Writing We seek definition

The Software Developer’s Career Handbook

I am delighted to announce The Software Developer’s Career Handbook has been published. I call it the Bird Book because, well, there’s a bird on the cover.

The Bird Book is the second edition of Being Geek. The absence of the words “being” and “geek” in the title hints that something is up. Reading the entire book is a requirement for revising an edition. During this process, I discovered there was a lot to like. In particular, the first chapter has a five-line declaration that explains how I think… all the time:

We seek definition to understand
the system so that we can discern
the rules so that we
know what to do next so that
we win.

Every word in that 26-word run-on sentence is chosen carefully. Same with the italics. And the line breaks. These words describe a virtual machine constantly running in my head. What does it mean? How does it fit into my model of how it works? How must I update my understanding to predict this in the future because I need to win?

You can understand why I didn’t like the first edition using those five lines. It’s right there in the first line: definition. It muddied the system of understanding I wanted to provide. If you purchased and read the first edition (thank you), you quickly realized that I wasn’t writing about geeks; I was writing about software developers. I realized this when I discovered I could replace every occurrence of “geek” with “engineer”, and it was better writing.

Here’s the rest surgery I performed:

  1. I added eight new chapters to the book, bringing us to a healthy 48 chapters. For those of you who purchased the atomic version of this book, you’ll enjoy the heft of holding this book. I know I do.
  2. I edited the hell out of all existing chapters. The best example is “The Business”, which must address companies’ new compensation strategies and cooling start-up marketing. Other chapters received less attention, but all were modernized.
  3. I removed two chapters from the book. They were no longer relevant or straight up didn’t make sense. Sorry.
  4. There’s a new cover with a bird on it. I love the bird and the color scheme, but will miss the Being Geek cover. Those sneakers tucked between the black business shoes will always be a favorite.

The Yellow Book, the Bird Book, and the Bee Book. They have names, but I always think about how the covers make me feel. The Yellow Book’s cover has evolved from frenetic scribbles and scratches to a more calm and professional vibe. Don’t worry; the pen is coming back in the next edition. The most recent book, the Bee Book, delivers a classic O’Reilly cover. Simple, clean, and an animal to convey… a hint of the theme. We repeated this vibe for the reboot of Being Geek.

The trilogy documents different parts of my leadership career. The Yellow Book continues to capture my thoughts on becoming a leader. The most recent book, The Bee Book, focuses more on senior leadership. This book, The Bird Book, documents the struggles with the job of middle management. These leaders are the connective tissue that holds the company together. They do this not with fancy titles but with the satisfaction of building the product with their hands. They do this in the middle. At a distance, with influence, partial information, intuition, and an evolving sense of strategy.

I document more of the story of how this edition started in the preface, but I want to thank the Rands Leadership Slack for reminding me of the good writing in this book. If you hadn’t asked, there wouldn’t be a new edition.

Management Topically irrelevant foreign lands

The Seven Meetings You Hate

Why Are We Here? Seems like a good set of people, but everyone is looking at each other, wondering what is happening. It’s nefarious; it’s just.. confusing and agenda-less.

Why Am I Here? It seems like a good set of people, but I have no clue how I’m relevant to this meeting. I will sit here a bit and nod, but mostly, I’m wondering why someone thought my presence was a good idea.

We’ve Always Done It This Way Every week. Same time. No matter what. Why? Well, you know, I don’t know why. We’ve always done it this way. Is that a problem?

This Isn’t a Meeting; It’s a Lecture Bunch of people. Check. In a conference room. Check. He’s talking now. Still talking. It’s been 30 minutes, and no one else has said a thing. Why are we meeting? Why is there only one human talking? Not a meeting, by the way.

We Can’t Make Progress It appears that we have a diverse set of humans, but we neglected to invite the humans who could help us make progress, so we’re going to have this meeting again, no matter what.

We’re Aimless We know why we’re here. We have the right people, but no one is referreeing, and now we’re off into topically irrelevant foreign lands.

It’s Everyone Someone was super aggressive about inviting anyone with any possible opinion about the topic, but we cannot make progress with this ginormous crew.

Writing Bear just gets me

300 Times a Day

When your favorite software tool receives a major update, it’s all dread. It’s not you expect them to ruin the application (although possible); it is because it’s your favorite tool, you know all the intricacies of how it works, and you know exactly how you need it to work.

This is not a casual tool. This is crucial. This is a piece of software you use 300 times a day, which means one subtle, seemingly meaningless change could ruin your workflow forever.

I use Bear 300 times a day. Probably more. I could sketch their five preference screens from memory. I’ve written and edited two books in Bear. I’ve spent hours understanding how tags propagate through the system. Ask me about their sync system. Quiz me on their keyboard shortcuts.

When the update landed earlier this week, I held my breath for five minutes straight. The Verge article claimed a “rewrite from the ground up1,” which sets the stage for a worst-case scenario for a critical tool. I fired up the updated app and watched them migrate my thousands of notes for a few seconds. The window appeared, and my first delicious thought was, “Wait, what’s different?”

Thank god.

Much is Different

My first reaction2 was the best because Bear is my home. It’s not a place I occasionally frequent; it’s always open. It’s where articles begin and finish. It’s where I capture random bad ideas. It’s where the first drafts of complex emails are created. I’m a word guy, and this is my word place, so a “nothing’s changed” first impression on a “rewrite from the ground up” narrative is a comfortable starting point.

