Cater to Your Personal Pathologies

Managing your time, I’ve found, is mostly a psychological problem rather than a logistical one. Many books lay out a particular system – from the Covey quadrants to David Allen’s 43 folders to a sea of nifty acronyms. What I’ve found from trying them out, and watching others try to use them, is that a system only works if it matches your particular needs. More specifically, if it caters to what I call your pathologies.

We all have some idealized version of ourselves that we aspire to be. This paragon of virtue may never procrastinate, or always rise above temptation .. whatever takes your fancy. Then there is the actual, flawed, imperfect person we actually are. Many people try to use a system that ought to work, rather than one that does work (for them). Hence a sea of unused DayTimer notebooks, mountains of abandoned organizational gear, and endless hopping from one To Do app to another. If cosmetics are “hope in a jar”, then organizational tools are “hope in an app” (or for the traditionalists, “hope in a binder”).

So what do I mean by pathologies? I don’t know what yours are, but I’ll share some of mine.

I Hate Clutter

Some people feel comfortable surrounded by things. They naturally keep papers in piles and leave lots of things lying out on desks. Not me – I like a spare and streamlined work environment. How does this relate to being productive? A friend of mine built an elaborate set of rules for sorting his email. Messages were passed automatically to a lovingly organized cascade of email folders. It worked well for him and was really cool, and I thought I’d give it a try, too. Result: disaster.

All my mail would come in, be sorted into the appropriate category, and I would look at it and be soothed by its orderliness. The problem is that I achieved this calm and pleasing result without actually doing anything. I had to throw away the whole thing and go back to having everything pour into my inbox and annoy me. Then I would be motivated to clean it up, by actually looking at the mail, making decisions, and taking action.

I Like To See My Whole World in One View

When I’m figuring out what to do, I like to see everything that matters all at once. I get stressed out when there are things I need to be thinking about, but they aren’t in front of me so I’m not sure I’m remembering all of them.

I like to plan out my week every Monday morning, and for many years, I have used two facing pages in my notebook to show: the big projects I’m responsible for, any deadlines for the week or in the near future, active to do items, key appointments, top priorities for the week, and top priorities for each day. It is a challenge to capture all that in two pages, but I’ve found it to be a really good exercise – it forces me to think about what’s important and distill it. Each time I have a new kind of role, I have to change those two pages. What I needed to capture when I managed a big team was radically different than when I’m a team of one in a startup and mostly work by myself on a set of projects. I keep those two pages open on my desk most of the time, so I’m always reminded of the most important things that I’m supposed to do that day and that week.

I could keep going for a while (I like to write and draw on paper, I can’t use bound journals because pages can’t be inserted or rearranged, ..), but I’ll spare you, because the important thing for you is to figure out what your pathologies are.

Sleuthing Them Out

A good way to start is to ask yourself:

  • What system has worked well for me? What did I like about it? Why did I like using it?
  • What didn’t work? Did it fail (you kept forgetting to do something important), or was it too much overhead, or did you just stop bothering with it? Why?

Remember, this is not about some idealized vision of yourself, or what works for somebody else – this is all about you. When you answer these questions, especially the second one, try to avoid value judgments – it’s not constructive to beat yourself up with things like “I’m lazy” or “I suck at organization”. Stick to thinking about what you have tried, what worked, and (for the things that have not) why they failed you.

The answers might be psychological (“I like writing things on paper because it is more visceral and I feel more committed to getting it done”) or mundane (“I didn’t carry around the binder because it was heavy and didn’t fit in my bag”). Don’t scorn the details – your whole system can founder if you just don’t like using it. If the color of the notebook bugs you, or you have a fetish for fountain pens, pay attention. If you are using an app, the details of the user experience matter a lot. “This app made me set up all these categories and I just got lost – I need something simple.” Or “I hate looking at the interface – it’s ugly”.

Your “system” might be very informal – maybe you like post-it notes on your monitor. Or piles on your desk organized a certain way. As long as it works for you, that’s what matters. Try to figure out how to eliminate any friction that prevented you from using (or wanting to use) some solution. Try to enhance any quality that you really like.

