The Challenges faced by the CEO of a Startup in Growth-Mode (and how to Overcome them?)

Tarun Kohli
May 1 · 7 min read
Photo by Ian Parker on Unsplash

As a startup CEO, I slept like a baby. I woke up every 2 hours, and cried.

Ben’s quote isn’t only applicable to startup CEOs but the ones managing high growth companies.

While growth is extremely gratifying, it brings along something pernicious — the dramatic change in its CEO’s style. Because, let’s face it, the kind of style that worked in a close-knit twenty-people startup wouldn’t necessarily work when the company scales to hundreds of team members.

The leader of a band-of-twenty-odd-friends who chugged beers every Friday evening — a concoction divined to elevate any engineer’s motivation to pay off the entire technical debt in an evening, listened to Time while doing pair programming because like Roger Waters they didn’t want to fritter and waste the hours in an offhand way, cracked some wickedly terrible nerdy jokes, must now reinvent to be a business savvy CEO — A leader who can effortlessly manage a mid-size enterprise, without breaking a sweat, making everyone feel like that s/he was born to do this.

All the books and guidance out there in the leader-verse talk about evolving and managing aspects of the organization like strategy, execution, culture, and so many other thing that leads to a successful venture. But nobody talks about the evolution of the founder or the CEO. The hardest part, if you were to ask me (in the words of Marshall Smith), is -

We spend a lot of time teaching leaders what to do. We don’t spend enough time teaching leaders what to stop. Half the leaders I have met don’t need to learn what to do. They need to learn what to stop.

I so wish I had had the benefit of learning not only new things but dropping the ones that don’t work anymore. So for all those of you who have been nodding in affirmation till this point, here are a few challenges that I faced.

Learning to zoom out instead of zoom in

I was totally comfortable swimming in the world of binary and envisioning delightful user experiences. I’ve always believed that God is in the details and would take immense satisfaction in working through the intricate details of the architecture, code, and user interface design.

Those skills helped me ship successful software releases and build the initial credibility for the company, but one needs a totally different focus when the company starts growing past that stage.

When I went past that stage, I couldn’t focus only on building products. It was equally important to focus on nurturing the culture , hiring the right people, scaling processes, managing people, managing the partner ecosystem, sales, marketing, and gazing in the future to make sure that we will have a spot in the sunlight.

All these aspects of a company need to work in tandem, otherwise a steep fall into some dark abyss full of startup skeletons is inevitable. And that is one of the most important things I or any founder has to learn.

Running all the things in tandem felt as if I was raising quadruplets. No matter the time of the day, there was always one that needed attention. I had just gotten comfortable with the calm waters of Uni Oceania, and all of a sudden, I had to learn to swim in the turbulent waters of Multitastic Sea.

The thing that smacks you right in the forehead is training your mind to go from one thing to another without losing focus and enthusiasm. You can’t have a sales meeting and attend the following marketing strategy meeting with droopy eyes, or hunched shoulders or you can’t have one product design review meeting with laser like focus, and be completely checked out for the second one.

After swimming in the tsunami of meetings, executing, retrospecting, and people seeking my attention to unblock them, frying my brain cells dead, you think to yourself — did I sign up for this? When would I actually do my job? Forgetting that all of this was my job now. That it was no longer about the adrenalin thrill of solving architectural and code problems. Now my main responsibility was towards managing all aspects of the business to create a respectable company.

Managing the beautiful inner conflict

In the growth phase, there is a chance that you would be stuck with a personality disorder. Not like having a medical condition but having the voices of two people inside you — your natural self who helped you to get to this fortunate place, and the one that you are trying to become. My, oh my!

For example: one would want to quickly reach out to people to check on the status of a project, the other would want to set up a meeting lest they were to disturb the team member’s momentum. One who would want to share thoughts at the speed of light for a given situation, and the other who would want to involve all the right people lest they were to think why were they hired in the first place. One who would want to check in with everyone in the company, and the other who would want to respect the organization hierarchy. One would want to crack a silly joke from the old times, and the other would frown at the seeming inappropriateness of it for those who are new.

The list goes on.

Being constantly aware of one’s own words, and actions is really hard. Not that it isn’t the sensible thing to do, but the transition from informal structure of startups to organized processes of growing companies, creates conflict with your natural style.

A larger group means there is more diversity of thinking patterns, and sensibilities within the group. So the CEO has a far bigger responsibility at the growth stage — There would be an astronomical cost of falling from grace if someone was to misconstrue your actions or words. And worse if someone misuses the camaraderie, informality and breaks the culture of high trust.

The sooner you realize the company is growing, and you need to pivot your style to suit this new stage of growth, the better chance you give to your company to keep on chugging along in the right direction.

Adopting a new interpersonal communication

Every stage of the company demands its own communication style. What worked in a startup stage might not work in growth mode. A small close-knit group remains cohesive with informal communication but larger groups need to have a different process for sharing information.

For example: your thinking-on-the-toes skills which enabled you to share new creative ideas to run the business, give suggestions in fixing broken processes/systems, now need to be first introspected, and then, maybe, restrained lest they become official decrees.

And, whether you like it or not, agree with it or not, even some of your suggestions would be taken as the gospel truth. No matter if your internal compass makes you believe that you are just one of the team members whose job profile requires them to be the face of the company and make it scale, the new people who join the company after traction will always look at you as the-authority-figure.

You would never ever be one of the guys again. Period. Like, James Hetfield said — Sad but true.

Thus, you would have to quickly learn the art of minimizing the HIPPO Effect.

Change of relationship dynamics at work

The new people look at you like Boss Man. But what about the older ones? Does that change too? It does, but not the way you think.

When I started, I was part of everything. The ‘God is in the details’ philosophy made me the partner-in crime of every crime scene. That made me present at all times for everyone to discuss anything at any time, just when they wanted. But now with so many things vying for my attention, and slotting even lunch breaks in the calendar, has an adverse impact on old timers.

I found that when you ask the old timers to follow a process, you spiral down from the best friend to the best manager to the best ahem..nobody — In like, nobody who wants to talk to you. And when the next year appraisal cycle hits, and it’s announced that you are still the CEO — you hear the collective sigh of the people’s emotion of “ This has made a lot of people very angry and been widely regarded as a bad move.” ( From the Hitchhiker’s guide to the galaxy )

People get upset at you for not caring enough while you are knee deep in juggling multiple things to make the company scale. People get upset about how ‘things are not the same’ and how you have changed. The sighs down the hallway reaches the dark recesses of your heart and while you also want to reciprocate with an Anulom Vilom sigh, you know that it will not solve anything.

Communication is the only thing that helps. As a CEO, know that while you are managing your own inner conflict, the old timers also need to be helped with theirs. So get together on beers again and talk about the change. The need for it. Explaining the reasons for the new processes go a long way in making sure everyone understands the philosophy behind the change. It’s equally important for the old timers to understand the need for this change because this ‘growth’ of your startup was the dream where you began this journey together. So it’s your responsibility. Together.

In the end, if I was to pick one character out of the X-Men franchise, I would say that every CEO should be like Mystique ( blue skin, and yellow eyes are optional). Always changing, and shifting their style on the outside to the level of growth while retaining their personality on the inside to the heart of their core.

how hackers start their afternoons.

Tarun Kohli

Written by

Founder & CEO of Quovantis, an avid book reader and a student for life

how hackers start their afternoons.

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