That first day as the Head of Engineering at a fast-growing startup is always glorious.

Not an engineering manager anymore, but a Head Of. The non-technical-at-all founder hired them because they *really* needed someone to get sort the eng problems.

A new story starts today:
The first week is done, and it's exciting. Well, a bit annoying as well. The founder keeps checking in, and talking about how they see this role, and what they want the EM (not Head of Eng) to do.

Problem is, much of it is not how the EM worked in the past, and it doesn't work.
Like the obsession the founder has with what are essentially micromanagement practices.

"This is how we work. High autonomy+high accountability is our culture". But then eng is told the work they should do, given deadlines with no input, and judged on "getting shit done".
Anyway, the EM is now Head of Engineering, so they know they'll change this. Once they gain trust.

Which is getting harder, every week.

An outage happened yesterday, taking down the product for hours. The founder is furious and is publicly blaming the EM already.
"Well, no one said Head of Engineering is easy" justifies the EM. Ok, so first, no more outages.

They announce all production pushes stop until the outage root cause is fixed. Engineers can't believe they finally get to fix things.

Neither can the founder. They summon the EM:
"Stopping shipping to production is ABSOLUTELY out of the question. And don't you pull something like this in public without checking with me again. I hired you to fix engineering, not to make things worse."

The EM tries to explain but gets shot down.

This is not looking good.
A direct message on LinkedIn from the previous Head of Engineering. "Want to hear some advice?" it reads.

They meet up, the Current and Former.

"Look for a new gig, I'm telling you. I wish someone told me what I told you 12 months ago." the Former concludes after the catchup.
The EM is not giving up on the Head of Engineering role though.

The next months are hell.

Hands tied, their role is relegated to carrying out whatever the founder approves of. When hiring, they feel like a fraud, describing the culture of the old place, not the current one.
After six months, going to work fills them with dread.

The founder is getting more unhappy is a reason for it.

On the first performance review, the rating is "below". "Since I hired you, we had two massive outages and work is still slow. You have one more chance. Do better."
The decision to quit when an engineer shares they're leaving to their former company, taking a cut in title, from Principal to Senior.

"It's the dev culture. No offense, but I hoped you coming would make it better. I feel like a second-class citizen here. I don't want this."
This is when they realize that the founder will not change.

No matter what they tried, it got shot down when it went against ideas the founder had on engineering. They'll never succeed here.

Months later they accept an EM position at a larger company, with double the paycheck.
The founder is not surprised when the EM resigns and goes on to repost the exact same job description from 8 months before. The EM wonders if they should also message the next Head of Engineering.

They leave. The Head of Engineering is back to being an EM, but is happier for it.
And the new job is *great*. The EM is on a highly performing team, working with great people. Two years alter, one of their products gets lots of press, the EM being featured in the article.

A flurry of congratulations and private messages follow. One of these stand out.
It's a message from a startup founder who just raised $17M. A coffee follows, where the founder offers the role of heading up the eng team to the EM on the spot. They need someone technical.

The EM hesitates, but just for a second. This will be different.
Within minutes, multiple Head of Eng’s messaged how this was all too real for where they are at… which is, on one end, funny, and sad, on the other.

Unsure if I’ll cover this specific topic at newsletter.pragmaticengineer.com but working with non-technical stakeholders will be one.

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More from @GergelyOrosz

29 Sep
While there are many posts criticizing how difficult hiring processes are, especially for entry-level roles, it's only in private you hear interviewers and hiring managers talk about the other side.

Here's a short thread on a few observations that also explains some criticisms:
1. Entry-level applicants are on a very wide spread skillset-wise. They range from people who can only follow a tutorial to those who are hands-on with production-ready code. It skews towards the former though.

This is one reason there are so many automated closing assessments.
2. Resumes don't tell you much about entry-level people. Within the same bootcamp grads, there will be some strong candidates, and plenty of week ones. Same with colleges. It's impossible to predict how well a person will do on a coding exercise.
Read 8 tweets
28 Sep
Engineer: "Can I expense this $500 noise-canceling headphone? Makes it easier to focus."

