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The Magic Tomato

October 2, 2012 by 2 Comments

A new productivity idea has been making the rounds lately, called the “Pomodoro” technique.  I’ve been using it quite a bit at our startup, and it’s been a great help, so I thought I’d share it on the blog.  The name comes from the Italian word for “tomato”, because the inventor (Francesco Cirillo) had a kitchen timer in the shape of a tomato that he used when he was coming up with it.

Pomodoro is really helpful for doing focused work on important projects, especially when they require creative or deep thinking.  It’s so easy to get distracted by easier work or email or interesting discussions with co-workers.

I use Pomodoro for projects that

  • Don’t have clear short-term milestones.  For example, I spent a number of weeks diving into the latest techniques in machine learning and figuring out how to apply them to our product.  This project took hundreds of hours and I just had to chew away at it day after day, working through the algorithms and how we can use them most effectively in our application.
  • Are hard.  In most jobs, there are a myriad of useful and productive things to work on.  A few of them are really important … but the others are often a lot easier.  It takes very little intellectual effort to update the feature spreadsheet, or answer some emails, or do a QA pass over the website – all fine and useful things to do.  But they aren’t the projects that are going to yield huge amounts of value.  Often, a project is “hard” because you don’t know what to do.  You just have to bash away at it until you figure out how to get traction (possibly using some of the ideas from the “crack the nut” post).  Or, it might be hard because you are trying to create something new, and that can be scary.

So How Does It Work?

There is a detailed online guide, which is well worth looking through.  I do find that it can be overly prescriptive about how you are supposed to use the technique, and my approach is somewhat simpler.

Say you have a project that you want to focus on.  The basic idea is that you tackle it in blocks of time, choosing the block size that works for you.  The guides recommend numbers like 25 minutes; I have found that 50 minutes tends to work best for me.  You commit to working for that long without stopping – no answering the phone, no getting up, no checking email, no distractions.  You just work.  If anything comes up that you need to attend to, write it down and get right back to work – don’t do anything else about it.  At the end of the block of time, you stop and get a rest period, where you can deal with things that came up, check email, etc.  The rest period might be 10 or 15 minutes, or whatever works for you.  Check off the Pomodoro when you finish it, and it doesn’t count if you didn’t spend the entire time on your project without stopping.

At the start of the day, I might decide that my goal is to do (let’s say) four 50-minute Pomodoros.  Maybe I’ll spend two of them on machine learning, one designing our user profile system, and one on learning about business metrics for SaaS companies.  I find this approach works really well, because it makes it pretty easy to line up my time against the really important priorities.  The chunks of time are big enough that you can make decisions about them pretty easily.

At the end of the day, I’ll look at how I did.  If I didn’t get very many Pomodoros checked off that day, I know that I wasn’t able to focus on the projects that I wanted to.  I got interrupted, or other things came up.  That’s ok .. the point is not to beat yourself up, but it is important to be honest with yourself about whether you are really moving ahead on the things that matter, and if not, figure out what to do about it.  You’ll also be surprised at how few Pomodoros you can really get done.  In a multi-tasking environment with meetings and so forth, you might get zero significant blocks of utterly focused, undistracted time.  In a startup with virtually no meetings, I’m able to get several 50 minute Pomodoros done on a really amazing day, which is an incredibly good feeling.

Why It Works

One of the things I really like about this technique is that it makes an open-ended project quantifiable.  A multi-week or month project that doesn’t have a lot of interim milestones suddenly has a countable milestone every 50 minutes of work.  You can plan in terms of these chunks of time, you can check them off, and you get a feeling of progress even if there isn’t anything else you can really point to.  I think most people find it much easier to work on a project when there are tangible results along the way – I know that I definitely do!

It also makes it much easier to psyche myself up for a big hard task, because I know that I can stop in 50 minutes – it’s a real comfort to know that no matter how bad things get, I only have to push for that long and then I get to stop.  What almost always happens in practice, of course, is that once I get going, the project sucks me in and I pound happily along, annoyed when I’m “forced” to stop at the end of the work period.  But there is a lot of research that you are most productive if you do sustained bursts of work with breaks in between.  It’s also healthy to get up and stretch regularly.

