Seven Questions: Interview Yourself for Your Home Business

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The idea of working from home sounds heavenly to many of us. We get to work in our pajamas (as you can tell from my domain name that’s my biggest goal), set our own hours and feel the freedom of not reporting to anyone except clients we choose. I’m still a nine-to-fiver, slowly building my online empire on the side. However, every few months I check back in to make sure I still have what it takes to be my own boss. Because, really, with that freedom comes a huge amount of responsibility and accountability.

If all we ask ourselves when deciding to work from home is if we want freedom and to do something we love all day, then of course we will always consider ourselves ready to cut ties with our nine to fives. Several months ago when I began reading up on the business end of internet business – perhaps the “unfun” piece for most of us – I decided that a good way to find out if I really wanted to be my own boss was to interview myself.

I found a couple of sites that listed basic interview questions; designed to help folks prepare for the interview process. Using those as a baseline and tweaking a bit to make things fit together, I came up with a list of seven interview questions that I run through from time to time just to see where I am at. Yes, these are those cliched, annoying questions that you hate having to answer in an interview. This is the sort of thing you think you will be escaping when you set out on your own.

Here’s my reasoning for this: working at home is still a job. At the point where you quit your nine to five you need to have a clear plan, know how to be a boss (even if it’s just your own) and basically prove your skills on a daily basis just as you would if you were working for anyone else. Answering these questions often annoys me, but every time I run through them I feel better knowing that I am approaching this realistically. When I am ready to leave my nine to five I want to be completely prepared for all aspects of running a business. So here we go:

Why Do you Want to Work for Your Own Business?

This is a take on the “why our company?” question, not the point where you talk about pajamas and laptops on the porch. You already know the fun perks, this question is more about the branding and culture of your business. What is it about what you have built (or are building) that makes it a good fit for you? Even if your internet endeavors grew out of mindless web-surfing, think about what it is that makes you want to be a part of this business.

What Can You Offer Over Other Candidates?

There are two main reasons why I include this question. First, it is a great way to highlight your own strengths. Consider what you are best at and what makes your product or service necessary, especially if you are in a market where similar services or products are already available. The second reason for asking this question is that it is paramount when it comes to marketing yourself. Clients want to know why they should choose you over everyone else. It’s best to answer this question before they even ask. But if they do ask before you can offer up the information, you need to be ready with a strong, clear answer that let’s them know you are the real deal. If a client asks you why they should choose your business over Widgets R Us and you don’t have a quick, convincing answer, you aren’t likely to land the project.

What Most Attracts You to This Position? What Sounds Least Attractive?

It is so easy to get caught up in the excitement and momentum of starting a new business that you really can lose site of why you started it. So make sure you keep that in mind for the times when it seems like you’re just not sure it’s worth all your time and effort. As for what is least attractive, that same excitement and momentum can leave you blind to the tasks that you do not enjoy. Don’t forget that pulling profits in means paying taxes out, that keeping a database of customers means staying in regular contact and that once you have committed to a deadline you might need to skip Sunday brunch and Sunday dinner to meet it. In my experience so far, I find that as long as I am conscious of the tasks I don’t like and am prepared to accept that they must be done, I can complete them. Also, many of the most mundane tasks can be outsourced. So if you have the cash to do it, pay someone else to take the least attractive activities off your plate.

What Do you consider important qualities of a job?

When this question is asked of me in a job interview (and it has been several times), I explain that my top two qualities in a job are that it is busy and challenging. The worst thing for me is a boring job that leaves me clockwatching. I hate it. Asking yourself this question will help you look at the big picture of what you look for when you are job hunting and compare it to the position you have created for yourself in your business. The answers you give to this question can bring some serious clarity and help you decide if any changes need to be made to your business plans as you move forward.

How Would you Rate your Managerial Skills? Why?

As a small business owner, you might not have any official employees, but you will still be doing a lot of managing. Just managing yourself, your projects and client load can be too much for some folks. There are some people who really need someone else to direct their activities and there is nothing wrong with that, it just means that running your own business probably isn’t the best fit for you. As your business progresses, you may also need to manage employees or at least outsourcers, guest writers and other people you will depend upon for the completion of projects. Some people are natural managers, but don’t worry too much if you aren’t. If you really want to run your own business you can learn the art of management.

Why are you Leaving your Present Job?

My first answer to this is, of course, so I can work in my pajamas. However, the seriousness of the possible answers shouldn’t be overlooked. If you plan to become a full-time blogger just because you hate your boss, then you might want to reconsider. Are you full of entrepreneurial spirit or just pissed off that some a$$hole gets to tell you what to do. If it’s the latter than you need to keep in mind that when you work for yourself you really aren’t working for yourself. You are working for your clients. If you have trouble following directions or meeting expectations, these issues will interfere with your client relationships the same way they do with your current relationships with management. This is one of those questions that you really need to dig deep or six months after quitting your job you’ll feel the same way about some a$$hole client asking for revisions as you did about your a$$hole boss.

Where Do You See Yourself Professionally in Five Years?

Oh man, doesn’t this question suck? I hate it. But it is critical that you have a long-term plan when you set out on your own. Not only should you set a financial goal, but your business plan should span at least five years. Yes, you will have to go with the flow, especially with the quickly changing nature of technology and the internet, but you need to set out with clear goals so you don’t lose site of where you are headed. Map out your income streams, consider long-term marketing plans and keep a list of ideas that can be implemented in the future. It is perfectly normal to have problems answering this question at first, but it works as a great prompting tool to get you thinking less about today’s Adsense earnings and more about 2012’s overall profit.

And there you have it. A simply annoying list of questions you can ask yourself to make sure you’re still sure you want to be your own boss. You don’t have to go through them all at once. In fact, I recommend that you don’t. I suggest you take time with each one, at least the first time you go through them. Trying to answer all seven in one sitting can be overwhelming. Just keep in mind that if you aren’t thorough and honest with yourself, then you will just be wasting your time with this tool. On the other hand, if you invest the thought and time to really answer these questions, you will be better prepared to manage and succeed with an online business of your own.

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