What makes a successful IT contractor?

Posted: October 17, 2011 in Information Technology, Rants

Only recently (the past couple of years) have I entered into the domain of the “IT Contractor”. After a reasonably successful transition and subsequent progression within my field, I’ve often been asked by peers, colleagues, friends, parents and even just random people at parties, something along the lines of, “What is the key to making the transition into contracting?” I’m no expert on the matter, but I have some fairly strong opinions on this question and perhaps the fact I’m willing to talk about it openly, highlights just one of them…

Most people I talk to, believe that to be an IT contractor, you must of course be the foremost expert in the sub-section of IT that you have been put forward for. I smile politely, agree with them and quickly move onto another topic of conversation. While I disagree with their premise, their logic is not without reason. If you are the foremost expert in your particular area of the IT sphere, you could make a great contractor.

The problem I see is that people, employers and – I guess – society as a whole, see academic progression as analogues to personal and professional progression. Personally I couldn’t disagree with this more. All three of these areas need to be aligned to obtain a balance to make them all work… exceptions to every rule of course.

So if pure knowledge/certifications/qualifications makes for a great expert… why doesn’t’ it make for a great contractor? From my experience, the answer is simple, you need two more things to make it is an IT contractor; people skills and business acumen. If you lack these skill sets, it doesn’t matter how great your genius is, the rest of the staff won’t get onside with your ideas and your concepts, in general, won’t align with the business goals.

I could probably end it there, leave you with the point that it takes more than “knowing your s*&t” to make it as a contractor. But what good would that be? I’m going to hit you with some dot points, or rather numbered points, because I believe these are actually in order of importance. The line between them is pretty thin though.

1. Autonomy
a. General
If you can’t march to the beat of your own drum, contracting is not for. This is by far the most important factor that I rate as a contractor. Remember, as a contractor, you are paid by the hour. If you can’t take a task on board and move it forward in some way, then you might want to go back to being a permanent.

b. Obscure
Now when I say “move it forward”, most people assume I mean make some leap in technology… do some voodoo magic to get a system working. Again, way off the target here. For me, moving forward, can encompass a whole range of things and one of the most significant challenges is getting people involved (other staff members, business units, managers, CIOs, CEOs). So somehow, being autonomous is the one skill that should actually get you involved with more people… go figure!

2. Adaptability
a. General
The IT industry demands a certain rate of change if you want to remain a player in the game. Be prepared to change and alter your thinking to new situations and scenarios as they arise. Yes, best practise dictates that you run up 50 servers in a farm immediately, but best practice doesn’t have the advantage of front line in-site, you do. Adapt to where you are, the people you are with, the budgets you have to work with, the technology you are permitted to use… these can all change from contract to contract… don’t be too set in your own ways.
b. Obscure
You may find opportunities to do things you were not hired to do. For some reason – and I still don’t understand this one – most contractors will not take a single step outside of their contract specifications. At the end of the day, you are being paid to be there, so if they need you to sweep the floor of the data centre… do it. If you see some area of the business that is lacking and you have the skills to fill the void, make it known. You need to be ready for any opportunity that presents itself. While your immediate supervisor may see it as just a convenience, the manager’s to his side or the CIO or the project manager, etc, etc, may see those skills as something they can use on their next project.

3. Honesty
a. I’m annoyed at the human race in general that this should be a quality that does not need any reminder. That annoyance aside, honesty is one trait that I find lacking everywhere in a corporate environment. From a contractor’s point of view, the most basic form of honesty (assuming you didn’t lie your ass off at the interview) is your time sheet. Be diligent with your time recording. Most agencies will only ask you to track down the 15 minute intervals, which are fine, do that for your time sheets. But, keep your own records of actual minute times you entered, minute times you left, any extra time you worked, times you log on from home, answering calls from employees after hours, etc, etc.

It’s not my belief that we should be end-billing like lawyers, for every three minute block. But, if you don’t keep track of the extra minutes you do, no-one will. Conversely, if you bill even one minute extra on your time sheet, assume that someone will pick it up. Trust me; keeping track of your pure time will save your skin in the long run. At some point, a manager or director will come along looking to cut costs and contractor times are always first on the radar (I’ve been on both sides of this fence).

b. Obscure
Own up straight away to any mistakes. This is one of the hardest things I’ve ever had to do in any role. But when you do it, it proves not only that you are an honest person, but that you are also capable of identifying when you did something wrong. Is there anything more frustrating that an employee who doesn’t even know why they are in trouble?

4. Money Management
a. General
Money management isn’t something that will aid you in performing your day to day tasks better, but without it, you won’t last long as a contractor and will return to the relevant comfort and security of full-time employment. Good money management does have the side effect of fostering good discipline as well.

Contracting offers better outright cash returns! This is no secret. If you are looking at contracting, this is most likely one of the factors driving your decision. The problem of course becomes one of security. You could take a three-month contract and then be without a job: what then?

Well, firstly, rested assured, if you make it through your first contract, your chances of getting you next contract increase significantly.

I have the advantage of being married to a bookkeeper so, for me, this part wasn’t really an issue, she just said: “OK, we have enough saved for you to give it a crack now”.

What she meant by that though is a great guideline. As an effective money management tactic, make sure you have enough money in the bank to cover at least three months of your current full time gross wage (wage + Super).

Now, when you start contracting, you should be looking for at least +30% above your current salary package. This was my guide to looking at moving out. You take on a lot of risk when you first start so you need to make sure you cover it with extra money.

b. Obscure
This is not to be considered as financial advice. I am not an authorised financial planner and any information provided is for educational purposes only.
Look at setting up a company and billing your recruiter through it. It takes more work, more initial investment (set aside $2,000 at least) and extra work from month to month, but the tax benefits are amazing and well worth-it in the long run.

I wanted to go for “5 traits”, just because it’s a nice number. But I can’t justify any other qualities outside of what I have mentioned. There are of course other personality traits that could be detailed, but an exhaustive list was not my intention. Ideally, I’m hoping that somewhere out there is an IT professional considering the switch from permanent employment the potentially lucrative contracting world and that this post will help them decide whether they are in fact ready to make the switch.

To wrap things up, I’d like to leave you with a couple of quotes that for me reflect some of the above points and help motivate me and keep me focussed. The key aspect of both of these quotes for me, is that the quantitative component (what you say/skill) makes up only a small portion of the total.

“This is 10% luck,
20% skill,
15% concentrated power of will,
5% pleasure,
50% pain,
And 100% reason to remember the name” – Mike Shinoda

“It’s 70% how you look, 20% how you sound and 10% what you say” – Eddie Izzard (original source unknown)

  1. Terrific post, Dylan.
    I think people from all professions would be able to relate and it would be helpful to anyone thinking of doing contract work (not just IT professionals).
    In relation to IT professionals in particular, I think what you have to say about ‘people skills’ is extremely important. It is always refreshing when an IT professional makes an effort to speak in language we ‘mere mortals’ can understand. There are many who insist on using ‘tech-talk’ only which can be very frustrating.

    • dthomo says:

      Hey Karen,

      There certainly are a lot of IT staff in general who like to really “tech it up” and I’m yet to see an instance where this is beneficial. From my experience, the more people do this, the more likely it is that they don’t really know what they are doing and they are trying to baffle people with bullshit, instead of blinding them with brilliance.

      It’s surprising how engaged people can become with IT and technology in general when they have someone break down the costs and benefits into simple terms. That’s the real, getting people excited about technology changes and updates. Making them see how the technology can work for them!

  2. Tom Chov says:

    Awesome post dylan, since starting my first contracting job whole heartly taking everything you have just posted.

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