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Becoming a leader, the hard (and only) way

If you want to be a leader, start leading. That’s it. There’s no shortcut.

Stop waiting for someone to give you a leadership opportunity. Leadership is not a thing you’re handed, it’s a thing you take.

There’s no white horse of truth and justice to come down and make everyone believe you’re a leader. That’s your job. I don’t care if your CEO says “OK everybody, this person is your leader now!” People will only think of you as a leader once you’ve shown that you are one.

So speak up. Be the first to support, unblock, advise, answer, volunteer, plan. Find the cracks in the project that need filling, and fill them. These are the things that make a leader.

Start leading, and leadership will follow.

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How easily our lives could have gone differently

I met my wife when I was 15. She didn’t go to my school but she was friends with a girl I sat next to in math class. I was in a chat room with that girl on a lazy Saturday afternoon when my future wife joined.

Everything about my life ended up depending on moment. My kids, my career, my house, my wife, the college I went to, the car I drive, how I spend my free time, who I spend it with, the food I eat, the clothes I wear. Everything.

I would have gone to a different college and never found the CS course that decided my career path. I would be single or with someone that I wouldn’t like as much. Would I have different kids? What would they look like, those little strangers? Would they also argue about who gets to sit next to me on the couch?

Who knows where I’d be living, what I’d be doing, what I’d want out of life, what I’d be missing.

Who knows what I’m missing now?

And yeah I know, the butterfly effect is a thing that people have been talking about for decades. But this is my life. It’s all I’ve got. And everything about it came from my seat in math class and an afternoon when I was bored enough to join a chat room.

Sometimes life just slips in through a back door, and carves out a person and makes you believe it’s all true.

She Used To Be Mine, Sara Bareilles

Or should I go back further? Was it that my parents moved to a neighborhood zoned for that high school before I was born? Was it that my parents met each other in the first place, at the same college that I ended up going to?

There are so many things that had to happen just so to make us who we are. Too many things. How did I ever feel like I had power over my life, when it could be decided by a chat room on a bored Saturday afternoon in high school? How lucky am I to be happy with the life that chat room gave me?


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Should bug tickets count towards velocity?

No. No they should not. Here’s why:

Reason #1: We already earned those points when we built the feature. We don’t get more points because the feature is buggy. An 8 point feature is 8 points no matter how much time it takes or how many bugs we introduce.

Reason #2: Bugs should hurt velocity. If we count bugs toward velocity, then we’re rewarding bug-riddled features.

Reason #3: Estimates for bug tickets are random. For most bugs, 90% of the effort is the investigation. There’s no way to know how involved that will be. Any estimates we give those tickets are guesses, so why bother?

Reason #4: Velocity measures complexity, not value. Bug fixes can be as valuable as new features, so why shouldn’t they contribute to velocity? Because story points don’t estimate value, they estimate complexity. If we want to measure value, then that’s what Value Velocity is for.

If you disagree, then consider whether your definition of a “bug” is too loose. A requirement that changed or was never documented is not a bug. A feature that doesn’t work how someone wants is not a bug. Those are changes. A bug must contradict the requirements as written when you built the feature.

If you’re still objecting, then let me know why! I’d love to hear your thoughts.


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Guerrilla productivity tactics

Does your productivity ever come at the expense of your team? Mine does, sometimes. I like the term “guerrilla productivity” for these tactics.

Guerrilla productivity tactics burn relationship capital. Use them too much and people won’t like working with you. But when used rarely and with caution, they can save a deadline.

Here are some examples I use:

Block off an entire day per week on my calendar. Some people call this a Focus Day. No meetings, no Slack, no emails, nothing. As far as my coworkers are concerned I’m on PTO, but I’m actually getting crap done.

Ask someone to yell at me until I’m done. I’ve done this with my boss a few times. If there’s something I’m putting off, and nobody is watching over my shoulder to motivate me, then I tell my boss to be that person. He bugs me off and on until I get it done.

Delegate my “Ugh Tasks” to someone else, anyone else. This one can feel especially jerk-ish, but wow is it effective. When there’s something I’m dreading and avoiding, I can make someone else do it.

Block Slack except for 5 minutes every hour. I’ve written about this before. When it’s blocked, it’s blocked. I can’t open it even if I want to. I only have a brief window every hour to respond to messages before it’s blocked again. This saves me from myself.

These tactics run the risk of annoying my team. They’re all obnoxious things to ask of people. That’s why they’re guerrilla productivity tactics. They’re good for me and bad for everyone else.

