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Failure to Onboard

Failure to Onboard

Don't doom you entire time at a new company by failing to onboard

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BowTied Fullstack
Jul 29, 2025
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Failure to Onboard
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In the last post, we went through how critical it is that you onboard quickly when joining a new company.

The first step to building social capital which will let you get promoted, push technical direction, and have influence in the company, is being seen as baseline competent, which requires onboarding successfully.

So, what happens if you don't?

You don't kill your ego, so your onboarding goes a bit rough. It drags out for a few months, you're on track for your first performance review being "doesn't meet expectations".

Well, this post will go through a few stories of how it played out for some colleagues who failed to onboard.

Safe to say if the carrot of the last post didn't motivate you, maybe the stick of this one will.

Onboard quickly and successfully, anon.

The rest of time at the company may depend on it.


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New Grad

I knew a girl, fresh out of school, first job. Data analyst role though she ended up needing to do some some basic Python programming.

She got along well with her manager, and the team. Quickly understood the social dynamics and the high level overview of the first task assigned.

But, when it came down to the actual programming she hit the usual predictable onboarding roadblocks.

The laptop had data analyst permissions, not the standard looser programmer OS image. So, she couldn't install Python or run her code at all.

It was a small innovation team in a sprawling organization, so there was no starter template repo or new engineer documentation.

She didn't know how to setup a fresh Python project for use with Jupyter for prototyping, and then a production data cleaning executable.

So, what did she do?


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She worried and became an anxious mess.

Googling in vain for almost 2 weeks, never once letting her manager or teammates know that she was hard blocked.

Finally, after almost a dozen stand up meetings just stalling – politely, confidently, and initially believably – the manager assigned someone to pair with her and figure out what was wrong.

Sure enough, there was some JIRA ticket that had to be filed to grant her permissions. But, of course that took another few days to get approved.

By then, she'd spent the first 3 weeks hard blocked and producing nothing. Her manager was not impressed.

8 Ways To Spot An Annoying Manager | Camilo RIO

Freaking out, she came to me.

I shared the same recommendations from the [last post](LAST POST). Timebox all efforts to 15 mins - 1 hour. Then, immediately escalate, say you're hard blocked, and ask the team or someone to pair program on getting unblocked.

It took her a while but she finally started to get the hang of it.

But instead of 1 hour to timebox, it'd still be 1-2 days. And through it all she was unable to undergo the necessary ego death to become comfortable asking for help.

She ended up convinced that she couldn't be a programmer. When really, she just was unable to admit that after her Bachelor's and Master's degree, she still needed to ask for help and had a lot to learn.

She quit 6 months later and struggled to get a recommendation letter from her manager, which obviously made it a bit more difficult to find her next position as a non-technical policy analyst.

If you're not willing to ask for help and continually learn, you'll never succeed.

Intermediate Engineer

A new guy joined a sister team one day. He'd been hired as an intermediate, well paid for his age. He had I think 4 or 5 years experience.

But, immediately he had a hard time fitting in socially on the team.

He was a sports bro, betting on every game, loud, Eastern European, upbeat & positive. A stark contrast to the much more subdued, level-headed, traditional nerd interests and mannerisms of the existing team.

He talked a good game technically, but soon that was the only thing he had a reputation for. Talk. He couldn't ship.

His manager was exceedingly aloof, so he was able to fumble around nearly a year before the tensions rose.

I was called in to pair program on his latest project and help fix his "velocity issues".

We started pairing once a week, then twice. Soon it was nearly every day.

He had an awful habit of drilling down for days, layer by layer in the code. Endless pointless goose chases.

Constant complaints about how the existing code had been written. Some of it valid complaints, some of their code was horrendous. But many complaints, simply were protecting his ego with endless accusations that his colleagues were idiots.

And through it all, still no PRs submitted.

I pushed hard coaching him for many months on the previously mentioned tactics of time-boxing, cleaning up other's bad code as you encounter it, but for him there were other big issues.

For one, scoping.

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