Startups: how to join the "Big" Fish in the Little Pond
When you bail from big tech to startups, ego management of the veterans (tenure: 18 months) often is harder than wrangling their rats nest of a codebase.
Moving from big tech to a startup is a shock to the senses in many domains.
In the most literal sense, you are jumping to a small pond from a big one, you can often be moving from a company with thousands of engineers to one that has ten.
The big fish in a startup, may still be good engineers, but are they great? Their ego would often be in for a bruising if they were dropped into the competitive hierarchy of a big company with industry leading experts on staff, which you have just left and were particularly adept at managing.
In the up close and personal ego management of startup engineers, “what got you here, won’t get you there”.
Like any W2, the move from big tech to startups isn’t from hell to heaven, but simply to a different set of tradeoffs, a different list of things to resent, a different motivation to build your eventual escape.
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Fast Feels Good
All the rumors, movies, and Silicon Valley Seasons 1 through 6, are true.
Startups are the wild west.
Certainly from day 1 until product market fit.
But often well beyond that, until dozens or hundreds of employees, where you still have that chaos, the dynamism, the lack of rigid process and structure and malaise that sets in for big enterprises.
At the first startup I switched to after my first stint in big tech, the first few weeks were a breath of fresh air.
Pull requests didn’t even require reviews, merge when you were “confident”
No expense reports, toss it on the corporate card and say sorry to the part-time CFO if you spent too much
Rapidly changing roadmaps
Endless new projects landing on my plate
No HR training, let alone any HR!
The speed of it all was really exhilarating after the soul-numbing HR training days, waiting for PR stamps from slow teams, endless discussions on quarterly and annual planning and strict adherence to meeting the agreed upon OKRs, regardless of if that was the right course of action anymore.
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Everyone’s Line is Different
Unfortunately, when the “move fast and trust me” culture breaks down is when the veterans – who have been there 18 months instead of your 18 days – decide that your line of when you felt “confident” to merge your code, was deliberately and clearly malicious, since it is different than their line.
How could you ship this?
Don’t you know this is bad code?
How could use AI for that? We only use AI for this?
You’re not done yet? Are you sure you’re cut out for startups?
The whiplash of being told from different people simultaneously that you work too slow but also too fast and reckless, that you don’t use AI enough to improve your velocity but also you’re using it too much for the wrong things, and on and on gets old real quick.
How about we require PR reviews? More feedback to easier onboard new folks to coding patterns?
“Fuck no, that’d slow me down”
How about we have a docs site where we document architecture, best practices, how-to guides?
“Sounds like a lot of work, who’d ever read it?”
What if we have an onboarding doc for our business domain which reviews basic lingo and doesn’t assume every hire has decades of industry experience?
“Yeah but we need my custom acronyms so my Typescript file name isn’t longer than 20 characters.”
Without the more professional atmosphere and larger organization forcing normalization, better onboarding practices, stronger documentation culture, and compliance mandated PR reviews which also allow for better cross-pollination of best practices, startups regress to the lowest common denominator of whatever the loudest veteran voices agree to hold themselves to, which can often be an impossibly high bar for new engineers to quickly onboard and meet.
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Managing their Paranoia
Managing upwards, peers, and down ends up requiring a slightly different set of skills in startups.
While you’re still obviously working with humans, startups can tend to quickly develop cult-like niche cultures, with the corresponding paranoia of outside forces and new hires.
Some big companies maintain that level of commitment and buy-in, but most as they grow slowly lose the white hot passion, fury, and schizophrenic detachment from reality which can come to characterize startups.
When confronted by a particularly paranoid colleague or boss with accusations and suspicions that you are a malicious actor, it’s important to take their concerns seriously, even if they are patently ludicrous.
Non-judgemental serious listening will do wonders to soften interactions and improve outcomes at work, and in all relationships. Judge all you want after the fact, or in your mind, but if people feel you won’t judge them, they will blab away all their closely held, dirty secrets, many of which can be critical knowledge for you to capitalize on in the future.
For example, one senior colleague hired me largely under the delusion that I could effectively be his clone and enforce similar standards and best practices as he was burning out trying to enforce amongst the growing engineering team.
When he saw some code I shipped that wasn’t quite perfect in his eyes, he came to me visibly emotional, feeling betrayed, let down, disappointed, regretting why they even hired me when I could ship something so bad in his eyes.
(I hadn’t discovered a custom method that they preferred to use over the language standard library version.)
I listened to his concerns intently, and agreed with his premises and goals, but acknowledged the current gap in execution and my intent to improve on it with continued feedback and guidance.
His eyes softened and the paranoia faded away.
It’s in the little interactions that you can build or burn social capital at your W2. Every moment counts.
Slot Machines: Expectations Management
Furthermore, what works in the interview to get the job and close the offer, can slowly lose it’s effectiveness once on payroll.
The mirroring of opinions, tone, and priorities which is much easier to do in short initial interactions during the interview process, must gradually be phased into a more lasting persona which you can sustain long term.
Managing that transition and ensuring it is slow enough to not cause alarm requires great tact.
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