01 · STAND-UP
“Give me six hours to chop down a tree and I will spend the first four sharpening the axe.”
— Abraham Lincoln (Kind of...)
Most hiring managers spend zero hours on the axe.
They open a role, start sourcing, and wonder why the first ninety days feel like a slow-motion stumble.
The sharpening isn’t the job description. It’s the question nobody asks before the search opens: what does success actually look like — and on whose timeline?
02 · SPRINT
I live in a tech-forward apartment building in the heart of downtown Oakland. What does "tech forward" mean, you ask?
In short, it feels like a startup. Kind of cool, actually.
But it's not the building itself and amenities that stand out; it's the people that live here.
People in tech, some founders of startups, some who've traveled across the country (and in some cases, the world) to be in the thick of it all - San Francisco's startup ecosystem.
It's a unique community where I've been so fortunate to meet amazing human beings I now call friends.
One of those humans, is Venkat.
He's an incredibly gifted young man who works as an engineer at an ed tech startup, and happens to be one of my newsletter subscribers.
Every week, he pings me on WhatsApp and shares his feedback directly.
Unsolicited.
He just loves the content (and I'm so glad it resonates!)
He’d read the last issue (#002) about design docs for engineering roles and where the 30/60/90 plan usually breaks down.
His response had me thinking 🤔
“For a new hire to really fit into the role they were hired for,” he wrote, “it takes at least six months of doing their job and slowly understanding the processes and systems already in place — while leaving room for the new hire to bring their own energy to the table.”
He’s two or three years into his career. He’s not a hiring manager. He’s never opened a role, and he got it more clearly than most of the engineering leaders I’ve worked with for a decade.
I’ve sat with founders who genuinely believed a new engineer would be fully contributing by week six. Move fast and break things (over and over again).
I’ve watched EMs build sprint plans that had a new hire carrying real load by day forty-five. I’ve seen onboarding decks with thirty action items in the first two weeks and nothing — nothing ⚡️ — about what month three looks like.
The gap between what companies plan for and what actually happens isn’t a performance problem. It’s a timeline problem.
Company roadmaps are put together without truly understanding the product, market, or audience; and that's a frustrating conundrum for new engineering hires.
The 30/60/90 framework exists for a reason. It’s a good structure.
But most teams use it backwards as they plan the output first and forget to plan the context. They forget that before an engineer can write good code for your system, they have to understand your system. Your architecture decisions. Your tech debt. Your deployment habits. The informal rules nobody wrote down. The reason that one service is still running on the old stack.
That takes time. Not because the engineer is slow. Because systems are complex and trust is earned incrementally.
Venkat put it simply: “Having that outlook and tasks planned around such a timeline — to gradually help them grow as well as get the work output required — is such an important thing most companies sadly miss.”
He’s right.
The companies that get this right don’t just have a 30/60/90.
They have a 30/60/90/180. The first three months are about context and contribution. The second three are about ownership. And the boundary between the two is defined before the offer letter goes out, and surely not after the first performance review.
The design doc for the role, the success criteria, the ramp timeline aren’t HR formalities (especially in early stage startups). They’re the sharpened axe. The thing that makes everything after the hire faster, cleaner, and less likely to cost you someone good six months in.
That’s the part most founders miss entirely. They view hiring like a secondary lever for growth, expect a unicorn candidate, and by the time the new engineer shows up, nobody in the room helped define what success looks like.
And the engineer is already looking elsewhere wondering what planet they landed on.
Fix that first. Everything else gets easier.
Sharpen the axe.
03 · RETROSPECTIVE
✅ What went well
A reader (and friend of mine) early in his career, paying close attention pushed back thoughtfully on something I wrote and made the point sharper. That’s the whole point of this newsletter. Not me broadcasting. A real conversation. Thanks, Venkat!
🔧 What could be improved
I want to write more issues that start with a reader’s voice instead of my own. The best thinking in this space isn’t just mine. It’s in the replies. Send me your problems, thoughts, and successes!
⚡ One action item before next week
If you’re an EM or founder with an open role right now: write down what “fully ramped” means for that hire. Not at 90 days. At 180. Need help? Hit reply, and I'll share my thoughts.