Another good thing is that it gives you permission/”coerces” you into ignoring potential interruptions.  When you are doing something intense or creative or hard, it’s death to be constantly starting and stopping – you don’t get into that flow that is so magical.   When you are in the midst of a Pomodoro and you know that you won’t get to count it if you let yourself get pulled away, you actively resist interruptions.

Tools

You can do a fine job of using the Pomodoro technique with nothing but a piece of paper and a watch or a kitchen timer.  I do use two pieces of software that I find helpful:

  • My Little Pomodoro – a cute little app for the Mac that will time your Pomodoro interval and chime at the end.  There are several apps like this, or you can also use a kitchen timer, or just your watch/smartphone.
  • Omnifocus – a great productivity tool I’ll write about in another post; the key thing for Pomodoro is that any time I want to note something, I just hit a quick key combination, type in a phrase, and hit return.  The window disappears, and I know the note is squirreled away where I can (and will!) deal with it later.  A lower tech solution is a piece of paper that you scribble a note onto.  Anything works if it is a quick and dependable place to jot down an idea or task, so you can forget about it and get back to your Pomodoro work.

Since I work in an open office, I have a bit of a ritual for starting the Pomodoro.  I put on noise cancelling headphones, start up a special playlist of music (my favorites are choral pieces from the 16th and 17th century), start up the Pomodoro app timer, set the program I’m using to full screen so no other software will be visible … and WORK.

When To Use It

Paul Graham wrote a wonderful essay about the difference between a “maker’s” schedule, and a “manager’s” schedule.  When your time is divided up for you, where things are very structured, and you go from meeting to meeting or activity to activity, you don’t need Pomodoro.  But when you are taking on something open-ended and creative, or you have to think really hard about a problem you don’t know how to solve .. give it a try.  Perhaps you will find that it is as magical for you as it has been for me!

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The Rip Van Winkle Question

July 18, 2012 by 2 Comments

Several years ago, I become responsible for a reasonably large business.  As you’d expect, the team regularly reviewed progress using a series of reports full of numbers.  Page after page of them, with thousands of numbers, analyzing performance by region, by pricing level, by licensing model, by customer type – you name it.

To an expert, these reports were filled with wonderful nuggets of insight.  Wow, what happened to sales in Germany last quarter – why did they tank even though the competitor’s results were strong?  Clearly, the Japanese sub is the only one leveraging the price increase – their average revenue per unit is spiking while everyone else is just plodding along.  And so on.

To somebody who was not expert (i.e. me), it was just a wall of numbers that didn’t convey much of anything.  To get a sense, check out a report like this one.  If you are an experienced investor, or used to reading accounting statements, you can glance over it and almost instantly you know a lot of interesting things about Google as a business.  If you aren’t, your eyes probably glazed over and you are hoping there won’t be a pop quiz at the bottom of this blog post.

In my case, I didn’t even know what half of the numbers on the business reports were about.  What the heck was the “PSP attainment vs. seasonality adjusted target”?  Did it matter that we seemed to be below what we had originally expected?  But I had to get smart quickly – these reports were the lifeblood of the business.  It’s like a medical chart to a doctor; they can spot patterns that reveal what is happening to their patients.  I had just become the doctor for this business, and I needed to know if the patient was suffering from any serious illnesses, so I could do something about them pronto.

So How to Start?

The best technique I’ve found is what I call the “Rip Van Winkle” question.  If you aren’t familiar with the short story, Rip was a man who fell asleep for twenty years, and found that the world had changed dramatically when he woke up.

What I did was to take every important angle on the business and find somebody who was really smart about it.  Then I sat down with them and asked the key question: “if you fell asleep for a year or two, when you woke up, what are the first things you would look at on this report to understand how the business is doing?”  Over and over again, I got amazing insights by asking this.  “Well, the first thing I’d do is look at new sales in the enterprise segment to make sure we are getting growth instead of just milking the installed base.  Then I’d divide that by the number of units for a quick check that our price was holding up and we’re not jacking up sales with deep discounting.  Then ….”

