How to answer where you see yourself in five years

Where do you see yourself in five years? What’s your five year plan? These are variations of a common job interview question. I don’t like that question. Here’s some advice for interviewees on how to answer that question. And some advice for interviewers on why that’s a bad question and what you might ask instead.

The problems with “What’s your five year plan?”

Where do you see yourself in five years
Where do you see yourself in five years? What’s your five year plan? I don’t like those interview questions because they can limit you and make you miss opportunities.

Five years can be a long time. It’s long enough for an industry to undergo serious change, especially anything involving computers.

Disruptive technology

And the problem with disruptive technology is that you can’t predict when the next one is going to come along. That’s why it’s disruptive. You can go five years without a disruption happening, but that doesn’t mean you will.

Here’s one example. In 1997, I was a budding network administrator. Novell Netware was a viable career path at the time. It’s popular now to say Windows NT was a juggernaut and Novell never stood a chance, but in the late 90s, it wasn’t unusual for people to tell me they wished I knew Netware. If I’d listened to them and made Netware part of my five year plan in 1997, I would have been in serious trouble in 2002. I’d already bet wrong on OS/2. I would have adjusted if I’d bet wrong on Netware as well, but at that point I would have been competing with people who had five or more years of experience with Windows NT.

Unexpected opportunities

Five years is a lot of time to learn, even if the industry is in a fairly stable period at the time. Between 2005 and 2010, the PC market was pretty stable. Microsoft and Intel were dominant in spite of some missteps. Apple shook up the mobile space but that wasn’t affecting anything I was doing just yet.

But when I look at what I was doing in 2005 versus what I was doing in 2010, I had no idea how to get there from where I was in 2005. I met people along the way who steered me in directions I wouldn’t have otherwise known existed. I was fully capable of doing the work, but you can’t really plan for something you don’t know exists.

It’s a good thing I threw out the plan.

And that’s not the only time that’s happened to me. In 2011, my then-supervisor was interviewing me for a promotion. He asked me where I saw myself in five years. What I told him didn’t remotely resemble where I ended up. Circumstances beyond my control–cutbacks in government contracts–sent me elsewhere. Along the way I learned a new product I’d never heard of in 2011. I turned out to be very good at using it. So much so, by 2016 I was working for the company that makes it.

How I answer the question of where I see myself in five years

I’m not sure anyone’s asked me where I see myself in five years recently. Of course I have a general idea of what I want to be doing. I like what I’m doing now, so I want it to be related to that. And with five more years of experience, hopefully I’ve helped out a protege or three along the way.

That said, I don’t want to have tunnel vision. Something disruptive can come along and change the direction of the industry, and I always need to keep my eyes open to that. Or I could pick up a new skill that makes something completely different possible. Both things have happened to me, so I want to be ready for either possibility. There are times you throw out your playbook and write a new one.

Not everyone will like that answer. If you find one of those, you probably don’t want to work for that person.

When the five year question is a trick question

Some interviewers will use this as a trick question. I know some hiring managers local to me who use this question to locate a specific kind of individual. If they’re looking for a certain kind of ambition and you answer correctly, that’s a good thing.

If you give a good answer to that question and don’t advance in the interview process, that’s not a bad thing. If you were a manager who was interested in their own power, and concerned about hiring someone who might someday overtake you, this question is a fairly easy way to weed out someone who might be too ambitious.

What I ask instead of where do you see yourself in five years

When I interview a candidate, I look over his or her resume and look for experience that’s relevant to the position. Then I ask them about the situations they found themselves in. I’m far more interested in someone’s war stories than I am in their ambitions. And since I (probably) have similar experience, I can tell if the stories are legitimate, or if they’re making stuff up.

For example, by asking people who say they have API experience what they do when they write a line of code that doesn’t run, I’ve been able to distinguish between people who just run examples provided by the vendor from people who write original work.

When I need someone with experience with a particular technology, I’ll frequently ask what their least favorite thing is about that technology. This weeds out people who haven’t really used the product much. It’s also a good way to find zealots. No product is perfect, and I don’t need people on my team who can’t be honest about a product’s flaws. If the person launches into a rant and completely trashes the product, that may also be a bad sign. When someone gives a thoughtful answer, and can discuss possible workarounds, then I know I’ve found a gem.

I’m not terribly interested in a person’s ambitions. When I interview a candidate, I want to talk shop. I want to hear about problems they’ve solved and how they solved them. I’ll ask some leading questions, but then mostly I want to hear war stories.

There’s a fair bit of talent out there who doesn’t always interview well.

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