My ideal role


This post follows on from my previous where I explained that I was leaving Elcom, and the reasons behind that decision. This post covers my thoughts on the ideal role for me. But if you don’t have time to read it all, here’s the summary:

Ideal role: Looking to contribute at a senior management level in a growing Microsoft technology focussed company, located either here or in the United States.

What am I looking for?

It’s taken me a little while to get my head fully around what I’m after, and I thought some readers may be interested in the process I’ve been through. Here’s how it started… I put together a simple Venn diagram of my skills and passions. This is a simple technique, often referred to as the hedgehog concept (although usually related to companies). My ideal role, is where all three circles intersect.

Hedgehog concept


Circle 1: What am I passionate about?

The aim of this circle is to think about the areas of my life that really get me excited. What would I do if I didn’t have to work, and could spend my time doing whatever I wanted? This was actually pretty simple for me.

In a nutshell I love learning, playing, investigating, understanding and implementing Microsoft technology. There are two main components. There’s the playing part, and there’s the implementing part. So, whilst many would be happy just playing with the technology, to me there needs to be more. I need to see it implemented and used. I get excited when a piece of technology is used appropriately to enhance an organisation’s productivity, efficiency, product offering, infrastructure, etc.

I love answering the question of ‘Why?’. Why use this piece of technology? Why implement it? What business value will it bring? What problems will it solve? And so on. The most satisfying times in my career have been after discovering a technology (or new use for a technology), incorporating it into a solution for the business (or a client), and seeing their world change. Seeing technology enable a company is a wonderful thing.


Circle 2: What can I be the best at?

This is tricky because you need to take an honest look at yourself and your abilities. You need to admit your weaknesses, and you need to be comfortable talking about things you are good at. I’ve tried to look at myself objectively, plus I’ve asked the opinions of a few people I trust and here’s what I’ve come up with. I’m OK at a lot of things, but I’m really good at two key things:

  • Broad understanding of Microsoft technology
  • People management

Let’s go through each of them:

Broad understanding of Microsoft technology: I’ve worked hard to understand as much as I can about Microsoft products in a broad overview sense. In some areas I have a deep knowledge, but in general I have a broad, high level understanding of the capabilities and appropriateness of each of their spaces. It’s about understanding the business value of each technology, as opposed to the nitty-gritty of how the code works.

I’m across almost all of the Microsoft developer space (.NET, desktop, web, database, connected systems, Office+SharePoint, etc), the server and IT platforms, games, home entertainment, cloud and Live offerings, mesh, etc (Admittedly there’s areas where I’m weak and currently improving including mobile and unified communications). I spend most of my spare time reading, investigating and playing with Microsoft offerings. And most of my work time in charge of implementing it.

People management: I think I’ve made the transition from developer to manager reasonably well. Part of the reason I like managing people is because I’ve had the opportunity to work for great managers in the past. Coming from a developer background I understand what it is that developers like (and dislike).

The key concept that I woke up to years ago was that developers are all individuals. Most (bad) managers make the mistake of thinking their staff are simply greater or lesser versions of themselves. But good managers understand that people are complex and individual packages, each with their own needs and wants. Getting the most out of people really is as simple as asking them what they want, and doing everything you can to provide it. A good manager is a facilitator – they free up their team to concentrate on what they do best. Often it is just a matter of removing simple frustrations in their daily work. This sounds like common sense of course. The skill though is in applying this individually across a team whilst still focussing on company goals.


There’s plenty of other things I can do well (including project management, client management, pre-sales, business development, presentations, proposals, analysis & design, coding, community activities, talking with people at all levels from user to CEO, etc) but the above are the two that I can, and aim to be the very best at.


Circle 3: What can I make money from?

And here’s where I need your help and inspiration dear reader.

I think my skill set is appropriate for a number of scenarios. I’ve been working in CTO and Technical Director roles for the last few years. This has been in medium sized technology companies. And I’m happy for that to continue. However I think I’m most valuable to a company that is much larger, or perhaps on a rapid growth path.

I’m ideal for a company that needs someone to come in and sort out their technology strategy, and then execute it through a team(s) of developers and technical staff.


With all that covered, here’s how my 3 circles look when filled in:

Craig Bailey's ideal role

What format will it take?

I’m open to all kinds of roles that include the above.

General CTO and Development manager roles would be appropriate, and I’m also looking at a consulting type of arrangement – eg I think I’d be good at short term temporary CTO assignments. Throw me in a company that needs someone to sort out their technology strategy, manage the team, report to the board, communicate the vision across the company and execute the plan, all the while mentoring key team members to take over the role once I left (whether that’s 3, 6 or 9 months later).

Other options might see me in a company like Microsoft where I could work with corporates to help them understand the best way to utilise their Microsoft technology options.

Yet another option would see me looking after development and IT teams in a growing software company or multi-national.


So, what else am I looking for?

The above covers my skill set and passions. But there’s a few other items to mention.

One thing I’ve always encouraged in my teams is for them to think big and state their dreams. We often hold back on stating our dreams because we think they are unachievable or we’ll get laughed at. Instead we tend to tell our managers and prospective employers what we think they want to hear! But that shouldn’t be the case. If there’s something we’d love to achieve, then we should make it known.

So, I’m going to do the same. The following are ideals. I don’t expect to achieve them all immediately, but I’d be foolish not to state them:

Smart people

I subscribe to the ‘be the dumbest person in the room’ strategy. I want to be working with exceptional management and development teams. I want to feel intimidated by the intelligence and wisdom of the people I work with. I understand that getting the opportunity to work in these kinds of environments is a privilege, and I’ll happily undergo any type of testing (psychometric or otherwise) required to gain entry.


Michele (my wife) and I are keen to move to the US in the short to medium term. We’d ideally like to live in New York for a few years, but will happily embrace any location along the way. Seattle and San Francisco are obvious candidates, as are LA and Chicago. Michele runs a number of internet based businesses and is thus completely mobile. We have no kids. We have family in Minneapolis and friends in New York. Australia has a nice little E3 visa arrangement with the US, so many of the usual hurdles have simple solutions.


I’m at that stage of my life when I’d like to take a greater interest in the company that I work for. In a large corporate this is likely to be through employee share schemes and the like. But in smaller companies and even startups I’m keen to contribute in an ownership role. I fully realise that equity is not something that is given lightly, and not something that I’m expecting for free. Michele and I have finance behind us, and will happily invest in the right company if that suits all concerned.


What now?

If you’ve read this far, then I thank you.

If you think I might be a fit for your company please drop me a line or call me on 0413 489 388 (+61 413 489 388 if calling from overseas). If you have a suggestion for someone you think I should contact, I’d really appreciate it. If you think there’s someone who may be interested please send them a link to this post.

I’m on LinkedIn here. My CV is available on request. References are also available, or alternatively just contact anyone at Elcom and ask about me (John Anstey is the CEO and Anthony Milner is the Projects Director if you are after them specifically).


Closing thoughts

I’m excited and optimistic about the coming months. I’m also keen to learn – I welcome any advice or suggestions.

I thank you for your consideration.

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By Craig Bailey