You need a list of specific unknowns we may encounter? Huh?

Hey CIO, if you want my advice… oh, you don’t

Something for the Weekend, Sir? The CIO flew in the other day. I am just a contractor so I only hear stories but so mythical is this fellow that I get the impression he must have flown in by winged chariot and would be trotting across town to our office on a company-funded unicorn.

His arrival would then be announced by a fanfare of trumpets and a team of scantily clad women would scatter petals before his bronzed, sandalled feet as his godlike being strides across the marble floor. Butterflies would flit around his golden hair as he turns his majestic head towards the mystical glowing screen bearing the glorious legend: “An unexpected error has occurred. Please contact your administrator.”

Replace the marble floor for static-inducing carpet tiles and this is pretty much how it turned out. It took ages to clear up the petals.

I have been told I lack respect. I call it an inability to brown-nose.

Freelancer, independent contractor, casual worker… call me what you will. I tell people I can’t hold down a proper job due to my low boredom threshold but the real problem is that I have an aversion to managers, especially senior managers. The further they are from the coalface, the cleaner their complexion and yet the more likely they will be invited to deliver a gobshite TED talk about pickaxe handles.

They may not all look like the pointy haired hate-figure in the Dilbert strip but that’s what they are inside. Dear reader, you know what I’m talking about.

My freelance status puts me in a situation that is simultaneously enviable and precarious. Managers understand that I don’t have to put up with the same shit as employees and I could just turn round and walk out the door. How enviable! They also know that by the time I have reached the entrance of the car park, another contractor will have been hired to replace me. How precarious!

As with all contractors, experience has taught me to keep my head down and mouth shut. This wasn’t so easy in the early days, when it used to make me anxious that big companies wasted so much money on poor decisions. Foolishly, I would try to help them curb the waste and suggest ways of improving their productivity and profitability. Oh yes, I truly was that naïve.

Since then, I learnt that big organisations would rather flush vast sums of money down the drain getting things wrong again and again before hitting on a winning formula than spend a fraction of the cash getting it right first time. They would also rather take one or two of your raw ideas and hand them to their “own people” to fuck up than pay you to complete the job effectively.

On one project back in the day, I was hired as a minion on a major project that was struggling to stay on the rails after a series of development delays was pushing it nearly a year behind schedule. The project manager, in the spirit of cultural revolution, invited those of us working with the poor sods who had to use the system to raise issues about which we felt concerned.

Picture the scene. It’s a morning stand-up meeting, the sun is out but everyone is down in the dumps. How did we get into this mess?

Me: The new system doesn't work as described. It’s poorly designed and badly implemented. It falls over every half hour. It randomly deletes user files. Everyone involved in user acceptability testing hates it. It’s not fit for purpose.

Project manager: (looking at everyone else but me) Any constructive comments?

Me: Ditch this turkey, get your money back from the dishonest salesman who sold it to you and buy something that works off the shelf. At least you’ll know it’ll work.

Project manager: (still looking at everyone else but me) Ha! Tell that to the board of directors!

Me: No problem. They're the dickheads who signed the contract on buying this bag of turds. Which room is it?

Cue hard stares and red faces around the room – specifically, their stares, my red face. I realise I will not be around to see the end of this contract. Thus put in my place by Those Who Know Better, I learn a lesson. When asked to point out where a project is going wrong, don’t for god’s sake try to tell them.

This causes problems on those occasions when I’m asked to supply references, as you can imagine. My CV is littered with short-term contracts on publishing launches and IT media projects on which my advice was ignored and which eventually went wildly over budget or failed entirely. Instead of a summary reading “I saved ABC company £150,000 on its roll-out of XYZ”, my CV goes along the lines of “I recommended and offered to help implement XYZ for ABC but they chose UVW instead, ignored my advice on sales promotion, wasted £0.5m and ended up making 50 staff redundant.”

Full of myself? Hell yeah. I have 25 years of proof to show for it.

Conversely, I adore working with bosses who are said to be “difficult”. Not the passive-aggressive bullies (who are just sad bastards with low sexual self-esteem) but the generally shouty, rude and sarcastic ones.

They are great fun to work for and remarkably easy to please. All you have to do is get stuff done and they love it, which is both refreshing and immensely satisfying for temporary casuals such as me. I suspect, deep down, their noisy and abusive behaviour around the office is due to their own frustrations in getting anyone else to do anything how they want it to be done. I know what that feels like and I can’t help but fantasise what it might be like to storm around an open-plan floor, shouting at no-one in particular for no specific reason.

My relationship to some of these ghastly people borders on hero-worship. They make me laugh, treat me well AND they pay me money. What’s not to like?

So I have mixed feelings when our Apollonian CIO enters the room for his 10-minute demo of a new system we are about to roll out. He sits down before shaking my hand – not a good sign but it might be part of the act.

Some 30 seconds into the demo, he declares a Commandment From On High. The one thing he absolutely insists on, he says, is that staff training on the new system must ensure… (wait for it)… that staff learn how to use the new system.

Embarrassed silence. A tumbleweed rolls by.

Me: Thanks, that’s really useful to know. Any other gems of the bleeding obvious that you wish to impart? Teacups are more effective with the open ends pointing upwards? Avoid handstands while using a toilet? Get a top job by talking utter fucking bollocks?

Of course, I say none of these things. I just hide behind my display and concentrate on getting the job done.

Alistair DabbsAlistair Dabbs is a freelance technology tart, juggling IT journalism, editorial training and digital publishing. His first full-time job involved working as personal assistant to the loudest, scariest two men in the building, one of whom admitted it was an act and confided: “I’m just a lamb, really.” And he was. And probably still is. Bribes will be considered to reveal the name of this mighty boss within the London publishing scene.

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