Aviv Ben-Yosef
@avivby.bsky.social
Because life's too short to waste them running *average* product-engineering teams.
https://avivbenyosef.com
https://avivbenyosef.com
180 Observations and Thoughts from 180 Days in Rome
It’s been six months since we moved to Italy. I’ve been collecting different thoughts and thought I’d share some of them. Disclaimer: This is what we’re seeing in our nice neighborhood in Rome. Our private experiences. YMMV.
It’s been six months since we moved to Italy. I’ve been collecting different thoughts and thought I’d share some of them. Disclaimer: This is what we’re seeing in our nice neighborhood in Rome. Our private experiences. YMMV.
January 16, 2026 at 3:35 PM
180 Observations and Thoughts from 180 Days in Rome
It’s been six months since we moved to Italy. I’ve been collecting different thoughts and thought I’d share some of them. Disclaimer: This is what we’re seeing in our nice neighborhood in Rome. Our private experiences. YMMV.
It’s been six months since we moved to Italy. I’ve been collecting different thoughts and thought I’d share some of them. Disclaimer: This is what we’re seeing in our nice neighborhood in Rome. Our private experiences. YMMV.
Let's continue improving the relationship and alignment between CEOs and tech execs. You don’t have to feel like you have nothing to show, that your value isn’t understood, or that you don’t know what to do. As a tech leader, you can bring more clarity to the situation.
January 15, 2026 at 1:59 PM
Let's continue improving the relationship and alignment between CEOs and tech execs. You don’t have to feel like you have nothing to show, that your value isn’t understood, or that you don’t know what to do. As a tech leader, you can bring more clarity to the situation.
It’s the season: we start see people lament their objectives and planning processes. Were you handed OKRs that you don’t really understand? Or that you don’t believe in and know will be changed by the time you’re back from the New Year’s vacation? It doesn’t have to be that way.
January 8, 2026 at 2:02 PM
It’s the season: we start see people lament their objectives and planning processes. Were you handed OKRs that you don’t really understand? Or that you don’t believe in and know will be changed by the time you’re back from the New Year’s vacation? It doesn’t have to be that way.
Every end of the year, I sit down to do some personal reviews, as well as collect my notes. Since I have hundreds of meetings with founders and tech leaders worldwide every year, looking at it all from a higher altitude helps me notice themes and trends.
January 1, 2026 at 2:04 PM
Every end of the year, I sit down to do some personal reviews, as well as collect my notes. Since I have hundreds of meetings with founders and tech leaders worldwide every year, looking at it all from a higher altitude helps me notice themes and trends.
Let's exploit the fact that this article goes out on Christmas for a light read about the 𝐂𝐓𝐎 𝐒𝐜𝐫𝐨𝐨𝐠𝐞. Did you become a grumpy tech leader? Without planning it, you've ended up in a position you don't really like? Let's quickly see how it happens to many good people.
December 25, 2025 at 1:56 PM
Let's exploit the fact that this article goes out on Christmas for a light read about the 𝐂𝐓𝐎 𝐒𝐜𝐫𝐨𝐨𝐠𝐞. Did you become a grumpy tech leader? Without planning it, you've ended up in a position you don't really like? Let's quickly see how it happens to many good people.
Italian progress: actually made people laugh this week, including a pun in Italian! Love it when I'm able to use a bit of my humor. Also, always glad when I find the right word/idiom and people are positively surprised. Piano piano!
December 20, 2025 at 11:20 PM
Italian progress: actually made people laugh this week, including a pun in Italian! Love it when I'm able to use a bit of my humor. Also, always glad when I find the right word/idiom and people are positively surprised. Piano piano!
Working with tech executives, one thing becomes obvious very quickly: the CEO relationship is the most important one you have, second only to Product. And yet, it’s often fragile, strained, or quietly dysfunctional. Even among co‑founders. It doesn’t have to be that way.
