A Framework for Prioritizing Tech Debt

The Importance of Leverage

Having spent over a decade building tech startups, I’ve come across my fair share of tech debt: The gnarly Ember.js code no one wants to touch, the bespoke cloud infrastructure maintained entirely by hand, or the solitary Elixir service left behind by a long-gone former teammate.

While these may be painful today, at one point in the past they were likely important accelerants that pushed the product forward in a meaningful way. In fact, tech debt is arguably a necessary evil–if a growing company isn’t taking on some measure of leverage, then it’s likely not shipping as fast as it should be. However as a company begins to see traction, there will come an inflection point where it becomes important to start prioritizing tech debt.1

Playing Long Games: Focus on Companies With Moats and Relevant Products

3 February 2023 | by Todd Wenning, CFA

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The longest nine-inning Major League Baseball game took four hours and forty-five minutes to complete; the shortest took just fifty-one minutes. Suffice it to say the concession stands had a much better day for the former than the latter.

Baseball analogies are used too often in investing, but the concept of innings is a worthy one. Unlike most sports, where games have a time limit, baseball is measured in innings rather than time.

The Latest Synthetic Base Layers Have Surpassed the Performance of Merino Wool

I’ve stopped wearing merino base layers. The change wasn’t deliberate, sudden, or driven by a deep concern for the wellbeing of rare sheep. Instead, it happened naturally over time, because the latest generation of synthetic next-to-skins genuinely offers superior performance.

A unique mix of performance attributes have always made wool the go-to long underwear. It remains warm when wet, resists odor, actively wicks moisture away from your skin, and helps regulate temperature, keeping you warm when you’re resting and cool when you’re moving.

Too Busy

Too Busy

For the last handful of years I’ve been too busy to do a lot of things. Too

busy to launch new products on my free time, too busy to go on trips for fun,

and too busy to spend time with family and friends.

I’ve spent the better part of the last few years working on company projects,

trying to leave a lasting impression with my work. While this has been

My Ambient Information Display

I like to be immersed in useful information, and often dreamed of ways to have it literally floating above me so that I could glance up and see something new and interesting.

A few years ago I mounted a 43″ Fire TV above my desk, tie-wrapped a Raspberry Pi to the back of it, and used MagicMirror to create the display of my dreams. I have spent several years improving my display and am finally ready to tell you all about it!

Developer Relations, where do you start? – Prashant Sridharan

I spoke with someone recently who didn’t know where to start with their first hire in Developer Relations. As folks who know me appreciate, I think of the Developer Relations organization as the following distinct functional areas:

• Developer Advocates: they’re the spine of your Developer Relations program. They’re technical experts, content machines, top-gun spokespeople, and the primary community interface. As I always say, “Trust and integrity are your primary currency, not your products or services.” Developer Advocates ooze trust and integrity, always speaking honestly and on behalf of (advocating for) the developer community.
• Developer Product Marketing: the ringleaders of the circus. They coordinate consistent positioning and messaging, launches, customer feedback and discovery, and imbue the rest of the organization with mission and purpose.
• Developer Growth: campaigns, SEO, and digital marketing.
• Developer Marketing: events, social media, comms, and content program management.
• Developer Education: documentation, training, and (if you’re big enough) certification.

In later posts, I’ll dive into each of these functional areas and ways for you to improve each.

Management Debt

Teams naturally start to incur management debt as they grow and become more complex, just as codebases incur tech debt. The combined weight of past decisions creates a web of precedents and exceptions that can cause problems of varying size over time.

For a concrete example of management debt, consider a team that’s never had performance reviews. They’ve saved time by skipping reviews, but have taken on significant management debt by not setting expectations or addressing over/under performance. When they kick off performance reviews they’ll have to pay down this debt with overdue promotions or performance management.

How to handle a reorganization as an engineering manager | LeadDev

We’ve all been through reorgs before. When you’re an individual contributor, they tend to be mysterious, often frustrating management exercises. Your boss changes suddenly, or your team is dissolved into other teams, or you’re moved into an entirely new organization and even though your job is the same, everything feels different.

Many of us go into management having had negative reorg experiences, and the first time we find ourselves on the other side of the process, it can be jarring. When you find yourself part of the group that’s in the know about a pending reorg, what should you do?

The Engineering Manager’s Tools

What is in a manager’s toolbox?

I’ve been writing about how to use systems thinking in software engineering management. I want to continue addressing a practical point: how to make change happen as an Engineering Manager (EM).

One of the realities of being an EM is that you constantly work on improving your team’s situation. For example, you can try to make your team more effective, help a team member grow, or improve your organization. Ultimately, being a change agent is a large part of the role.