At the end of the day, the measure that your approach works is that you know what is important and you get it done. Then you have created a magical accelerant for your life.

Kissing Frogs Part 3: Frog Dos and Don’ts

The first two posts in this series were from the point of view of the interviewer.  But suppose you are on the other side of the table?

Do’s

Do your research.  It’s really disappointing for an interviewer when a candidate doesn’t have the first notion of what the company or the team does, and it’s great when they have intelligent questions.  “I tried out your product, and it seems like one of your big challenges is integration with systems that customers are already using.  Is that right?  How are you handling that?”  So much better than somebody who doesn’t have a clue.  These days you can learn staggering amounts about almost anything on the Internet.  So check out the company, the project, and the people.

Do practice.  Interviewing is unnatural for most people.  You won’t have concise soundbites ready to roll out about the work you did in previous jobs.  You may be rusty or misremember the details.  It’s very, very useful to have some mock interviews before you go into the real thing, especially if you can do it with experienced interviewers who will be honest enough to give you candid feedback.

Do interview them.  You are preparing to commit huge amounts of your time to this team and this project.  It’s probably the biggest investment decision you are going to make – your time is your biggest asset.  So learn as much as you can while you are there.  Are these people you actually like?  Is the work inspiring?  Will you learn something and stay engaged for the long haul?

Do prepare.  Be ready for hard questions.  “Why didn’t you finish school?”  “Why do you jump from job to job?”  “Why have you been unemployed for the last two years?”  “Why did the product you worked on get panned by every review?”  Look over your resume through the eyes of a stranger (or ask another person), and think up the most difficult questions you can.  Answer them honestly, be open about mistakes (if appropriate), and tell people what you learned.  Don’t be bitter, don’t whine about your past co-workers .. be constructive.

Do be concrete.   I think the best questions are not open-ended and general.  But lots of interviewers use them, anyway.  Don’t meet vague questions with vague answers – ground your answer in detail.  Tell stories.  Not “I think I’m very results-oriented.”  Ugh.  Instead, “in my last job, I drove the marketing campaign for Jumble.  It was a tough push, but we delivered on time into five different channels, driving a positive awareness of 44% – the best result of any campaign our company had done.”

Do be passionate.  It’s deeply dull to listen to somebody drone on in a monotone listing facts and figures about their career.  Boorrrrinnngg.  It’s very interesting when somebody’s eyes light up as they share personal stories about things they’ve done that inspired them.  Find things to talk about that you are excited about, that you loved doing in previous jobs or educational experiences.  You’re a human being, not a resume – let people get to know you.  Share yourself and what you love.

Don’ts

Don’t assume!  If you aren’t sure you understand the question that you are supposed to answer, don’t launch off and answer it anyway.  You can ask, or you can explain.  Start by asking: “when you asked me to design an operating system, did you mean something like Linux, or something else like an embedded system?”  Some interviewers want you to dive in and don’t want to be interrogated, however.  You can usually tell immediately based on their reaction to your first question.  In that case, I’d stop asking and make some assumptions, but I’d be explicit about them.  “Ok, I’m going to assume unless you stop me that you want an operating system like Linux.  That means a general purpose server OS that …”  Then you are diving in and moving forward but are clear about the assumptions you have made.  In any case, don’t ask too many questions – the purpose of the interview is not to collaborate with your interviewer on defining an extremely precise question, it’s to show that you are good at answering them.  So make sure you spend most of your time on the answer.

Don’t be prickly.  Interviews are inherently awkward, and some people like to put you under pressure to see how you perform.  I don’t like that approach as an interviewer, and don’t use it, but many swear by it.  That means they are going to push you.  They’ll ask tough questions or brain teasers and watch you sweat.  They’ll push back on your answers, with varying amounts of respect, to see how you handle it.  Don’t freak out .. just stay calm, and focus on the answer, not how you feel about the situation.  That doesn’t mean that you should allow yourself to be abused or mistreated, but keep your cool even if the other person is pretty hard on you.  If you think of it as a test, and letting yourself get emotional is failing the test, that might help.  Don’t let them throw you.

