Difficult Decisions


Many times in your career or your personal life you’ll face difficult decisions. When you face a decision where the consequences of making the wrong decision are serious. You feel sick in your stomach as you think about even making the decision.

So how do you make the decision?

The first thing to acknowledge that it’s often less about the decision itself, it’s more about  the consequences of the decision. Deciding what to wear is a trivial decision, but it might not feel so trivial if you’re going to give a speech to 1000 people. Then you might really care about what your clothes.

When I face difficult decisions, I find it helpful to be able to understand what kind of decision it is. Putting the decision into a box helps you better understand how to handle making a decision.

I see difficult decisions falling into three basic categories.

Hard to call

These are decisions you’re genuinely not sure what the right decision is. You’ve done the analysis, written lists of pros and cons, asked for advice, run scenarios over the different outcomes, and … it’s still a 50-50 decision.

So what do you do?

This is actually really simple: you flip a coin.

If you genuinely cannot choose between two options, then it isn’t worth the time to agonise over it. Choose at random and move on. Put your energy into your chosen path rather than agonising over the decision.

If you find out later you made the wrong decision based on new information, rest easy. You can only make decisions based on the information you have at the time.

Not enough time

This is a decision with a time limit. If you don’t make a decision soon, you’ll miss an opportunity or suffer some consequences.

You don’t have the time to gather enough information to feel comfortable you’re going to make the right decision. What do you do? You simply don’t have enough information to be sure you’re going to make the right decision.

You need to recognise also that not making a decision is still a decision, it’s just a decision to do nothing. You will always be forced to make a decision, even if that decision is to delay making a decision. You need to seriously consider whether deciding to delay is better than actually making the decision.

Not making a decision is almost always worse than making a decision. Often your initial reaction is the best one, so make the decision and move on.

Decisions With Consequences

These are the decisions where you know what the right choice is, you just don’t want to do it.

This is the kind of decision where you find out that someone senior at work bullying a junior staff member, and it’s not the first time it’s happened. You know that you should speak up, you know it’s the right thing to do. Maybe you just aren’t sure if it will make any difference. You might be seen as someone who isn’t a team player. Maybe you’ve seen what happens to people who speak up.

It could be something more personal, something closer to home. You discover a well liked family member is abusing their spouse. If you speak up, that would make you very unpopular and create a real divide in the family. Maybe it would be simpler to pretend you hadn’t seen anything? Or that you might have been confused.

It’s the kind of situation that can make you feel sick in the pit of your stomach. You know what you should do, but you fear the consequences.

When you’re faced with a decision like this, the only real choice is to do what you know is right. You need to live with the consequences of your decision.

However, you can be wise how you do this. You can collect evidence, ask others for advice and prepare how you want to approach it. Maybe you can find some allies. You can choose how and when to address the issue. Take the time to manage the impact of your decision.


When making decisions, I find it gives me comfort to be able to understand what sort of decision you’re facing. If in doubt, aim for making a faster decision over a slower decision. For 2 out of the 3 types of decisions a faster decision is the best option.

Most useful skills in technology

Over time, I’ve developed some pretty strong views on what skills are most useful in technology. I’ve developed these from 20 years of experience in different roles from hands on development, staff management and strategic leadership positions.

Without a doubt, the two most important skills are:

  • The ability to learn
  • Communication

These two skills are far more important than skills in a particular technology, language or certifications and it’s well worth concentrating on developing these skills above others.

Why are these skills so important? Let me explain.

The ability to learn

The one certainty in technology is change. As Stewart Brand says:

Once a new technology rolls over you, if you’re not part of the steamroller, you’re part of the road

The rate of change in technology is relentless. For example, in my career I’ve seen us move from:

  • physical machines to
  • virtual machines to
  • containers and now to
  • serverless.

In any other industry you would see just one of those changes every 20 years, in technology, it’s more like every 5 years. While this example is more infrastructure focussed, the rate of change is just as high across the whole industry. Changes aren’t limited to new technologies, processes change too. How we build software and communicate about it, have changed completely

In order to thrive in constant change, you need to be able to learn, and learn fast.

What does this mean for you? If you are in technology, you need to build this skill by exercising it. The best way to do this is to learn new things. Take the time to learn a new language or platform. Even better, teach someone else a new technology. Teaching someone else forces you to learn this better than you otherwise would.