At the core of my love of the Bear is a line from an article on How to Write a Book: “Features create choice and choice is a dangerous distraction, and the last place you want to find distraction is in the tool you use to write.”

I began my exploration of Bear 2 within the preferences; first noticing was that there were fewer preferences. Same number of sections, but less choice in each section. Less choice, yeah, you read that right. I want talented designers and engineers to make choices for me. I want them to do this because I trust their judgment, and I don’t want to spend my time fussing with knobs and dials in my favorite tool; I want to spend my time writing. Tinkering with a tool isn’t productive; it’s procrastination.

This is the core of my dread. I need application owners to continue demonstrating incredible product judgment so I can use the tool and not worry about how the tool could work.

Bear 2 continues to demonstrate fine judgment.

Nips and Tucks

Given it took seven years to get a major revision to Bear, it seems disrespectful to call the set of changes I’ve noticed nips and tucks. There is confirmed a considerable amount of engineering and design that went into Bear 2, but as noted above, they’ve made these changes subtle and unobtrusive.

BearSansUI Within the editor, the first and most noticeable change is Shiny Frog introduced BearSansUI (and BearSansUIHeadline) as part of this release. This default new font replaces Avenir Next. It also accompanies a significant typography change for the product in that you can use any typeface instead of six in the original version of Bear. But why would you not stick with BearSansUI — a typeface designed specifically for Bear? I don’t know. I trust the experts.

Here’s a comparison of BearSansUI with Avenir, which I suspect is its core inspiration:


Avenir Next:

My go-to letter of comparison for typefaces is the ampersand. Go compare. The BearSansUI ampersand softens a complex swishy character and makes it calm. You can see this intent in capital Q, as well.

Bear has always supported Markdown, but my impression is the developers picked and chose the parts of the fractured standard that suited them. As a non-power user of Markdown, this didn’t annoy me because I’m not tinkering with Markdown; I’m writing. For Bear 2, Shiny Frog now adheres to the CommonMark standard, which is “a strongly defined, high compatible specification of Markdown.” This will please the standard folks but mostly means my highlight syntax changed from :: to ==.

More important to Markdown is Bear added a preference to Hide Markdown. Enabled means that once you’ve finished bolding or italicizing a bit of text with the appropriate formatting, the markdown vanishes, leaving you with styling. Markdown purists may take issue with this because they always want to see the formatting, but I love this option because writing a piece involves an entirely different part of my brain than editing.

When I’m writing, I need as little distraction as possible; I need to get the words out. I do Markdown, but asterisks, octothorps, and other formatting text are visual noise. When I get to publishing the piece, yes, show me all the formatting details because I need to see these details to edit and format it properly, but when I’m in the zone, I need sweet, sweet, cleanly formatted words.

Bear 2 also introduces a formatting toolbar that allows you to do formatting, insert todos, and, as a new feature, tables. I’ve tinkered with the new table feature briefly, and it’s impressive. It gives you all the necessary options to add, remove, and move rows and columns, and copies in various formats (Markdown, CSV, and HTML). Still, I wonder how many folks are keen on littering their beautiful text with tables. I’m a sample of one, but in my extensive usage of Bear for seven years, I have never not once considered adding a table to my documents.

I won’t be a frequent user of the formatting toolbar because if my hands leave the keyboard, well, I’m not writing.

Additional observations:

  • My impression is every bit of artwork, like the typeface, has been either replaced or touched up.
  • Bear has three views: edit, notes, and editor and notes, editor, and tags. I swap between editor (focused) and editor and notes (organizing). The note view has been visually tightened up and now includes options to sort this list and adjust the preview style. Use large. Turn it off when you don’t need it. You’re welcome.
  • Bullets now indent text as opposed to outdenting in Bear 1. I didn’t know how much this bugged me until I created my first bullet in this version. Bullets also follow CommonMark rules and can nest blockquotes and titles.
  • Footnotes are now also supported. No clue how these behave when exported to publishing platforms.3
  • Sync continues to just work. This is an invisible but essential feature because Bear is vital to all my Macs, iPhones, and iPads.
  • There are six additional themes. I am frequently theme-changed-based-on-mood and am delighted to have more moods.
  • Finally, a dedicated panel within preferences to select your app icon. This seems like a waste of real estate until you remember I’m the guy who changes his template based on his mood.

What you are reading is my first significant piece of writing completed in Bear. The next step will be passing it through Grammarly to tidy up grammar and spelling. I will then post to WordPress. These final production steps might teach me more about Bear 2, but I doubt my opinion will change significantly:

  1. Solid update. Didn’t adversely affect any of my writing workflows.
  2. Intense attention to detail. They took a significant risk introducing a new text and headline typeface, but it’s instantly appealing and gives a subtle application more personality.
  3. My bar for paying a monthly fee for an application is high. Bear 2 greatly exceeds that bar.

301 Times

My final compliment for my favorite applications. When these applications release anything, I first pour over the release notes to read what has changed. When I’m done with that, I walk through the entire application, every menu item, every preference, and everything I can click to see how the documented changes work and discover undocumented changes4, which always exist and often surprise.

Yes, it starts with dread, but that rapidly turns to joy and hope because these applications are my favorite because I’ve learned designers and engineers just get me.

