No Silos = No Strategy

And other startup mistakes

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Hello and welcome! I’m Phoebe: a writer, strategist, mom & nerd in Brooklyn. This newsletter is mostly about startups, culture, creativity, and modern motherhood with a critical side-eye and some hopefully helpful — or at least entertaining — takeaways.

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Toxic Startup Mantras, Wrapped

When “Lateral” Goes Sideways

I began working at/with startups in the early aughts when everyone was terrified of “silos.” It was not cool to run a departmentalized business with strict roles, specialties, or jurisdictions. The fear was that each department would become a mini-business-within-the-business with conflicting goals, and never communicating except to fight over resources.

This new de-siloed world meant most employees had to be generalists and form opinions on everything: product people wanted to user-test editorial packages, growth marketers tried to drive brand strategy, entry-level assistants made demands for headcount, etc.

This “lateral” organizational structure also gave rise to the “open plan” office, where provincial cubicles disappeared along with privacy, focus, and noise reduction. I remember asking my doctor in Brooklyn Heights if I might have ADHD and his first question was, “Do you work in an open-plan office?” (Most of his patients with new trouble focusing also worked in open-plan offices.)

The Fees of Flattening

There are of course cost benefits to hiring young non-experts to “wear many hats.” You get a hard-working team willing to do anything at all hours because they don’t have much else to do besides work. It’s quantity over quality, which works when you’re throwing spaghetti at the wall to see what sticks. Get a lot of noodle throwers on the cheap.

And in pre-remote days, piling a bunch of desks into one room and calling it a collaborative design solution is less expensive than adding upholstered panels to your budget. (Now we save even more by keeping everyone at home, and Slack is the open-plan office.)

It’s also easier for “leadership” to spend less time galvanizing, communicating, and getting their various teams on the same page (also known as “leading”) and punt the dysfunction back to their employees (“You need to get on the same page!”) while they chase their next round of capital.

Regardless of what drove the anti-silo ethos of the last 20 years, the pitfalls seem worse than what happens at a siloed organization:

1. Everyone is pulled in different directions. When employees are forbidden to say, “That’s not my job,” individual contributors who should be focused on their craft are forced to manage themselves. They also manage up by explaining the limits of their time and skills to superiors (usually met with a frown or a firing), and manage down or sideways with an unending flow of requests from their non-maker colleagues. They must guard their time, figure out priorities, and play office politics without the aegis of a traditional manager.

2. No one can focus or specialize. This is actually a perk for a young generalist at a small new company. They get to do everything and figure out what they’re good at. The downside is once they find their specialty, they may not be able to focus on it. If the company doesn’t invest in specialists in the first place, it certainly won’t invest in hatching them either. This leads to an outflow of talent once it starts to take the shape of expertise.

3. Strategy becomes an afterthought. Along with “no silos,” the “launch-test-iterate” style of product development becomes the standard procedure across all operations. Everything is experimental; every project and new hire is “a little test” to see what works, with the hope that the company’s general idea for what they’re doing in the market will become clear.

   Put another way: when no one defines strategy from the top down (“top-down” is another cultural bogeyman at startups), it puts the onus on each individual to make up their own vision for the company, usually with themselves as the ICP. It’s all noise, no signal.

Quick refresher: There’s a difference between choosing a strategy without knowing if it will work out (that’s the nature of good leadership and making big bets for business growth) and choosing not to put a stake in the ground until you’ve done enough “little tests” to know what you’re doing.

Strategy should be tweakable, not negotiable and open to everyone’s interpretation.

4. When no one is allowed to be an expert, everyone becomes an expert. This might be most accretive to burnout and general mental health concerns that pervade #startuplife. When each person’s non-expert (or wholly unqualified) opinion is valid and equal, everyone becomes a stakeholder and decision maker in everyone else’s work, and by extension, their career and status at the company. We all know it’s impossible to make everyone happy, so this makes contributors and young managers (especially the highly attuned ones) spread too thin and hyper-vigilant as a default, paranoid at worst.

When you lack the guardrails of clear strategy, defined roles, strong management, and departmental solidarity you see at larger companies, it turns into every person for themself. Then the open-plan office starts to feel like an open plain in a nature documentary.

Solution: Get Comfortable with Discomfort

Unlike other endeavors like writing or going for a run, the easiest part of starting a startup is starting. It’s all blue sky, a big idea, possibilities, and if you can assemble a team of “good people,” you can imagine deploying them in the right direction/specialization once you’ve found your focus.

This works during the honeymoon phase of a seed round, but there comes a point when you need to invest in expertise, either as an outside consultant or bringing someone in-house to do nothing but obsess on your positioning and strategy.

Resources

If you’re going the DIY route in the meantime, here are a few holy grails to check out:

• HBR Series: What is Strategy?

• Anything April Dunford says about Positioning

• Strategy vs. Planning (also HBR, also linked previously)

• Lords of Strategy: The Secret Intellectual History of the New Corporate World

That’s where this one ends. See you next week!