Proof That Positive Work Cultures Are More Productive

Too many companies bet on having a cut-throat, high-pressure, take-no-prisoners culture to drive their financial success.

But a large and growing body of research on positive organizational psychology demonstrates that not only is a cut-throat environment harmful to productivity over time, but that a positive environment will lead to dramatic benefits for employers, employees, and the bottom line.

Although there’s an assumption that stress and pressure push employees to perform more, better, and faster, what cutthroat organizations fail to recognize is the hidden costs incurred.

Framing → Shaping

Over the last few months I’ve worked with teams to help them adapt Shape Up to their specific context. Talking to a wider variety of teams has been eye-opening. It’s helped me discover many hidden factors that were present at Basecamp when I first wrote the book. This is now leading to a whole new iteration of the process and steps that I’m teaching teams to improve their product development.

A Mental Model for Addressing Burnout

It’s not you.

A mental model for addressing burnout

Last week I was on a panel addressing the topic of burnout. It’s a topic that pops up with some frequency, yet the misconception that burnout is a personal problem seems to persist.

Burnout isn’t something you can solve by doing breathing exercises or starting a bullet-journal. Burnout is a systemic issue which the WHO now classifies as an organizational phenomenon, and which therefore requires systemic change to address.

How to Lead Strategically Every Day

Strategic leadership can often sound abstract and hard to put into words. Not only that, the majority of the CTOs, VPs and engineering leaders I work with are so busy running from meeting to meeting, handling team issues or trying to scale, that they have zero time to work on the most important aspect of their job: strategy.

The higher your leadership position, the more strategic your role becomes, and in turn the greater the impact your decisions will have on the business as a whole. The ability of a leader to always see the big picture, identify trends and patterns, and consider a range of perspectives is critical to strategic leadership.

The Pros and Cons of Working Directly for the CEO

Pros of working directly for CEO:

– Turbocharges learnings
– Accelerated decisions + impact
– Lifetime relationship
– More rewarding

Cons of working directly for CEO:

– Feedback can be too direct
– Appreciations only for results
– Not available enough
– You’ll need to grow

— Jason ✨BeKind✨ Lemkin ⚫️ (@jasonlk) August 2, 2020

I remember the first time I worked directly for a CEO. I’d reported to leaders before, and a VP before, but never the CEO.

My Take on Why Goal Cascades Are Harmful and What to Do Instead

If collective goals matter, you need some way of creating coherence.

“The very business of getting an organisation made up of individuals, no matter how disciplined, to pursue a collective goal produces friction just as surely as applying the brakes of a car.”

Stephen Bungay, The Art of Action

As long as it’s more than one person AND it’s important that we achieve some collective goal THEN we need some way of facilitating coherent action across an organisation. Without coherence, you’ll see a lot of duplicate, competing, or missing efforts.

What a Healthy Team Looks Like

The concept of “healthy teams” is something I stole from the Engineering Org at Pluralsight before the Vista acquisition. Most people attribute healthy teams to buzzwords like “collaboration” or “psychological safety.” The people who had been a part of healthy teams know what it feels like, but they can’t distill it into a recipe. There is no recipe for culture.

I’ve told this story before but I was initially a team of 1 on the Search team, and in the next 3 years, we grew into a data platform with 5 engineering mobs. Those of us who have left often refer to the Discovery team as “THAT team.” I was very proud of the products that we built together, but I am far more proud of our culture, the invisible thread that connected us beyond our tenure at Pluralsight.

Guiding Principle: Cross-Pollination Over Imposed Standards

Guiding principle in effective product development culture.

There are many ways to say it: de facto over de jure standards, natural over imposed consistency, cross-pollination over imposed standards. They are all describing the same way to answer the question: how should standard ways of doing something be spread more broadly?

So why might a standard be valuable enough to bother trying to spread?

Standards are useful to simplify learning and address variation of performance

Standards are useful to avoid everyone having to learn a new way of doing things every time they interact with a new team.

Skyrocket Your Productivity With the ‘Touch It Once’ Rule

When work is coming at you from all directions, it’s easy to push even the simplest tasks aside. You may find yourself repeatedly looking at the same paperwork or email and promising to get to it later.

However, this form of procrastination can really tank your ability to get things done, says productivity expert Nicole Bandes.

“We take so much time doing something and then redoing something because we didn’t really do it fully the first time,” she tells CNBC Make It.

The Scoop: Netflix’s historic introduction of levels for software engineering

👋 Hi, this is Gergely with a bonus, free issue of the Pragmatic Engineer Newsletter. We cover one out of five topics in today’s subscriber-only The Scoop issue. Subscribe to get this newsletter every week 👇

In April of this year, I covered how Netflix intended to introduce levels for software engineers in The Scoop #9:

“Netflix is considering the following leveling system:
– Engineer 1
– Engineer 2
– Senior
– Staff
– Principal

(more…)

How to Hire for Director+ Roles?