  1. I pinged the developer regarding why they did a rewrite. They have a forthcoming version of Bear for the web, and the most performant strategy was building C++ compiled to WASM. The web version has yet to be released. 
  2. This article was written and edited entirely on the Mac. I haven’t evaluated the iOS version of Bear 2. 
  3. Let’s find out. Just works with my WordPress setup. Sweet. 
  4. I keep the prior version of the application around — network disabled so it doesn’t update — as a means of comparison. 
Tech Life You know you rock, but they don't yet

The Business 2023

You’ve had a small number of career-defining moments. These are the select few moments in time when the trajectory of your career changed instantly and drastically. I have two buckets of these: ones I expected and ones that completely blindsided me. While the surprise and subsequent scrambling involved in being blindsided are chock full of delicious adrenaline, I highly recommend the moments you can predict.

One such predictable moment is the first glimpse of the offer letter for your new gig. This is the culmination of hours of résumé tweaking, a series of phone screen gymnastics, and two grueling days of in-person interviews. This is a rare moment where you can answer the question, How much does the world think I’m worth?

Fact is, you should already know. You’re the business.

You Are the Business

Before I break down the offer and offer negotiation process, I want to reset your head. I’ve no clue how badly you need your next job, and the degree of your need will affect your negotiating position, but here’s some reality. You are the business. If you get an offer and take the gig, I think you should pour your heart into it, but I want you to remember that you’ll have 5 to 10 other jobs in your life, just like this next one. This means that for each moment you spend being pumped about the new gig, you’ll have an equal and opposite moment at the end of the gig where you can’t wait to get the next gig started.

Among these 5 to 10 jobs you’ll have, there is one constant: you. You’re the one who has to pay rent, ride the subway, buy a condo, get married, have some kids, and build your dream house. Your welfare is not your employer’s first priority. It takes one layoff to figure that out.

You are the business; the one consistent metric business is measured by is its growth. A new gig represents one of the few moments in your career when you can directly and forever change the trajectory of that growth. It’s backward to think of an offer as a true estimate of your worth; it’s one piece of data in a larger story that is your responsibility to define. Let’s do it.

Actual Earnings

The offer negotiation process has changed significantly in the last decade. In many US states, employers cannot ask about your current salary. If you volunteer this information, employers are not allowed to use this information in setting your offer.

You still have a chunk of work to do; you need to figure out what kind of offer you’d accept, starting with figuring out what you’re currently earning. Go ahead and say your current earnings out loud. I won’t tell.

What’d you say? $104K? How’d you arrive at that number? Oh, it’s your base salary. You actually earn just over $200K.

I’ll explain.

What Am I Earning?

Like frequent résumé updates, this career maintenance exercise is designed as a professional checkpoint that answers the simple question, How am I doing?

Let’s start by breaking down how I calculated what you are earning:

  • Base salary: $104K
  • Benefits: 30% of $104K = +$31K
  • Bonus: +$10K
  • Stock: +$60K
  • Total: $205K

There are likely two surprises in this framework. First, if you haven’t worked for yourself, you probably haven’t considered benefits as part of your compensation. That 30% is an educated swag that most companies use to account for health and life insurance and 401(k). You spend much time ignoring this 30% because it involves retirement and health benefits, and you’re immortal. There will, however, be a time, probably sooner than you’d like when you fully appreciate this portion of your compensation.

The other area: stock. This $60K represents a total swag. Levels.fyi claims that stock grants range from $20K to $100K per year for your average engineer in the US. I combined the high and low and divided it in half. Do not confuse this sloppy math with the importance of your stock grants; they often have the most direct effect on your compensation. Much more on this later in this article.

Ok, grab a piece of paper and use this rough framework to figure out what you make. Don’t sweat perfection. You just need to be close.

The Swag

Fast forward. You’ve just finished the interviews. Traditionally in high tech, the recruiter is the last interview of the day, and their job is to get inside your head and take your temperature regarding the gig. The guiding rule here is: the more they know you want the gig, the less they need to offer you.
And they haven’t offered you a thing yet.

There’s a time and place for negotiation, and it’s not at the end of six hours of interviews on a Friday when you don’t even know if you’re getting an offer.

So, you wait. You send off a set of references, lie in bed replaying interviews in your head and send thank-you emails to the interview team. All professional karma-aligning activities, but what you really need to do is build your own offer letter. Like you built your compensation, I want you to build your offer.

Base Salary

The business model everyone loves is built on recurring revenue streams. This is why you can get a good smartphone for nothing. You’ll pay for that phone many times over with your monthly subscription of $39.95. You’re still happy paying that much a month because that feels like a deal, but carriers don’t see $39.95; they see the $1,500 you’ll spend over that three-year contract.

While it is often not the biggest potential impact on your salary, your base salary is your recurring revenue stream. It’s your financial lifeblood, and we want to get it as high as possible because getting them to add a 1% increase doesn’t affect this year; it affects every year after.

For the swag, you need to figure out what you want to be paid in the new gig, and my first question is, “For someone doing exactly the same job as you, how much are they being paid?”

When I originally wrote this article, I found the internet surprisingly useless in figuring out salary ranges. There are multiple relevant information sources these days, but even better, you can ask your potential future employer. Many states in the US have passed laws that require them to post job descriptions with salary range information.

Don’t get too excited. They are required to post ranges, which include what they pay an engineer in this role for 1 year or 10. Other companies have chosen to combine two jobs into a single role. The result is you’re going to discover absurdly large salary ranges.