I did this walk-through with around 30 people, for a total of some sixty hours of discussions.  Finance people told me how they analyze the finance numbers.  Customer service showed me how they track and assess problems and customer satisfaction.  Sales managers talked about the pipeline and performance and hiring.  Often, different people would take me through the same report, and come at it from radically different directions.  I took copious notes, but I always asked for the top 2-4 things they would look at first.  I would highlight and number the places that held the answer.

Vital Signs

It turns out that for just about any report, even if it has hundreds or thousands of numbers on it, there are a handful that really tell the crucial story.  The rest of them might be useful to support the story or diagnose a problem, but you mustn’t get distracted.  In medicine they call them your vital signs – tell me your pulse and whether your eyes dilate and a couple of other things that can be measured by an EMT in seconds, and I will know if you are basically ok or deeply traumatized.  I may not know if you had a stroke or a concussion, but I’ll have a good basic sense of how you are doing.

This technique hinges, of course, on finding insightful people with an intuitive mastery of the numbers.  I could never predict who it would be from the org chart – they might be high up or buried deep.  But the people who worked in that area almost always knew whom I should talk to.  Ask around!  Once I found the right people, they were usually happy to share some wisdom with an interested and enthusiastic listener.  Buying them lunch never hurt, either.

By the end of those sixty hours, I was pretty darn good at diagnosing the business from the numbers, because I had learned from such a wide range of experts.  The process also turned out to be a useful diagnostic tool in its own right.  If I couldn’t find anyone in an area with great insights to share, chances were pretty good this was a side of the business that wasn’t being managed very well.

What I’ve learned by doing this exercise many times is that project reporting is almost always far too detailed – it’s like the old story about writing a shorter letter if you had more time.  It’s very hard to distill a lot of complexity into a tight report that shows only the key things – that means you have to figure out what those key things are (and have confidence that you didn’t miss anything vital!) – so most people cop out and throw in the kitchen sink.  As you are ramping up, think about how to cut way down on the amount of information being reported.  More is definitely not better, when it comes to metrics.  Einstein’s famous dictum applies perfectly here – “make things as simple as possible, but not simpler”.

The next time you have to get smart about a report full of numbers, give the Rip Van Winkle technique a try, and see if it works as well for you as it has for me.

Filed Under: 1000x, 100x, 10x, 1x, Rhythms of Business Tagged With: , ,

As the leader of the forces opposing evil in the universe .. you’re fired!

June 7, 2012 by Leave a Comment

Epic tales are a lot of fun to read – the struggle of good and evil, the climactic moment of truth when the future of humanity or the world hangs in the balance.  They also can provide good insight on managing complex projects .. or rather, how not to.  There are some great lessons to be learned from the bungling incompetence of fictional heroes (and yes, this point of view can make you a real buzzkill, so you might want to keep these thoughts to yourself!).

Risk Mitigation and Contingency Planning

The worst sins of omission are basic risk analysis, mitigation, and contingency planning.  Very brittle plans are made, with no effort to figure out a Plan B if something goes wrong.  That makes for great drama, but it’s lousy planning.

Let’s start with Lord of the Rings.  It’s a great story that I have loved since I discovered The Hobbit as a ten year old – it has edge of your seat excitement with a richly detailed universe as the backdrop.  But come on .. what kind of a grab-ass plan was that for saving the world from evil?  We’ve got a group of clueless hobbits wandering to Bree with the Nazgûl charging around and almost catching them. The hobbits are supposed to hook up with Aragorn, but they don’t even know what he looks like – would it have killed Gandalf to give them a description?  How about an escort?  The great civilizations of Middle Earth are facing Armageddon, and they can’t scare up a couple of people to help out?

On Star Trek they are always beaming the ship’s top officers onto a potentially hostile and unknown planet, leaving the Enterprise with mostly junior people to run it.  What’s up with that?  They probably shouldn’t be sending most of the senior officers into harms way in the first place.  And, a Constitution class starship is a massive investment and a jewel in the crown of the Federation .. how come they don’t have enough seasoned officers on board to be fully covered even if four or five of the most senior ones insist on wandering into danger all the time?