Don’t be desperate.  This is easier said than done, especially if you ARE kind of desperate to get the job.  But realize that the odds may well be against you in any particular interview.  They may have a favored candidate lined up and are just checking to make sure they aren’t missing a bet.  You may be a bad fit for what they think they need in the role.  The more you build up the job in your mind and get wound up about how you absolutely have to get it, the worse you are likely to perform.  So be hungry, give it your best shot, but don’t think it all rides on that one interview, because life is mostly not like that.

Don’t lie.  This should go without saying, but a lot of people seem to think it’s ok to fudge on a resume.  Who is going to find out, right?  Wrong.  In the age of Facebook and blogging and LinkedIn, it’s crazy to be confident that you can get away with it.  If the employer finds out that you have been deceptive, that’s probably game over.  And the world is a small place, so there is every chance that they might tell the next company you talk to.  So in addition to it being immoral, it’s also dumb.  Just don’t go there.

I hope that these ideas help you prepare for your next interview .. good luck!

Kissing Frogs Part 2: Conducting the Interview

You’ve done all your prep, and now the candidate is sitting there looking at you.  You have an hour, at the end of which you are supposed to have a smart and insightful analysis on whether to hire them or not.  How do you spend your time?

Have Them DO Something – Don’t Ask General Questions

One of the most common mistakes is to ask open-ended softball questions.  “What are your strengths and weaknesses?”  The candidate then babbles on about how disciplined and passionate they are, and how their big weakness in life is that they just work so hard, and take things so seriously – they struggle under the burden of an extreme work ethic that was just the despair of their former managers.  And now several precious minutes of your interview are gone, and you haven’t learned a darned thing.

I think it’s infinitely better to ask them to create something.  Write code on the board for a multi-threaded lock implementation.  Write the Javascript code to update the notification count when a new message arrives.  Design a UI for managing notifications.  Design a set of metrics to monitor the state of the business.  Create a plan to track and land a milestone.  Whatever is appropriate for the job you need them to do.

If the design involves a skill they need to have, you will quickly see whether they really have it.  Many people can do a lovely job describing a design they know but are lousy at creating one.  Confronting a blank white board and having to invent something on the spot cuts through a lot of blather.  If it’s a skill they are still learning, you will also discover a lot in watching them try to tackle a real problem.

What To Look For

When I pose a design problem, whether the result is an algorithm or a visual design or a report or anything else, beyond the quality of the work, I’m assessing a number of other things:

  • Do they like solving this kind of problem?  Of course there is some added stress because it is an interview, but you can usually tell if they are enjoying the opportunity to dig into the problem or not.  I try hard to make an interview feel as much as I can like the real job – sometimes I will pose a problem that I’m actually trying to figure out at the time.  If they hate doing it in the interview, they probably aren’t going to love doing it all day long.
  • Do we make each other smart?  If we’re going to be working together in the future, hopefully we have a good working rapport.  Did the design conversation zip along efficiently and cover ground well, or were there constant misunderstandings and false starts?
  • Do they handle pushback well?  I always question some of their decisions (politely, of course).  How they handle that will tell you a lot.  The worst reaction is if they get mad, or they dogmatically insist that theirs is the best approach without explaining why.  Almost as bad is if they cave immediately and ask what you think they should do instead.  A great reaction is to explain the rationale for the original design, and to list a couple of alternative approaches and why they seemed less effective.  I hope they welcome new data, if I share something useful that would influence the design in a better direction.  In general, I want to know if they are passionate about finding the best answer, or about moving forward with their answer.
  • How do they handle underspecified problems?  I like to ask design questions without providing enough information, to see what happens.  The two most common failure modes are to flail around and to make wild sweeping assumptions.  If I ask you to design an airport, do you just freeze up, do you assume that it is LAX (rather than, say, an oilfield airport in Alaska), or do you ask?  In general, I’ve found that people who fall into either of those traps often have trouble if they get hired.  The freezers aren’t good at taking on hard new problems without having their hand held, and the assumers bull off in wrong directions and get themselves (and their teams) into a mess.