I have three pieces of advice for your swag. First, talk to friends with similar jobs and figure out what they’re making. Salaries vary greatly depending on the industry, geographic location, and specific company, but after you’ve talked with a few folks, you will have a rough feel for the base salary. Second, ask the recruiter and confirm the salary range and see what else they can tell you about this range. Does it encompass multiple jobs? Or just one? What are the expectations regarding years of experience from the low range to the high? What is the company’s philosophy on promotion? How long are folks expected to perform well in a role before they are promoted?

Finally, if you don’t have a good signal, take your current salary and add 10%—that’s your very low signal salary swag.


Titles, like salaries, vary from company to company, but what you’re looking for in a new job is a sign that you are growing. Associate software engineer now? OK, drop that associate title. Stuck as a software engineer for three years? I’d be looking for that senior prefix when I jumped ship.

Like salaries, the internal value of a title varies wildly by company. A director at a startup is an entirely different role at a public company. The good news is the legal requirement of published salary ranges has forced many companies to normalize jobs and titles, which means there are fewer aberrant jobs and job titles, which means senior engineer at Company X is likely a very similar position to a senior engineer at Company Y.

Your swag goal: What title do you believe needs to be added to your résumé for this new job to demonstrate that you’re actively growing in your career? You need to have a defensible opinion regarding why this is an appropriate title.

Sign-On Bonus

It’s difficult to swag a sign-on bonus because this type of incentive is often used to augment weak parts of an offer, and you don’t have an offer yet. If a recruiter knows you’re keen on stock and you’ll be disappointed with a lowball stock offer, they might dazzle you with a large sign-on bonus.

Pro tip: sign-on bonuses are one-time cash windfalls that may never appear again. For now, all you need to know is that they’re often a short-term Band-Aid, and the question will be: What are they hiding?


While representing the largest potential for financial gain, stock grants are also the hardest to swag. There are two likely initial scenarios here: public companies and startups. I’ll explain likely stock structures for each.

A public company is public, meaning anyone can buy and sell their stock. More importantly, you can do a deep dive into their financials. You can get a sense of how the company is performing, usually, by how their stock is performing. I like to look at the last five years. What’s the average stock price over that time? That’s a good swag price per share for your model.

As a full-time employee, you will likely receive a restricted stock unit (RSU) which vests over three or four years with a one-year cliff. This means your initial ⅓ or ¼ of your stock vests yearly, but you won’t be able to sell any for a year because of the cliff. After that, you are likely to vest quarterly.

RSUs replaced hard-to-understand stock options grants and are—important point here—just straight-up stock, usually with restrictions regarding voting rights and dividends. Unlike salary ranges, companies are under no legal obligation to tell you stock ranges for a role. Sure, ask. Know this: per-job ranges exist and are far more predictable for public companies versus startups.

Your potential stock situation at that startup is more complicated. First, they might use stock options versus RSUs. Smaller startups tend to offer stock options and then transition to RSUs as they prepare to go public or seek additional funding. Second, and more importantly, how do you evaluate the value of a startup? You can’t check the stock price. Yes, you can.

A public 409A valuation assesses the fair market value of a privately held company’s stock. A third party defines this price, and the asking price; “What’s your last 409A?” is a question you must ask because you need to place a value on the stock. Now, unlike publicly traded companies, the 409A is only done once a year or when there are significant changes to the business (funding events, strategy shifts, or other major changes to the business). In my experience inside these companies, the 409A is often a stale number that does not reflect current company reality, but it’s better than nothing.

Even with this information in hand, you don’t know one of the most important pieces of information. When is this startup going to go public so you can sell your shares? The IPO market is based on market conditions. After the dot-com boom, the IPO market cooled for two decades until 2021, when it exceeded the dot-com bubble. At the time of this writing, in 2023, the IPO market has again cooled significantly. When will it heat up again? If you find out, tell me.

For both public companies and startups, you are speculating about the stock, but I see no scenario where you don’t focus most of your attention on the size of your stock grant. Better said, why would you ever go to a company where you didn’t believe in the opportunity? In your growth? And the growth of the company?

Yes, any value you place on stock or options is speculation, but it should be informed speculation. Your value on the stock is one measure of your belief in the company.

Negotiating Roles

You’re done. Two phone screens, two rounds of interviews, reference checks, and much waiting have paid off. Before considering your offer, let’s determine who you will negotiate with.

In any reasonably sized organization, a strange switcheroo occurs when you start talking money. If you’ve reached the offer phase, it means you’ve likely professionally connected with your potential future manager. She’s sending you follow-up emails and generally paving the way for a clean transition to you joining the team. The moment you start talking compensation, she might vanish.

This far into the process, you’re probably pretty close with the recruiter. You’ve probably had a couple of professional heart-to-heart conversations and might be under the impression they’re representing your best interests.


The recruiter’s role in negotiation is the bad guy and deliverer of bad news. Recruiters are measured not only by the number of hires they make but how the compensation for those hires measures up to the rest of the company. Yes, recruiters want to make the hire, but they’re also driving toward internal corporate hiring standards that may or may not be aligned with your ideal offer letter.

Your future manager’s role is to make a great hire; the recruiter’s job is to make that hire and negotiate it so it’s fiscally responsible.

You need to be prepared to dig in your heels and fight for what you want. This may be uncomfortable and might involve tense moments with the recruiter, but if you’ve done your work above, you have the upper hand.

