Should I ask for a raise for myself AND another manager?

Question

Small Business of 40 employees. I am #2 person in charge (under the owner). I was given a raise a year an a half ago of 10%, however, the owner asked that I would not ask for another raise for 2 years. I agreed. (didn't feel right)

My coworker is below me, but is an integral part of this company. He is one of the most deserving employees here or anywhere that I have ever seen. He is also in charge of about 6 employees himself. The owner also recognizes this employees worth and knows that the company would not be what it was without him. I was able to help get this employee a 10% raise about 2 years ago.

We both have just absorbed another employees responsibilities. In fact, this ex-employee could have been considered the #3 person in charge and worked under myself. He quit his position and now his work is my and my "integral employees" responsibility. This ex-employee made the most money in the company. Even though he was the #3 person in the company, about 40% more per year than myself / my "integral employee". Reason being, he was experienced in areas that I was not. I have had an issue with this as I am and have been experienced in areas that he is not. Either way, this employee is now gone and we are responsible for his work. We each have absorbed about 40% of his duties and the owner of the company absorbed about 10%.

First Question: Do I ask for a raise for myself and my "integral employee"? I believe this is the right thing to do, both as a human and as a boss.

Second Question: Do I ask for a specific percentage? I believe that we both should be making about 20%-30% more than we make currently.

Our boss isn't one to hand out raises. There are no bonuses, perks, PTO, or anything like that. I have been here for 5 years and the other employee has been here for 9 years. The owner, however, is amazing. My "integral employee" and I have believed in this company since its inception. We both would love to work together with the owner to build something that we are not only proud of, but super succesfull. Our intention was to work here until retirement, but within the last year, we both have felt under-appreciated and have begun looking for other options. Neither of us really wants to go though. Please help!

Answer 1

First Question: Do I ask for a raise for myself and my "integral employee"?

When you feel underpaid, you should seek a raise. There is nothing wrong with informing your boss that you believe you're worth significantly more and are unhappy with how your paid. You can inform the owner that you will look elsewhere if you don't get an adequate raise as long as you can communicate that in a way that is not a threat or an ultimatum (in my experience if you have to issue ultimatums, you probably just want to leave because it usually damages relationships).

As a boss - especially if you're aware that one of your reports is looking elsewhere - you should let the owner know that the person is underpaid and that you feel it's time to remedy that. With your direct report, you should definitely let the boss know that you're worried the person is leaving if not more adequately rewarded.

Second Question: Do I ask for a specific percentage?

There is nothing wrong with asking for a specific percentage. I don't know that I've ever seen someone get a 20% raise without specifically asking for it and making a compelling case for why he or she deserves it. That being said, taking over responsibilities for someone who was paid significantly more than you is absolutely a reason I would seek a raise.