Other Questions I Like

 Once you have figured out whether they can do the work that is most important for your role, there are other questions that I’ve found effective:

  • Teach me about X.  Pick something that looks interesting in their resume – a skill they say they have, a project they worked on.  Have them teach it to you.  If it involves a design they did, ask them why they made certain decisions, and what they would have done differently in retrospect.  At the end of the discussion, do you feel well informed about the topic?  Any job I hire somebody to do will almost certainly involve explanations of complex topics, so it’s an important skill in its own right.  And, it will help you figure out how well they actually understood what they were working on.  If a very attentive listener can’t get a decent grasp of it quickly, they probably didn’t.
  • How would YOU interview somebody for this job?  This is a fun question, and I’ve found it is really useful.  It helps me understand what they think is important about the role and how thoughtful they are about testing for those characteristics.  It also reveals whether they have insight into other people and how to work with/manage them.
  • Share a great success and a disappointing failure in managing other people.  What did you do, how did it come out, and what did you learn?  If the person is interviewing for a management role, I want to know how they think about other people.  Are they insightful?  Do they passionately identify with the success of the people whom they managed?  If you are an experienced manager, you are pretty much guaranteed to have succeeded with somebody and failed with somebody, so you should have some interesting stories to talk about.  I also often pose a scenario – “Margaret is a superstar but runs roughshod over others, and you are going to give her a tough review calling her on it.  How do you prepare, what do you say, how do you handle it when she attacks you …”

Making the Call

At the end of the interview, you have to make a decision – “hire” or “no hire”.  Often, it’s obvious.  But if there is any doubt in my mind, I find it really useful to write down the reasons and talk them through with somebody else who has made a lot of hiring decisions.  By the time I finish explaining the analysis, I almost always realize that I’ve made up my mind, and can ground the answer in solid reasons.

The people you hire will largely determine how successful your team is, so choose wisely.  Good luck!

Kissing Frogs: Preparing for an Interview

One of the most important things you ever do is to interview people for a job on your team, and it’s hard to do it right – people don’t come neatly labeled.  But somehow, you need to figure out if this person is that great ingredient you can mix into the stew of your team and make it better.  I’m going to spend the next three posts on interviewing, and we’ll start with getting ready.

What Kind of Prince Do We Need?

We work at FriskyCo, a small technology startup, and we need to hire a great database engineer to design, build, and run our back end storage systems.  Let’s start out by making a very short list of hard requirements.  And really, these supposedly “hard” requirements are just “highly desirable” – somebody who has some other amazing strength might be a good bet even if they look very different from the person we thought we were looking for.

We’ll start with skills they need to have.  Ideally, our new hire would already be an expert in building, using, and maintaining highly scalable storage engines.  In fact, they’d have already done the job, with the same technology we want to use, for some other company.  Unfortunately, if we insist on that, there are a tiny number of people in the world who would qualify (the so-called “albino unicorn”).  We can hold out for that miracle, or we can accept more ramp and risk to get a broader candidate pool.

On the flip side, setting up a system like this is not for amateurs, so we aren’t willing to hire just any competent developer.  After a bunch of debate, we’ve decided we should look for these “hard” requirements:

  • Has built and deployed some kind of highly scalable system.
  • Is an expert at some industrial strength database system.
  • Is a skilled systems programmer.

But skills are not enough; it’s vitally important to assess team fit – whether the candidate will flourish in our team’s culture.  FriskyCo is a startup, which means we move fast and change our minds as we evolve the product.  They have to be able to handle uncertainty and not freeze or freak out.  They have to be inspired and passionate about the mission we’ve undertaken – we’re too small to have people who aren’t bought into the adventure.  We have a standard set of things we always look for as well around their nature – they are smart, not too arrogant, can handle pushback, and are driven to get things done.

Now we have a bottom line on what we need in a candidate (or at least what we think we need).  Note that we don’t have any requirements around education or “years of experience” – those can be useful indicators that somebody has what you actually need, but I think it’s a big mistake to focus on them rather than on your true requirements.