Offer Compromise

I’ve never received an initial offer that I loved. There has always been an aspect that has disappointed me. The stock is off, the title is unexpected, or the base salary isn’t that close. I’ve always needed to construct a counteroffer, and I’ve done it using facts.

As a hiring manager involved in many offer negotiations, the safest way to get me to ignore any counteroffer is to make it without data.

Recruiter: The candidate wants a higher base.

Me: Really? Why?

Recruiter: He just does.

Me: Grrrrrrr.

Negotiation is a discussion of facts. Any counteroffer must be constructed with data. “I want a 10% raise because, based on my research, that represents the average salary for this gig elsewhere in the industry.”

Sure, it’s still a swag, but your swag demonstrates a defensible opinion. In an interruption-driven industry full of bright people racing around yelling about the last interesting thing they heard, I’m a fan of research. It demonstrates that you are curious and care about your career, and that’s someone I want to work with.

As I don’t know your problem with your particular offer, I can’t advise what you need to say specifically, but here are some common frustrations and a plan of attack.

Lower base salary

If you’re staying in your industry and at an established company, I can’t see how a pay decrease is ever a positive sign. Yes, if you’re moving to a startup, you will trade your base salary for stock. You need to figure out if you’re cool with that.

You wanted a 10% increase, and they returned with 5%? Why? Sure, perhaps your 10% was a pie-in-the-sky swag, but how is the recruiter justifying this base salary? They’re probably saying something about comparable salaries across the company and how you’d make more than 90% of the people in your grade. That’s a warm fuzzy, but I call it shenanigans: you’re in the wrong grade. Push for a higher grade with more compensation headroom.

But it’s OK; here’s a bonus

If the recruiter is pitching this bonus as a fix for your low base, I call shenanigans again. A sign-on bonus, like a bonus plan, is a finicky thing that has a habit of vanishing. You can’t count on them. There’s nothing like an instant pile of money to distract you from the fact that, over the long term, you’re bringing less money home.

There are two questions you have to ask yourself: What are they covering up for with this sweet bonus, and how will you feel when that bonus money is gone?

Even better, here’s a pile of stock

How big of a pile? Your public company offer will likely come with justification for the grant amount, and you can plug that number plus your five-year average and get an idea of potential yearly returns. As I wrote above, you can ask and should receive a 409A number from the startup to place on a number on the private shares. You can also ask about the number of shares that are issued to get a sense of how big a slice of the pie they are offering.

Again, this is speculation. The amount of shares and their future value is a guess, but if you aren’t happy with the amount and place a high value on the stock, you can ask about trading base salary for stock.

And this is our final offer

If some part of the offer is below expectations and there’s absolutely no way to fix it, you have two options: walk away or find another way to ease the blow. We’ll talk about walking away in a moment, but have you considered the following to ease the blow?

  • Asking for additional vacation hours right out of the gate?
  • A start date a month later than they’re asking? There’s nothing like 30 days of work-free bliss to improve work-life balance.
  • What their work-at-home policy is? Suggest an adaptation that better suits your particular work setup.
  • My favorite move is to negotiate a six-month performance review. You know you rock, but they don’t yet.

Walk Away

The final strategy I suggest is one that you might think is hard, but if you’ve done your work, if you have a defensible opinion regarding both what you are worth and what you want out of your next role, this move is simple.

Walk away.

Please note: I didn’t write ghost them; I wrote walk away. If it is clear that this job offer does not meet your expectations, you do this: write to whoever your point of contact an email that says:

  • Thank you.
  • Clearly explains the aspects of the offer that do not meet your expectations and why. Note: if any of this context surprises the other party, you’ve missed a couple of key steps above.
  • Thank you. Yes, again.

This email does not say anything suggesting that “If we can address this gap, I’m in.” While this may be an outcome of this step, it is not the content nor intent of this mail. You must be clear in your own head about why you are walking away and be 100% committed to doing so.

You are not buying a used car. This is your professional life.

I walked away from what became one of my favorite jobs—twice. The first time was early in the interview process when my spidey sense was tingling: “The job responsibilities aren’t right.” I told the recruiter briefly, said thank you, and said goodbye.

Recruiters as a species won’t take no for an answer. This recruiter quickly got on the phone, tap-danced his way into my head with promises of further conversations and other assurance, and did just enough thinking to convince me to continue. When offer time arrived, all of my responsibilities and cultural concerns remained, so I followed the process above. I sweated every single word of the email. There were very specific concerns I documented, and none of them—none of them—had anything to do with compensation. There were clear concerns about their interview process( and why it was a red flag for the culture) and there was a lack of definition of responsibilities. I included in my email why I believe these concerns would set me up for failure.

When I wrote “thank you” again and hit send, I was content. I believed in my choice and was ready to continue my search. Yes, I was eager to hear a response, but I was fine if the answer was “Thank you.”

The specificity and clarity of my concerns gave them a very obvious response framework. The fact that this was not the first time they’d read any of this information gave my response gravity. Yes, they did respond, and they responded thoughtfully, in person, over multiple conversations. We cleared the air long before it had a chance to become hazy.

And remember, my concerns had nothing to do with compensation.

My single worst gig was one where I got everything I wanted out of the offer letter. A raise, a promotion, ample stock, and a sweet sign-on bonus. In my exuberance for this compelling offer, I totally forgot that my gut read on the gig was “meh.”

Ninety days later, I couldn’t care less that I got a 15% raise and a sign-on bonus. I couldn’t stand the mundanity of the daily work, and I happily resigned a few months later, taking both a pay cut and returning my sign-on bonus for the opportunity to work at Netscape.

