Somewhere in the COVID-19 pandemic "Occupational Burnout" entered my vocabulary. I'm a empathetic manager. I read Harvard Business Review articles about supporting colleagues through mental illness. I took mindfullness and inclusivity online training courses. In stilted, awkward ways I tried and failed to support my teammates.

In the first half of 2025 I was leading product, design, engineering, and QA for a rapidly growing startup. I was also singlehandedly the IT and Security team. This was about 2 years into tenure. My mental health ebbed and flowed, but the last few months had been unbearable. Burnout was no longer an abstract concept. I was burned out.

One Saturday morning an IT contractor botched our internal email migration. I found myself uncontrollably scream crying. That afternoon I wrote in my journal, "Haha this is the burnout I've read about." Through this period I was catastrophically depressed, unable to eat, exercise, or enjoy anything. I suppose I'm privileged to say this was the worst I'd ever felt.

To avoid burnout a workplace needs:

1. Autonomy
2. Commensurate reward (social and financial) for efforts
3. Community: trust, respect, reciprocity
4. Fairness and consistency

The worst part of burnout is you'll blame yourself. This happens to everyone. You'll think that you could fix it if you only worked harder or did something differently, but systematic failures are not personal failures. In the midst of burnout you won't know the difference.

To fix burnout you have to stop. Full stop. Depending on your employer or country of residence stopping may be difficult. I quit. I took six months off. It took me three months of aimlessness to rediscover joy in living. It's the manager's job to stop burnout. Recognize the signs and offer real support.

YouTube videos to watch:

• Burnout - When does work start feeling pointless? DW Documentary
• Occupational Burnout in Games: Causes, Impact, and Solutions

I was a happy customer of MENSCIENCE Advanced Deodorant for almost fifteen years. Amazon's order history lists my first purchase in January 2011. For the last two years I ordered directly from MENSCIENCE's website. In August their e-commerce site stopped accepting orders and their products were removed from Amazon. I emailed all the addresses on the MENSCIENCE website. There was no reply. The men scientists had abandoned me.

My criteria for deodorant is simple. It should have no intrinsic odor. It should prevent me from developing an odor. It should not make a mess. And, most importantly, it should be a deodorant (not an antiperspirant)!

Some people believe that aluminum in antiperspirant causes cancer. There is no evidence to support that. I avoid antiperspirants because I sweat more when I use them. There is no evidence to support this except my anecdotal experience through my teens and twenties. And Reddit. There are plenty of posts on Reddit that corroborate my experience.

My first stop was Walgreens. Their selection of deodorants was slim, and their selection of unscented deodorants was nil. I would prefer not to smell like Old Spice, lavender, vanilla, nor Cool Rush™.

Amazon, The Wirecutter, Reddit, and the open web brought me to a short list of viable candidates: Vanicream, Lavanila, Tom's of Maine, Native, and Lavilin. I ordered one of each for testing. Vanicream and Tom's were ineffective. Lavanila was not unscented. Lavilin, not to be confused with Lavanila, was effective, but more expensive. Native won for being entirely unscented and effective, with bonus points for low price and plastic-free packaging.

I wrote this as a public service. I don't make any money of these links. I only hope this saves you the time I spent triangulating options between websites and ordering five options for testing.

ELC is the leadership community I've sorely needed. Leadership is already a lonely position, but these days it can be downright depressing: anxiety of ongoing Big Tech layoffs, existential AI dread, and the current culture of anti-leadership.

Community is the only cure I know.

For the last two years I've been a fixture at ELC's local meetups. Last week I attended the ELC's annual conference. It exceeded all my expectations. The agenda was all AI, but content and perspectives varied greatly. In conversation and presentations the firsthand experience of leaders at other organizations mirrored my own experience. My leadership, technical and cultural, was in good company. The resounding choir of my peers brought me back to life. I returned to Chicago with renewed enthusiasm for my chosen vocation.

On the second morning I was surprised when James Birchler's presentation moved me to tears. His story wasn't sad. No one else cried. James fixed a few teams at Amazon with good leadership. I was beyond relieved to hear the fundamentals of Google's effective teams research are still true. Good leadership is not dead. I hadn't realized how lonely I had been in the wilderness.

I'll be at ELC Annual next year. In the meantime, I hope I see you at a local meetup. Whatever you're dealing with – Community is the cure.