Architecting the Interviews

This is a crucial hire for us and we’re going to have a set of people talk to the candidate.  We’ve done a number of interviews together, so I have a pretty good sense of what each person does well.

  • John, the head of engineering, is a good all-around interviewer and does a great system design assessment.
  • Mary, the front end dev, has a good set of questions around designing a well factored database schema and a solid API.
  • Rajiv is good at straight coding questions.
  • I’ll test to see if they can handle our environment, if they have passion for the product, and if they have design insight.

By thinking about what each person should focus on, we are much more likely to get decent coverage.  Otherwise, everybody may ask coding questions and we won’t know if we have a good fit for the team.  Or, even worse, most people spend their time on team questions, and we don’t know if the candidate can actually build anything.  Also, the team is crazy busy, so giving each interviewer a concrete set of things to probe is much appreciated.  It isn’t a straight-jacket – if an interesting digression comes up during the discussion, everyone knows they can and should pursue it.  But each interviewer should really try to nail those one or two things that we’re counting on them to test, and have a firm opinion at the end as to whether the person is a hire from that perspective.

One tricky situation is that you are hiring for a skill that the team doesn’t have yet.  Suppose in our FriskyCo example, we don’t have anyone who knows databases well.  What to do?  Sometimes you can wriggle around this (maybe one of the folks can assess a schema, even if nobody knows how to design one).  But that’s pretty risky – it’s often possible for a glib person with weak knowledge to snow somebody who has even less.  So I always try to draft somebody from outside the team to participate in the interviews.  Maybe somebody from elsewhere in the company, if you are part of a larger organization.  A contractor you’ve worked with.  A friend who will pitch in as a favor.  There just isn’t any true substitute for somebody who is an expert at the thing you need to evaluate.

Interview Etiquette

Every candidate is interviewing us as much as we are interviewing them.  How they are treated will strongly affect whether they accept an offer, if we extend one.  So:

  • Don’t be clueless.  It’s really irritating when the interviewer isn’t sure what position you are interviewing for.  They haven’t looked at your resume.  They putz around, trying to figure out what to talk about.
  • Don’t be a jerk.  Enough said.
  • Don’t dither.  One of the most annoying things you can do is not to make a decision.  Interviewing at some places is like dropping a rock into a bottomless pit .. you wait, and you wait, and nothing seems to happen.  Get all the information you are going to get, and then make the damn decision.

Next, we’ll look at what to actually do during the interview.

Photo credit: Nickodemo

The Magic Tomato

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 distractionsYou 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!

The Rip Van Winkle Question

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.

Manage Your Firedrill Capacity

Ah, the firedrill – that urgent project that your team has to scramble to get done by the deadline.  Everywhere I have been, they are an inescapable fact of life.  “We just got a key customer meeting and we’ve got to have that demo ready!”  “There is a VP review of the project next week and we have to nail it!”  “I need this analysis done tonight for the board meeting – they said we have to cover this compete angle!”  “Our customer’s site is down and we have to get them back up ASAP – drop everything!”

Some of this is inevitable – things come up, so you have to rise to the occasion and get it done.  But some teams seem to exist in perpetual firedrill – life is just an endless succession of crises and it feels like a treadmill; you never get the chance to move forward on the really important projects that could be game changers, because you are running as fast as you can to handle the constant stream of do-it-now projects that bombard you.

How much you can control this problem depends on the role.  If your job is to fight fires (literal or metaphorical), then maybe the firedrill is what you do.  But if your work is more project-oriented, my guess is that a lot of them could have been anticipated and avoided.  That’s been my experience.  Test it for yourself – keep track of the firedrills you are pulled into for a couple of weeks, and look over the list.  How many of them really came out of the blue and could not have been avoided?

The Magic Wand: Designing Good Systems

Systems and processes can make life miserable and are one of the things that people complain most about.  They can get rigid, bureaucratic, and generally suck the spirit and energy out of life.  BUT … they are the critical tool that can eliminate firedrills, if they are done right.  What I’ve found is that you must design them thoughtfully, hone them until they cause the minimum of friction, and throw them out when they are no longer adding value. You probably will benefit from a system when something is predictable, repeated, and complex.

