Product Management

My last job title at Trade Me was ‘Head of Product’.

If you say you are a ‘Software Developer’ or even a ‘Development Manager’, then most people working in technology will know what that means.

But, I’m not sure I’ve ever heard a succinct definition of what makes a ‘Product Manager’. In fact, I’m not even sure I’ve heard a succinct definition of a product, in this context.

I thought it might be useful to try and describe, at least as I’ve experienced it, for those who might be interested in this sort of role.

Some long time readers (there are a few of you left, right?) and a handful of former Trade Me employees may recognise this old diagram:

Product Management Process

I used this as part of the induction of new employees into the development team at Trade Me, to try and describe the broader product management process that we were part of.

There are six links in the infinite loop, so let’s go through them.

Actually it’s two somewhat separate loops: the smaller software development loop and the larger product development loop.

The work involved in the smaller loop is pretty well understood, I think, and widely documented elsewhere, so I won’t spend much time on that here.

Let’s pick it up at the point where you are ready to deploy a new feature out into the wild…


The first important thing to realise about a release it that it’s not an end point. It’s just another link in an infinite loop.

This can be tough to understand for technical people who have predominantly worked in a project environment, for example as you would commonly experience in a consulting business. In that world projects have a defined beginning and end and then everybody moves on to the next project, and the software moves into “business-as-usual” mode.

In product management there is only business-as-usual. You are never “finished”.

This has a number of consequences, not the least being the importance of pacing yourself. Managing a product is a never ending marathon, not a sprint.

The second important thing to realise about the release cycle is how you win.

It’s tempting to think that you win by doing a good job and getting everything “right”. But, remember, I just said that you will never be finished. There is no such thing as “right”.

However, there is such a thing as late. The trade off between right and late is what makes product management more art than science. The best product managers typically have a bias to roll the dice and just try stuff – “If you’re not prepared to be wrong you’ll never come up with anything original”, “if you launch and you’re not a little embarrassed then you launched too late”, etc etc.

In other words, the challenge is not to necessarily navigate your way flawlessly once around this loop, but to navigate your way around this loop as many times as you can, getting a little bit better each time.

In order to achieve that you need to make sure that the release process is baked into your tools and process. You should be able to deploy and roll-back often and easily, ideally with one click.

I’m also a fan of a bit of release theatre, so that everybody is aware when changes are deployed and can celebrate the progress that represents.


As soon as changes are released, the next challenge is to create a feedback loop.

This is where you get to listen to what people do rather than what they say. If you can start to understand how people are really using your product then it helps you to cut through debate in the next two steps of the process with facts rather than feelings. It’s how you build confidence in your theory of what users will respond to (which doesn’t always mean what users will love, by the way – often it’s a product managers job to do what is best for the system as a whole, rather than for individual users).

I think it’s really important that everybody in the team understands how the business wins. It’s the product managers job to make sure that all of the developers and testers know what the key metrics are – for example, with a big screen on the wall showing these values and trends. But, more than that, they should be able to articulate how the features they are working on will positively impact on those numbers.


Broadly speaking the first job of a product manager is to keep lists.

You have to be able to take inputs from lots of different and often competing sources and constantly organise these so that the important stuff bubbles to the top, while at the same time not drowning in the long tail of less important stuff.

I recommend a “Now / Next / Later” approach.

Firstly, you need to be aware of all of the things that are underway, ideally with some idea for when they should be completed so you can keep a schedule in mind.

Secondly, and most importantly, you need to have a strong focus on what’s next. You should be able to list the next top three, four or five projects from memory, so you can stay focussed on those.

There will constantly be competing suggestions, of course. In that situation, provided you can list off the current priority projects, the question is simply: “which of these existing projects gets bumped by this new suggestion?” That usually puts new ideas in their place (on the later list).

It’s really powerful if you can have consensus from the whole team on what the next priority projects are. A useful technique for getting to that is to organise a prioritisation session where everybody is asked to bring their top two or three project to the table and advocate for them, then as a group rank them in terms of bang (i.e. expected impact on key metrics) vs buck (i.e. expected cost to implement), then pick the ideas which have the best ratio. Ideally nobody leaves until everybody has agreed what those are.

Finally, you need somewhere to dump everything else. It may be that you don’t even need to write these things down – if you’re prepared to assume that the good ideas will keep coming up. Or, maybe having a long shopping list is handy to have, so that you can fill any gaps that come up with something useful. Either way, the key is to ensure that these don’t become a constant distraction or an overwhelming background fear (remember you’ll never be finished, so getting to the end of the list isn’t the goal).

Once you have priorities agreed you also need to consider the order. There are two different approaches to scheduling projects that I’ve seen used effectively:

The Riverstone Model

Think of your schedule as a riverbed, and your job is to cover it in river stones. You’ll start by placing the big stones, picking the most important big projects to go first. Then you fill in the gaps between the big stones with some medium stones, again picking the highest priority medium projects first. Finally, in all of the little gaps between the medium stones you scatter some little pebbles – you probably don’t have to pay too much attention to which of these go first, it could be a simple as first in first out, or whatever else works. Or, you can live with the gaps and leave some slack in the system, which is often not a bad thing.

This model is recommended if you have more priority projects than development capacity.

The Train Carriage Model

Think of your schedule as a series of train carriages. On a regular timetable one will leave the station. Your job is to make sure that all of the seats on the carriage are filled. When a new project is agreed you also pick a carriage to target for release and reserve a seat in that carriage. Once a carriage is full you need to pick the next one available. And, if a carriage leaves the station with empty seats then that is a missed opportunity, so you always need to be thinking ahead to make sure that doesn’t happen – if there are no big projects ready to fill the space available then put some medium or smaller projects in there.

This model is recommended if you have more development capacity than prioritised projects.

Scope & Design

This is where a product manager will probably end up investing most of their time.

Everything should start with the user experience. I recommend having designers in the team, so you can be constantly working on this, starting with wireframes and high-level designs and later moving onto more detailed mocks which demonstrate the intent of the user interface.