PGraham’s post was unavoidable last week. I have many complicated feelings about it. It’s difficult for me to fairly parse the article. He made good points, but his perspective is so deep in the Silicon Valley “we’re so smart and we improve everything” mentality. What he described is good management, overcomplicated by hype and reinvention from first principles.

I've been a “professional manager” working for founders for the last 15 years. My perspective from the other side of the org chart is a snippy “well, duh. we all knew this already!” Who is PG's advice for?

1) Don’t get hamstrung by the org chart.

Getting the “100 best” people together regardless of org chart is a good practice that lots of companies do. It’s not just a Steve Jobs thing. Understanding the vibe of your organization is essential. Any leader, founder or not, struggles to balance hands-off versus hands-on. Knowing when to delegate and trust is complicated. Most founders fail to operationalize interactions and fall into surprise inspections.

2) Apply leverage where leverage needs applying.

If something in the organization isn’t working then somebody needs to fix it. If something’s important to the business, it should get the appropriate level of time and attention. A good founder or professional manager would dig into the things that need attention. Only a bad leader would sit back and let the organization fail because it’s not their job.

3) Most advice is bad and wrong.

LinkedIn lunatics, scam artists, and frauds are everywhere in every business. PG makes a good point, but he leans heavily on the myth of the founder, as if they have innate business magic. Trust no one. Only the heart of a founder can succeed.

The special thing about a founder is that they care the most. In software and management we have academic research and best practices at our fingertips, but almost nobody looks at them. Most of us are reading blogs and buying self-help books at the airport bookstore. Most of our problems were solved already.

It starts with a REPL or the compiler. An engineer hammers at their keyboard and waits for the result. Does the code run? Is the result correct? The next loop might be tests or quality assurance. The next loop might be integration testing. The next, user acceptance testing, design review, and then? Releasing to customers!

Now the loop is out of your hands. Do your customers get what they want? Does your business get the desired outcome?

At each loop you will be wrong. We write bugs bugs, we misundertsand the problem, and sometimes customers simply surprise us. An effective manager can't do everything themselves, but they can build processes to tighten feedback loops and a culture that thrives on feedback.

The examples thus far are Technological and Product loops. There's another software loop that's far more difficult to measure and often ignored: Social/Organizational.

Team cohesion, psychological safety, and individual performance can be slippery measurements. Even worse, most of your colleagues will tell you what you want to hear. Quantitative survey tools can help, but there's no substitute for authentic relationships, trust, and candor. Don't overlook the social and organizational feedback loops.

In 2010 I got serious about running with a training plan and a half-marathon. The first injury came right after that first race. I had to take weeks off for iliotibial band syndrome. The cycle repeated itself. Every year mileage and intensity would increase until something in my body broke. Every time I looked for a reason. Every time I worked with physical therapists. It was always the same.

The worst year was 2021. I took 6 months off running.

Every runner has a cache of advice. Try orthotics, run barefoot, do this one weird stretch, get a foam roller, and always strengthen your hips. I tried it all. Stretching, strength, and massage all helped. It was one piece of advice that fixed me:

Consider a career instead of a year.

I don't remember where I heard it and I haven't been able to find it again. In hindsight my running "career" was laid bare. Short-term goals led to overtraining which led to injuries.

Imagine how your behavior would change if you knew you had opportunities ahead instead of a single shot. Imagine abundance instead of scarcity. That's the change I found.

High-falutin Theory of Knowledge comes up at work when I stumble over things I thought I knew or what I thought other people knew. We each have models in our minds – models of our customers, our software, our teams, and our business. Some models are good and helpful while others are misguided. How do we share the good models? Imagine if the experts could effortlessly transmit their mental models. We’d be unstoppable!

A few years ago I spoke about the topic of knowledge transfer and skill acquisition at one of ActiveCampaign's Brown Bag Session. I’m a tourist in the field of pedagogy, but I can point you towards my sources:

• What Everyone in Tech Should Know About Teaching and Learning is a video Benjamin Doherty brought to my attention. It's an engaging and fast-moving overview of effective teaching and learning.
• Weien Wang pointed me towards a summary of Accelerated Expertise. The book came from the Defense Science and Technology Advisory Group (DSTAG) as they tried to accelerate skill acquisition. The secret is simulations!