  • Predictable: hey, it’s a new year and we have to get our plan landed – wow, who could have seen that coming?  Excuse me, but it’s been on the Gregorian calendar for around 430 years, so this really shouldn’t catch you by surprise.
  • Repeated: if you do something once, then designing a system may or may not pay off.  If you do it over and over again, you don’t want to lose the hard-won lessons of the past.  Figure out how to do it well and bake it into a system so that you don’t have to think about it.  We’d never be able to function as human beings if our bodies didn’t do this constantly – we couldn’t walk, talk, eat, read, or write.  We spend much of our early childhood evolving our neural systems to master the key activities needed for life – think about how helpless an infant is.  Reinventing the wheel every time you do something keeps your team in perpetual infancy.
  • Complex: if it’s trivial, you may (may!) not need to remember how to do it.  But as things get complex, you are wasting enormous amounts of time and operating very inefficiently if you don’t capture that knowledge into a system.

Firedrills are a great indicator that you need to do something – jotting down a line or two about each one will take you less than a minute a day and looking the list over will help you diagnose places where you have a missing system or a failing one.

Don’t Waste Your Firedrill Capacity

Every team has some capacity to absorb firedrills.  That capacity increases as people are more committed to the mission.  It increases with confidence in the team leadership – people figure that if the leaders say something is important, it probably is.  But if you burn through that capacity too often, or you waste it on things that are obviously just screw-ups in planning that could have been prevented, you’ll pay the price.  People will get grumpy, cynical, burned out .. and eventually will leave the team.

So manage that capacity.  Fill the tank by fostering trust and commitment.  Avoid burning it up on dumb things that you could have avoided with some thoughtful planning.  Come clean when you screwed up and the team has to pay for your mistake.  And then when you really do need them to commit heart and soul to pulling off something heroic, the team will be right there with you, ready to dig deep and gut it out.

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

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.

Eyes of a Stranger

I’m always looking for best practices to adapt and adopt, and I got an idea that I really like from a mentor.  It is a way to combat the complacency that sets in as we settle into any role – that tendency to become accustomed to the way things are, even when they are pretty screwed up.  “Well, of course you stand on one foot and tug on your left ear with your right hand .. that’s just how things are done here.”  With fresh eyes, we might ask “but, umm, isn’t that kind of stupid?”  And, “about the fire burning over there .. maybe throwing some water on it would be good?”

So periodically – maybe once a quarter, or once a year, the idea is to do an exercise I like to call “eyes of a stranger”.  Pretend that you just got your job and are figuring things out – you are in your “first 30 days” and are coming up to speed on the important things you need to focus on.  What is a top priority issue or opportunity that you would see and decide that you absolutely have to pursue?  What inefficiency would you discover that would just bug you until you got it fixed?  What joy-killer is afflicting the team (or you) that needs to get taken care of?

There’s a scene from a book that got stuck in my mind; it’s in Kon Tiki, the really fun story about an anthropologist who gathers a set of kindred spirits to prove that it is possible to sail a raft from the Peruvian coast to the Polynesian islands, using only the technology available in ancient Peru.  At the end of the book, they have crashed on a reef and the raft is smashed, they are pinned down and waves are pounding over them, and one of the people clinging to the remains of the boat says calmly “This won’t do.”  I try to apply that same calm but determined spirit to situations at work that feel desperate.  As you look at your job and the environment around you, what “won’t do” that you’ve gotten used to and have been letting slide?

I’ve found that you probably want to come out of the exercise with a very short list of things you are going to pursue more aggressively than you have been – one is good, three is probably an absolute max.  If you come up with a longer list, revisit it after you do something about the top ones.  I tend to find that you get wildly more bang for the buck by focusing on a couple of things (or one!) rather than dutifully writing down ten “priorities” and feeling overwhelmed so you just go back to ignoring them.