There is always going to be a blurry line between design and development in any product team, and it’s important that there is a good working relationship between them. I’ve seen examples where this breaks down and developers treat the designs they have been given as a broad direction rather than a detailed specification. It’s better if the designers are responsible for the design, and developers are responsible for the code, but with a lot of communication in both directions – the developers need to loop back regularly with designers to make sure that what is implemented is as intended, and designers need to be constantly talking to developers so that specifications take into account development constraints.

I recommend putting together a project team at the very beginning of the scoping stage. This should include designers, developers and operations people as well as testers and/or support team members who bring an understanding of the current business rules and likely pot holes from dealing more directly with end users.

One of the important questions for this group to consider is: what change are we expecting, and how are we going to measure that? As we discussed above this creates a feedback loop after the feature is released, where you can confirm that the work you’ve done has had the intended impact, or not, and learn from that for future scoping and design work. If you can’t clearly articulate what the intended change or benefit is, then you probably need to go back and think about the feature some more before you start designing the user experience or cutting code.

As scope and design bleeds into development and testing the product manager will hand over to a development manager to make sure that the build runs smoothly, and will likely become a “customer” in that process. In a smaller team the product manager and development manager are often the same person, so it’s important for them to realise the two competing roles they fill in that situation.

Everything & Nothing

To do all of these things well demands a varied and interesting set of skills from a product manager, including a lot of soft skills that are not always easy to find in technical people – you need to be able to put yourself in the shoes of an end user and have empathy for who they are, how they think about your product and how they are likely to respond in different situations; you need to be able to think analytically – you’ll probably spend more time looking at spreadsheets than looking at code; but, on the other hand, you need an aesthetic judgement, a sense of style and an understanding of design trade-offs; you need to be able to write authentically and succinctly (writing is a muscle and one of the main reasons why I maintain this blog); you need to think like a marketer, because making things that people will love is hard; you need to be able to work with a variety of different people, both technical and non-technical; and, last but not least, you need to understand that you can achieve a lot in this sort of role provided you don’t need to take all of the credit for it.

In my experience the best product managers are heads-up developers who can code but don’t want to anymore.

If that sounds like you then think about how you can get involved in some of the areas that I’ve described above within your team, so you can build your skills and over time move from a software development role into taking responsibility for product management.

I’m interested in your thoughts, especially from those who have been a product manager or worked with one. What are the other jobs of a product manager that I’m missing?

Of course, the problem with an infinite loop like this is that there is no obvious beginning. This all assumes that there is an existing product that needs to be managed and developed. It doesn’t talk at all to where the idea for the product comes from in the first place, so maybe that’s where we’ll turn out attention next…

Be a good dictator

At Webstock ’08 Michael Lopp (aka @rands) gave a great talk about the three components that are needed for any successful product team:

  1. A designer
  2. A developer
  3. A dictator

There is no shortage of advice online about how to be a good designer or a good software developer. But what about advice for those who aspire to be good product dictators? Guidance seems pretty thin on the ground.

Perhaps it’s the name? It’s fair to say that, historically, dictatorship has some PR challenges. Who wants to be a better one of those?

Maybe it’s the lack of role models. After Steve Jobs, who is the most successful product dictator you can think of? Daylight is in second place.

Whatever the reason, let’s think about what an aspiring dictator can do to improve themselves.

Starting with the fundamentals: how do you choose the best thing to dictate?

This great quote from Seth Godin has the answer, in my opinion:

“Change gets made by people who care, who have authority and who take responsibility

So, ask yourself:

What do you care about?

What do you have authority over?

What will you take responsibility for?

(the most important word in all three questions, by the way, is “you”!)

The intersection of these three things is where you’re likely to find the best opportunities to be a good dictator.

Let’s look at four different aspects that are important for good dictators to work on:


A good dictator is careful about the language they use.

There is one word especially that you need to eliminate from your vocabulary, and from your team’s: THEY

Think about how you describe the other people in your team.

Think about how your team describes the other teams in your company.

If you’re working in a technical team there is a variant of “they” which is very common and not so obvious, but just as dangerous: “the business” (as if the business is something external and separate from what you’re working on, and usually not so on to it).

Of course, the word dictators need to use instead is: WE.

Being a good dictator means building a great team, and good teams need all sorts of skills.

This is well understood in the sporting arena. Former All Black coach Graham Henry, for example, has a simple way of explaining his success as a coach:

“The key to being a great coach is coaching the best players”

On first reading that seems unnecessarily humble or flippant given his recent achievements. But, he’s genuine, and making a useful point: when your team is great they make you look good. It’s important to surround yourself with winners because your success is likely to be an average of theirs.

Think about your leadership style. There are alternatives: you can be a sergeant major or a coxswain. My experience is that you can achieve a lot more if you don’t feel that you need to take all the credit, but your mileage may vary.

And then, once you’ve done the easy part of putting the team in place, you need to get on with the much more difficult job of getting them all organised (no, not organised into departments just pulling in the same direction).

Which is a nice segue to the second thing…


Tim Cook, the CEO to replace Steve Jobs at Apple, is quoted as saying that the #1 thing that he learned from Steve was: FOCUS.

After that interview, I spotted this witty response from @cdixon on Twitter:

“As opposed to all of the people who think being unfocused is the key?”

He’s right, of course. But, if we all know that focus is important, why is it so uncommon?

Perhaps part of the reason is that focus is hard to describe:

Source: Indexed by Jessica Hagy

We often don’t recognise when we’re not focussed until afterwards.

For technical people a common reason for losing focus is boredom – we feel we need to be challenged by the technology we’re working on, so we keep adding unnecessary stuff to keep it interesting. Good dictators understand that what matters is not what the software does but what the user does.

For non-technical people it’s more often simple flailing (take a few minutes to read that post so you understand what I mean by that … I’ll wait right here).  Good dictators don’t keep thrashing and splashing and hoping for the best, they work out what moves them forward.

Keep in mind, you don’t have to be awesome to succeed, you just need to find a niche to focus on.

This is what I think Tim Cook means when he talks about focus:

Whether you’re a designer, developer or business person, the more your satisfaction is derived from shipping something, the more your success will be correlated with the success of your venture.

And for dictators that’s true not only of yourself but of your whole team. You need to narrow your collective focus to those things that move you forward.

