Find your cohort. The generous ones.

Seth shares a great story about an author called Robert Caro in “The Practice.” Caro had quit his job as a reporter and begun writing his first major biography – “The Power Broker.”

He took a modest advance and moved his family to a tiny apartment. But, years later, the end didn’t seem in sight. In 1975, he wrote a poignant story for The New York Times describing his despair.

Then, he was given a key to a back room at the New York Public Library. Only eleven writers had keys, and each was given a desk to write.

One day, he looked up and found James Flexner – one of his idols – ask a question he’d come to dread – “How long have you been working on it?”

“Five years”

“Oh, that’s not so long. I’ve been working on my Washington for nine years.”

The next day, another of his idols said quietly – “Eleanor and Franklin took me seven.”

He could have jumped up and kissed them. In a couple of sentences, both men – his idols – had wiped away five years of doubt.

The lesson “Find your cohort. The generous ones.” resonated deeply.

Turn it off and then back on

It is amazing how often a technology problem is solved by turning off the device and turning it on.

I think it works similarly in our lives. When we aren’t feeling our best or behaving as we’d expect, the best thing we can do is to turn off. Take a break and get some rest.

We’ll work better on the other side.

Privacy rights notice friction

I received a “privacy rights” notice from a financial service provider who collects payments on a loan. They notified me that I had the right to tell them to not share my data with other financial services companies. However –

(a) If I didn’t explicitly say no, they’d assume I am supportive.
(b) If I did want to say no, I can’t just do it via my account online. No, I’d need to mail in a response.
(c) They graciously added an envelope. However, I wouldn’t just be able to drop it in the post box. I’d need to get a stamp.

I marveled at the thoughtfulness that went into adding just enough friction for me to discard the mailer and thus give them what they want.

Imagine if we all applied the same amount of thought to adding or removing friction to drive better habits/behavior.

Missing commitments to recommit

Once I make a commitment, I hate missing it. But, every once a while, I find it helpful to miss a commitment to recommit to a better process. Here’s an example.

I used to host this blog myself. A few years in, I started experiencing a spate of phishing attacks from some Russian bots/. This led to a predictable pattern – I would realize something is wrong (included the blog going down/an inability to post), go back and forth with my hosting provider requesting for help to clean up the Russian files, and then call one of my trusted developer friends for help to save the day.

Eventually, we’d get it back up and I’d sneak in my post for the day and not miss my commitment.

After this had happened a few times too many, I decided it had to stop. So, I missed a day.

Instead of the usual short-term fix, I used the day to stop hosting the blog myself and handed over the reins to WordPress.com. Safety/security came with the package. And, for $40 or so per year back then, I bought myself peace of mind.

I thought of this incident recently as I found myself contemplating yet another last-minute sprint for a project. But, instead of doing so, I decided to miss my commitment (it hurt!) and, instead, commit to a better process.

Here’s to that.

Effective 1:1s – a field guide

A note for new subscribers: This post is part of a series on my notes on technology product management (this is what I do for a living). You might notice that these posts often link to older posts in the series on LinkedIn even though they are all available on this blog. That is intended for folks who only want to follow future product management related posts. Finally, for all those of you who don’t build tech products for a living, I believe many of these notes have broader applicability. And, I hope you find that to be the case as well…


A quick overview of what we’ve covered on “Notes on Product Management” so far – 

Take a look at an IC product manager’s calendar and it is likely you’ll find a number of 1:1 meetings. These meetings are an important part of a Product Manager’s life. So, I thought we’d spend time on lessons I’ve learnt about 1:1s.

 We’ll do this by talking about the 4 types of 1:1s – (1) Introductory 1:1s, (2) Manager 1:1s, (3) Recurring 1:1s, (4) Ad hoc 1:1s. You’ll see 3 principles at play:

(i) 1:1 time is precious. Intentionality when we set them up and thoughtfulness/preparation when we show up to them go a long way. Between the two, I’d prioritize intentionality.

(ii) Go deep and talk about things that matter as quickly as possible as often as possible. This doesn’t mean you don’t kick 1:1s off with personal updates. It just means you talk about what you’re actually feeling/going through vs. the weather.