December 18, 2025 at 1:56 PM
Working with tech executives, one thing becomes obvious very quickly: the CEO relationship is the most important one you have, second only to Product. And yet, it’s often fragile, strained, or quietly dysfunctional. Even among co‑founders. It doesn’t have to be that way.
Lighting the first candle, last night at Piazza Barberini, Rome. One day, we'll be able to do this without dozens of police officers locking us behind barricades for protection, my daughter repeatedly asking if it's safe, and people discussing where it's less risky to stand. 🕎🇮🇱
December 15, 2025 at 9:35 AM
Lighting the first candle, last night at Piazza Barberini, Rome. One day, we'll be able to do this without dozens of police officers locking us behind barricades for protection, my daughter repeatedly asking if it's safe, and people discussing where it's less risky to stand. 🕎🇮🇱
5 months into this Rome move, I still get stuck in front of an aisle at the supermarket trying to make sense of a shelf of a type of sausage, cheese, snack, etc. I've never heard of. I need Hello Fresh but just with a weekly interesting local recipe to try at home myself.
December 12, 2025 at 8:04 AM
5 months into this Rome move, I still get stuck in front of an aisle at the supermarket trying to make sense of a shelf of a type of sausage, cheese, snack, etc. I've never heard of. I need Hello Fresh but just with a weekly interesting local recipe to try at home myself.
Your team’s running along and getting work done. You’re busy supporting all of that, which is great. But don’t lose sight of the longer-term leadership work of shaping the org, or you’ll waste the current momentum.
December 11, 2025 at 1:59 PM
Your team’s running along and getting work done. You’re busy supporting all of that, which is great. But don’t lose sight of the longer-term leadership work of shaping the org, or you’ll waste the current momentum.
Little Italian progress: I find myself in my writing reaching out to an Italian word and having to reverse lookup it to English/Hebrew to find the right word with the right sfumature.
December 11, 2025 at 7:01 AM
Little Italian progress: I find myself in my writing reaching out to an Italian word and having to reverse lookup it to English/Hebrew to find the right word with the right sfumature.
Random thing we noticed: many of the canned goods we get here in Rome supermarkets don't… stack? Like, you get a pack of tuna cans and they wobble when you try to put them one atop the other. Just… odd?
December 10, 2025 at 3:00 PM
Random thing we noticed: many of the canned goods we get here in Rome supermarkets don't… stack? Like, you get a pack of tuna cans and they wobble when you try to put them one atop the other. Just… odd?
I think xmas raffles are kinda a thing here in Rome? One of our fav gelato places has one, and the nice employee there asked my son to write not just in Italian but also in "Israelish" (Hebrew…). Che carino!
December 6, 2025 at 8:58 AM
I think xmas raffles are kinda a thing here in Rome? One of our fav gelato places has one, and the nice employee there asked my son to write not just in Italian but also in "Israelish" (Hebrew…). Che carino!
Took the kids for a stroll over the weekend. On a whim, they wanted to explore Circo Massimo. We snap a photo and later realize other than this millennia-old spot, one can also see the Jewish ghetto and the Vatican in the background. Rome is still mind-boggling.
December 5, 2025 at 7:04 AM
Took the kids for a stroll over the weekend. On a whim, they wanted to explore Circo Massimo. We snap a photo and later realize other than this millennia-old spot, one can also see the Jewish ghetto and the Vatican in the background. Rome is still mind-boggling.
Most leaders I meet are shallow. Not because they lack care. They’re shallow because they’ve stopped treating their role with the same urgency, curiosity, and responsibility they had as engineers.
December 4, 2025 at 1:57 PM
Most leaders I meet are shallow. Not because they lack care. They’re shallow because they’ve stopped treating their role with the same urgency, curiosity, and responsibility they had as engineers.
Today in memos-everyone-in-Rome-got-except-us: Like magic, natale (xmas) decorations appeared on half the apartments in our building. I like these traditions!
December 3, 2025 at 8:07 PM
Today in memos-everyone-in-Rome-got-except-us: Like magic, natale (xmas) decorations appeared on half the apartments in our building. I like these traditions!