Innovation vs Execution

Is it enough to ship?

Often when we talk about successful products and product businesses we think about innovation.

But, good dictators are seldom innovators.

Here is a quick list of things that Steve Jobs didn’t invent:

  • Desktop computers
  • GUI
  • Computer animation
  • MP3 players
  • Smart phones
  • Tablet computers

Of course, in all of those cases his teams were pioneers in working out how normal people could be made to desire those things. That’s really what good dictators need to do.

This is much more about execution than innovation.

Execution is one of those words we all use, often without thinking about what it actually means.

The clue is in the name: an innovative idea is like a computer program that has never been run on an actual machine. Anybody who has written any non-trivial code will know the likelihood that this will work as intended is infinitesimally small.

Execution is turning plans into actions. It’s tactical. It’s all about making assumptions and testing them and adjusting as you learn and as the environment you work in changes. It’s getting thousands of little things right, rather than getting one big thing right. It’s HARD!

As Derek Sivers explains, a killer idea is a multiplier, but execution is where the value is. (imagine if we had a Ministry of Execution rather than a Ministry of Innovation – then government funding might make a difference!)

How do you measure execution? The easiest way is to look at sales.

Interestingly, most good dictators don’t seem to be primarily motivated by money. But they know that is how a good dictator keeps score.

All of this begs an interesting question for good dictators with a technical background – because so often teams of designers and developers look down their noses at sales people (think about it: are the sales people in your company WE or THEY?)

Look around: if you don’t have a sales team then you are the sales team!

If you want to be a good dictator the most important question to keep in the front of your mind is: How will you market and sell your product or service? How will you overcome your obscurity?

Being a Polymath

Steve Jobs famously described Apple as operating “at the intersection of technology and the liberal arts”.

Here is a longer quote from Wired Magazine where he explains why this is important:

Creativity is just connecting things. When you ask creative people how they did something, they feel a little guilty because they didn’t really do it, they just saw something. It seemed obvious to them after a while. That’s because they were able to connect experiences they’ve had and synthesize new things. And the reason they were able to do that was that they’ve had more experiences or they have thought more about their experiences than other people. Unfortunately, that’s too rare a commodity. A lot of people in our industry haven’t had very diverse experiences. So they don’t have enough dots to connect, and they end up with very linear solutions without a broad perspective on the problem. The broader one’s understanding of the human experience, the better design we will have.”
~ The Next Insanely Great Thing, Wired, February, 1996

So, ask yourself: What else are you good at? Being a deep expert in just one area is not enough for good dictators. You need to be a polymath living at an intersection.

Think about all of the things that you care about, have authority in and are prepared to take responsibility for.  Then work out what the intersection of those things are, for you and for the team you build around yourself.

Narrow your focus to those things that you can prove move you forward. And don’t forget that, when it all boils down, sales is how you know that you are winning.

Happy Dictating!

When technology gets out of the way

I’m a sucker for sport generally and live sport especially – see previous posts here on Olympics, Football World Cup & European Championships and even previous Rugby World Cup events.

If they keep score I’ll probably watch it, and might even get up in the middle of the night to make sure I can influence the outcome.

Indeed one of the all-time top posts on this blog is Just tell them it’s sport – although that appears to have more to do with the fact that it contains the words “shower naked with a group of men” and “dress up in lycra” which are apparently both popular Google search terms!

The big downside of watching these big events live on TV is having to deal with adverts, which I otherwise mostly manage to avoid.

Here in NZ we haven’t quite descended to the depths of US sports coverage, where networks have the ability to call time-outs during the game if they are not getting enough stoppages. But, we are slowly getting closer.

The latest slippage is the insertion of a 90 second ad break between the anthems/hakas and the start of the game. It’s an annoying intrusion after all the ceremony is completed and everybody is ready to get going. Even more so at the ground, where all of the players are left standing in position waiting for the referee to get the signal from their TV overlords so they can start the match.

It wouldn’t be so bad if the ads themselves weren’t so terrible.

For example, this horrible “advertisement” for a Panasonic television, which is featuring here during the Rugby World Cup:

The first 20 seconds are a long list of irrelevant and intimidating technical jargon.

The last 10 seconds are even worse, portraying their target customer as a freak who is more than a few biscuits short of a full packet.

The number of people who care if their television has a “built in high definition SD card viewer for media playback and program recording” is infinitesimally small.

Rather than trying to impress with the advanced componetry they should focus on what the technology allows real people to do – surely the manufacturer can think of something more inspiring than barking at your dog over Skype?

The benchmark in this area continues to be set by Apple. The repeated message in the iPad adverts is “it’s going to change the way we do things everyday” – in other words: it’s not what the software/hardware does, it’s what the user does.

So, I’m agitated that Panasonic have chosen to intrude into an event I’m excited about watching and having been force fed their marketing I’m left with the impression that the Viera is a complicated overspec’d piece of technology that only propeller heads and nutbags will love.

Nice job!

Previous Rugby & World Cup Posts:

  • Are the All Blacks winning more than ever? July 2007 – yes!
  • Dark Days October 2007 – thoughts following our exit from the previous World Cup in 2007, in which I pin the blame on all of us (see also: Whatever makes you nervous) and also predict a NZ vs Australia final in 2011 based on historical patterns – before the draw was even made.
  • Re-invigorating the All Blacks December 2007 – more is less and variety is the spice of life.
  • Third Largest? September 2008 – yes, it’s exciting to have it here, but let’s not get carried away!
  • Rugby World Cup 2011 December 2008 – after the draw was made, in which I predict the semi-finalists and finalists three years out (not actually looking too bad at this point, with the exception of under-estimating Australia)
  • 31-December December 2008 – further proof that Richie McCaw is exceptional.

LOAD * ,8 ,1

“Took my iPad out into the outside world earlier. Was weird, I felt like I was from the future.”

“The iPad is bad for computer science in the same way that the availability of aspirin in bottles has killed industrial chemistry.”

Atari 2600

The dark ages, circa 1985, from memory…

The state of the art, in our house at least, back then was an Atari 2600, a simple game console, with a slot for game cartridges which were sold separately.