 (iii) Invest in ad hoc 1:1s with people in your broader organization (a.k.a. serendipity 1:1s). These often help you develop empathy for the challenges others face, help you connect the dots, find future collaborations, and can even the source of lovely friendships.

 With that said, let’s dig in.

 (1) Introductory 1:1s

 There’s a simple guideline with introductory 1:1s – meet people 1:1 before you have to ask them for something. So, as part of your onboarding into any new role or project, figure out every person you expect to work with and meet people 1:1 first. Do this early. It always helps.

Now that we’ve gotten that out of the way, let’s get to the purpose of the introductory 1:1. It is to help us get to know people well enough so we can begin to understand them. That paves the way for trust – and, in occasional cases, mistrust. Either way, it is in your interest to make this process happen fast.

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I’ve found 3 questions to be particularly helpful in the introductory 1:1s –

(a) I’d love to get to know your story – from when you were born to how we’re having this conversation. This generally results in a chuckle as folks are used to introductions about their work experience. However, I prefer the story outside of the work experience. With the right follow up questions, this question helps get to what matters to them and why?

(b) If you had a few hours of free time, what would you do? Hobbies tell us a lot about what matters to a person too.

(c) What’s the dream?  The most common follow up question I get to this is – “Do you mean my work dream? or life dream?” To this, my response is always that it is intentionally ambiguous. Again, this provides more insight into what matters.

Typically, working through these questions takes a good 15-20 minutes. That’s perfect. It then flips over to us to share our story. And, if our story has everything we hoped to hear – starting with why we do what we do, our influences, and how we approach work and life – we’re off to a great start.

(2) Manager 1:1s

The sign of a good manager is someone who (i) wants to help you be the best PM you can and (ii) has the skills to help. If this is your manager*, your manager 1:1 is among the most important meetings in any given week. It is the time in the week when you invest in your own development and get unstuck.

(*On the same token, if the description above does not describe your manager (or in some cases your manager’s manager), it may be worth finding a new team/company. More on this in a future note.)

 So, given this context, how do you make the most of a manager 1:1? Ensure the agenda covers what is top of mind for your manager (which should align with your priorities) while providing all the context they need to be helpful. If possible, share a pre-read so they have time to process.  

Here is a template with the structure I use for my 1:1s. It is right out of Andy Grove’s “High Output Management” playbook where the 1:1 agenda is driven by the director report vs. the manager.

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As you can tell, I do the following –

  • I share how I’m doing, review my development areas (typically from my last review), have a standing update on the top priorities we agreed on for the quarter (or month), and then add a collection of miscellaneous updates and questions.
  • I then use highlighting to call out what I want to discuss. Anything that is not highlighted is FYI.
  • I also end with a note of gratitude and call out any and all feedback that helped me learn.

The key with these 1:1s is giving your manager all the context you can for them to help you with help, direction and coaching. Successful 1:1s aren’t just a pat on the back (though these feel good from time to time :)) – they involve “aha” moments that help us operate better.

(3) Recurring 1:1s

Many product teams have an unsaid expectation about recurring 1:1s between PMs and cross-functional lead. And, while you can use a simple shared doc where you add in topics for the week to be productive, I’d like to add some more color on these 1:1s.

Early in our life as an IC PM, these recurring 1:1s help a lot. On the one hand, they help us understand and empathize with challenges that our cross-functional partners face. That understanding and empathy makes us better PMs – or in many cases, PMs. We don’t become PMs when we are handed the title. Our early cross-functional partners teach us to become so.

On the other hand, they also often give us much-needed connection in a job that can feel challenging and lonely when you’re expected to provide direction while you’re still figuring out what to do.

But, over time, these recurring 1:1s also become the biggest obstacle to enabling us to scale. This typically happens to folks when they begin handling the responsibilities of a senior PM. These responsibilities can include multiple engineering teams and multiple sets of cross-functional partners. When this happens, it won’t be feasible to have recurring 1:1s with all 12 of your cross-functional partners.

At this point, they aren’t just a sub-optimal use of time. They also get in the way of the flow of information. When you find yourself responding to the same types of questions 1:1, it is a sign that you need to get the group together more and ensure everyone has shared context.