  • If my team can’t reach me for an entire day for questions or support even though I’m not on PTO, that’s annoying.
  • If someone has to spend their valuable time making sure I’m focused, that’s annoying.
  • If I hand off my most dreaded task to some poor unsuspecting coworker, that’s annoying.
  • If I’m in a conversation with someone on Slack and poof, I disappear for 55 minutes, that’s annoying.

That’s why I have to tell my team what I’m doing. I tell them I’m blocking Slack to get ticket 1234 done. I tell them I’m taking a Focus Day on Tuesday to finish the Sprint. I tell them I need to delegate an annoying task, and I ask for volunteers.

It’s still obnoxious, but I’m admitting that up front so nobody can hold it against me (as much). So far, that has shielded me from being hated, at least to my face.

What are your guerrilla productivity tactics?


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Write 5x more but write 5x less

There are 2 things I have come to believe about writing:

  1. The average person should write 5x more things than they do.
  2. The average written thing should be 5x shorter than it is.

See? Write 5x more but write 5x less. Write more often, but make each thing you write shorter.

I don’t care what it is. Blog posts. Novels. Google docs. Articles. Wiki pages. Write more of them, but make them shorter.

Why write more often?

  • Because writing helps thinking.
  • Because practice will make you better.
  • Because writing is more shareable than speaking.
  • Because humans are worse than computers at storing knowledge.
  • Because writing your old thoughts frees your brain to think of new thoughts.

Why make them shorter?

  • Because the shorter it is, the more people will read it.
  • Because of the Pareto principle: 80% of the value is in 20% of the length (hence “5x shorter”).

So write more, but write less.


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Process Teams

Slide deck presentations are the worst way to share knowledge remotely

Nobody is paying attention to your remote slide deck presentation. In person? Sure. But not remote. They’re distracted. They’re multitasking. The internet is irresistible when there’s nobody watching over their shoulder.

They’re catching up on email or checking Slack or playing online poker or getting some actual work done. At best, they’re listening to you in the background.

Give it up. Stop spending hours putting together presentations that help no one.

Instead, write up a document and share it around ahead of time. Let people read it and understand it on their own. Or, do what Amazon does and set aside reading time for it at the beginning of the meeting to remove all excuses.

Then the meeting itself can be a Q&A or a discussion instead of a presentation. You can use your time together to be together and to dig into the topic as a group. It’ll be more valuable for everyone, including yourself.


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Self Help

Skill stacking

Scott Adams, the creator of Dilbert, wrote about how to reach the top:

If you want something extraordinary, you have two paths:

1. Become the best at one specific thing.
2. Become good (top 25%) at two or more things.

Scott Adams (source)

Number one, he says, is as good as impossible but number two is easy.

It’s called Skill Stacking. I went down the rabbit hole and found this excellent post with this image:

See that little fella in the middle there? That’s the sweet spot.

I will never be the best in the world at running or programming or writing or agile process. But I can be in the top 25% of each. If I can find a way to combine two or more of them, then I can be the best at that combination.

I could build an audiobook reader app specifically for runners. I could create a niche blog for programmers who run. I could apply for Strava’s engineering team. I could write a book on how to apply agile principles to running.

Here’s another example, plucked from a random Hacker News comment:

I learned this lesson from Clifford Stoll. He said that astronomers figure he must be an exceptional programmer, since he’s clearly a mediocre astronomer. While programmers figure he must be an exceptional astronomer, since his programming is strictly middle-of-the-road!

samatman on HN

Of course, there are different types of skills. You’ll have trouble combining some skills, but others are universal. Public speaking, writing, marketing, programming, charisma; these can stack with almost anything. Scott Adams says this about public speaking:

I always advise young people to become good public speakers (top 25%). Anyone can do it with practice. If you add that talent to any other, suddenly you’re the boss of the people who have only one skill.

Scott Adams

It’s a fun thought experiment. List the things you’re pretty good at, and brainstorm ways to combine 2 or more of them. What do you come up with?


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“If you want a task done quickly, ask a busy person to do it.”

That quote has been around since at least the 1850’s. I heard it a while back and immediately rejected it as nonsense. Then it kept bugging me for another week or two, so I tweeted about it.

I got exactly 3 responses, and they’re all fascinating:

The assumption here is that busy people are do-ers, and non-busy people are watchers. And you’d trust a do-er with your task more than a watcher, even if the do-er is busier. Seems reasonable to me.