We had a few of the classics – Pac Man, Space Invaders, Missile Command.

This was hours of fun for all of us.  You just inserted the game you wanted to play and it magically appeared on the screen.  It had a grand total of four switches – on/off, colour/black+white, game select and game reset.  In other words you could pretty much turn it off and on, start and stop games and not much else, so there was no learning curve and it was pretty bullet proof.

However, I naturally started to wonder: how does it all work on the inside? (as I am now discovering for myself, little people can be annoyingly curious beyond their station, and I was no exception).  Who made these games we were playing?  And, how?  I enjoyed using the games we had, although to be honest I never was and still am not much of a gamer, but it felt like it would be more fun to try and make my own.

Around the same time I was given some old BYTE magazines, which were full of articles about “computers” like the ZX Spectrum and Commodore 64.  At the back there were pages and pages of goobledegook which were apparently the instructions you could type into these machines to make them do different and interesting things.  That all sounded intriguing to me, so I started thinking of all of the things I could build and tried to convince my parents to let me buy one.  However, they didn’t see the need for another “game machine”.  The distinction between a console which you could play games on and a more expensive computer which you could type the code for games into and then play was a bit subtle and I struggled to make the case (something I’m still pleased to remind them of whenever I get the opportunity, given how things have worked out for me since!)

Eventually I saved up enough money to take the decision out of their hands.  I purchased a second-hand Commodore 16 off a family friend (he was no doubt upgrading to something even more powerful like a Commodore 128 or maybe even an Amiga?) and started to teach myself BASIC.

It was pretty slow going to begin with.  My first project was to try and build a system that would emulate the statistics shown on TV during a one day cricket game, with run rates for each batsman and manhattan graphs and worms etc.  It turned out to be far too ambitious.  I eventually got it to work for a full 50 overs, but it would always crash at the change of innings.  In hindsight I suspect that I may have needed more than 16K of memory to achieve my vision.  But either way I never let it defeat me.  There was always a new technique to learn (discovering if statements and while loops was a revolution!) and I enjoyed the challenge of creating something of my own from scratch.

iPhone 3GS & iPad

Fast forward a few years…

The state of the art, in our house at least, today is an Apple iPhone or iPad.  These are simple mobile devices, running applications which are sold separately.

We have a few of the classics – Flight Control, Skype, Shazam.

This is hours of fun for all of us.  You just tap on the icon of the application you want and it magically appears on the screen.  It has a grand total of four switches – on/off, volume and mute and a home button model.  In other words you can pretty much turn it off and on, start and stop applications and not much else, so there is no learning curve and it is pretty bullet proof.

However, I naturally start to wonder: how does it all work on the inside?  Who makes these applications we use?  And, how?  I enjoy the applications we can download, to be honest I’m pretty addicted to and dependent on some of them, but it seems like it would be more fun to try and make my own.

I found a few websites with articles about developing applications.  They were full of square brackets and semi-colons that you could type into a computer to create an application that you could then transfer to run on your device.  That all sounded intriguing to me, so I started thinking of all of the things I could build.  Thankfully this time around I didn’t need to convince anybody other than myself that this was a good idea. :-)

Eventually I saved up enough time to begin experimenting.  I installed XCode and the SDK and started to teach myself Objective-C.

It was pretty slow going to begin with (it was a few years since I had to allocate and deallocate memory, for goodness sake!)  My first project was to try and build the Flower Power Meter Reader (download now).  It probably took me about 10x longer to get it working than it should have, while I came up to speed with some of the unique problems of designing and developing for a mobile device and a touch interface.  But, either way, I haven’t let it defeat me.  There is always a new technique to learn (discovering autorelease was a revolution!) and I continue to enjoy the challenge of creating something of my own from scratch.  My second project, by the way, is called Top Three and will hopefully be approved soon – stand by for an announcement on that.

The Post-PC Era?

At the recent D8 conference Apple CEO Steve Jobs compared a PC to a truck – i.e. a heavy duty vehicle that has its uses but is not the standard transport mode of choice for most people (watch the video).  Is he right?  Are we at the beginning of the post-PC era?

It doesn’t seem to me to be an either/or situation.

A couple of years ago I got fed up with providing tech support for my parents and replaced their PC with an iMac (yes, they eventually realised that computers are not only about games but also useful for sharing photos of your grandkids!)  This is much more of a controlled computer experience than they were used to – maybe a minivan, to extend the analogy?  They love it.  I imagine that the next computer they get, when the time comes to upgrade, will look a lot more like an iPad than like a PC.  A car will suit them much better than a truck.

So, there will no doubt be more cars by popular demand.  The iPhone a couple of years ago, and the iPad more recently, are both so simple to use that a much broader group of people have inadvertently started to carry a computer around wherever they go.  In terms of putting more useful functionality in more hands, that has to be a good thing, doesn’t it?

But trucks aren’t going away either, as long as there are people like me who want to find out how things work and are tempted to create things of our own.  If you believe that the relatively closed platform of the iPhone and iPad is a threat to computer science all you need to do is ensure that people generally, and kids especially, remain curious.

Distribution, Distribution, Distribution

Chris Dixon recently tweeted:

“In video game industry, it is widely believed that Atari died because of explosion of crappy games.  Hence platforms have been curated since then.”

Is that correct?  I don’t know.  But, either way, it is true that the iTunes App Store is tightly controlled by Apple (is “curated” the right word?), and that is a source of frustration for many developers who are forced to wait for them to approve every application and update.  Brad Burnham from Union Square Ventures recently compared the system to a “monarchy”, which I thought was a good description, although I guess nobody likes to think of themselves as a serf or worse, find themselves banished from court for befriending a rival kingdom.

On the other hand, I struggle to get angry about the app store.  It’s an amazingly popular venue full of people who have already demonstrated a propensity to pay for software.  It’s an awesome opportunity for developers to tap into, and a significant step up in many ways.