I'm doing my best to reserve judgment, but it looks like it's going poorly. The company, the application, and the societal impact – It all looks bad. In the midst of this mess I’m not sure how it'll turn out. SRE buddies say the systems are doomed. Acquaintances in marketing tell me advertisers will evaporate without content moderation. Reuters warns Musk has $12.7 billion in debt to juggle. Governments and individuals around the world are suing. Real people are suffering because new ownership underestimated technical, social, and political complexity.

There's a scene in Star Trek Into Darkness where Capt. Kirk loses his command (spoiler alert). The admiral berates Kirk. He closes with "you don't respect the chair" and I love it. I wish I had a more academic reference for the responsibility of leadership, but pop culture will have to do.

It’s easy to get cocky. It’s easy to take success for granted. Luck can be mistaken for skill. When I’m tired, lazy, glib, or preoccupied I remember responsibility. We depend on one another.

Kirk, you, me, and Musk are in command of something. We make software and we work as teams. You may be responsible for a few people or a lot of people. Your impact may be a line of code, facilitating a meeting, or pointing a teammate in the right direction. The scale doesn't matter, the crux of responsibility is the same. Colleagues and customers depend on us every day in ways big and small. Please don’t underestimate the impact of your contribution. Keep up the good work.

Existentialists believe we are each responsible for creating purpose and meaning in our own lives. A long time ago I decided I would try my best to build good things with good teams. I know what we’ve done together isn’t everything, but it certainly is something

One will weave the canvas; another will fell a tree by the light of his ax. Yet another will forge nails, and there will be others who observe the stars to learn how to navigate. And yet all will be as one. Building a boat isn’t about weaving canvas, forging nails, or reading the sky. It’s about giving a shared taste for the sea, by the light of which you will see nothing contradictory but rather a community of love.

https://quoteinvestigator.com/2015/08/25/sea/

A group of people gather together for synchronous verbal and visual communication. The communication can be one-to-one, one-to-many, or many-to-many. Generally the setting is formal. Meetings are scheduled in advance and imply mandatory attendance. They are synchronous multimedia experiences.

What is “effective communication”?

Effective communication is the right message delivered through the right medium at the right time for the right audience. That’s a lot of pressure! It gets worse! Consider the preferences of your audience and realize everyone absorbs information in different ways. Should your message be written, visual, performed, spoken, folksy, well-rehearsed… the variations in communication are infinite.

Therefore:

What is the problem you’re trying to solve?

Before any communication, please consider the problem to be solved. Perhaps you’re meeting out of habit. That’s fine, but do so with intention! Don’t fall into shitty meetings.

What is the point of your meeting?

Consider these possibilities:

• Casual time with the team to build rapport and relationships
• Status updates
• Providing context through storytelling, allegory, and myths
• Reading slides to each other
• Marking time on the calendar (two weeks have passed again!)
• Discussion towards a decision
• Discussion away from a decision
• Venting frustrations and commiserating
• Hyping and repeating some recent news/change

The audience, medium, timing, and content varies for each of these examples.

What are the tools at your disposal?

You have more tools at your fingertips than any manager in human history! Email, Slack, phone calls, video calls, recorded presentations, blog posts, slides, polls, collaborative doodleboards… AND you can use any combination of these to communicate. You don’t have to use just one.

But what did Sean do?

The purpose of my Teams Meeting™ was to tell stories to build a culture and provide organizational perspective. I make that clear in the agenda.

The meeting is always optional and sometimes canceled. If a meaningful message hadn’t naturally emerged since the last meeting I’ll cancel. If the message doesn’t benefit from my live performance I’ll send an email instead.

What about your problem?

I don’t know your job! Pick the tools that work for you and your audience! My friend Benedict gave me great advice about 8 years ago: Try thinking and writing before you start whatever you’re doing.

If you agree with Joel and Steve then you, as a manager, should not be making decisions. Managers, by definition, have the least amount of direct information about any implementation details. Managers, leaders, and executives may have broader understanding, but that’s no reason to make the decision. It is the leader’s job to set the culture, values, and expectations. You should share the broader context so the lowest possible level of the org chart makes any given decision.