If you are managing a team, you need to think about what people you bring into the team. You should hire for the ability to learn over current hard technical skills. Look for how people demonstrated the ability to learn in their career. The skills you are looking for now are less valuable than the skills they will learn.


Communication is a much underrated skill. People tend to focus hard technical skills over softer skills. This isn’t helped by the image many have of people technology: the brilliant lone coder, hunched over a keyboard, building the next facebook.

The reality is that software development is collaborative. The broader technology space is just a collaborative, as no single person has all the skills to build the kind of complex products that are used today. That takes a team.

For a team to collaborate effectively, communication is key. Communication skills help other team members to understand what the work is and how each person is contributing to that. Without communication work is duplicated and people head off in different directions rather than working towards the same goal.

Communication is equally important outside the team. This can help bridge the gap in understanding with less technical people, so that they can better understand how to work together. For example, if there is good communication between a sales team and a development team, then the sales team isn’t going to over promise beyond what can be delivered. Well, at least they’re less likely to.

At some point, you will need to convince someone of an idea or proposal. Often you will need to sell the idea to people who might not truly understand the technical details or agree with you. Communication skills will help you pitch the idea and translate your proposal into the language your audience understands.

So, how do you build those skills? Look at other people who communicate well and see what you can learn from them. Ask for feedback on how you can improve. Follow up with people later to see whether they understood the idea you were trying to communicate.

Consider how you best communicate (face to face, written text, diagrams?) and look at how you can improve areas where you are weaker. If you have something particularly important to communicate, consider leaning on areas where you are strongest.

Above all, practice, practice, practice.


If you are looking to be more effective in technology, you should look at building your ability to learn and communicate. These skills transcend almost all other skills and will serve you throughout your career, far beyond any hard technical skills you might learn.

Working with Remote Development Teams

Over my career I’ve worked with a number of remote teams in different contexts. From this I’ve collected a few lessons I’ve learnt. Like the best lessons, some of these have been learnt the hard way.

The TLDR version is: working with remote teams is similar to working with any development team, with some additional challenges. You have the same issues as you have with other teams, just with the added distance caused by timezones, communication and culture.

This advice is based my experience of working with teams that have been split between multiple locations, offshore development contracts or remote teams. There are real benefits to improving the working relationship, even if this is a shorter term contract relationship on a fixed price contract.

If you share an office with your team, you won’t have to think about these things, they come naturally through daily contact.

1. Remote people are people too

It’s easy to treat remote people as though they’re just the service they provide. The distance makes it so much easier to treat them as just a service. You feed them jira issues/Trello cards/emails, and they deliver the work. Simple, right?

That’s not how you’d want to be treated. There are people behind the code (or testing). Don’t think of them as a machine that you feed work into and get a result.

Unless you’re a sociopath, you wouldn’t think this of people you see every day in the office. However when you have no face to face contact with people, it’s easier to de-personalise them.

You need to actively strive to understand who they are. What do they enjoy doing most? How do they like to be managed? Where do they want to go with their career? What do they do outside work?

You know, the kind of stuff you’d do with someone who works in the same office as you.

2. Actively communicate

The reality of the distance between remote and local teams is such an issue that you need to take active steps to bridge the gap. The area where this is most seen is in communication. You need to build in processes that help people to communicate. This can be a real challenge when working with developers as they’re not the most communicative people in world to start with.

Some ways you can actively build this include:

  • Have a standup (this is really a basic)
  • Schedule one on one catch ups with them
  • Use more personal forms of electronic communication. Video is better than audio, audio is better than chat, chat is better than email.
  • Use tools that make keeping in contact easy, eg slack
  • Foster a shared culture
  • Ask for their input as much as possible

Of course, the best form of communication is still face to face. So if possible, either go and meet the people of your team or have them come to meet you.

3. Include them in your plans

Communication works both ways, so you need to look at communicating to them what is on your mind. Tell them what is important to you, tell them where you’re going.

Again, if you all work in the same office, people often learn this without having to be told. They overhear conversations and hear the emotion in people’s voices.

If you need to hit a critical deadline, explain what the impact is if they miss it and ask them to surface issues early. If quality is important, then make that clear, and explain why.

It’s important to help them understand not just what you want to do, but why.

