Lessons From A Failed Founder #11: Baby Steps On The Road To Greatness

How the ‘easy does it’ approach can be the key to sustainable growth and development in a world full of startup hype.

Failed Founder
failedfounder
6 min readAug 21, 2019

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Photo by Marjorie Bertrand on Unsplash

Hockey stick graphs. Promised exponential growth. Break-even before the year’s over. Founders are pulling out all the stops to win an investor or a corporate partner. Not even the skies are the limit these days, and every entrepreneur is expected to be a big-picture visionary. This way of talking works great for a pitch, but you’re people aren’t having it.

In fact, if you are the proud founder of a startup, your employees are likely to feel stretched thin. Everybody is busy extinguishing fires, nobody has the mental bandwidth to think strategically. Knowing full well your team is this close to a burn-out, you try to make “something big” happen. Or maybe you are attempting to introduce new ways of “collaborating”.

Everybody is busy extinguishing fires, nobody has the mental bandwidth to think strategically.

My fellow founders, I am telling you: Our biggest handicap isn’t money. Nor is it the lack of time. Those who have been following me from the beginning will know where this is going: Our biggest handicaps are 1) focus and 2) expectations. The first will cause project groups to run in any direction but the right one, the second will hamper even the most optimistic team.

Photo by Aditya Romansa on Unsplash

“Let’s do a hackathon!” “We should implement OKRs for every department!”
“Let’s do an all-hands brainstorming session every month!” Do any of these lofty ambitions sound familiar to you? Of course, they do: We are founders, we don’t limit ourselves to the status quo! Why, we are pushing the boundaries, disrupting the markets, saving the world!

But that hackathon didn’t go so well, did it? The objective wasn’t clear, participants didn’t show up, and the other teams had no idea why they couldn’t rouse the Dev department that Friday. And that first OKR meeting was also the last OKR meeting: Nobody dared to follow-up. The monthly brainstorming session? Meh — all you heard was a deafening silence.

Start small. Execute. Measure. Learn. Repeat. Add something on top. Execute. Measure. Learn. Repeat.

Why do so many initiatives and ambitions fail? Well, chances are you lost sight of the number one rule in founding a company: Give, give… and then give some more. There is no such thing as simply setting the stage. And when you set the stage, make sure it’s a tiny one. Don’t get the entire team involved the first time you try something new. Start small. Execute. Measure. Learn.

What you sow is what you’ll reap… Photo by Paige Cody on Unsplash

Let’s go back to the idea of organising a hackathon. I failed miserably the first two times. I actually demoralised the few people that really wanted to be involved. The idea was shelved and I never talked about it again. The same applied to my other, hopeful initiatives. They bombed, big time. But the third time, at a different company, was truly a charm. Here’s what I did:

  1. I pitched the idea to a couple of key developers: People who take a genuine interest in others and are always up for a new challenge. They liked it.
  2. Those three developers immediately became part of the task force. We would meet on a weekly basis to review progress and to pitch ideas.
  3. We set a date for the event, and we limited the number of participants to ten. Now all we had to take care of, was location, catering, and a prize.
  4. One week before the hackathon, the three devs would secure buy-in and commitments from the 10 participants. It was really a thing now.
  5. We printed posters to inform our colleagues about the hackathon: Those 10 participants would not be available for regular work that day!

We let the participants decide on the goals and team structures. Your colleagues are full-grown adults running their own lives and households: I’m pretty sure they got this. Catering, organised by task force member #2, arrived well ahead of schedule. The little trophy, purchased by #3, was kept in a secure place. #1 would act as ceremony master and call out the winner.

Your colleagues are full-grown adults running their own lives and households: I’m pretty sure they got this.

The hackathon exceeded our expectations: People loved it! Every Developer wanted to take part in the next hackathon, and our task force has grown to five. Those five people will not only act as organisers, but also as advocates, lobbyists, and even mentors. It’s amazing to see people’s attitudes change from cynical to “Hey, this might work!”

Photo by Ben Wicks on Unsplash

We used the same “start small, grow together” approach with our road towards implementing OKRs: The entire company now gets together every Monday where one “Ambassador” shares their team’s biggest tasks and challenges for the week. On Friday, every Ambassador announces their department’s biggest “win” for the week.

Your colleagues are full-grown adults running their own lives and households: I’m pretty sure they got this.

Discipline is key, and by consistently maintaining a weekly cadence of people getting together and sharing ideas, we are well on our way to introducing OKRs for each and every department. But first, we need to establish a culture of trust, discipline and widespread participation. Again: You have to give, give… and then give some more.

Start small. Get your people to buy into it, then turn them into responsible advocates with clear goals and expectations. Let them run the show, don’t try to prevent things from going astray: You can voice your observations in a post-mortem. Don’t point fingers, turn it into a learning moment! Then, stand back and watch your people rise.

Empower your people to take small steps on their way to greatness.

Lessons From A Failed Founder is a series of blog posts by a thirty-something entrepreneur who made all the mistakes in the big startup playbook, and then some. My posts are no pearls of wisdom: Consider them the cautionary tales of a young founder who wants you to avoid making the same mistakes.

Feel free to reach out to me at failedfounder{AT}gmail.com

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Failed Founder
failedfounder

Lessons From A Failed Founder is a series of blog posts by a thirty-something entrepreneur who made all the mistakes in the big startup playbook, and then some.