Chris Dixon again:

“The people griping about Apple’s “closed system” are generally people who are new to the industry and didn’t realize how bad it was before.”
— Steve Jobs single handedly restructured the mobile industry

If only there was such an accessible and well trafficked distribution channel for web applications.  Many of the early stage companies that I’ve been working with over the last couple of years would certainly benefit from something equivalent that makes it easier to reach the customers they are targeting with their products.  If you begrudge paying Apple a 30% success fee, consider how much you would spend on sales, marketing, distribution, payment and fulfillment via any alternative channel.

I don’t know what the future of getting applications onto mobile devices is.  Perhaps it’s iTunes?  Perhaps it’s a decentralised and more open equivalent of the app store, without the oversight of a single company?  Perhaps it’s just the web?  Who knows?

Google recently announced the Chrome Web Store, which will be a place for developers to distribute (and sell?) applications.  It will be interesting to see how they approach the job of curating listings within the store when it launches.  If they get it right they could well end up doing for web applications (both desktop and mobile) what they have spent the last several years doing so successfully for web content: separating the wheat from the chaff.

History Only Ever Repeats

Here is a quote I read recently, from a 1996 issue of Wired Magazine:

“The Web reminds me of the early days of the PC industry. No one really knows anything. There are no experts. All the experts have been wrong. There’s a tremendous open possibility to the whole thing. And it hasn’t been confined, or defined, in too many ways. That’s wonderful. There’s a phrase in buddhism, ‘beginner’s mind.’ It’s wonderful to have a beginner’s mind.”
The Next Insanely Great Thing, Wired 4.02

That’s Steve Jobs 14 years ago talking about the coming wave of web applications, as he saw it then.

I was lucky enough to be part of that wave.  It’s been a fun ride so far, and has some distance to run yet, I think.

But, let me revise the quote sightly, for these modern times:

“Mobile devices, and the iPhone and iPad especially, remind me of the early days of the web.  No one really knows anything.  There are no experts.  All the experts have been wrong.  There’s a tremendous open possibility to the whole thing.  And it hasn’t been confined, or defined, in too many ways.  That’s wonderful.  There’s a phrase in buddhism,’beginner’s mind.’ It’s wonderful to have a beginner’s mind.”

Amen.  Or, namaste, if you prefer ;-)

Related Reading:

When I was searching for Atari 2600 links I found this great post by John Gruber, who makes a similar point…

The Kids Are All Right

“40 years ago you could open the hood of your car and see and touch just about every component in there. And you had to, because many of those components required frequent maintenance. To properly own a car required, to some degree, that you understood how a car worked. Today, you open the hood of your car and you see a big sealed block and a basin for the windshield washer fluid. You can buy a new car, drive it for years, and never once open the hood yourself.  That’s the iPad.”

Garmin Lock In

I’m a big fan of Garmin.

I acquired a Forerunner 405 about 18 months ago from Chris Auld (even the toys he doesn’t want any more are cool!)

I have been raving about it to everybody ever since.

It’s a standard ANT+ sports watch which connects to a heart rate monitor and cadence/power meter on my bike, but also includes GPS built in.

The killer feature in my opinion is Garmin Connect, a website where you can upload data from your device.  This gives you a great view of the information collected while you’re training or racing (including plotting routes on a map) and let’s you keep track of this over time.  For example, here is a replay of the bike leg I did at Challenge Wanaka earlier this year (please focus on the first half of the race when I was flying, not the second half as I was dying up-hill and into the wind!)

This site has a really clean and simple design, and is a great example of a site that fades nicely into the background putting the focus on your data.

And, now that they have proper support for OS X, the integration is super slick – I simply put the watch in the same room as the computer at the end of a run or ride and the data is automatically sucked out and uploaded.

So, all was good.  Until…

I was on a long training ride a couple of weeks ago and noticed that the display on the watch was starting to fade in and out.  By the time I got home it was so faint that you couldn’t really see the details anymore.

As I write it’s less than 20 days until the Taupo Half Ironman, so (if you’ll excuse the pun) it couldn’t be worse timing.

The next day, I took the watch into a local shop to get the battery replaced, only to be told that they couldn’t help me.  So, I called the Garmin service department, and it turns out that the battery is not replaceable.

I have to say, they did everything right.  The lady I spoke to was very friendly and helpful.  Even though the watch was outside of its warranty period, once they checked the serial number they offered me a replacement at a significant discount to the normal retail price which arrived by courier a couple of days after I returned the faulty one.

But, I couldn’t help feeling like I was the sucker – somehow I’ve become locked in by an eco-system of accessories, online services and persuasive support staff.

So, I guess I need to add Garmin to the list of companies that has earned the right to tax me as they see fit.

Google Alphabet for NZ

Google Suggest

Here is a list of the top suggested term for each letter in the alphabet, from the Google NZ home page:

A: air new zealand
B: bebo
C: currency converter
D: dictionary
E: ebay
F: facebook
G: gmail
H: hotmail
I: ird
J: jetstar
K: kiwibank
L: lotto
M: miniclip
N: nz herald
O: online games
P: pacific blue
Q: qantas
R: runescape
S: stuff
T: trademe
U: university of auckland
V: vodafone
W: white pages
X: xtra
Y: youtube
Z: zm

Some observations:

Surprisingly, four airlines make the list.  But only one bank, Kiwibank, although all of the others were in the top few results.

Lots of online gaming sites make the list, including runescape and miniclip, as well as the generic “online games” – club penguin and mathletics also featured in the top results for their letters.

Some local sites beat out well known international competition – e.g. “ird” over “itunes”, “air nz” over “amazon” and “white pages” over “wikipedia”.

Apart from “currency converter” and “online games” all of the other terms are brand names which the person doing the search could have reached directly just by adding a “.com” or “”. (see related: Where do I find Google?)

What do you make of this list? Any obvious omissions?

How many letters do you have to type into Google Suggest before your site shows up?

I’m in fourth place, behind Rowan Atkinson and his daughter.

How To

I’ve been trying to write fewer posts that are simply re-quoting stuff that others have written.

Instead, if you want to follow some of the links I come across which I think are interesting, feel free to check out my Delicious bookmarks, or FriendFeed.

Today is the exception.

Here are some quote from three excellent “How To…” articles that I’ve stumbled across in the last few weeks, written by Paul Graham and Joel Spolsky.

If you’re working on, or investing in start-up companies, or would like to be, I recommend you read all three…  


How to be a Start-up Founder – by Paul Graham

“I’ve figured out how to express the quality [of being a good start-up founder] directly. I was writing a talk for investors, and I had to explain what to look for in founders. What would someone who was the opposite of hapless be like? They’d be relentlessly resourceful. Not merely relentless. That’s not enough to make things go your way except in a few mostly uninteresting domains. In any interesting domain, the difficulties will be novel. Which means you can’t simply plow through them, because you don’t know initially how hard they are; you don’t know whether you’re about to plow through a block of foam or granite. So you have to be resourceful. You have to have keep trying new things.  Be relentlessly resourceful.”

“If I were running a startup, this would be the phrase I’d tape to the mirror. “Make something people want” is the destination, but “Be relentlessly resourceful” is how you get there.”


How to be a Program Manager – by Joel Spolsky

“Having a good program manager is one of the secret formulas to making really great software. And you probably don’t have one on your team, because most teams don’t.”

“[Jabe Blumenthal, a programmer on the Mac Excel team in the late 80s] noticed that software development was getting so complicated that none of the programmers had the time to figure out how to make software that was either usable or useful. The marketing team was ranting and raving about customer needs and nobody had time to talk to them or translate their MBA-speak into actual features. There was a lot of product design stuff that took a lot of work: talking to users, running usability tests, reviewing competitive products, and thinking hard about how to make things easier, and most programmers just didn’t have the time (nor were they particularly good at it).”

“A good rule of thumb is that it takes about one program manager for every four programmers.”

“The number one mistake most companies make is having the manager of the programmers writing the specs and designing the product. This is a mistake because the design does not get a fair trial, and is not born out of conflict and debate, so it’s not as good as it could be.”

“… being effective as a program manager means you have to (a) be right, and (b) earn the respect of the programmers so that they concede that you’re right.”


How to be an Angel Investor – by Paul Graham

“Don’t spend much time worrying about the details of deal terms, especially when you first start angel investing. That’s not how you win at this game. When you hear people talking about a successful angel investor, they’re not saying “He got a 4x liquidation preference.” They’re saying “He invested in Google.”  That’s how you win: by investing in the right startups.”

“How do you decide what valuation to offer? If you’re part of a round led by someone else, that problem is solved for you. But what if you’re investing by yourself? There’s no real answer. There is no rational way to value an early stage startup. The valuation reflects nothing more than the strength of the company’s bargaining position. If they really want you, either because they desperately need money, or you’re someone who can help them a lot, they’ll let you invest at a low valuation. If they don’t need you, it will be higher. So guess.”

“Ultimately it doesn’t matter much. When angels make a lot of money from a deal, it’s not because they invested at a valuation of $1.5 million instead of $3 million. It’s because the company was really successful.”

“To be a good angel investor, you have to be a good judge of potential. That’s what it comes down to. VCs can be fast followers. Most of them don’t try to predict what will win. They just try to notice quickly when something already is winning. But angels have to be able to predict.”

“The most successful angel investors I know are all basically good people. Once they invest in a company, all they want to do is help it. And they’ll help people they haven’t invested in too. When they do favors they don’t seem to keep track of them. It’s too much overhead. They just try to help everyone, and assume good things will flow back to them somehow. Empirically that seems to work.”

Now what?

“I reckon an education notice can’t just say “don’t do that”. It needs to include what to do instead otherwise it’s not education. “

Br3nda via Twitter

“The biggest threat to an author is obscurity, not piracy.”

– Tim O’Reilly

I was overseas and missed the bulk of the debate about Section 92a of the new Copyright Amendment Act.

But the outcome was pretty interesting, even from a distance.

The #blackout campaign, initiated by Creative Freedom NZ and supported by a huge number of people, managed to get a lot of coverage of the issue and convinced the government to delay the implementation of this part of the Act.

And then, earlier this week, they announced that they were scrapping this altogether and going back to the drawing board.

So, here is a question for everybody that supported the campaign (i.e. everybody who changed their avatar in Facebook and/or Twitter):

Now what?

The current wording of s92a is dumb.  All agreed.  But, how should it read?

I’m not sure that I’ve heard anybody propose a solution that everybody would support, which I assume means that this is a much more difficult problem than we think.

The Creative Freedom site lists three goals:

  1. No “guilt upon accusation” law
  2. DRM Free NewZealand
  3. No companies snooping on your internet 

These are fine goals.  

I think everybody would nod in furious agreement as they read those.

(If you haven’t already I encourage you to follow the links above read the details).

And I think that most people would also agree that the groups representing the various rights owners have to be part of the solution, even though they have not seemed very willing to engage in the debate (for example, when RIANZ CEO Campbell Smith describes a requirement to provide evidence of copyright infringement as “impractical” and “ridiculous” he just looks silly).

There just doesn’t seem to be a middle ground at the moment.  

So, it’s a stalemate.

On one side we have people who consume content who, it seems, would probably prefer to keep the status-quo where they can reasonably freely download and share whatever without risk of being caught (it’s hard to beat free, eh!)

That might be unfair, but I haven’t really heard anybody on this side of the debate come out strongly against copyright infringements and say “we think it’s terrible that it’s so easy to steal, and we think it should be enforced like this …”.  

Perhaps it’s a case of people in glass houses being a bit cautious about throwing stones?  

On the other side are the content producers and rights owners who seem incapable of grasping the size of the opportunity they are missing out on by sticking to their old business models and a mindset of having to hold on so tightly to the content they own.  

As Elan from Plex said so well in his recent open letter to media companies

“You have to stop being scared that I’m going to steal your content, because I’m already stealing your content. Your goal should be to get me to give you the money I’m already giving to others.”


“There is a holy trinity of things I want desperately from you, because I can’t get them anywhere else: availability, quality, and metadata. By availability I mean give me access to full catalogs of content. More is more. If I can’t get it from you, I’m going to have to go elsewhere, and you don’t want that. Secondly, give me quality: why would I go to you for SD content when I can get HD content elsewhere? Why would I go to you for ad-laden content when I can get ad-free content elsewhere? Lastly, give me rich metadata: reviews, related content, recommendations, transcripts, and credits. And give me an API interface to that data. In return I will give you my money every month, and I’ll rub your feet at least once a week.”