4. Understand the culture

While people are basically people no matter where they are in the world, the culture people live in has a big impact on how they see the world. This is often the culture they have grown up, been educated in and worked in. It shapes how they work.

While not everyone is the same, people from the same culture often have a lot in common. The culture they have in common might be very different to your culture. You need to work at this, as by default you tend to assume that people will approach things the way you do.

For example, as someone who has grown up in Australia, I tend to have a lower respect for authority than many other cultures. As a result I’m inclined to challenge people more senior than me. As an Australian, I assume that other people will challenge me when I’m wrong. In Asian cultures, authority tends to be much more respected. If I were managing a remote team in Asia, I’d need to be very careful to ensure I gave my team lots of space to give feedback and encourage it when it’s given.

Read up about the cultures you’re working with and be aware. One of the best questions to ask yourself is: What do they value (achievement, impact, family, education, status etc)?

5. Be Genuine

Be yourself. Don’t pretend to be someone else to try to build a connection with the team. You might have to moderate how you express yourself, but you should always be yourself.

You want to build relationships with the people you’re working with, and you’ll only do that if you genuinely show who you are.


Working with any team of developers is often quite challenging. Working with remote teams can make some of the challenges even harder. However with it can be a very rewarding experience, where you learn more about other cultures and your own biases.

Windows 8

Now Windows 10 has been released, I feel it’s worth putting together a highly subjective review of Windows 8.

What does it feel like?

For me, from the first preview buil, Windows 8 felt like the movie From Disk till Dawn.

For those who haven’t seen the movie, it is a collaboration between Quentin Tarantino and Robert Rodriguez. Quentin Tarantino is best known for gangster movies, Robert Rodriguez (at that time) was best known for horror movies.

The movie starts like a normal Quentin Tarantino movie, guns, hold ups, tough talk. Two fugitives are on their way to Mexico. They fight their way over the border to a bar.

Suddenly half the people in the bar turn to Vampires and the movie switches to a horror movie. The survivors band together to fight the vampires.

It’s not really one movie. It’s two movies with two directors with an abrupt transition from one to the other.

We’ve got Tarantino:

Then Rodriguez:

It’s a great movie. You should see if if you haven’t already.

Windows 8 isn’t one operating system

I do have a point here, I promise.

Windows 8 isn’t one operating system, it’s two. On one hand you’ve got the traditional windows desktop, largely the same sort of experience since Windows 98. You know, windows, desktop, explorer.

Then you’ve for the Metro Modern interface. This is the full screen, touch optimized interface.
There is zero continuity between them.

So what does it feel like?

This depends on the device you are using.

Tablet/Convertible – hey this is pretty neat
Laptop – doesn’t really make sense, but ok
Dual Screen Desktop – I want to stab someone

This didn’t really come home to me until I started using windows 8 on a dual screen desktop extensively. The metro modern interface, optimised for touch, doesn’t translate well to large screen displays. Or more than one screen.

The start screen taking over the whole screen is hugely jarring.

My pattern of usage is to start apps using Windows Key + start typing app name. Prior to Window 8, this was a relatively unobtrusive start menu. With Windows 8 it takes over the whole screen. And on a 24″ monitor I hate it.

With the release of Windows 10, it looks like Microsoft has acknowledged this.

Fixing a broken windows installation

I recently had a rather sick server that was exhibiting all sorts of weird behaviour. Applications pools under IIS were shutting down as soon as the site was hit. All sorts of weird stuff was happening. Event logs were providing nothing useful. Even trying to install IIS diagnosis tools failed.

Clearly a very sick machine.


One of the challenges was what to trust. Clearly there were some underlying issues with the operating system. Once you go down that rabbit hole, where do you stop? Is the event log still working?

Where do you start?

I had the following info:

  1. A web application that was working 6 hours before was now failing, without any useful errors in the event log. There was an exit code but I couldn’t find any info.
  2. Diagnosis tools were failing to install
  3. A colleague was reporting that some apps wouldn’t run

My best guess was that some of the operating system was corrupted in some way.


In my extensive research (googling frantically) on this, I came across System File Checker. This runs through all system files and finds any files that might be corrupt.
I also found this rather helpful link that covers how to read the log files.


The scan indicated an issue with a specific dll. I passed this onto a colleague who was able to fix the issue by uninstalling and re-installing windows updates. It’s a great tool to add to the toolbox.


System File Checker

System File Checker