Hiring folks in leadership roles is very challenging. One difficulty is that almost every candidate who gets to that level is generally good at communication, charismatic in their demeanor, and well trained to say the right things to get the job. Nonetheless, there is a huge difference between how people interview and how they deliver once they get hired. In my interactions with folks in Director+ roles, I generally find a very strong dichotomy, with a few individuals being superstars and a large majority having some level of non-pathological narcissism, where they got to a leadership position primarily because they knew how to play the game of visibility. Given all this, how do you break the level of information asymmetry in interviews and hire exceptional leaders for technical roles?

PM & EM: Rules of Engagement

Picture this: you just landed the Product Management (PM) job of your dreams. On day one, you meet your partner-in-crime Engineering Manager (EM) at your new gig. Before you know it, you’ve been assigned your first problem to solve. Now, it’s time to get to work.

Naturally, as you get started, you realize there’s actually a ton to work out. What exactly are we building? How are we going to build it? What’s the timeline? You schedule time with your EM to work out how to tackle these questions. In both of your heads, the same questions start to percolate: Should I be responsible for all of this? Maybe just some of it? Should everything be shared? What do we collaborate on vs. own individually?

WordPress.org is ineffective for plugin distribution in 2022 – Ellipsis Marketing

We’ve seen sharp focus pulled onto the growth of plugins on WordPress.org in the last couple of weeks. For many years, it’s been possible to see a plugin’s active install growth rate on the Plugin Repository.

Public plugin active install numbers only change at pre-set intervals (1k, 2k, etc) and these intervals get bigger as a plugin gets bigger. The active install growth chart was thus useful for plugin developers to see whether their product was growing or shrinking, and at what rate.

The Builder’s Trap

Every developer knows the satisfaction that comes from building a software system. Type in a stream of characters and somehow you’ve built something that appears magical to others. This is the Builder’s dream. The thrill about learning something new. The satisfaction of solving unknown problems through building code. But, the Builder’s dream can quickly become the Builder’s Trap if you’re conscious of the context. In this article, we will explain the Builder’s Trap, where it comes from and three steps to avoid it.

Your Career Is Just One-Eighth of Your Life – The Atlantic

Career advice as a genre is almost fatally flawed. With 160 million American workers across thousands of occupations in hundreds of industries, saying anything that is of use to all of them is practically impossible. The most common counsel is almost always too personal to be broadly applicable. My toes curl with embarrassment when successful people say anything along the lines of “Just do these three things I did.” Autobiography is not advice. Given how poorly most people understand themselves, it’s barely even autobiography.

Matter is now official! – Stacey on IoT | Internet of Things news and analysis

The Connectivity Standards Alliance has certified and released the first version of the Matter smart home interoperability protocol Tuesday and I couldn’t be happier. This means that member companies can now put their devices through the certification protocol and get a badge showing that their products are Matter compliant.

The Matter logo on a smart bulb. Image courtesy of the Connectivity Standards Association.

How to Plan?

How to plan? How hard could it be? 4k words on sunny October afternoon for people in tech observing the Season’s Traditional Annual Planning Process, inspired by a recent interview question (and 25 years of variously painful planning processes).

I was in a job interview the other day when I got asked about planning, and so I decided I’d turn the question into another “plucked from the interviews” blog post. (see also Interview Question: Why do leaders keep disempowering their teams?) To be clear this is a significantly expanded answer than the one I rattled off from the top of my head on Zoom, but I think the themes are roughly the same.

On the team as a system | ★❤✰ Vicki Boykis ★❤✰

Crowded Boat II, Robert Goodnough

I read this great post over the weekend and this sentence is the heart of understanding how to operate a great software team:

Software quality is more the result of a system designed to produce quality, and not so much the result of individual performance. 

The whole post is good and you should read it, but for me it immediately brought to mind a podcast from 2019 called “The Dysfunction of Organizations” on the same topic. The content of that podcast has become an important part of my development philosophy. Unfortunately, it is only in Russian (unless someone wants to entirely transcribe it, which they should, because the content is really good), so I re-listened to it and took key notes.

Build Your Career on Dirty Work

The Dirty Work Theory: The lamentable work that many people avoid are great places to look for high impact, low hanging fruit.

Whenever people ask me for advice on career growth, I share what has worked reasonably well for me: find a growth company, one that really needs you to get work done, and then tackle the unpleasant work that everyone avoids. I think this is a broadly applicable path: