Paolo’s Handbook

I published this document internally at Automattic to be used by any colleague curious about how to interact with me. I am sharing it here as I want to be able to reference it publicly, and access to our internal P2s is limited.

Version 20240817.2

What is this?

This is my instruction manual. As your team lead, I serve you. I work for you, and try to make your life easier and your work better. For that, it’s crucial that I remove any friction in interacting with me.

No one should wonder, hesitate, or have to ask questions about how to do our best work together.

I’m sharing here how I function (or at least, I think), and how to interact with me.

This is a live document, feel free to react, comment, and ask questions, I’ll revise it regularly.

Who is it for?

I am writing this for every Automattician I interact with, but also as a template for other team leads. You are welcome to inspire yourself from it.

Tech Specs

• I talk, a lot.
• I write succinctly.
• I am impatient.
• I pay attention to details.
• No task is beneath me.
• No goal is unreachable.
• I take time off, and so should you.
• I have a strong product sense.
• I have strong opinions.
  • Loosely held in the front of real user experiences.
  • Strongly held in front of other opinions.
• I am data-informed, not data-driven.
• Some people think to talk, I talk to think.

Principle vs. Rules

I value principles because they are adaptable and a guide through new situations. I dislike rules because they assume the future will behave as the past did.

Feedback

I value receiving feedback like a gift.

I can take criticism as long as it is about my actions and not my person.

I practice radical candor, and appreciate it in others.

I believe no problem can’t be solved by talking through it.

I think feedback should be timely, but delayed just enough to guarantee it’s not a knee-jerk reaction.

Meetings

1-1s

I love 1-1 meetings, they are the highest signal/noise ratio.

I also value reconsidering my positions, so I am currently experimenting with optional 1-1 meetings open to the whole Jetpack team.

Larger meetings

With very rare exceptions, I try to avoid larger meetings unless they are team meetings. In the case of team meetings, I particularly appreciate the social, and bonding, aspects. I hate when important decisions are made in large meetings.

If a meeting has no agenda and I am leading it, I’ll shorten it.

If you find yourself in a meeting with me and have no idea why you are there, ask me. If after that, you still don’t know, feel free to leave.

Town Halls

I appreciate the town hall format for its efficiency in sharing a message to the entire team or company.

Communication

API

I Assume Positive Intent and count on you to do the same.

P2

You may at times find me a bit absent from P2 threads, then be frustrated if once in a while I jump in too late to criticize a choice or a decision.

This happens particularly while in this my current interim-GM role.

I can be on top of every single P2 post and reply to all, but I found that the result of that is too often to shut the conversation down. I trust the team and the fact that the hive mind is smarter than individual ones, and reverting a decision once in a while is a low price to pay to benefit from a larger diversity of opinions.

I believe the role of a leader is to start more conversations than they end.

Slack

Never hesitate to ping me. Preferably on public channels.

If privacy is a concern, DMs are fine.

With few specific exceptions, I dislike private channels and multi-person DMs.

Notifications

You can ping me on any day, at any time. It’s my responsibility to manage my notifications so that they do not interfere with my life when not working.

Don’t expect an immediate answer. I value async communication.

I also do not expect an immediate reply from you to my messages. While I’ll message my peers and managers liberally at any time. I’ll refrain from doing so with the team members reporting to me because no matter how much we repeat that asynchronous communication is the way, that will always create some unwelcome pressure or discomfort. I love scheduling messages in Slack.

Boundaries

I work for Automattic, not for Jetpack or .blog. I expect the same from you.

This means that I will always privilege the path that maximizes value for Automattic even if it comes at a local cost for our team.

My toes are very agile, it’s impossible to step on them. I count on the same agility from you. There are no walled gardens, no gatekeepers.

I trust. Upfront and fully. And I verify.

It’s difficult to lose my trust, but it can happen only once.

My Work Style

How I work best

I don’t multitask, but I can switch context frequently and quickly.

I time-block my calendar so the current week looks incredibly busy, but that’s because I allocate almost every moment to a specific purpose. Check a week or two in the future, you’ll see there is flexibility.

I spend my life trying to understand problems and solving them, so, if you need my help, make obvious upfront if:

• You just need to inform me about a problem.
• You are presenting me a solution.
• You are presenting options for me to choose from.
• You need my help to figure it out.

Otherwise, I’ll systematically switch to solving mode, and it may not be what you wanted.

My weaknesses and a few workarounds

I tend to dive into tasks that I should ask someone else to perform, becoming a bottleneck.
→ If you are waiting for me on anything, just ping me in a DM or public channel.

Giving positive feedback is an acquired skill, I wasn’t familiar with the concept growing up. I learned that in my early Automattic days. (Thank you, @loriloo, I’ll never forget our conversation in Montreal, circa 2013).
→ I think I have improved on this aspect, but if you disagree, you should feel free to let me know.

The same goes about saying “no” to good ideas. I am learning, but it is still hard, and I say yes to too many things.
→ If you find a workaround, let me know 😉

My strengths and how to leverage them

I am excellent at logistics and operations.
→ Ask me for help if you need any.

I see patterns in chaos (with numbers more than people).
→ Show me your numbers.

I am persistent and perseverant, but also impatient.
→It’s a marathon, but at a sustained pace.

What I value in others

Drive: I love working with people who move autonomously towards the goals we defined together.

Adaptability: re-evaluate position and options at all times. The (road)map is not the territory.

Humility: the ability to ask for help is one of the most important qualities on a team.

Transparency: deliver bad news like the good ones, as soon as you learn about them.

How do I view success

I know that perfection doesn’t exist, and that trying to reach perfection is a recipe for frustration.

I also know that everything can always be improved, and that settling for “just ok” is a recipe for apathy.

I prefer to split my work between the things I won’t do and the ones I’ll do really well, than try to do everything at an average level.

The only value we create, is value for our users.

• I measure success as the outcome our work generates. Did we positively impact our users, and our business?
• I measure the quality of our work as our output. Did we work on the most essential things, did we do an outstanding job?

The two are only loosely coupled, and that’s fine.

I accept that randomness is an integral part of life and work. We can only do our best, and results may vary. If we do our best, we’ll have no regrets. If we succeed, that’s even better.

In the end, I remember that we are here, on this pale blue dot.

From this distant vantage point, the Earth might not seem of any particular interest. But for us, it’s different. Consider again that dot. That’s here. That’s home. That’s us. On it everyone you love, everyone you know, everyone you ever heard of, every human being who ever was, lived out their lives. The aggregate of our joy and suffering, thousands of confident religions, ideologies, and economic doctrines, every hunter and forager, every hero and coward, every creator and destroyer of civilization, every king and peasant, every young couple in love, every mother and father, hopeful child, inventor and explorer, every teacher of morals, every corrupt politician, every “superstar,” every “supreme leader,” every saint and sinner in the history of our species lived there – on a mote of dust suspended in a sunbeam.

The Earth is a very small stage in a vast cosmic arena. Think of the rivers of blood spilled by all those generals and emperors so that, in glory and triumph, they could become the momentary masters of a fraction of a dot. Think of the endless cruelties visited by the inhabitants of one corner of this pixel on the scarcely distinguishable inhabitants of some other corner, how frequent their misunderstandings, how eager they are to kill one another, how fervent their hatreds.

Our posturings, our imagined self-importance, the delusion that we have some privileged position in the Universe, are challenged by this point of pale light. Our planet is a lonely speck in the great enveloping cosmic dark. In our obscurity, in all this vastness, there is no hint that help will come from elsewhere to save us from ourselves.

Carl Sagan—Pale Blue Dot