And stuck in the middle of all of this are the ISPs of various flavours, who would, I suspect, much rather just invoice monthly than have to get involved in the messy business of being adjudicator and enforcer.

That seems like quite a big gap to try and bridge.

How do we break this deadlock?

What’s the next step forwards?

Are there examples from overseas that we think would work here – i.e. the American model (which gives a bit more power to the rights owners) or the European model (which gives a bit more power to the consumer)?  

Or perhaps we try our own hybrid, with some form of industry self-regulation?

Would that work?

Or do we just think it’s all too hard, and so stick with the status-quo by default?

Interested in your thoughts.

OSX for Windows Refugees

Macbook in Trash

If you’re a Windows refugee and Santa bought you a new MacBook or iMac, then you might be feeling a bit duped by now.

When I first switched to using a Mac I really struggled for the first month or so. Prior to that I’d been a Windows user for getting onto 10 years (gulp!) and during that time had become a power user. Now all of a sudden I felt like I had been dropped blindfolded into an unfamiliar place without a map.

Watching somebody who is not a confident computer user playing with OSX for the first time is amazing. Things work, everything is where they expect and nothing gets in the way.  They land on their feet.

But, for somebody who is an experienced Windows user, it can be a little intimidating and frustrating. There is a dip to go through, and you have a lot of old habits to break, but once you come out the other side it’s a beautiful place. :-)

I thought I’d share some of the things that helped me …

Keyboard Shortcuts

I eventually realised one of the main reasons for my frustration: none of my keyboard shortcuts worked any more … not even Alt-F4 to close applications … so I was forced to use the mouse a lot more than I was used to.

As Phil pointed out, in this situation you really need a fanboy to show you “all the secret five fingered key commands, hidden settings and special software that makes working with a Mac tolerable”

Your chief weapons are fear and surprise … and the “command” key (this is the key with the Apple logo either side of the space bar).

These three shortcuts work in pretty much all applications:
  • Command-Q = Quit the current application
  • Command-W = Close the current window
  • Command-` = Toggle between windows within the current application
    You’ll find the “`” key next to the “1” key in the top-left of the keyboard
This last one is especially useful if you use for your email.
Some others that are specific to mail:
  • Command-N = Create a new message
  • Command-Shift-N = Get new mail
  • Command-Shift-D = Send current message
  • Command-Option-F = Search (very handy – see below)

Here are a couple of other keyboard shortcuts that I’ve stumbled upon since then, which (as far as I can tell) are not widely known. The first two apply to text fields within all Cocoa applications:

  1. Escape or Shift-F5 to display an auto-complete spell checker (from Dave5).
  2. Option-F8 to insert a stylised bullet point – discovered completely by accident (try holding down option and typing random characters, you’ll be amazed what you can find)
  3. In Excel: Command-T to toggle a cell reference to be permanent – e.g. C8 to $C$8 – this one dove me crazy for quite a while!
  4. In Firefox: Command-L to jump to the URL and Command-K to jump to the search box – for some reason the search shortcut doesn’t seem to work in Safari?

I’m sure there must be heaps more that I haven’t found yet.

What secret keyboard shortcuts do you use all the time?

Feel free to share your discoveries in the comments below.


One of the things that continues to surprise me about OSX is the number of quality third-party apps that are available. These are usually pretty cheap, and generally really well built.

Typically they just do one simple job, but do it well.

Here is a quick list from my applications folder, roughly in order of usage:

  • Yojimbo – Simple note keeping app.
  • Things – Simple to-do list app.
  • Quicksilver – Hard to explain in one short sentence, but I’m much slower without it.
  • RescueTime – Data entry-less time monitoring.
  • TextMate – Text editor which is as powerful as you want it to be.
  • 1Password – Cross-browser password manager (also syncs to iPhone).
  • VLC – Media player which can handle more-or-less any format, including streaming audio/video.
  • Pixelmator – Photoshop-lite – nice for quickly editing photos etc.
  • VMWare Fusion – Virtual Machine, run Windows and Linux apps in OSX.
  • VectorDesigner – Simple vector design file editor (great for quick mock-ups)
  • StuffIt Expander – Zip utility.
  • Switch – Audio converter.
  • Paparazzi – Web page screen-shot taker.
  • AppFresh – Scans apps and tells you when a newer version is available.
  • Transmission – BitTorrent client.
  • Handbreak – DVD utility.
  • Scribbles – Nice-n-simple drawing app for kids.

Two others from my downloads folder that I haven’t played with myself (yet), but which come recommended by others:

I have both iWork and Microsoft Office.  I find I use Excel more than Numbers, Keynote more than PowerPoint and Pages and Word hardly at all.  I used Entourage when I was working at Xero, but thankfully no longer.

I also know others who are fans of OpenOffice, which also seems to work nicely on OSX.

fluid-apps-in-dockAlso, as I’ve mentioned previously I’m a fan of using Fluid to create site-specific browser based apps.  I currently have five Fluid apps in my dock, each with a sexy icon:

Note: If you look closely you’ll see I’ve moved my dock on the left hand side of the screen.  I figure that screen are wider than they are taller, and web pages and documents run top to bottom, so there is generally more free space on the sides than at the bottom.

Finally, if you’re into Media Center type apps, then have a play with:

What applications do you use the most?

For those who have recently switched, do you find you spend more on apps now than when you were a Windows user?

Unfortunately since my switch to OSX I’ve done very little coding, but I’d also be interested to hear what tools people use and can recommend I check out.

Your suggestions for other things I should try are welcome, as always.

UPDATE 20-Feb:

Jean from SmileOnMyMac has been in touch to let me know about their Mac Switcher Bundle, which includes two of the apps I mentioned above (1Password and TextExpander) as well as another I didn’t know about previously (Witch) which looks like it solves the window/app switching problem.

She has also kindly offered a free copy of this bundle for me to give away to a lucky reader.  I thought that I’d give it to the best comment on this post.  Just add your best tip now to be in to win!

