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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.

That’s what I mean by “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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“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.

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Declare bankruptcy and don’t be ashamed of it

I’m not talking about financial bankruptcy. I’m talking about all the other kinds of bankruptcy:

  • Email bankruptcy (anything important will come back up)
  • Backlog bankruptcy (because Backlogs are not idea buckets)
  • Books-to-read list bankruptcy (if your TBR list is 100+ books long, it’s not doing you any good)
  • Slack inbox bankruptcy (i.e., the first-day-back-from-vacation feeling)
  • Wiki bankruptcy (I wrote about this one before)
  • Social networking notification bankruptcy (this shouldn’t even be a question)
  • Browser tab bankruptcy (you can find stuff again when you to, but you won’t)
  • Garage/attic bankruptcy (don’t try to go through it, pay someone to haul it all away)

If you feel like declaring bankruptcy is a failure, stop that. It’s not a failure. It’s a fresh start. It’s a powerful tool and we should take advantage of it. It’s a weight lifted.

If your washing machine breaks, you can spend hours and hours learning how to fix the stupid thing, or you can toss it and buy a new one. Buying a new one is nothing to be ashamed of. It’s practical. You’re declaring dryer bankruptcy (I know the metaphor is a stretch, shut up).

Sure, if you declare bankruptcy on the same thing over and over, then you should examine your patterns about that thing. Bankruptcy is a voice that says “what can you do to make it unnecessary to do this again?”

Try it. Declare bankruptcy and come tell me if you don’t feel ten times better afterwards.

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Employee growth vs. project smoothness

The situation: Sandra builds polished, awe-inspiring features but she’s terrible at demoing them. Each Sprint Review meeting, she stumbles over her demo and speaks like she’s half asleep. She makes exciting new features feel boring and uncomfortable. What do you do?

  • The “project smoothness” option: have someone else demo her work for her.
  • The “employee growth” option: let her keep doing it for experience and give her lots of feedback.

Sometimes, employee growth is bad for the project.

The classic example is the battle between velocity and learning. Say George wants to learn React, and Sheryl has lots of React experience. Do you let George build the React-based feature to learn it? Or do you let Sheryl get it done in half the time?

If you’re up against a tight deadline, of course you’d let Sheryl take it. But I find that many companies would want Sheryl to take it regardless. “Faster is better, right?” Better than what? Better than people growing and learning?

It’s short term vs. long term thinking. Project smoothness leads to short term success. Employee growth leads to long term success. Long term success can be painful in the short term. If it wasn’t painful, then everyone would eat a perfect diet and exercise every day.

It’s hard to choose awkward Sprint Review demos now so that Sandra can be great at them later. But the alternative is that she stays bad at them forever. Is that a tradeoff you’re willing to make for a little short term success?

Think of it like a spectrum. Companies on one end value employee growth at the cost of everything else. Companies on the other end want each project to cruise at the cost of everything else. We could call the metric the “growth-pain-threshold”.

Where would you like your company to be on that spectrum? And where is it right now?

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Interviewing just because

I’ve been at my current company for 7 years, and I’m a raving fan of it. But when a decent looking job opportunity comes my way, I apply. Whenever I can interview for something interesting, I do it.

Why? A few reasons:

  • The only way to know if my company pays me fairly is by comparing to offers I get from other companies. Without that, how would I know my worth to the market?
  • Low stakes interviews are good experience. Whenever I do eventually need a new job, I’ll be better at interviewing and less stressed about it.
  • Interviews are efficient at pointing out my weak points. If I stumble on questions about roadmapping or testing automation or whatever, then I know that I should beef up those skills.
  • A job offer is proof that I’m not trapped in my job. If I turn it down, I’m staying because I want to, not because I have to. The opportunity to leave makes staying more fulfilling.
  • Interviews are fun when my livelihood isn’t on the line. I get to talk about the stuff I love with someone who is asking to hear about it. How often do you get that in everyday life?
  • Someday I may get the killer offer that I can’t turn down, and if I don’t interview then I’ll never know.

Am I wasting the interviewer’s time, when I have no plans to quit? No, I always tell them that I’m happy at my current company. If they still want to interview me, they know that I would need a killer offer at the end to make the leap. So far, no one has said “never mind” after hearing that, but they have an out if they want it.

Do you interview when you don’t need a job? Why or why not? Tweet me and let me know.

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Experimenting on myself

A couple months ago I wrote about how teams will let you try any crazy idea if you pitch it as an experiment.