All of this important compensation strategy ignores a simple question you need to be able to confidently answer long before you decide on an offer: What do I love about this gig?

Better, Faster, and More

I want a better job. I want a role providing me with challenges I have not seen before. I want to work with a diverse and talented team that, by just existing, teaches me new ideas and makes me better. I want a better company that has figured itself out and is heading, no, charging toward building the next thing.

I want to move faster in my career. I have been doing the same thing for the last three years, and my career is decelerating because my daily learning is decreasing over time. I always have the next goal for my career, and I want to have a job accelerating me toward that goal by providing me with new opportunities with new humans on different products. The speed with which I’m heading toward the next goal should be… breathtaking.

I want more. More accountability means more potential for the products I’ll be building. More visibility into how the product is built and how the company is shaped to support building the product. More features that help more humans.

You will note that nothing I listed under my better, faster, and more job goals mentions compensation. This is not because compensation isn’t essential; it’s because the things that will matter most in your next job have little to do with how you are paid. We gravitate toward compensation as the measure for the next gig because it’s so wonderfully measurable and comparable. However, who you work with, how you build, and what you build are aspects of the job you should be assessing.

But how? There are no structured rubrics for evaluating and comparing people, processes, and products. This is why the best word in your response is feel. I know your feelings about the compensation, but how do you feel about the humans you will be working with? How do you feel about how they work together? How do you feel about what they build and where they are going?

Feelings are observations collected, compiled into opinions, and finally transformed into an emotion. I want you to feel your offer is fair, but I want you to feel this is a fantastic opportunity to grow.

For any new job, you should be able to quickly explain to anyone why the new job is more compelling than the last and why you will love it. Whether they believe you or not is irrelevant. You’ve got to believe it because you’re the business.

Management Humans tend to tweak information in their favor

The Contagion

In the hallway, late on Thursday, someone tells a bit of information about your product that is 100% provably not true. You laugh, wink at the person, and say, “That’s goofy. What reasonable human would believe that?” And that conversation moves on.

Two hours later, different locations, different humans, and different contexts. Same exact piece of provably false information is shared with you. Your brain mentally perks up because here’s this laughable bit of data you’ve heard twice in the same day. Now, you’re curious. Now, you ask questions, “Weird. Where’d you hear that?”

To which they honestly say, “I don’t know.”

Twenty-four hours later, this silly bit of information is your entire life. It’s all you are focused on. You’ve had two meetings with stakeholders to strategize how to counteract this immortal lie.

It’s a Contagion, and while I can not tell you how to fix it, you must understand the rules, behaviors, and personalities influencing and contributing to its creation and why it thrives.

An Incomplete List of the Communication Rules

There are rules which govern communication in large groups of humans. Habits or tendencies are a better word, but I call these rules because of the significance of their impact. While these certainly apply to very large groups of humans, for this piece, I’m focused on the groups of humans within a company. This is an incomplete list of rules.

  • The amount of information created, interpreted, and shipped around a group of humans is a function of the number of humans in the group.
  • Similarly, the amount of noise introduced into a given piece of information increases as a function of the number of humans exposed to it.
  • Simpler thoughts travel farther faster.
  • The higher the perceived value of a piece of information, the faster it moves amongst a group of humans.
  • The perceived value of a piece of information is terrifically situational. For example, you would care a lot to know a layoff is coming to your company. You’d be curious to learn there was a layoff in a different but similar company, and you wouldn’t care much to learn that a jean factory in Austin, Texas, had a layoff.
  • Humans hate (hate!) not knowing things. In the absence of information, humans tend to make things up to fill the vacuum. This is generally considered but is not always framed as gossip.
  • The further information travels from the source, the harder it becomes to confirm its veracity and source.
  • The higher the stress of a group of humans, the more they are willing to accept increasingly goofy explanations for that stress.
  • The quality of a piece of information decreases by 10%1 each time it crosses a significant communication membrane. These significant membranes are: from one team (or organization) to another, up or down one level of an org chart, or when information is transferred between humans who are strangers. There are many contributions to the degradation, including the complexity of the thought, the transmission medium (in-person — low degradation, email — higher), the distance from the source, and, sadly, the time it takes to explain the thought.
  • With each hop, humans tend to tweak information in their favor.
  • Finally, humans tend to create echo chambers full of partial truth because: Humans like to hear things they agree with from people they know, and humans don’t want to hear things they don’t agree with, especially from strangers.

Network Nodes

I will describe two critical information networks in a moment, but to understand their construction, you need to understand the constituent parts of a network. There is the information traveling the network, the rules which govern how the information moves (described above), and finally, there are the nodes, the humans, which comprise the network. I see four types of nodes:

Basics The majority of the nodes. A human who is capably receiving, interpreting, creating, and transmitting information in any direction. Good job.

Our next three are exotic nodes, and they exhibit very specific behavior worth understanding:

Gossips/Mutators. These humans infect the communication network with speculation and half-truths for sport. They like the high when they speculate on a thing, and you immediately remark, “Wait. No way?”

Nodding happily, “Way.”

Don’t judge this node too harshly. It’s clear that if you stand right next to them and hear them speak, they think they’re just having fun making up tantalizing bits of information. The problem is that each time they construct something super juicy, it travels further and mutates more.