Advanced Search

I don’t bother with an elaborate directory structure.

For my emails, I just have a single local folder, called “Keep” which contains all of the messages I choose to hold on to for whatever reason.

I’ve been using more-or-less the same approach ever since I’ve been using email (and I’m not as young now as I used to be then!) so I have a lot of emails.

I rely on search to make it all work.

The search within the default Mail app which is part of OSX is pretty good (even though my email accounts these days are all Gmail of one form or another, I still prefer to use Mail as my email client – how about you?)

As mentioned above, the Command-Option-F keyboard shortcut jumps you straight into the search field.

From there I tend to use the name of the other person and a single keyword. Generally this will quickly uncover the message I’m after.

But, where a more detailed search is required there are a couple of tricks that you might find useful …

Firstly, you can narrow search results using prefixes:

  • “email:” will search for a specific email address
  • “from:” and “to:” will search for a specific sender or recipient
  • “subject:” will search for a word in the subject field only

These work in the search built into Mail and also in Spotlight.

Similarly, within Spotlight you can use “kind:” to limit the results to a specific type of file (e.g. “mail” or “word” or “pdf”).


Secondly, you can use the “Smart Mailboxes” feature in Mail to give you a more detailed advanced search.

Just create a new smart mailbox and call it “Advanced Search”. Then whenever you want to run a search with multiple criteria you can just double click on it and it will open up the standard filter options screen.


Finally, unrelated to email, but nonetheless a nifty little time saving feature built into Spotlight: type an equation as a search and the top item displayed will be the result:

All good.

What other advanced search tricks do you use?


I hope that helps?  But, what else am I forgetting?

I’m interested to hear any other suggestions that long-time OSX users might have for the newly converted!

Photo Credits: Schlock, by -nathan

Two Small Email Improvements

On the surface email seems like a mature application, without any obvious ways to make it better.

At least that’s what everybody thought until Gmail came along, with a bunch of excellent innovations: threaded conversations, automated archiving and labels rather than a folder structure, etc, etc.

So, what would you do to improve email even further?

Here are two simple ideas that would make email much better for me:

1. Hide until

This would simply allow me to “hide” a selected message until some date in the future.  Then on that date the message would re-appear in my inbox.

I try and keep my inbox empty.  In practice, that means at any given time my inbox contains a handful of messages which need a response.  It would be nicer, where I’m waiting on somebody else, or need to respond, but not straight away, to be able to get that message out of the list temporarily.

This seems like it would be pretty easy to implement.

2. Auto-scan for forgotten attachments

This would scan each message when I click “send” and if the body of the message includes the words “see attached” or something similar and there is nothing attached, it would stop and confirm that I didn’t forget to actually attach the document.

If I had a dollar for each time I had to follow-up with a “doh – actually attached this time” message …

Likewise this doesn’t seem that hard (famous last words, those!)

What do you think?

Would those be useful to you too?

Perhaps they already exist?

What other little ideas do you have for improving email and some of the other tools you use everyday?



I was in Auckland last week and spotted this ad in the business section of the Herald:


The small print at the bottom reads:

“People seem to be investing more than ever in TVs.  So it doesn’t take a rocket scientist to figure out where to invest your advertising dollar.”

Now, I realise that I’m far from the target audience for this ad – given that I’m not the sort of person who’s likely to buy TV advertising.

But, it still made me angry.

Our big LCD TV is hooked up to a MySky box, which means most of the things we watch are available in HD.

But, not the TVNZ channels, which look like rubbish in comparison.

So, instead of expensive ads in the newspaper, I wish that TVNZ would put their energy into sorting out their petty differences with Sky and making their content available in the best possible format however people choose to access it.

Then, ironically, more people might watch their channels.

Which will make it easier for them to sell more ads.

Which will mean they don’t have to spend so much money on newspaper ads.

Everybody wins. Except the newspapers, I suppose.

Network Time Machine

If you have any important files sitting on a single hard drive somewhere, disaster (or at least disappointment) is never far away. 

If you’re an Apple user then you can use Time Machine, a simple backup tool which is included as part of your operating system, to help solve this problem.

However, there are several limitations to Time Machine which make it a bit useless – not the least that you either have to splash out on a Time Capsule or use a USB or Firewire drive which is directly connected to your computer.

To get around this restriction, here is a simple hack that let’s you backup to a network drive:

Setup Time Machine on a NAS in three easy steps

Alternatively, there is a free utility called iTimeMachine which will do the setup for you.

I use this to backup my laptop to a ReadyNAS at home, which is also where we keep all of our photos and music etc.  It would work even better in an office environment where you could backup the whole company to a single server. 

A setup like this doesn’t have to be hugely expensive.  And, anyway, the peace of mind in knowing that I can recover important files if when my hard drive craps itself is worth a lot.

If you’re one of those people who think that putting a good system in place for backing up your important data is something that you can do tomorrow, then keep your fingers crossed that the dreaded blinking question mark doesn’t appear today. :-)

PS The next step beyond this is to setup an offsite backup.  The ReadyNAS supports rsync, which should allow me to do this pretty easily.  If anybody has something like this up and running already, or would be interested in helping me with this get in touch.

Where do I find Google?

Google has published their list of the top search terms for the year:

Top 10 searches on in 2008

  1. games
  2. bebo
  3. youtube
  4. trade me
  5. lyrics
  6. google
  7. map
  8. hotmail
  9. tv
  10. weather

Half of these are site specific brand names (in bold) – meaning that rather than using Google the person doing the search could have simple added .com or to the term and entered the URL directly into their browser and found the site they were looking for directly.

(the same trick would actually also work with most of the other terms too, but it’s not so obvious that people searching for these things were after the corresponding .com)

The one that will really surprise many web developers, I suspect, is “Google” itself – the sixth most popular search this year.  

How do you explain that?  What’s the mental model those users have of the web and of search engines specifically?

Most technology people will, I suspect, find it difficult to understand the sort of person who does this sort of search, but that’s exactly what we need to do if we’re going to build products these people will like to use and will tell their friends about.

Now Hiring: Web Designer

Interested? Check out the job description.