The Pioneer’s Dilemma

To leave the chasm behind, to cross it and not fall back into it, involves a transformation in the enterprise that few individuals can span. It is the move from being pioneers to becoming settlers. — Geoffrey Moore

I’m a startup junkie. I’ve learned to appreciate uncertainty and thrive in disarray, figuring things out without being hindered by bureaucracy. However, once the startup crosses the chasm and settles into something that resembles an enterprise-level company, I get cold feet.

These days, the word disruptive is usually depicted as something good. It has generally fueled tech startups and their thirst to unseat the incumbent. It also makes of a good David versus Goliath story if the startup succeeds. Clayton M. Christensen initially coined the term disruptive technology— later to be replaced by disruptive innovation.

Like most people working in tech, I drank the magical Kool-Aid and was hooked to everything that has anything to do with the tech startup scene. One of this was Christensen’s book, The Innovator’s Dilemma, which ended up as mandatory reading in our startup.

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Frugality was the name of the game. Instant coffee in a disposable cup and stirrer.

Being disruptive is great. You get to explore and experiment with new ideas — not to mention create jobs while doing so. You take advantage of oversights made by incumbents and pray they don’t notice you.

But there’s another side to being disruptive and it’s not as pretty. One day, a colleague messaged me on Slack: You busy? I need your wisdom. I was just finishing up with an email so I told her I’ll be free in five minutes. We went into an empty meeting room and started talking.

We are part of the pioneers. The ones present at ground zero. The ones who literally built the company with basically nothing but crappy software and Microsoft Excel. We started very small so we were used to being in the loop with just about everything that it feels weird these days how things magically get done without us knowing.

The Pioneers

A truly sad reality—at least for me—is when the startup starts to not feel like a startup anymore. More so if it’s a startup you’ve actually helped build — a startup you’ve been with from the very beginning.

But I guess that’s just the nature of every business. Everything will eventually have to settle down. Even the most powerful engines can’t survive running at full throttle perpetually. Facebook had to eventually change their mantra from “move fast and break things” to something more subtle.

However, the pioneers — the ones running around and making things happen in the very beginning — are usually stuck in startup mode and it’s somehow hard for them to let go and transition into the new environment.

In his book Crossing The Chasm, Geoffrey Moore describes pioneers as follows:

In the development organization, pioneers are the ones who push the edge of the technology application envelope. They do not institutionalize. They do not like to create infrastructure. They don’t even like to document. They want to do great deeds, and when there are no more great deeds to be done, they want to move on. Their brilliance fuels the early market, and without them, there would be no such thing as high tech. Nonetheless, once you have crossed the chasm, these people can become a potential liability.

The pioneer will most likely stick to his guns, doing things the way it was done before — when the business was just starting up — instead of trusting the [often slow] putting in place of processes which, in essence, should make things much more effective.

“First, you download the file, open it in Microsoft Excel, save it as as a comma-separated values (CSV) file, and then run this macro from another Excel file..”

They get lost in the transition and, as Moore suggested, quickly become liabilities instead. They’re usually not the types to agree to just wait for the engineering team to come up with an automated process — or with being looped out of certain things. They relate bureaucracy with a inefficiency and they’ll wreak havoc if they’re not put at ease the soonest.

This is what the colleague earlier wanted to consult with me. She was getting the impression that her opinions were being set aside as processes and more senior people were being put in place. She wanted to get my take on whether she was being too disruptive and whether she should explore other opportunities or stick it out for a couple more months.

That guy over there

Blame it on a broken onboarding process for new hires, people mostly spend their first days at work clueless — trying to find the correlation between what they thought they signed up for and what they’re actually doing.

Most of them spend a couple of weeks trying to learn the ropes and it’s only a matter of time before someone — usually their immediate superior, also new — tells them to come see me.

I stay at a corner with my computer and an external monitor as I am now in charge of multiple projects. Someone I was never introduced to — not even by an email from Human Resources — appears in front of me and I slowly remove my headphones from my ears.

I usually start the conversation with, “Hey! I don’t think we’ve met. I’m Mike,” and shake their hands. They then introduce themselves and we exchange pleasantries.

I miss the startup days. When every conversation — regardless if it’s about work or not — was looked forward to. When everyone was interested in what the other person had to say — sharing ideas, throwing all of them against a wall and see which ones stick. Days before unnecessary red tape and make-believe org charts.

My attempt at a decent conversation and slight reminiscing comes to an immediate halt when they say, “My boss told me to ask you about this.”

Welp, fun’s over.

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If this doesn’t look startup-y, I’m not sure what does. Peep the mandatory reading at the upper right.

To be or not to be?

Every startup has to eventually cross the chasm but not every team member will be capable of making it to the other side. Reid Hoffman put this into perspective quite perfectly. He says, “In the early startup stage you need all-rounders who would love to get their hands dirty. Later on you’ll need polished managers who know how to delegate.”

“This balancing act between who you need now and who you’ll need later is no small feat. In the early startup stage you need all-rounders who would love to get their hands dirty. Later on you’ll need polished managers who know how to delegate. Not everyone makes it through every company turn and not everyone is destined to be a manager. Some people are best as individual contributors — as an engineer, not as a VP of Engineering.” — Reid Hoffman

More often than not, the pioneer wouldn’t like to be in a position where she is just delegating tasks. This is not her cup of tea and is somehow contrary to her intuitions. You’d think after working 50- to 60-hour weeks building the startup she’d at least try to slow down and start reaping what she initially sowed — bask in her glory, sort to say. I might be speaking for myself here but this is almost never the case. You’d always want to be involved in things. You’d want to be part of most decisions and you take offense in getting looped out of conversations.

And that’s where it usually concludes. It’s up to the pioneer to decide whether she can see herself in a more toned down role — a cog in the wheel — or if it’s time for her to move on to something else. Perhaps another startup that needs building or pursuing a childhood dream.

In the end, I do hope she chooses to give another startup a go — whether her own or someone else’s. I believe the need for more people to be taking risks and creating opportunities further outweigh being stuck in unnecessary meetings over whole wheat sandwiches, expensive coffee, and hifalutin conversations.

As for me, well, that’s another story to tell.

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