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From self employed to working for an organization

by Joan Tabb in Uncategorized

Dear Coach Joan,

After decades of being self employed and successfully owning and running my own small business I am ready to call it quits. I’d like to move into to a full time management position in an established organization. I look forward to being part of a team and having a regular paycheck and benefits. I’m tired of always having to chase business. The problem is that I’ve done some informational interviews consistently get the question of how I would fit into an organization and work for a boss after so many years of being independent and on my own.

How can I satisfactorily answer that concern as I truly do feel I would be an excellent employee and had a couple of years in a large organization at the start of my career.

Thank you,

Susan in Santa Rosa


Dear Susan,

I can understand that the grass looks greener at this point. You have probably had to hustle to keep your business going for all those years. Plus, health benefits, vacation and sick pay are something you have probably had stretch to provide for yourself. That is often the lament of independent business owners.

That said, I hope your motivation is a lot more than just getting benefits and having dependable work.

Let’s look at your candidacy from the perspective of a hiring manager within an organization. They are looking for candidates who have the skills to do the job, the ability to work in a large organization, understand the business that you would be entering and have true enthusiasm and interest in the job.

Here are the top 4 things they’d be looking for and ways you might position your background in a positive way:

  1. SKILLS – The job description will list the skills and experience they are looking for. If you look at the skills themselves it doesn’t matter whether you did those things in a small or large company. For instance, if they are looking for project management skills, you might well have demonstrated those on your own. If they are looking for financial management skills, you must have had those in running a business. It’s important that you stress the SKILLS more than where you did those.
  2. UNDERSTANDING OF THEIR BUSINESS/INDUSTRY – If you are applying for a job in a new industry, either read up on it, attend some professional classes, go to the web sites of notables in that industry and show you are conversant in the issues, challenges and opportunities that are happening today. Be up to date and current. Perhaps you can even volunteer at a professional organization in that industry to show your interest and knowledge, your network of people in that industry can  expand.
  3. MANAGEMENT EXPERIENCE – If you are looking for a management position it is imperative to show your management capabilities. Even though you ran your own business you must have had vendors to manage and perhaps assistants as well. Be conversant about your management style and give examples of how you have successfully managed people and how you have recognized potential and developed people, too.
  4. WHY THE TRANSITION AND WHY NOW: Think through the reasons you are attracted to being a part of a large organization. You needn’t mention the benefits or time off, that is obvious and not an attractive reason for an employer to hire you!! You might talk about looking forward to being a part of a team of smart, energetic people and that you enjoy working with various types of people and getting work done as a team. You might talk about the respect you have for that particular company and mention key reasons you are impressed by them. Talk about their competitors, too, and why you are much more interested in their company and this position. You might also touch on your early on experiences in a large company and how you feel that at this point you’d like to return to that, but this time in a management position.                            Susan, be clear about all of the successes and achievements you had as a business owner. It’s very impressive to have had a decades long business! And make sure to go into meetings with very clear reasons you’d be a great fit and that you’re a  proven winning professional.                                                                                                                           Onward in your successful career transition, Susan.  Coach Joan