It may make you nervous to give up control, but no matter who makes a decision there is a chance of failure. Any decision, no matter how well informed, could be a mistake. Remember failure is a great teacher. Letting someone decide, be wrong, and learn from the experience is the best training. And, as Jeff Bezos says, there are very few decisions that can’t be undone.

Additional Reading

• What do executives do, anyway?
• A Framework for Making Smarter Decisions and Fewer Errors
• 3 Ways Amazon CEO Jeff Bezos Makes Tough Decisions

The correct mix of teammates will require hiring and firing. A rigorous interview process should ensure you only hire “the best”. If you hire the wrong person a quick separation will minimize the impact and allow the team to find the right person.

Unfortunately interviewing is an imprecise instrument. Research shows that we often fall back on our biases when hiring. We look for people like ourselves. Research also shows that interview performance has no bearing on job performance. The sad truth is that a few hours of conversation is no way to judge a candidate.

The most effective interviews are job simulations. Create an exercise that simulates the job to be performed and you’ll have a much better idea of the candidate’s aptitude. Use the real tools of the job if possible. For example, solving an algorithmic problem in a web browser is a bad test. Solving a collaborative problem with future teammates would be a better test.

When interviewing, try to test for traits and values. Almost anyone can learn a new skill. Traits and values are much more difficult to change. This will require you and the team to seriously consider the traits and values you’re looking for in a teammate. Its difficult work, but more introspection now will pay off with better teammates in the future.

Additional Reading

• Unconscious Bias @ Work | Google Ventures
• https://www.forbes.com/sites/danschawbel/2016/02/02/adam-grant-why-you-shouldnt-hire-for-cultural-fit

Communication in a small tribe is straightforward. Everyone in the tribe knows everyone else. Communication happens as needed. Relationships are direct.

How do cities, states, nations, militaries, and multinational corporations communicate? Fractal, often hierarchical, tribes. You know your family, maybe neighborhood, some of them know someone else. Spiraling and unfurling webs of implicit and explicit relationships.

Efficient organizations require some structure to formalize relationships. Formal relationships will codify expectations. Clear expectations will engender trust. Abstraction of trust is the key to scaling relationships across large groups of people.

A hierarchical organization is not necessary. There are other ways to organize a large group. In this curriculum we will only be considering management in hierarchical organizations. Leadership topics should be universal, but your mileage may vary.

A manager’s job is to improve outcomes. On the way to improving outcomes a manager may hire and fire, teach and train, delegate, or do it themselves. As a manager you’ll have to manage up, manage out, advocate, and advertise. No one will care about your mission as much as you do, but that’s the job. Do whatever it takes to improve outcomes.

Technical managers often ask “should I write code as a manager?” It depends! The manager is one person among a team of many. Managers should seek out activities with the greatest leverage. Leverage means maximum output for minimum effort. Writing one line of code to fix a bug is good, but teaching a team to build resilient systems is great.

Should managers protect their teams? It depends, although I tend to think not. A manager can only block bad news and negative feedback for so long. Eventually the truth will come, breaking through like water over a dam. Direct and timely feedback is essential to growth and learning. Failure is the best teacher. Please don’t hoard the gift of failure.

There are many management styles. Joel Spolsky (linked below) has a trilogy of essays that explain the history, intentions, and outcomes better than I could.

Additional Reading

• Joel Spolsky's Management Trilogy 1
• Joel Spolsky's Management Trilogy 2
• Joel Spolsky's Management Trilogy 3
• The First-Time Manager by Loren B. Belker

1on1s are for building and maintaining personal relationships. Anything beyond that is icing on the cake. If you’re not meeting this minimum requirement you are wasting your time.

Personal relationships are important because they engender trust. Trust is important because it is the foundation of organizations (as covered earlier).

I struggle to offer advice on building and maintaining personal relationships. For some, relating to others is natural and effortless. For others, it's a confounding puzzle. I am only sure of this limited advice:

1. Care about the other person. If you can’t find a way to care, genuinely, then there’s not much you can do. Find a way to care about the other person and the rest will fall into place.
2. Be authentic. Don’t try to fake your way into a relationship. Other people will know. Be yourself and be honest.
3. Lean into the awkwardness. Say the thing or ask the question that you would rather avoid. Be so explicit that it makes you uncomfortable.

