John Cutler Profile picture
Sep 11, 2021 11 tweets 2 min read Read on X
I've met with ~70 teams in the last three weeks.

One thing that sticks in my mind.

Paradoxes.

1/n: you can have...

a mid-stage startup team that is highly dysfunctional

...but due to timing and early product/market fit, they succeed (by some measure) for years
2/n: you can have...

a team of incredibly thoughtful, experienced, people

...but due to disruption of the business model and the inertia of the legacy business, they go circles.

They're stuck.
3/n: you can have...

a bunch of new hire team contributors (engineers and designers) that are excited to tackle the new strategy

...but middle-management is severely underpaid, and burnt out by buffering "the teams" from "the biz".

The new hires leave quickly.
4/n: you can have...

"very junior engineers"

...but the codebase is incredibly accessible, and there are safeguards in place to make sure people don't break anything
5/n: you can have...

a "highly successful leader who has a track-record doing X"

...but the company isn't, in fact, doing X. They are doing Y. It is just that almost no one has realized that yet.
6/n: you can have...

an "amazing company culture"

...but at a certain point, it becomes stale. People don't leave for new opportunities. It is amazing at _______, but not longer amazing at _______.
7/n: you can have...

a team of the "best engineers money can buy"

...but there is a lack of team cohesion, and those advantages quickly become big liabilities.

The codebase grows to reflect this issue.
8/n: you can have...

a team of "newbies"

...but they have a single experienced leader who encourages access to customers, and that customer connection inspires a great product.
9/n: you can have...

An executive team of leaders who don't really like it each other much. That are highly competitive.

...and it works, the incentives magically balance

...until it stops working
10/n ...

So:
...performance is a not a linear thing
...strengths have corresponding challenges
...today is a the sum of countless days
...a company is not a monolithic "culture"
...paradoxes abound
...puzzles abound
...messes abound

• • •

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More from @johncutlefish

Apr 2, 2023
The “messy middle” problems is one of the biggest impediments to product success. Here’s what it looks like:

The strategy and vision is somewhat clear.

Teams have specific features they’re working on.

But there’s nothing in between.

Why does it matter? 1/n
High level visions and strategies are helpful, but they lack the specificity to guide teams.

Specific project-based roadmaps feel “actionable” but they are very fragile—they don’t inspire aligned autonomy.

You need a linking mechanism 2/n
Some teams use goal cascades

The problem is the classic MBO problem: goals get more specific & prescriptive as you move down the stack. And by definition they should be “time bound”.

They too are fragile and foster “figure out what you want to build AND THEN tack on goals” 3/n
Read 5 tweets
Mar 26, 2023
I was reading the transcript of a work presentation. Then I watched the presentation.

The transcript was filled with issues / logical fallacies / open questions.

While watching I noticed very few.

I think this is the root issue with presentation culture.
I noticed different parts of my brain firing in each context. When slides had lots of “stuff” it felt like a sense of “oh they’ve figured this out” even when the words did not match.

If you pay attention you can feel this happening.
The confident voice of the presenter made the “three focus areas” feel certain, clear, and logical.

In writing it felt incoherent.

I guess this is a point for “a compelling visual” but still it’s interesting.
Read 6 tweets
Feb 12, 2023
Your team is burnt out. They are not getting anything done. Work is "low quality". You can see and feel those things.

But what you are seeing is an output of something—the downstream effects of other things happening.

In some companies this is a black box

1/n Image
…they don’t have visibility into what’s happening.

But it is not that simple (of course).

The outputs are inputs into the black box. And the outputs input into the inputs.

2/n Image
Say the team reactively addresses quality issues.

This creates more “work” (the output inputs into the input), but it also leaves the team more burnt out and they make less-good decisions on whatever is going on in the box.

3/n
Read 10 tweets
Jan 29, 2023
Product Management is an exploration of time.

In product we are always jumping between "Time-full" things and "Time-free" things.

Example:
An improvement project to build a new AI irrigation system vs. the ability to irrigate our crops.

1/n
We project thing time-free things into the future, making them time-full.

Here we imagine our ability to irrigate our crops evolving from a watering can, to the new AI powered system.

And we imagine the capability level increasing.... over time

2/n
This is happening everywhere.

Right now your product exists, a jumble of current capabilities.

You work to improve those capabilities.

And, if you squint, you evolve the capabilities necessary to do that work, and support that product

3/n
Read 9 tweets
Jan 29, 2023
Why do attempts to "reign in" product processes involving multiple teams fail so regularly?

Well...

Here we have a list of features about "the work".

An example of a feature might be something like:

"Amount of customer education needed...."

OK...1/n
So imagine we collect data about our initiatives.

Example:

"Amount of customer education needed" = HIGH

OK, now we're getting somewhere.

Except... 2/n
Sequence matters.

In product, if we try to converge on everything way in advance, outcomes will suffer. We don't want that.

So the sequence...of when and how you attempt to collect data about the initiative matters.

But we're not done... 3/n
Read 9 tweets
Jan 21, 2023
I recently asked Twitter for words describing "great product managers". Here the results in pictures...

The diameter of each circle represents the number of *other* words that were related to the word.

Colors represent "neighborhoods" of words.

Lines = relationships

1/n
"Responsive" was not the most common response. But it was the word that had the most number of similar/related words

It is a broad word...for sure...but I thought that was interesting

2/n
Results and customer orientation...

3/n
Read 5 tweets

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