Manager: "Sure."

Compliance: "That's against policy."

Manager: "It's $500. 0.3% of their salary. It helps them do better work."

Compliance: "It's policy."

Manager: "Ok, how about this:"
Manager: "Can you remind me of team morale budget rules?"

Compliance: "$1,500/person, per year."

Manager: "So it comes out of team morale."

Compliance: "But..."

Manager: "But, indeed, if we don't buy this, team morale will plummet due to stupid corp policies."

True story.
This was how I went getting noise-canceling headphones in an open-plan office* for my team at my previous gig.

*corp policy was handing out $100, non-noise canceling, uncomfortable headphones, purchased in bulk for savings.

Policy still the same AFAIK, as is the workaround.
Read 4 tweets
27 Sep
A month into a paid newsletter for eng managers/engineers, it's taking off faster than I ever hoped:

~ 500 paid subscribers (thank you!)
~ 15,000 free subscribers
~ $62K ARR
- A top 10 @SubstackInc technology newsletter

Here's what I learned and advice on writing/newsletters 👇
1. Start writing. I started The Pragmatic Engineer blog years ago. At first, no one noticed. 70 essays later, a lot of people do.

If I started today, I'd join a community for feedback/encouragement like @bloggingfordevs by @monicalent (a community I'm a paying member of).
2. Write what *you* want to read. I always liked articles that shared observations on where tech is heading or explained important things with plain language.

So I wrote about this. Like equity in tech blog.pragmaticengineer.com/equity-for-sof… or product-minded engineers blog.pragmaticengineer.com/the-product-mi…
Read 15 tweets
27 Sep
My article on how big tech runs projects is on the frontpage of Hacker News (news.ycombinator.com), and the comments are really interesting.

I particularly like this one from a person at Shopify, who are out-executing most tech companies. How do they do it? Like this: Image
This is exactly how high-performing teams have always worked, from the teams at Apple building all their products to ones at Amazon, to those at Google etc.

Scrum, bundled with consultants can help, sure. But ever stopped to wonder about why many places never needed these folks?
And I'm not anti Scrum (with the capital S), and the article defends this practice that has its time and place: newsletter.pragmaticengineer.com/p/project-mana…

But here's an open secret Silicon Valley companies know that most other companies don't: blog.pragmaticengineer.com/what-silicon-v…
Read 4 tweets
26 Sep
When you ask "Why did Company build 7 of the same products that all failed?", it always starts with the current solution struggling. This is an opportunity. Not to fix - which doesn't get you promoted - but to start anew.

An all too real story about Promotion Driven Development:
1. Opportunity.

The PM identifies the opportunity as Company's current product(s) are struggling. The root cause? Incorrect positioning/not understanding new market dynamics.

Opportunity: build a new product that addresses all these issues (and can get the PM promoted)
2. Proposal.

The PM makes a business case and an investment ask. "If we fund a team of 10 engineers, 2 data scientists, 1 designer, and 1 PM, we can ship a new product in 12 months, and an MVP in 6. This will result in this many users/revenue/market share: 📈"
Read 17 tweets
26 Sep
On equity: "Our CEO doesn't believe in awarding equity to employees b/c it creates the wrong types of incentives. People stay hoping for a payday."

I hear you. Companies that obviously did not get this memo include Microsoft, Apple, Amazon, Google, FB, Tesla, Twitter, Slack...
... not to talk about most of the fastest moving & innovative startups.

What the same C-levels don't like to admit is how they *do* have large amounts of equity, and hoping for a payday is one of the many reasons they also stay.

Aligning company and employee incentives works.
My writeup on equity in tech: what you need to know and why it's (very) important blog.pragmaticengineer.com/equity-for-sof…

A recent, in-depth book I reviewed and recommend: Equity Compensation for Tech Employees by @mcdickenson gumroad.com/a/276534387/Eg…
Read 4 tweets

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