Additional Reading

• To listen well, get curious
• Balanced One on Ones by Lara Hogan [pdf]
• Questions for a First One on One
• How to Talk so Kids Will Listen...And Listen So Kids Will Talk by Adele Faber

A leader can’t be everywhere. They can’t do everything. An effective leader imbues their colleagues with the right information, right motivation, and correct thinking to execute without oversight. Bill Walsh, linked below, believes leader is synonymous with teacher. A leader sets the standard of excellence for their organization.

Teaching isn’t limited to the classroom. Your every word and action will have some impact on your colleagues (and this applies to everyone, not just leaders). The example you set is more powerful than any memorandum. Consistency is key. If you respond to feedback with pettiness instead of gratefulness what do you think will happen? People will stop giving you feedback. If your approach to decisions changes constantly, how could anyone rely on you?

The easiest way to be consistent is to be authentic. It takes much less effort to be yourself.

If you are authentic you will find consistency easy. Consistency will lead to clarity in expectations. Clear expectations will empower your colleagues to execute in your spirit without direct oversight.

Additional Reading

• An Interview with Bill Walsh
• Teach Them to Yearn for the Vast and Endless Sea (quote investigator)
• The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh

I wasted the a few years of my life following the false dichotomy between features and foundations. Everything is a feature. Specific customer use cases over everything! Foundations should emerge from features!

Please take the following points for granted as I make my argument:

• In product development you will always be wrong. The miss may be big or small, but no one hits the market perfectly. All the market research in the world can help, but never guarantee success.
• Tighter feedback loops mitigate the risk of wrongness. Agile development and the ephemeral nature of software let us all be wronger faster. Ship, learn, ship again.
• Delivering an outcome generally takes the same amount of time, whether you spend time planning or you get started straight away. The sum of time spent will be the same.

When I say “everything’s a feature” my engineering colleagues usually stand up a straw-man: But what about tech debt? This will never scale! I’m not saying foundations should be ignored, but generalizations should emerge from the specific features. Pour the concrete in well-worn paths. Before customers show us there’s no way to know how the foundation should be poured. Building an abstraction for problems that don’t yet exist will probably be a waste of time.

Engineers will demand: we need to redo this better! So we build a new generalized system without real customers in an engineering ivory tower. All our assumptions are wrong and we deliver a mess of a system that had to be crammed into real-world use cases. The business and the engineers hate the experience.

Instead, let's start with a single use case, then another, then another – generalizing as the engineers deliver. This delivers value faster, better, stronger.

The thought technologies that enabled success were deliberate iteration, expecting failure/wrongness, and the trust and space to pour foundations when appropriate.

Communication

Please default to asynchronous communication.

Set expectations as clearly as possible.

I’ve found that most communication doesn’t have to be RIGHT NOW REAL TIME. Look at this email! I wrote it earlier today and now you’re reading it. Before sending a message or scheduling a meeting take a minute to consider asynchronous communication. Other strategies include...

• Write a document and invite commentary
• Set deadlines for feedback (“I intend to do this 3pm Fri. Please speak up before!”)
• Collect all possible questions up front

If you think synchronous communication is needed try to schedule it in advance and be crystal clear on the medium of communication. Would you like a Slack chat or a video conference? What do you want to discuss? What are the outcomes? Set explicit expectations wherever possible!

Finally, if something is URGENT please say so!

Work

Our clients’ businesses depend on ActiveCampaign. Now more than ever we need to deliver correct quality software. If our clients are struggling, we're struggling. They're counting on us. They’re counting on you.

We must deliver software, but I’m not so foolish to believe nothing has changed around us. I ask that you do your best and deliver the appropriate level of intensity. “Your best” will be different for each of us. The appropriate level of intensity will vary depending on your work. I’m counting on you.

As far as businesses go ActiveCampaign is in the best possible position. We have millions in annual recurring revenue with millions more in venture capital. Our clients are diverse in every regard. No one industry, country, size, or shape dominates our customer base. Until you’re told otherwise we are continuing to hire. I know there’s a lot to worry about. Please don’t worry about your job.

Bullet Points in Case I Failed to Convey My Intended Message

• Default to asynchronous communication!
• Set expectations explicitly!
• Say what you’re going to do and then do it.
• Say what you want from others.
• Please do your best to be productive, but don’t beat yourself up if you aren’t.
• Our clients are depending on us!
• ActiveCampaign is in the best position possible entering this economic freeze.