What Entrepreneurs Can Learn from The Making of a Manager
Priya founded a logistics software startup after landing seed funding, and once she hired her first three employees she kept working the way she always had: heads-down at her desk, assigning tasks through terse messages, telling herself she was "too busy building" for regular check-ins. One engineer, Marcus, spent weeks quietly stuck on an ambiguous spec, afraid to ask questions because the only feedback Priya had ever given him was an offhand "just figure it out" in the hallway. When the feature shipped broken, Priya called an emergency meeting and criticized the team's work in front of everyone, having never once said what "good" looked like beforehand. Two engineers started job hunting within the month. Priya had assumed hiring capable people was the whole job. Instead, the culture calcified around fear before it ever had a chance to form on purpose.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
0 of 5 selected
The core lessons, applied to you
The founder check-in that actually helps
In a five-person company, informal hallway chats quietly replace scheduled one-on-ones, and founders assume this is even better than a formal meeting because it's constant. It usually isn't: hallway talk happens on the founder's terms, about whatever is loudest that day, and rarely leaves room for a quieter problem to surface.
A founder assumes silence means things are fine, while a team member has been stuck on a decision for a week and doesn't want to interrupt someone who always looks busy.
Put a standing thirty-minute one-on-one on the calendar with each direct report, protect it from being bumped by "more urgent" work, and open it by asking what's in their way rather than what they've finished.
Feedback that's specific and kind at once
Early hires often get either no feedback, because the founder is too busy, or feedback that arrives only in a crisis, sharpened by stress. Neither builds the ongoing signal a new hire needs to improve.
The first real feedback an employee hears is delivered publicly, after a failure, and reads as a character judgment rather than direction they could have used weeks earlier.
Give one piece of specific, behavior-based feedback per week per person, tied to something you actually observed, delivered privately and close to the moment it happened.
Trust built before it's needed
In a startup's early scramble, trust often gets treated as a nice-to-have that can wait until the company is stable. But the first hard conversation, a missed deadline or a role change, always seems to arrive before that imagined calm.
A founder asks a struggling employee to take on a smaller role, and the employee hears it as a demotion from someone who has never shown any real interest in their growth.
Spend the first month with each new hire learning what they actually want from this job, and revisit that answer out loud every few months.
Redefining your own success
Founders are trained to measure themselves by what they personally shipped, closed, or fixed, and that habit doesn't disappear the moment they hire someone. The hardest internal shift in early leadership is realizing your job has changed from producing the work to making other people's work possible, a trade that can feel, for a while, like doing less rather than something different and harder to see.
Weekly one-on-ones and specific feedback take real hours a founder could spend on product or sales, and in a cash-tight month it's tempting to cancel them first. The tension is real, but treating people time as expendable is exactly what let Priya's team unravel; protect a smaller, non-negotiable amount of it rather than dropping it whenever the calendar tightens.
Name one thing, honestly
Which of your current employees would say they know what you actually think of their work, and which would only be guessing?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
0 of 3 selected
Run this for seven days
Spend the first month with each new hire learning what they actually want from this job, and revisit that answer out loud every few months.