Perhaps the more costly behavior of the Gossip is that they also mutate incoming information using the same “skill.” Looks like this:

An intriguing piece of information X appears in front of the Gossip. They think: It’s interesting, but you what would be more interesting? If I tweak this fact a bit. Now it’s juicy. This variant of the Gossip, I call the Mutator.

Ok, you can judge them harshly now. They are mostly not helping by creating unnecessary confusion.

Amplifiers Similar to the Gossips, an Amplifier finds joy in knowing and transmitting things. Unlike Basics and Gossips, they work to transmit the information unaltered. We’ll discuss network construction in a moment, but — spoiler alert — Amplifiers are precious nodes in your network.

Black Holes This aptly described node eats information. Their motivation is similarly opaque. Maybe they are tired of the half-truths wandering the network. Perhaps they have strict principles regarding information transmission. I don’t know. What I do know is that information arriving at Black Holes never leaves. That’s an exaggeration, you can pry it out of them, but their desire to hoard information confuses me.

Types of Networks

Now that we understand the behaviors and the types of humans that comprise them, let’s talk about the networks they build. Like humans, there are infinite slightly different versions of these networks, but there are two you definitely care about:

The Leadership Network

This is the publicly visible network. I call this the Leadership Network because leaders in large groups are incentivized to seek, identify, and relay important information. Their job depends on the quality and the freshness of their information. To keep themselves stocked with the latest and greatest information, they build networks of humans that they trust. They also build elaborate processes, org structure, and meetings, ensuring that everyone has a good chance to learn about essential bits of information.

The Leadership Network is the backbone of communication of any large organization, but it is paired with another, which is more challenging to find and trust.

The Whisper Network

The Whisper Network is a rich tapestry of partially true information. My gut is to call this the Gossip Network, but gossip is just one of the information types that traverse this network. The Whisper Network is a semi-deliberate construction of humans who might trust each other but mostly wondering out loud what the hell is going on.

Remember the rule: humans don’t like not knowing what is happening, especially if it directly affects their professional well-being. They tap into their Whisper Network when they hear a whisper of an idea that hints at shenanigans. A collection of semi-trusted others who meet one or more of the following criteria:

  • They have some professional stake in the topic. They might not be domain experts, but they can comment.
  • They are known as Gossip or Amplifiers. Or both.
  • They’ve provided high-quality Whisper fodder in the past.

Conducting business on the Whisper Network feels shifty because it’s designed to operate outside of standard forms of communication, but this doesn’t mean it’s entirely nefarious or full of lies. It’s a rich tapestry of partially true information, half-formed ideas, and opaquely motivated uninformed opinions. Its lack of integrity does not mean it is bereft of signal.

The Whisper Network is wholly entangled with the Leadership Network because it’s the same set of humans. Yes, information is jumping back and forth between these networks. You can talk to the same person and change networks during the conversation. I consider it a separate network because of intent. When I’m participating in the Whisper Network, it’s a different mindset. There’s a reason I’m whispering.

I participate in the Whisper network because it often serves as an early warning system. It often alerts me to the Contagion.

The Contagion. Let’s Play It Out.

Large group humans. Thousands. Multiple huge programs. Months of complex development. Millions of dollars on the line.

One key project. One person. One person who has intimate knowledge of the state of development of that critical project is slighted. How? Doesn’t matter. You’ll never know who they are and why they feel this way. They will express their displeasure with this development quietly and privately. Their only motivation at this moment is therapy by venting to trusted others.

Thing is, it’s a good vent. It’s a compelling story that can be summarized elegantly… briefly, even though it’s an opinion… a ridiculous thought. I will call the summary of this vent The Defining Thought.

The Defining Thought checks a lot of the boxes from the communication rules above. It’s the answer to a question many folks haven’t even asked themselves, but they can sense it because… they don’t like not knowing things. It’s terse, and it’s pithy, which significantly reduces transmission costs. Finally, this Defining Thought involves a critical and high visibility program which means humans who are not remotely involved in the effort eagerly amplify it across the company.

It’s around this time when you first hear this ridiculous thought. Still, you don’t understand that it’s a Defining Thought until you’ve listened to this untraceable ridiculous nonsense from five other trusted others.

See, the Contagion is not this ridiculous thought. The Contagion is your culture. A unique combination of the communication rules allowed to exist, the types of obvious and non-obvious information networks that connect your teams, and the unique set of nodes that dominate those networks.

Why is ok for this vent to be transmitted? Who thinks it’s a good idea? Who did they share it with? What were they hoping to achieve? Once the thought started gaining traction, why did receivers not source-check? Why is it ok for them to tweak this information in their favor? It’s an unknowable list of questions and answers; the answers explain why the Contagion is allowed to exist and thrive.

  1. Some
Management Hard decisions are full of experience

Ask Questions, Repeat The Hard Parts, and Listen

One of my least favorite moments as a leader, specifically your leader, is when you ask me to make the decision.

First, yes, I know it’s my job to make these decisions, especially the complicated and high-risk ones.

Second, it’s true I’ve acquired ample experience over the last thirty years, and the chance I can make informed decisions on this particular topic is high. In the case it’s a novel decision, related experience probably gives me an excellent chance to make a prompt and quality gut-feel decision.

Third, and finally, I am 100% clear when a decision is mine and only mine to make.

These three qualifications do not change my discomfort, no… disappointment when you ask me to decide. Before I explain why I’m disappointed, I’ll explain three tactics I will take that might get you to decide.

