Interview Questions (and Answers) for the Previously Self-Employed
The Key Is To Overcome Suspicions About Why You Want A Job
Interview Questions and Answers
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.
Interview Question 1: Why did you leave your self-employment?
- 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?
- 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
Interview Question 1: Do you really think you can work under someone else now that you’ve experienced the freedom of self-employment?
- 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?
- 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?
- 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.
Tips for Writing a Letter Asking for Your Job Back
Did you just start a new job and are already regretting it? Or have you been demoted, laid-off, or fired from your job? You may not be able to get your old job back, but it certainly doesn't hurt to ask. You have nothing to lose by sending a courteous request to be rehired.
How to Write a Letter Asking for a Job Back
- Follow business letter format. If this is a written letter, use the official business letter format when writing your letter. Include your contact information at the top, the date, and the employer’s contact information. Be sure to provide a salutation at the beginning, and a handwritten signature at the end. If this is an email, begin with a salutation, and end with your typed name. For an email, also be sure to include your name in the subject of the message, so your request is read.
- Remind them who you are. Remind your employer of the department you worked in, and your job title. You might also mention how long you worked there. If you worked there for awhile, this will remind them of your dedication to the company. Start by sending the message to your former manager. You may also have to speak to human resources or upper management, but your boss is good a person to start with.
- Sell yourself to the company. Don’t expect that you will get your job back just because your employer liked you in the past. You need to convince your former boss that hiring you again is a great idea for the company. Tell them why you are a terrific fit for the job. If you achieved any big successes at the job (for example, if you helped the company save any money), remind them of this. If you have developed any new skills since leaving the job, mention these.
- Keep it brief. Don’t go into great detail in this letter. You can mention why you are leaving your new job, but keep it brief, focusing mainly on why you think you should return to your old position. If your former boss considers you for the position, you will likely meet with him or her in person. During that meeting, be prepared to answer more questions about why you left your old job, and why you want this job back.
- Ask about other opportunities. Your job might already be filled. Therefore, if you are willing to consider other open positions at the company, say so. Being flexible might help you get a job offer.
- Think twice. Make sure you really want to return to the company. You left for a reason, after all. If you are only going back because it is the easiest option, think hard before sending this letter. Consider making a pros and cons list to consider whether you should return to the job. Keep in mind that if you were to be rehired, you most likely would be starting over as a new employee. Your salary and benefits package may not match what you were earning before.
- Edit, edit, edit. This letter is what can get your foot back in the door at your old company. Therefore, take the time to make this letter as professional as possible. Read through and carefully proofread the letter for any errors.
Letter Example to Ask For a Job Back
City, State, Zip Code
City, State, Zip Code
Dear Mr./Ms. LastName,
As you know, I recently started a new job at ABC Company. However, I have realized that the job duties and the work environment are not what I expected. I am therefore writing to inquire about the possibility of returning to my position as Assistant Editor at XYZ Company, which I held for the past four years.
I sincerely regret my decision to resign and if I were to be rehired, I can assure you that I can offer a long-term commitment to the company.
In the interim period since I was Assistant Editor, I have gained experience with new content-management systems, including Drupal and WordPress. I believe these skills would be invaluable as ABC Company continues to expand its online presence.
If the company would consider rehiring me, I do understand that my job may have been filled.
If so, are the other open positions I would be eligible to apply for?
Thank you in advance for your consideration. I look forward to hearing from you, and I am available at your convenience for a conversation. I can be reached at 555-555-1234 or at firstname.lastname@example.org.
Sending an Email Request to be Rehired
A request for being rehired can be sent by email. List your name and former job title in the subject line of the message: Your Name - Job Title Question. Include your contact information in the signature of the message, so it's easy for your former supervisor to get in touch with you.
When You Have Been Demoted or Let Go
What should you do if you've been demoted, laid-off or fired? You may not be able to do anything about it, but it can be worth appealing the decision and writing a letter to ask the employer to reconsider.
Review tips for writing an appeal letter, with an example and a template to use for your own appeal.
Suggested Reading: What to Do When a New Job Doesn't Work Out | How to Reapply for a Job