Special and limited-time offer alert!
I got envious of my kids getting Advent calendars for the first time (Rome has these everywhere). I decided to offer the same for you all!
But some things are limited, and so you can only sign up in the next 24 hours! Hurry up!
I got envious of my kids getting Advent calendars for the first time (Rome has these everywhere). I decided to offer the same for you all!
But some things are limited, and so you can only sign up in the next 24 hours! Hurry up!
December 1, 2025 at 2:45 PM
Special and limited-time offer alert!
I got envious of my kids getting Advent calendars for the first time (Rome has these everywhere). I decided to offer the same for you all!
But some things are limited, and so you can only sign up in the next 24 hours! Hurry up!
I got envious of my kids getting Advent calendars for the first time (Rome has these everywhere). I decided to offer the same for you all!
But some things are limited, and so you can only sign up in the next 24 hours! Hurry up!
About two months into the school year, my children have already filled notebooks! Italian schools do a lot of writing, which I think is good. Back home, a notebook would take two years to be filled…
November 29, 2025 at 6:56 AM
About two months into the school year, my children have already filled notebooks! Italian schools do a lot of writing, which I think is good. Back home, a notebook would take two years to be filled…
Something changed this week, as if everyone in Rome got a memo. All of a sudden, everyone's wearing down jackets (piumini). We never needed those in the past. Time to do some shopping!
November 28, 2025 at 11:36 AM
Something changed this week, as if everyone in Rome got a memo. All of a sudden, everyone's wearing down jackets (piumini). We never needed those in the past. Time to do some shopping!
Working with many tech leaders, I've come to realize that while each one of you is a unique and special snowflake, if you squint, you can notice certain archetypes of behavior.
November 27, 2025 at 2:01 PM
Working with many tech leaders, I've come to realize that while each one of you is a unique and special snowflake, if you squint, you can notice certain archetypes of behavior.
Random thing I noticed this week, ~4 months into our move to Rome: Kids have started gesticulating more… 🤌
November 27, 2025 at 6:57 AM
Random thing I noticed this week, ~4 months into our move to Rome: Kids have started gesticulating more… 🤌
I was talking to someone here that it's surprising the amount of dubbing done in Italy. Most local cinemas here don't usually show movies in their original language (Wicked and similar not included). I believe this difference from other places affects proficiency in English.
November 22, 2025 at 9:58 AM
I was talking to someone here that it's surprising the amount of dubbing done in Italy. Most local cinemas here don't usually show movies in their original language (Wicked and similar not included). I believe this difference from other places affects proficiency in English.
The Notes.app on my Mac and iPad has lost highlights and markups on PDFs at least 5 times in the past week. Are people using something else that actually works?
November 21, 2025 at 8:58 AM
The Notes.app on my Mac and iPad has lost highlights and markups on PDFs at least 5 times in the past week. Are people using something else that actually works?
There's a great local restaurant we've gone to ~once a month since moving to Rome. It's nice seeing the progress the kids are making every time: the blank stares slowly turning into short answers, recognizing the different salami and asking for their favs, etc. Steady progress 💪
November 21, 2025 at 7:03 AM
There's a great local restaurant we've gone to ~once a month since moving to Rome. It's nice seeing the progress the kids are making every time: the blank stares slowly turning into short answers, recognizing the different salami and asking for their favs, etc. Steady progress 💪
Complexity is lazy. Coders spin up microservices on day one, and then spend years maintaining a distributed Rube Goldberg machine. Leaders fall for the same trap. It’s shockingly easy to grind a company to a halt not by being incompetent, but by being smart in all the wrong ways.
November 20, 2025 at 1:57 PM
Complexity is lazy. Coders spin up microservices on day one, and then spend years maintaining a distributed Rube Goldberg machine. Leaders fall for the same trap. It’s shockingly easy to grind a company to a halt not by being incompetent, but by being smart in all the wrong ways.