It’s not the busyness itself that makes a person a good choice for your task. It’s that busyness is usually a trait of a do-er. If you could somehow find a do-er who wasn’t busy, that would be ideal. But do-ers by definition tend to be doing stuff.


Ouch. Too real. The quote is from a bygone era, meaning it dates back at least 150 years. So that part is correct. But were people spending their time on more meaningful tasks back then? Did deep work vs. shallow work exist 100+ years ago like it exists today?

They didn’t have Slack, Zoom, email, or even telephones to fill up their days with shallow work. So it seems reasonable that “busy” back then meant something more than it means now.

Then again, they couldn’t use computers or robots to automate the monotonous parts of the job. Maybe “busy” 150+ years ago meant manual number crunching and hand writing and paper folding?

I’m not sure, and my Google searches about this have ended in frustration. Anyone have any insight?


I didn’t expect Parkinson’s law to make an appearance when I tweeted that. But that’s the thing about Parkinson’s law; it likes to sneak in when you don’t expect it.

The more time you have for a task, the longer it takes. If you want something done quickly, give it to someone who doesn’t have much time for it. I love that interpretation.


What do you think? Is this quote a relic, or is there still some wisdom to be had here? Tweet me and let me know!

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2 months of daily blogging

For the past 8 weeks, I’ve posted to this blog every weekday. That’s 40 posts and counting.

It started as a personal experiment (because personal experiments are my new thing):

By the time August was up, I was having too much fun to stop.


Here are a few of my original misconceptions:

I won’t be able to think of that many topics!” Turns out, the more I write, the easier it is to think of more things to write about. My ideas list is growing faster than my published list.

It’ll start to feel like a chore.” I’m not saying this will never happen, but it hasn’t happened yet. I still look forward to it every day.

It will take a lot of time, and some days I’ll be too busy.” I got around this by telling myself that it’s fine if some posts are only a paragraph or two. My rule of thumb is “anything longer than a Tweet is long enough for a blog post.” Everyone should write more, shorter blog posts.

Nobody will read it.” First of all, I was wrong. I got a lot more traffic than I expected (see the stats at the bottom). But it didn’t matter anyway, because traffic is irrelevant. Writing without an audience is better than not writing, which brings me to:

Writing won’t benefit me much.” Oh, past Critter, you sweet little idiot. Writing daily has helped me in two major ways:

#1: I don’t know what I think about something until I start writing about it. I make connections and discover opinions I didn’t know existed in my brain. Yeah I know, “everyone knows that writing helps you think.” But experiencing it firsthand has been bizarre and fantastic.

#2: It’s helpful to have a blog post handy when I get into a discussion with someone. Instead of summarizing my thoughts over and over again to different people, I can shoot them a link. Beware, it’s tricky to do this without sounding like a know-it-all jerk. But in the right context and with the right tone, it can work and save everyone a lot of time.


Finally, some stats for those 8 weeks, if you’re curious:

The Pareto Principle (i.e., the 80/20 rule) is popping up here. Out of those 40 posts, the top 2 brought in almost 2/3 of the views. In fact, the top 8 posts (i.e., the top 20%) accounted for 85% of the views. So instead of 80/20 it’s 85/20 so far!

Another example: Hacker News gave me almost half of my traffic.


I plan to keep the streak going as long as possible. Seth Goden says the first 1000 are the most difficult, and I’d like to see if that’s true.

If you’ve made it this far, I challenge you to write every day for just one week. If you want to stop at the end of the week, then stop. But if not, keep going and see where it takes you.

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If you want to be heard, listen

I’ve read a lot of books on dealing with conflict, helping teams to jell, giving feedback, heck even parenting grumpy toddlers. The one thing they all say is that nobody’s going to want to listen to you until they feel heard.

The book Difficult Conversations hammers it home particularly well. It talks about “learning conversations” where you listen, ask questions, paraphrase, and acknowledge.

Listen to understand their perspective on what happened. Ask questions. Acknowledge the feelings behind the arguments and accusations. Paraphrase to see if you’ve got it. Try to unravel how the two of you got to this place.

Difficult Conversations

The purpose isn’t to convince them that you’re right. It’s to understand their opinions and share yours. Once they’re sure you understand them, they’ll be in the right mindset to listen to you.

Maybe this is common knowledge to everyone except me, but it’s been huge in my life. I’ve had some breakthrough conversations with people based on this one simple concept.

Here’s a full outline of running a difficult conversation from that book, if you’re curious.