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Interview Questions (and Answers) for the Previously Self-Employed

Interview Questions (and Answers) for the Previously Self-Employed

The Key Is To Overcome Suspicions About Why You Want A Job


By the Monster Career Coach

At any given point in time, approximately 12 to 18 percent of the Canadian workforce is self-employed. This mainly includes people who have started their own small business or are classified as “independent consultants.”

Being self-employed can be wonderfully fulfilling and liberating. But it is also subject to sudden wild upswings and treacherous plunges, generally much more so than if you held a traditional job.

A number of people who’ve been self-employed for a period of time decide, for one reason or another, to either sell or close down their operation and return to the regular workforce. In doing so they face potential hurdles as employers may rightfully wonder why this recently independent person now wants to work within a more structured setting.

Below you will find some of the typical questions an employer might ask a job seeker who has recently been self-employed. A few potential responses for each query are listed in bullet-point style. See which answers best apply to you personally. If you choose to use one of the suggested replies, be sure to customize it to your own specific situation, and stick to the truth.

Easier Questions

Interview Question 1: Why did you leave your self-employment?

Possible Answers:

  • After being successful out on my own, I eventually found that I missed being part of a real team and working daily with multiple parties on a variety of assignments
  • I accomplished all that I set out to do, and now want to bring back all that great experience as part of something much larger than I could ever be on my own
  • In the years I was away from a traditional job, the whole area of Corporate Social Responsibility and Sustainability has begun to take root in traditional jobs. This is where I truly want to be and I wouldn’t have left to go out on my own if these types of opportunities had been around at the time

Interview Question 2: What would be the benefit to me of hiring someone who’s been self-employed?

Possible Answers:

  • Being on your own teaches you the true importance of meeting tight deadlines, satisfying the demands of your customers, and doing much more with much less. It is this high level of inventiveness and dedication I can bring to the position you’re hiring for
  • When self-employed you get to wear many hats. One day you are doing sales and marketing, the next you are creating a financial budget, scheduling your workflow, and meeting directly with customers. I can now bring all of these varied skills together to help your organization grow and be more profitable

Harder Questions

Interview Question 1: Do you really think you can work under someone else now that you’ve experienced the freedom of self-employment?

Possible Answers:

  • Actually, when you’re self-employed you still work for bosses. Each customer or client is like a mini-boss. You have to understand their individual needs and produce in a manner that satisfies their respective expectations
  • Keep in mind that before I went into self-employment I worked successfully as a traditional employee for years. My former bosses will tell you directly, if you’d like them to, that I was an excellent worker and very loyal
  • As someone who had to make difficult decisions every day when on my own, I now appreciate much more the pressures a boss like you must operate under. I want to help to take some of that pressure off of you so you can focus on other important matters

Interview Question 2: How do I know you won’t just join my firm, learn all my trade secrets, steal my customer list, and go off to start your own operation again?

Possible Answers:

  • I will gladly sign a confidentiality agreement and a non-compete contract so that you can be confident I will never be a threat to you or your organization
  • I actually never really wanted to be self-employed in the first place. It came about by chance when I was downsized from a job I loved a few years back. While looking for a new job someone who knew of my expertise offered me a bit of work on a contract basis. It paid the bills and the work flowed in more and more for a while, but I always knew I’d return soon to a regular job

Interview Question 3: Do you consider yourself a failure because you’re not still self-employed?

Possible Answers:

  • Quite the opposite. I think it took courage and determination to leave the relative comfort of an actual job to start something on my own. When you think about all that I’ve learned during that time, and the sales I produced, if anything I consider myself to be more of an asset than ever to an employer like yourself
  • In some ways I must admit that I didn’t fully succeed. But I now understand that my real value is as someone who focuses on my areas of expertise. When self-employed I was just plain spread too thin. I was wasting too much time on areas outside of my expertise, and on small things like ordering supplies, dealing with collection of invoices, and other such stuff I won’t need to bother with when I focus exclusively on doing the job you're hiring for

Reduce The Employer’s Doubts

Employers you are interviewing with for a new job want to feel comfortable that you are not a “flight risk” (that is, someone who will run off with company secrets and client lists to restart your own business). They also need to be convinced that you can work under layers of managers who call the shots, now that you won’t be the ultimate boss anymore.

Getting a traditional job when moving from being self-employed is something that happens all the time. You can boost your chances of succeeding by showing an employer that you have grown from your experience away from the mothership, and that you are committed to being the best employee this boss could possibly hire. Assist them in eliminating their concerns and you too can get back into a traditional role.

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