For each of the issues that you’ve picked, you need to figure out what concrete steps you can actually go take to deal with them.  I like to sit down with a piece of paper and do a mind map.  If the issues are worth addressing and you haven’t been doing it, it’s a good bet that you are a bit stuck in figuring out what needs to be done.  Maybe you just need to spend 30 minutes listing next steps or coming up with a plan.  Or, perhaps it will work better to pick somebody you have a good rapport with, and brainstorm about it together.  If it’s a really big issue, you might find it helpful to apply (some of) the framework that I outlined in the series on “Cracking the Nut”.

I’ve done this exercise over a dozen times, and each one has helped me get hard core about tackling something that needed doing and that wasn’t moving forward.  See if it works for you, too!

Relay Race vs. Diving Competition

When you are evaluating how people are doing, it seems reasonable to focus on the business results they deliver.  In my previous team, we called this the relay race model.  What matters in a race is finishing, and finishing with the fastest time.  Nobody cares whether your running form was good or terrible – you are measured solely on the results you deliver at the end.  In most work environments, this is appealing, intuitive, measurable … and wrong.

A diving competition is almost the exact opposite of a relay race.  After all, everybody is going to hit the water, and it will take about the same amount of time no matter what you do.  The score is based on your form – how difficult a set of moves you undertake, and how gracefully and perfectly you do them.

Why the Diving Competition Matters

So what does this have to do with measuring job performance?  It’s the difference between assessing the pure business results that somebody delivers vs. the way they delivered those results.

It’s easier to measure (and talk about) the results that were delivered.  Did the product ship?  How much revenue did it generate?  Did you hit your sales quota?  Was the code quality where it needed to be?  Is the product performance hitting the ship goal?  It depends on your job, of course, but in many cases it’s relatively straight-forward to tell whether the person and/or the team achieved the goals that they were striving towards.

But there is another side of things – the way you behaved in pushing towards that goal.  Did you help build up the team?  Do people find you a good person to work with?  Do you help make the whole team better, smarter, and more capable?  I’ve worked with a lot of aggressive young engineers, and they sometimes are very impatient when I bring up these questions.  “Hey, I wrote the code, the product shipped, and it’s good.  I didn’t have time to humor those other idiots – we were on a tight schedule.  And I was right, wasn’t I?”  Often, yes.  But you are still going to get dinged on your review, because you may have been right about the issue, but you didn’t handle it the right way.  By running roughshod over the other person and leaving them feeling dismissed and mistreated, you blew it.  Why?

Well, for one thing, you are only responsible for part of the project.  Checking high quality code into the build is important, but the crucial thing we need to do is solve the customer’s problem.  Which means we need to understand their problem holistically, build a complete solution that meets their needs, test it, explain it and then sell it to them, support it, and integrate with other products.  That calls for a group of people to work effectively together.

Also, a particular deliverable is just one in a long succession of business results that we have to achieve together.  Sure, we shipped the product .. but that was just the beginning.  Even with packaged software, we have to ship patches.  We immediately start building the next version.  If it’s a service, shipping is the beginning of the hard work, not the end – now we have to run it 24/7 and manage the business that is based on it.

All of these ongoing business deliverables rely on the team working smoothly together.  When you are working on a problem that involves groups of people, no single person’s work alone can make the whole group successful.  If you achieve the goal you are focused on but leave a path behind you strewn with dead bodies, you can easily do more harm than good even if you do achieve what you set out to do.  Every team member has as much of an obligation to help ship the team as they do to help ship the product.  Given our ongoing responsibilities, the team is often the more important deliverable.  In the software business, if we create an unpleasant working environment and everyone leaves, we’ll be left with a big pile of code and no ability to run it, fix it, evolve it, support it, and sell it.

So for very hard-headed business reasons, I think it is necessary to evaluate people based on both the relay race model (the explicit results they achieved) and the diving competition model (whether they work effectively with others).  If you only focus on one, you aren’t encouraging and rewarding the behavior that yields the most value for the organization.  And on a more personal note, who wants to be on a team that’s unhappy and mistreats each other?