What to Look For in a Small Business Boss

Certainly it is true that working for a small business is in many ways a very different animal than working for a large one; big businesses have processes, benefits, resources, packages, and programs that can’t be matched by small businesses.

Initially, I would suggest that working for a big business is usually a far more structured experience. People come into the job with a fairly good idea of what to expect, and what is expected of them. Pay raises, performance standards, and other processes are plotted. Oh sure there are surprises, but by and large, when going to work for a big business, the surprises come from people more than the organization itself.

That is simply not the case when going to work for a small business. Now of course, it all depends upon the size of the business as the term “small business” can mean anything from a solopreneur hiring her first employee to a chain of 10 stores with 100 employees adding seasonal staff.

So, while it is a bit hard to generalize, that hasn’t stopped me before, so let’s go!

One of the biggest problems small businesses have is that they are unlike big businesses in that things are more haphazard. At a small business, while you will be given a job and a job description, it is not unusual to be considered a jack-of-all trades. One day you may be doing the job you were hired to do and the next you may be the shipping and receiving clerk for a day.

So one thing you want to look for in a small business boss is someone who is organized, who works to run his or her business professionally and not as some fly-by-the-seat-of-the-pants experience.

You also want someone who is fair. Make no mistake about it, a small business is a little fiefdom for the owner. This is someone who broke away from the daily grind to start his own business and has succeeded; indeed, he is so successful that he is hiring staff – you.

So yes, there is an ego thing involved with small business owners and because of that you want someone who not only respects himself, but respects you too; a boss who knows that it is OK to expect hard work, but who also gets that there has to be some give and take. Look for someone who values your time and contributions.

Being respectful takes many forms. It is someone

  • Who doesn’t take joy in berating his staff
  • Who gives praise where praise is due
  • Who pays a fair wage, and
  • Who plays a fair game

Also look for an owner who understands that people work for many reasons and that money is just one. Ideally, you want a boss who helps you learn new skills and takes pride in challenging you to do your best.

Finally, and this is the same advice I gave the small business owner regarding potential employees, don’t underestimate the importance of chemistry. A boss with whom you click is employment gold, Jerry!


Steve Strauss

Steve Strauss is the senior small business columnist at USA TODAY, the Editor-in-Chief here at Small Business Connection, a speaker and spokesperson. He can be reached at

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