ASK QUESTIONS. Let’s start by setting some ground rules for this decision you are bringing to me. First, you’ve already decided you can’t make it because of complexity, experience, risk, or straight-up fear. Second, it is a hard decision. Just a couple minutes into your pitch, I can tell why you’re bringing this to me — it’s a big, not a little, decision.

I will ask you questions regardless of my experience, thoughts, and first impressions regarding this decision. Lots of them. These are honest; I don’t know; please educate me on the situation, and I’ve got a bunch of them. My immediate goal with these questions is to educate myself regarding these decisions. See, if it were trivial, low risk, or obvious to decide, you would not need me. You would’ve made it.

My second goal, and it happens more than you’d think, is that you make the decision. It doesn’t always sound like you decided as we go back and forth; it often sounds like:

“… and because of that critical architectural change in June, the performance has steadily decreased. It’s time to refactor the whole damned thing, right?”

To which I say, “Right.”

You might think I am making the decision, you might think I am giving you permission to refactor the whole damned thing, but what has occurred in this interaction is via our back and forth, you’ve made your case, and you proposed your next steps to which I said, “Right.”

You decided. Not me.

I served an essential role in this exchange. I did tease out the hopefully tricky bits of the decision. I also pointed out some nuanced political people’s pros and cons that we hadn’t considered but didn’t change the decision calculus. Yeah, I tasted the soup, but you decided.

It doesn’t always go this easily.

REPEAT THE HARD PARTS. Our question and answer session comes to a close, and we’re still staring at that decision. You might suspect the decision but are not yet confident in your reasoning. You might not be close to a decision. Whatever the situation, we don’t have a decision yet.

My next strategy. Repeat the complex parts of the problem. There are two reasons I’m doing this. First, if this were an easy and uncomplicated decision, you would’ve already made it. There is intricate detail to be understood here, and humans, especially when stressed, are fantastic at glossing over intricate details, so I will repeat any part that I feel might need more clarification. Barring that, I’ll repeat what I consider critical parts of this decision.

Second, I’m stalling for time. I still really want you to decide. It happens less than during question and answer time, but frequently when I clarify a missing detail or restate a core thesis, you decide, “It’s time to refactor the whole damned thing, right?”

To which I say, “Right.”

LISTEN. Having done this decision thing for a long time, at scale, and with everyone — everyone — staring at me waiting for a critical decision, there’s a good chance when you bring me your decision that I’ve seen it before. If I haven’t seen this precise decision before, I’ve seen enough like it to begin with a good understanding of the type of decision, its constituent parts, and the likely consequences of making a good or bad decision.

With all this, I still don’t want to decide. I want to listen.

This is how I listen. I bury all of my experiences with similar decisions, I clearly hear the urgency in your voice, and I understand and will acknowledge it. Still, I don’t react emotionally to it, and I clear my head and listen.

This mindset is equal parts for you and me. I want to approach this situation as a neutral blank slate initially. This is how I can ask questions thoughtfully. Yes, I know the humans involved and the history, but I am intensely curious. Yes, there are folks at fault, emotions running high, and mistakes were made. We’ll revisit all that at the right time, but not now… now we seek the joy of understanding.

For you, I want you to see me as support. I want to let the frenetic energy out of this situation, and I want us to find the facts. I need you to feel that we’re partners in figuring this out, even though my preference is you decide.

In an age where it’s become increasingly acceptable to sit at your laptop during a meeting or to check your phone mid-conversation, the act of someone giving you their full attention is precious. They are looking straight at you, clearly hearing every word, and then they say something, and it’s completely clear, “There is nothing else going on here except the two of us discussing this situation.”

Humans do their best work when they feel safe and supported. There is a contingent of humans who believe they do their best work when the stakes are high, everyone is yelling, and the deadline is imminent. This is called “surviving,” while survival is fun, it’s not good work.

So, I listen. I ask questions, and I listen to your answers. I repeat the hard parts, and I watch you listen to me. For the record, these moments are when I most feel like a leader.

So You Decide (Whew)

So you decide, and we eventually make one of three discoveries:

  1. It was a good decision. What we expected to occur occurred. No surprises.
  2. It was a bad decision. What we expected to occur did not. More work.
  3. You don’t yet know the consequence of the decision. In my world, this means it’s a poor decision, still waiting to become good.

Yes, ideally, you want to make more good than bad decisions. Yes, when we discover this was a bad decision, there is additional work, additional consequences, and often a sense of regret. You might even wonder, Why didn’t you decide, Rands?

Hard decisions are full of experience. Full of it. You’ve got everything that transpired before the decision was required. Then there’s the crystalizing realization a change must be made, and a hard decision is necessary to enact that change. Then we’ve got all the work we do to make the decision. That’s pressure, people, debate, data, feelings, agenda, and politics. We’re packing months of experience into a short, intense period. Finally, and hopefully, there’s the moment when I convince you to decide. That is your decision, and I trust you to make it.

Even though I can make this decision, I spent a good chunk of time convincing you to because the experience you will gain by being accountable for this hard decision vastly outweighs the experience when I decide.

Earlier in this piece, I wrote I was disappointed when you asked me to decide. I’m not disappointed in you; I’m disappointed with myself. See, my primary job as your leader is to give you the skills and experience I’ve gained over the years. If I cannot guide you toward making the decision, I’m reminded I’ve not yet achieved my primary goal in our professional relationship.

My job is to teach you not to need me.