Hiring (and managing) cracked engineers

May 23, 2024

Posted by

Charles Cook

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What’s not cracked?
Managing cracked engineers
1. Being cracked yourself
2. Spending most of your time generating enthusiasm
3. Getting out of the way
4. Prioritizing making cracked people more cracked
5. Eliminating pointless approval processes
6. Nailing hiring and context
Moar reading

We’ve become a bit obsessed with the notion of hiring cracked engineers at PostHog.

When we say cracked, we mean people who:

🙋‍♀️ Take extreme ownership of ideas. This means driving ideas to completion, even when others need convincing. And, yes, there’s a fine line between extreme ownership and being an asshole. Truly cracked engineers can tread it.
😄 Stay optimistic at all times. Cracked engineers aren’t intimidated by change, or new ideas. This doesn’t mean you have to agree with every change, but adopting a ‘yes and’ mentality helps new ideas get off the ground that might otherwise die in a committee somewhere, especially when they come from non-senior or new people.
🤩 Make people feel excited and energized. Every conversation with a cracked engineer should generate enthusiasm. Cracked engineers build people and their ideas up, and are generally perceived as very helpful.
😎 Behave in a completely authentic way. Cracked engineers don’t play politics – their work does the talking. For example, if you do marketing, talk like an actual human being. This doesn’t work in most large organizations, sadly.
👷‍♂️ Apply themselves to the craft. Joy comes from the craft itself, not creating shareholder value. Cracked engineers apply themselves to the craft of building products with a quasi-religious fervor, and love what they do.

What’s not cracked?

This sounds pretty ripe for a toxic monoculture of tech bros doing whatever they want while the founders arbitrarily pick new pet projects, right?

No! You need some anti-goals as well. For example, the following are definitely not prerequisites to being cracked:

🏢 Fancy companies on your resume. You don’t need to have worked at a FAANG/MAMAA/shit-hot SV-based company. We welcome cracked engineers who held together failing companies – we like their paranoia.
😏 Being an asshole. People need to want to work with you – saying “screw you, I’m doing this anyway” is uncracked behavior if you can’t back it up.
🐣 How experienced you are. There is no number of years of experience that correlates with crackedness, in either direction. See also: using rank / experience to get your way.
📈 A popular side project. To be clear, side projects are great signs of crackedness, but success is less important. An interesting project no one knows is about is just as valid. Remember: loving the craft of building something is cracked.

Adopting this mentality has noticeably increased the diversity of people applying to work with us at PostHog.

It ignores many of the traditional markers of status when it comes to job applications, helping us unearth great people who might otherwise miss out.

And we apply the same criteria to all our roles, including non-engineering ones.

Managing cracked engineers

This mentality also forces us to think about how to manage cracked engineers.

A lot of traditional management behavior doesn’t apply here, and can actively slow down or demotivate them.

For us, managing cracked engineers means:

1. Being cracked yourself

You need to demonstrate the behavior you want to see. Cracked people are extremely attuned to ‘do as I do’ not ‘do as I say’. This means spending a significant amount of time doing individual contributor work.

Do the stuff that arrogant senior people would find ‘boring’. Write tests. Respond to customer support queries. Go weirdly deep into some piece of analysis. Do something badly that’s not your job, so you at least understand it better.

2. Spending most of your time generating enthusiasm

It is unbelievably easy to find reasons not to do stuff at any kind of organization, including startups.

Inertia is the default state of most businesses. Overcoming it is mainly reliant on the enthusiasm of people to make new and cool things happen, and is far more important than their raw intelligence or competence.

This is why you should spend more time motivating people than trying to teach them new skills, or making them do training. If they are cracked and motivated, they will train themselves.

I don’t think I’ve yet read a blog post by someone I admire and learned from that says ‘I got good because I attended blah blah special leadership course on being great.’

3. Getting out of the way

Cracked people are deeply intrinsically motivated. This means that extrinsic motivation, while still present in some form (we’ve all got to pay bills yeah), is way less important.

Help cracked engineers take ownership of their own projects by encouraging them to make the decisions about what to do next. If they ask for help – i.e. they actively want you to get in the way – ask questions about what they think should happen next, rather than giving them the answers.

Setting deadlines, creating arbitrary reporting obligations, or saying ‘if you ship X, you will get to Y title’ are examples of trying to use extrinsic motivation. This is un-cracked.

4. Prioritizing making cracked people more cracked

Here is some subjective math:

The 20% of your team who are underperforming will take up 80% of your effort.
You may be able to get an underperformer’s output from 4/10 to 6/10 if you work hard with them.
Doubling down on a cracked person’s performance can improve their output from 8/10 to 9/10.
It’s the 9/10 quality output that will delight your users, so you should focus on that, even if the absolute increase in performance is less.

5. Eliminating pointless approval processes

Asking thoughtful questions and rigorously testing ideas? Cracked.

Long approval processes that exist for the sake of having someone senior sign off on something in order to kick accountability up the chain? Very un-cracked.

If you find yourself approving stuff for your team because of your position as their manager, remove yourself from the process.

6. Nailing hiring and context

The number one thing you can do to motivate cracked people? Find them more cracked people to work with!

(Yes, there are many other very obvious ways you can demotivate, like creating a shitty culture, making people burnout with unrealistic demands, pivoting aggressively every week for no reason, but I’m going to assume you at least have some semblance of managerial logic if you’ve read this far.)

Conversely, the number one thing you can do to demotivate them is to make them work with un-cracked people.

A close number two is setting the right context for them to do their best work. This means:

Clearly articulating your company and/or team’s vision.
Ensuring everyone understands it and their role in it.
Helping them pick between competing priorities when needed.

Above all, never use “setting context” as a euphemism for “work on the stuff I care about as a manager”. They are not the same thing.

Nailing these two things is the 80/20 of managing cracked engineers.

Moar reading

Got the interview? Here are the questions you should be asking.
Literally everything we've learned about hiring at PostHog
A bunch of myths and truths I've learned about startup hiring in the last 10 years