Around the same time, I discovered that the same strategy works on myself. I can convince myself to stick with anything if I tell myself it’s only a week-long experiment.

For the past 6 weeks, each Monday morning I’ve settled on a new weekly experiment. I commit to it for the next week, and then next Monday I decide whether I want to stick with it now that the week is up.

Here are the experiments I’ve tried so far:

  • Write a blog post every weekday. This has been life changing and I’m still doing it.
  • Stop eating and drinking all dairy. I didn’t notice a difference in how I felt, so stopped after the week.
  • Lift weights for 10 minutes before sitting down to work each weekday. I’ve stuck with this one. 10 minutes isn’t much but 10 consistent minutes is better than an hour that’s not consistent at all.
  • Set an alarm every hour to drink water. Still sticking with it. I am so hydrated!
  • Take baths instead of showers. I hated it. I almost didn’t make it through the whole week.
  • Keep my phone in the kitchen at all times so I’m not constantly distracted by it during family time. This is the one I’m starting this week – we’ll see how it goes.

A week is the perfect amount of time for me. It’s easy to say “for the next week, I’ll lift weights for 10 minutes before sitting down to work.” But without the “for the next week” part, it feels crazy.

Therein lies the power. Things seem possible for a week but impossible when I’m thinking long term. But once I’ve done it for a week, long term doesn’t seem so impossible.

Here are some ideas I have for future experiments:

  • Drink tea instead of coffee
  • Each day, send a quick thank you email or tweet to someone who’s work helped me that day (a blog post writer, a Stack Overflow responder, a book author, etc.)
  • Spend 10 minutes with YouTube videos each day learning to draw
  • Eat only plant-based foods until dinner
  • Track my time down to the minute during working hours
  • Every day, reach out to a different friend/acquaintance I haven’t spoken to in years

I’m excited to keep experimenting on myself and seeing where it takes me.

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Dating our clients

Client relationships have a lot in common with romantic relationships. This is well documented elsewhere.

Let’s start with the obvious parallels:

  • Flirting and courting = the sales process and trying to win the bid
  • Facebook official = signing the contract
  • The honeymoon phase = the first couple sprints when everything is still exciting and new
  • The first fight = the first disagreement (often about scope)
  • The messy breakup = using the termination clause in the contract
  • The amicable breakup = a successful completion of the project
  • The messy divorce = someone gets sued
  • The long term relationship = a trusting partnership with no end date (this is the holy grail for many people, but not all)

But romantic relationships are about love! Client relationships are about money! That is an important difference!” That’s why I didn’t say that client relationships are exactly like romantic ones. But to be fair, aren’t both love and money about mutual benefit?

I could keep going and start talking about where kids and joint mortgages fit in, but it all gets very boring.

It’s more interesting when we apply the power dynamics of romantic relationships. Esther Perel, a well known psychotherapist and speaker, was on the Tim Ferriss podcast a few years back. She said something that stuck with me enough to motivate me to spend 15 minutes finding the exact quote:

In every couple you will often find one person who is more in touch with the fear of losing the other, and one person who is more in touch with the fear of losing themselves.

One person more in touch with the fear of abandonment, and one person more in touch with the fear of suffocation.

Esther Perel (transcript here)

Are client relationships like that? I think so. It could go either way:

  • The client is afraid that the contractor whom they rely on will move onto a higher paying or more interesting client (fear of abandonment)
  • The contractor is afraid that continuing to work with their client will prevent them from growing and learning new things (fear of suffocation)

Or, going the other way:

  • The client is afraid that the contractor’s low quality work or outdated solutions will hold them back (fear of suffocation)
  • The contractor is afraid that the client will fire them and hire someone selling shiny new unproven technology (fear of abandonment)

Does any of that sound familiar? It does to me.

Who holds the most power in those situations? Obviously we’d prefer that whatever side we’re on has the power. But ideally both sides would hold equal power, so neither side needs to act out of fear.

It sounds like a chicken/egg problem: do we equalize power by getting rid of fear, or do we get rid of fear by equalizing power? But that’s a false dichotomy. Those are both symptoms of the larger issue: we aren’t communicating. Fix the communication and we fix both symptoms of it.

In a romantic relationship, we’d want to talk about this stuff, right? Get it out in the open and have a mature, honest conversation. Maybe even see a relationship counselor.

So why not do that with our client? It goes back to my post “Hide a problem from your client and now you’ve got 2 problems“. If we’re feeling a fear of suffocation or abandonment, or we suspect that they are, why wouldn’t we bring it up and talk through it with them?

What do you think? Tweet me!