-random” policy to give those who are shy or might otherwise not speak up the chance to have their voices heard.

It’s strange to lose that intimate connection with your employees. I can no longer manage closeness at scale. But I trust each manager to keep an eye on their team, and for employees to be honest and transparent when we meet. I don’t actually need to continuously monitor the pulse of the company, since I know that’s being done by people I trust who are better positioned to get an accurate read on that than I often am.

5. Interviewing New Hires

Every job candidate goes through a cultural interview before we make an offer here. We vet potential employees for their values, self-awareness, and transparency. It’s not just about the right skill set, it’s about finding the kind of people who put teamwork before their own talent.


As CEO, you want to share your passion with every person who walks through your door. But as the company gets bigger, it’s simply not possible to meet with everyone, especially when we have dozens of people in the office interviewing every week.

Instead, I’ve taken a step back and become the approver in the process. After hiring managers give their feedback, I spend a few minutes reviewing before signing the offer letter. Even this won’t be scalable forever. But I truly believe that people are the most important part of any company, and it’s exciting to learn who’s applying. So for now, I’m staying involved–even though I’m less involved in the hiring process than I once was.

Abandoning the habits that worked great when Leanplum was a smaller company actually helped it become a bigger one. These were the five most important changes I made, and as we continue to grow, they could very well become obstacles to reaching our next stage. As a CEO, it’s my job to always be ready to let go of something that once worked but no longer does, and to try something new.

Momchil Kyurkchiev is the CEO and cofounder of Leanplum.