In the wonderful fantasy series “The Dark is Rising”, they almost lose the ancient artifacts that determine the victory of good or evil because .. somebody left a note with a family and they happened to forget to deliver it.  Really?  Come on!  If that’s the best you can do, time for a new project manager who has a clue.  To drive a complex and crucial initiative, think about the aspects of your plan that are fragile and could easily go wrong, and build in defense in depth.

The Dark is Rising heroes not only made one dumb and potentially fatal arrangement, they keep doing it.  Don’t be like them.  If you see a particular breakdown, think about the underlying causes and address them.  Don’t settle for the obvious explanation – dig deeper.  Say you are running an online service and it went down .. why did it happen?  Well, there was a bug in the code.

  • Sure, but why did the bug slip through?  Do you need better tests?  More tests?  More realistic load testing?
  • Why did it happen in the first place?  Was there some communication breakdown?  Is the architecture of the system too baroque?  Are there missing levels of abstraction between system components?
  • Why was it hard to find and fix?  Do you need better diagnostics?  Better logging?  Better monitoring?
  • Why did it affect so many people?  Could you have a more loosely connected system?  Could components be more resilient when others fail, and degrade the user experience more gracefully?
  • Why were you down so long?  Does it take too long to deploy a fix?  Too much time to restart components that depend on it?

In running a project, you often have to make bets and take gambles – that’s part of the game.  However, you should think about the key bets you are making, and what will happen if your bet is wrong.  How quickly can you tell that you made a mistake (and be fairly sure about it)?  What will you do to reverse course or mitigate the failure?  Are you keeping anything in reserve so that you have some resources you can apply to help rescue the situation?  If you are making an unrecoverable bet, are you clear about that and about the due diligence you need to do up front?

Defining Roles

One of the common sources of confusion and inefficiency in a team is not knowing what role everyone is supposed to play.  Often, you can muddle along until something really important comes up, and then under stress the team works very poorly to resolve the issue.

Think about Boromir and Aragorn – after Gandalf fell into the cavern fighting the Balrog, they hadn’t resolved who was left in charge of the group.  Boromir deeply disagreed with the strategy Aragorn laid out.  Frodo decided he didn’t want to be with any of them any longer.  Since he was the ring bearer, ultimately it was his decision .. but nobody had given much thought to it.   It’s critical to figure out how the most important decisions are going to get made, and it’s a lot easier to do that before you are in the middle of a stressful situation with emotions running high (though hopefully you won’t be getting attacked by the Uruk-hai).

Thinking Out of the Box

It’s easy to get trapped into conventional thinking.  We’re all prone to unconscious assumptions – how things are supposed to be done, constraints we think we have to live with.  For example, Gandalf is close friends with the eagles, who can .. fly.  While carrying riders, and even outmaneuvering the fell beasts that the Nazgûl are riding later in the story.  So why is the Fellowship slogging their way through the mines of Moria and playing tag with terrifying ancient spiders, when they could get to Orodruin in a couple of hours?  Maybe with some Legolas-class archers along to provide suppressing fire in case anybody tries to interfere?  The whole thing could have been wrapped up and the hobbits tucked cozily back in their beds after a nice end of the day snack, before Sauron had a clue.  This idea is hilariously developed on “How it Should Have Ended”.

In life, it’s impossible to identify and question all your unconscious assumptions .. but you can tease out the most important ones.  Ask yourself what you are assuming, and whether you have the evidence to back it up.  Ask “what do I have to believe?” in order to justify a proposed course of action, and see if you can get some kind of backup that those things are really true.  Or a way to notice that they aren’t, so if you are on a delusional path, you’ll figure it out as quickly as possible.

Learn From Everything

I have found that there are great lessons to be learned about accomplishing your goals from every life experience.  Learn on the job, by all means, but I try to make everything grist for the mill – books, stories, movies, tales from history .. it all provides insight and inspiration to help you pick the goals that matter to you and to find ways to achieve them.  And before you decide that “actually, hope is the plan”, remember that in real life, you aren’t the main character.  There is no author who will turn your heedless folly into an exciting story of success against all odds.

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