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When you reach this point, it helps to have a clear and empathetic response to anyone who requests a recurring 1:1. It goes along the lines of – “I really appreciate you setting this up. At this point, I’m not able to do justice to recurring 1:1s as they get in the way of me being able to deliver the strategy docs and specs that we need. But, more importantly, they also get in the way of us getting time when something comes up. 

The approach I’m trying right now is to remove all recurring 1:1s so I can make space for all the ad hoc 1:1s we need. So, please know that we’ll still be communicating plenty – across our team meetings, docs, async conversations, and ad hoc 1:1s any time we need it.”

 That then brings us to ad hoc 1:1s.

 (4) Adhoc 1:1s

Ad hoc 1:1s are among the most valuable uses of our time. There are a few kinds of ad hoc 1:1 – all of which are useful in their own way. 

There are the “Let’s discuss” or “We have a problem” variants with our close working team to quickly align on something important or straighten out a disagreement. Then there’s catch up variant. While these can be with our immediate team including with relevant executives, they’re very useful when we done with folks in the broader organization.

These conversations can give you fascinating perspective into life on other teams. That can result in future collaborations and also helpful insight into teams you want to join or avoid whenever you consider switching teams next. In rare cases, they can result in lovely peer-relationships or friendships. As you grow in your career, they also take the form of folks who come to you for advice and counsel.

I think it is helpful to be proactive about making sure you have these 1:1s on your calendar. And, while it is possible to overdo these, most folks tend to under-invest. As a guideline, I’ve found that having 1 or 2 of these “serendipity 1:1s” over the course of any given week helps a ton.

(BONUS) Facilitate get-to-know each other meetings for your team 

The magic of most 1:1s is the time spent getting to know and thus understand each other. A simple practice I try to invest in every time I join a new team is to ensure we all spend a meeting just getting to know each other. The process is simple –

(1) Split folks into pairs (or 3s) and give them 10 minutes to introduce themselves to each other. The guideline for these is – get to know their story and understand what matters to the other person.

(2) The pairs then cross-introduce each other to the group. There’s something very special about cross-introductions. They feel even more special when others in the group add what they know to these folks.  

Depending on the size of the group, this will take somewhere between 60 and 90 minutes (it is on you to manage time with some reasonable nudging). It will also be among the best investments you make. I’ve been in groups where folks who worked together for many years suddenly realized they had so much in common. And, by bringing the magic of a great introductory 1:1 to a group, I’ve seen sessions like this completely transform the mood of the group.

All this brings us back to the magic of 1:1s. A recent post from Seth Godin’s blog explained why. 

Time doesn’t scale

That’s why it’s worth so much. 

Sure, you can outsource. You can look for shortcuts. You can hire folks. You can use mailmerge. You can even send it to voice mail.

 But all of these time shortcuts fail to express the thing we want the most. 

Your time, my time, their time–we all get the same number of minutes per day.

 If you spend them on someone, they can tell.

 Indeed.

 1:1 time is precious. Let’s use it well. 

Mistaking agreement for truth

“In fact, it’s Douggie’s growing conviction that the greatest flaw of the species is its overwhelming tendency to mistake agreement for truth. Single biggest influence on what a body will or won’t believe is what nearby bodies broadcast over the public band. Get three people in the room and they’ll decide that the law of gravity is evil and should be rescinded because one of their uncles got shit-faced and fell off the roof.” | Richard Powers in “The Overstory”

That line about our overwhelming tendency as humans to mistake agreement for truth hit me hard.

It is the best description I’ve heard of our fallibility.

Optimistic about ourselves, pessimistic about others

Gallup has been asking Americans for more than four decades, “Are you satisfied with the way things are going in the U.S. right now?”

The average percent of Americans answering “no” since 1969 is 63%.

What’s interesting is that Gallup asks a follow-up question: “Are you satisfied with the way things are going in your own life right now?”

There, the average “no” response is just 15.8%.

People tend to be optimistic about themselves but pessimistic about others. Social media probably supercharges that. Benedict Evans says, “The more the Internet exposes people to new points of view, the angrier people get that different views exist.”


Such a great factoid. It puts a lot of what we see on social media in perspective.

(H/T: Morgan Housel’s blog and his seemingly never ending reservoir of great stories)