You are not alone, I’ve always found it difficult to fire someone, fortunately is has been a rare occurrence. However, it has always been a huge relief once it was done. All of the tension is gone and the whole company can feel it around the office, just a better atmosphere. This presupposes that it was a legitimate firing of course.

My experience has actually been the other employees are even happier than I am the person is gone, no hard working honest employee likes it when a co-worker is shirking. If action wasn’t taken, you can be sure someone else would soon be saying to themselves, why am I busting my butt?

As others have mentioned, no firing should be unexpected if management has been doing their job…still doesn’t mean the person will take it reasonably…reasonable people don’t typically get fired from good companies. With time and distance you will gain ever better perspective on the whole situation/relationship and this experience will help you going forward.

It’s normal to an extent. I think there are kind of two ways a purchase of a small business can go and this one is going the less than ideal way. Pre-agreement, absolutely understand, no need spooking employees when even the owners don’t know the outcome. People like uncertainty even less than change! Post-agreement is ideally kind of a different story, and it may depend on whether the owner is “escaping” or capping off a successful run of ownership.

Less than ideal is a seller that has no intention of sharing the fruits of a successful sale with those that helped create it (maybe b/c they are only escaping and don’t consider it a successful exit), leaving a disgruntled group of employees behind that are now well aware that this is “just a job” for them. You mention the owner is hands-off and remote so there is a chance this is already the case and it’s a non-issue. However, many people choose work at a small business b/c its more than “just a job”…better atmosphere, less bureaucracy, more flexibility, more meaningful work as they can see the fruits of their labors, etc.

Ideal scenario is the owner brings talks to their employees about why they are selling. They explain how this is a positive thing for the business as it opens up future growth opportunities for the company and career paths…and oh by the way…everyone is getting a sale bonus based on their years of service or some other metric. Realistically, this will only happen after due diligence is completed as many deals can and do fall apart during due diligence, so it might only be a week or 2 before closing.

Not much the first few years as it takes time to get trusted employees and systems in place. It certainly helps to have a business partner. At some point you hopefully begin working on the business instead of in the business (cliche I know, but true) and after a while of that your vacation opportunities kind of explode. I imagine the timeline is different for everyone and every business, but doubt it’s overnight for any.

1. Yes 2) Most recent was 2 1/2 weeks, not the first multi-week one, but also I don’t necessarily do multi-week vacations every year 3) All in probably a month per year 4) October

*Again, we have been in business for over a decade now, I had no expectation of vacations the first few years. When we did go away I took my work with me, computer, customer service phone and all, and worked while the family went to the beach, etc. w/o me…but at least I was around and they got a break. Fortunately, that has all changed. Don’t get discouraged, it’s possible if you step out of the day-to-day long enough to create a plan and work the plan.

I would make the wild guess that you pay your office manager more than you pay him, he now knows this as the are a couple, and he would like to get on a more even financial footing (even though they perform totally different jobs).

As far as how to handle it, you’ve kind of answered your question. Employees are paid for value, if the $28 is replaceable at $22 w/o much hassle then maybe you offer $23. Replaceable at $20 then offer $21. We value low turnover so we try to pay better than market b/c it’s a hassle for us to hire, train and trust someone new. We are profitable so it’s worth it to us, but there is a point where it is not. It sounds like $28 is a point well above the hassle threshold for you, but maybe there is a number between $18 and $28 that is not so give it a shot. I don’t like the idea of canning someone just for asking for a big raise, unless “unreasonable” expectations/demands is an ongoing issue.

Then the question becomes will he stay for less and if he does will he be happy, and if he’s not happy do you still want him around? Research your labor laws in that case.

Final point, you may ask him to justify the $28 rate so that when you offer less he understands he is out of line with the market for his position (assuming he really is replaceable for much less).