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Don’t Act Differently After You Give Notice
Sometimes when people give notice that they are quitting they start acting differently:
- Some people get very bold. They start having stronger opinions than normal.
- Some people are obviously playing Mario Kart during team meetings.
- Some people start to spend more and more time talking in the br...
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Bottleneck Dirty Webs
Delegation, specialization, and federation are critical to scaling companies. But scaling doesn’t mean stepping back from everything. Especially for unsavory, cross-functional, time intensive tasks, leaders should position themselves as bottlenecks - owners that feel pressure when the work grows too...
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2024: A SaaSy Year In Review
Well SaaStronauts that’s another year in the books, which means it’s time for the Stay SaaSy Year In Review.
The Numbers
Our audience grew by about 30% this year. What is more valuable to us is the number of really impressive companies and people represented. It’s a joy and an honor to see the domai...
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Problem Driven Development
Figuring out what to do is a big part of senior tech roles. Senior Engineers and Engineering Managers often struggle to define technical roadmaps. Reasons include:
- There’s little industry training on how to do it
- It can be daunting to prioritize against professional PMs who are specifically sele...
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This Is How You’re Eroding Accountability
Accountability is the only way that anything gets done at scale. Businesses are complex and as any organization scales up, a larger and larger amount of work gets done out of the direct line-of-sight of senior management.
As a result, a culture of accountability is key. I’d define a strong accountab...
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Management Mantras
Don’t Do Me Any Favors
In the course of getting work done at a company, nobody should be doing anyone else any favors. Everything you do at work should be the most important thing you could be doing to add value to the business, and those things should be aided by people whose job it is to support t...
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Delegating Complex Tasks
Many leaders struggle with complex delegation.
Failure to delegate often makes you a bottleneck. There are few things more demoralizing for a team than spending days trying to get a leader to do something that takes them minutes,
Failure to delegate also creates key person risk, leaving you as the o...
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Mutually Assured Mediocrity
Maybe the worst state for a company to get in is what I call Mutually Assured Mediocrity.
This is where people are so holistically mid that they agree not to criticize each other for fear of their own mediocrity being found out.
And what’s worse is that leaders on top of MAM organizations are by def...
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Tips For Better Interactions
The following are an assortment of tips for having better interactions and better meetings.
Don’t Be Frustrated
Don’t ever agree to the premise that you’re “frustrated” or “upset” at work.
People will often consciously or subconsciously say things like “I know you’re frustrated, but…”
If you’re in a...
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Blameful Post-Mortems
Over the last decade, the concept of a “blameless” post-mortem has become a software industry standard. According to ChatGPT, blameless was introduced to the software world by a 2012 blog post:
Having a “blameless” Post-Mortem process means that engineers whose actions have contributed to an acciden...
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Managing People You Can’t Fire
One of the worst situations in management is needing to fire someone and getting blocked. This happens somewhat regularly and is one of the most trust-breaking experiences between a manager and their boss. Let’s talk about why it happens and how to right-size the situation
The Ingredients
Managers e...
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First Principles Problems, Secondhand Solutions
If you spend a lot of time in tech, you’ll inevitably hear people extolling the virtues of being a First Principles Thinker – that is, someone who analyzes situations in terms of foundational axioms and then uses their impeccable reasoning to determine a bold and original course of action.
But if yo...
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The Precise Language Of Good Management
As a manager, your words are your bond
In the squishy realm of managing humans, the specific things you say have specific outcomes.
Unfortunately, most managers are very bad at speaking precisely. Speaking precisely, especially about long-term, uncertain things, is not something many people do by na...
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Setting Startup Policies
One of your most important activities as an executive, especially at a startup, is to set policies: Sets of guardrails or rules for how company systems work, such as vacation policies, expense policies, WFH policies, or rules for how to get promoted.
Companies are just groups of people with money on...
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Leading From The Front
Leading from the front means leading where the action is happening.
Here we’ll talk about three critical aspects of leading from the front:
- Why you should do it
- Finding the front
- Leading when you’re there
Why you should do it
Leading from the front is important for two main reasons:
- It makes...
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We Tried That
A common logical fallacy is claiming something won’t work because a previous attempt failed.
Why It’s A Crutch
People often look to previous failures to set their future course for several reasons, including:
- Ego. If I couldn’t do it, nobody can.
- Negativity bias. Failure hurts, and people often ...
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Your Manager Is Not Your Best Friend
As people become managers, it’s quite common for their team members to want to commiserate with them. This is especially true for friendly, competent, reasonable-seeming managers – people want to commiserate with winners. This makes commiseration extra dangerous, as it comes with a hint of flattery ...
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AI Makes Bad Managers
It’s performance-review season and I’m watching managers kneecap their careers. Gleefully they share the best prompts to have ChatGPT write their performance assessments - exactly the sort of shortcut that guarantees they’ll never get better at the job.
Below, we’ll break down why AI’s leaky interfa...
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Naming Software Teams
Forming a new software team is easy to get wrong in many ways, including:
- Making a B team
- Making a low context team
Here, however, we’ll focus on one of the most important and often bungled aspects of team formation - the team name.
Let’s review how to avoid the common trap of naming teams poorl...
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You Know What To Do
One of the most consistent observations I’ve had in my time in startups, scale-ups, and public companies is that smart people with context on a tricky situation almost always know exactly what they need to do.
Teams obsess about company strategy, about data, and about frameworks for decision-making....
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