When a Contractor becomes a Client

A hired gun no more

For twenty years I was a mercenary. The contractor mentality was strong with me and I treated my career much the same way as a Mexican Bandito of old. With my gaucho mustache, giant sombrero and big belt of bullets strapped across my shoulders I hired my gun to any willing master that was prepared to pay my day rate.

Loyalty was not always in great supply.

These days circumstances have changed. The moustache has been shaved off while the sombrero is now safely packed away in the wardrobe, never to see the light of day again. I might keep a few spare bullets handy, just in case.

Maybe I'm stretching the metaphor thin but you get it: the life of a contractor can be isolating and choices are often short but swapping sides from being employed to being the employer has been eye-opening.

Here are my tips from being a contractor and how they compare with my experiences of being an employer.

Knowing when to shut up

In many respects, my circumstances have reversed. No longer the interviewee in an endless steam of contract interviews I now find myself in the strange position of sitting on the other side of the desk. These days I am the one asking the questions and making the decisions.

During my career, I participated in at least 200 interviews. From the plush corporate offices of the investment banks to the run-down garages of the startup crews. I did them everywhere. By the end of the process I like to think I got quite good at them.

It’s the art of knowing when to shut up. Understanding that sometimes you just have to listen to the internal politics or deal with the strange quirky process that they have invented for you. It’s about learning the phrases that push the buttons, having the confidence to say something funny or realising that it’s ok to disagree with the client because they are looking for you tell them the truth.

Be warned, that last one is quite rare.

By the end of the process I could safely say that in most circumstances the person conducting the interview was more nervous than I was. Practice brings comfort and in the end I had done so many interviews that it had almost become routine. Half of them I did in third gear.

A lot more difficult than expected

So imagine my surprise when I found out that its actually a lot more difficult than expected to sit on the other side of the desk. In previous years I would scorn at the ineffective interviewer who mixed his words and asked pointless questions. Imagine my horror to find myself, a hardened veteran of many a battle, doing exactly the same thing.

The thing to remember about conducting an interview is that it requires preparation. It’s always a really good idea to know what questions you are going to ask before you start. The interviewee has the luxury of strolling into the interview room without any real expectation of what is going to happen. Over the years I did so many that it was clear the process was going to be different every time and that worrying about it in advance was pointless.

Turns out, it’s very much the opposite case for the interviewer.

There are situations when the candidate makes a series of terrible mistakes and you have a very uncomfortable remaining interview. You already made the decision in the first few minutes that the candidate was not suitable.

Some of them clam up and say nothing and you have a horrible feeling that the candidate has not only suffered but perhaps been damaged by the experience. Some of them are hostile, some of them you want to hire just out of pity, some of them you just want to punch.

There was even one interview where the candidate was a fellow cutthroat like me. After a bit of confusion on my part and a question mark over whether I could really afford him I got that look of exasperation on his face. What the hell am I doing here? I think back to all the times that I must have given away the same signal when I was in his shoes.

It’s like falling through a strange portal into an alternative reality. It’s the same setting with the same people but the laws of physics have changed and everyone is now sitting on the ceiling.

The solution

I find myself having to go back to basics. Of remembering that the interview process is a two way deal. I think back to all the contracts I turned down because the person interviewing me was not someone I wanted to work for. I now try my hardest to be the person that I bought into, on the rare occasion that I did.

It was the one criticism that I used to have of the process. When potential clients got angry because I said no. I realise now that I must not be that client. This process requires preparation, focus and, most importantly, rules.

My confidence, even hubris, in the interview process worked against me. I had to be more reasonable, more forgiving and more understanding. As a time served professional with twenty years’ experience in the sector I had to become tolerant and understanding of those young people who are never going to have those kind of skills. I never had those skills at that age.

It is difficult in the technical community. Software developers are naturally insular, not because of their own personality but because of the highly focused work that they do. Programming makes us insular and locks us away.

As someone who experiences that on a regular basis himself I was angry that I had so easily forgotten it. You have to be tolerant of it as an interviewer.

The comfort zone

With some decent preparation and a healthy dose of humility I like to think I am beginning to return to the comfort zone in interviews. We forget sometimes how stressful the process can be for those not used to it and also just how much hope and expectation is riding upon it. On both sides.

As an interviewer I realise I have a duty of care to provide a reasonable experience and also to get to the heart of what makes the candidate tick. You are never going understand someone but to hire these days I realise there has to be some form of connection.

That connection needs to be two way and as an interviewer you have to make as much effort as the candidate does. Otherwise it just doesn’t happen.

We never stop learning. Even for those who have vast experience in an industry there are still moments of surprise and unexpected circumstance. It’s what makes the process of running a tech startup so much fun.

At least this time I am less likely to get fired.

Richard Norman is the CEO of Yatter, a collaboration-driven social media scheduling platform. Yatter is currently crowdfunding on Seedrs.