As the owner of your business, you should never feel threatened by the loss of an employee. Have a straightforward conversation with the employees to let them know that you are willing to take action if necessary. Work on assertive communication techniques that will help you hold the space. In my experience, some of the most challenging staff I have managed, have thrived after I have reset the expectations.

As far as the threat of losing his, keep your feelers out for a possible replacement and start building the systems and processes you will need in place to train the replacement in the shortest amount of time.

I work with entrepreneurs to build their businesses, address risk and strategy and work on leadership. I'd love to discuss this more with you and answer any questions you may have. Feel free to set up a call with me.

2 issues to address: (1) dependency on one employee and (2) dealing with a difficult employee. Both are addressed below.

(1) Ask yourself why you feel dependent on this employee. If it is merely because of what he does, then finding an alternative is not too hard. It may mean spreading the work between other people (you included), and it may mean others being busier for a while. Consider what you can outsource or automate, or hire a temp to cover. That is better than allowing toxic attitudes in the workplace.
If it is because of knowledge he has or relationships he has with clients, start working right now to change that. Find ways to capture and share information, make sure your clients associate positive experiences with the company as well as the people. If your employees capture knowledge in their heads then start new procedures to manage a CRM Or system to keep client files up to date.
Never let an employee hold your business hostage.

(2) Dealing with a difficult employee - there are good tips here already. I don't know how close your relationship with this person is but remember that the workplace is not the back-yard: loyalty is rewarded but loyalty is not the same as longevity or seniority. If he is causing damage to your business, that is not loyalty.
Have a clear conversation, talk about the work issues: is he dropping the ball? Is he not doing what is expected? Is he not performing to your required business standards? Ask him if there is something he doesn't understand, or if he wants more training. In essence: when you speak with him come to the table with solutions. If he refuses each one, then give him his warning and be explicit about what that means.

Best of luck with this difficult situation!

What so you mean when you say that your business "depends on him greatly"?

All team members, regardless of team size, can benefit from clear expectations related to their performance and professional demeanor. Expectations can be set formally, in terms of annual goals, and informally, in terms of company culture.

As a person who has worked for you for 10 years, do you have a relationship with this employee to understand id personal circumstances may have changed?

Sometime people outgrow companies and vice versa. Have job functions for this employee evolved and were these changes communicated to them?

Happy to jump on a quick call and discuss a few tactics to ease the tensions and retain good talent.

Dan

It’s hard to answer this question without knowing the nature of your business, but if his attitude is toxic then it will be affecting the work environment and ultimately the customers. At some point you need to assess whether his value to the company outweighs the damage he is doing to the company. If he is a valuable employee with a skill set that you can’t easily replace and he does a good job at a job that is isolated from others, then a bad attitude is something you need to address but maybe not worry too much about. If it’s going to make or break your business you need to do what’s best for your business.

It can be difficult when dealing with an employee upon whom you depend because they are competent, but on the other hand are not shored up in the area of manners and the etiquette of your office environment. My approach would be two prong, first of all, I would be very vigilant about finding a possible replacement for this particular employee, in case you need to eventually make that unfortunate move, and at the same time, I would begin an Professional Improvement Plan with said employee to help make them keenly aware of my concerns and expectations as an employee of our company. Starting an improvement plan with the employee will express the seriousness of your concern while also giving the employee specific areas to work on and a way for you to observe and measure if there is indeed improvement.
You can download a Professional Improvement Plan online. Hope this helps....All the best.

This is another similar question I answer this month. The previous question I answered was https://clarity.fm/questions/6150/new-coo-clashing-with-two-most-important-veteran-employees

I was requested for a call due to my answer in the above link. However, I asked him to follow my answer first and if he can solve the problem after using my answer then no need to request a call from me.

Luckily, he successfully used my method and save the money to call me. Thus I suggest you may click the link to read my answer, it may have some helps to you.

There is only one thing I like to highlight based on your case:
"you greatly depending on the employee really makes me wonder should you cease operation or if your profit still very attractive, then treat that employee as a customer and bear with his nonsense (although I feel quite ridiculous, if he really indispensable, you can't do anything much but just have the two options I suggested above)"

"if you disagree that he is indispensable, then my link above will be useful"

Hi! First of all, your business can never depend on nobody, even if this someone is yourself.
It looks like your employee knows that he is essencial for your company, and it makes him powerfull.
If I were you, I would try to understand what is happening with this employee. He is human, not a robot, and everybody has problems in some moments of lives. Maybe he is going trought some difficult moments that are changing his behavior. It could be a disease, a family problem, a financial problem, or it’s just a problem with the job. However, the first step is have a professional conversation with your employee to understand what is going on.
If you the problem is the job, try to understand which facts are making him unmotivated and what could you do to make him feel better. Sometimes a salary rise or new beneficits will solve the problem. Sometimes you should review the company environment, culture, relationships…
But one thing is certain, you gotta have a honest and open mind conversation with him. Show him that he’s important (not dependent), reconized and valued for your company.

Why is your business so dependent on this one person - what if he decides to quit of his own accord, or becomes sick, or has an accident?

I think you should plan as if he were to suddenly become sick - e.g: get any passwords, or access that he has made generic, or transfer ownership or admin rights to you, so that you aren't locked out of your systems, any information that he has needs to be made available, whether that's writing it down, or getting him to record his screen using something like Loom - so that you have processes documented, and put on a shared drive?

In terms of his behaviour, you could either speak to him about it, maybe things have changed in his personal life and its affecting him at work, or decide that the best course of action is to let him go.

Hope that helps, and I'd be happy to chat further on a call if you wish!

Have you tried getting to the root of his lack of respect? I suggest having a one on one conversation as a peer rather than a boss. He may be going through something and he’s taking his frustrations out at the work place. He’s been with you for 10 years for a reason either he really likes the job or he’s really good. Also he may have lost interest in the job as well. But sometimes employees avoid conversations with their boss because it becomes to work related rather than just two people simply having a conversation. I can see you care and value him as an employee since you haven’t gave up on him due to his behavior but before throwing in the towel I suggest getting to the root of it. I’ve had a manager that was sending me to become one as well but a lot was going on. When I did try to tell her how I felt it went left and I ended up leaving a great paying job because I simply couldn’t deal with managements lack of communication. Feel free to give me a call if you want to ask other questions that may help get your employee back on track. :)