Waiting and hoping
- What it fixes
- Nothing, though it spares you a hard talk this week
- What it leaves
- The same work undone, and him still not told
- Who still pays
- You, and whoever picks up the slack
Straight answers: problems
How to Tell Whether He Is Falling Short or the Job Grew Past Him, and What Fair Looks Like
For the owner with a team who has spent a long time working around someone who stood by them.
"Great guy, very loyal. And he's not getting it done." You have said it to your spouse, or your accountant, or yourself on the drive home, and then you stopped, because you do not like where the next sentence goes. He was there the year you nearly went under. He told you to pay him next week, and he meant it.
So you work around him. You fix his schedule after he goes home. The big customer now calls someone else on your team, and nobody says why. You stopped asking for the report two years ago, because it is faster to build it yourself. Owners say this to Max Koz in almost those words, and what they are after is rarely how to fire someone. They want to do right by him and stop pretending the job is getting done.
Below is how to tell whether he is falling short or the job grew past him, without being unfair to someone who stood by you and without living with this for another year. It starts with putting him next to everyone else who reports to you, on the same questions, at about two minutes a person.

Start with your own week. The schedule you fix, the report you build and the customer call you take are his job, and you are doing them on top of your own. You stopped noticing, because it grew a little at a time.
Your team knows, too. Someone picked up the work he dropped, and she has noticed that she gets more of it for the same pay. The others have watched how long this has gone on, and they have learned that this level of work is allowed here.
Then there is him, and this is the cost owners tend to miss. He is the one person in the building who has not been told. He still thinks he is doing the job you gave him ten years ago, and he is, but the company needs a different job from him now. The sooner he hears it, the more time he has to do something about it.
Doug and Polly White, writing in Entrepreneur, say owners keep long-time people who no longer add value because they fear the disruption and the hit to the culture, and that there is never a convenient time. They put it this way: "Loyalty is a fine quality unless it is killing your company." In most companies we would say the damage comes more slowly than that. A job the company needs goes half done, you fill in the rest, and nobody says so out loud.
If you want to put a number on those hours, read What Is Your Hour Worth as a Business Owner?
None of these makes you a bad owner. Every one of them comes from caring about him and not wanting to hurt him. Each one also puts off telling him one thing: this is what the job is now.
You give it another quarter, because he has come through before. It feels kind, and it costs nothing today. EOS Worldwide's piece on this, "Firing Uncle Joe," says waiting for a long-time employee to improve is not a good plan, and we agree. He cannot fix a problem nobody has told him about.
You say "we need to tighten up" in the meeting, looking at nobody. You mention how late the report was. He nods, because he thinks you mean the others. Monroe Porter, writing in Roofing Contractor, says complaining about it does not work, and that you have to say the problem and what you expect to his face. His line is "workers need bosses, not buddies." After fifteen years you are his boss and his buddy, and that is why this is hard.
This is the road that lasts longest, because it works. The work gets done this week. You redo his part, or you route it to someone else, or you stop asking. His job no longer matches what he does, you cover the difference, and he is the last to find out.
You bring in a younger manager and call it more help. Now two people each have part of a job, and he has worked out what it means before you have finished explaining it.
If you have already added people and it all still comes back to you, read Why Hiring More People Didn't Fix It.
Director of Special Projects is a generous thing to offer, and it comes from a good place. Entrepreneur's writers say moving a struggling person sideways without cutting pay usually drains money and leaves everyone uncomfortable. We would add that he is no fool. After all these years he can tell when the work is not real.
Someone tells you to start documenting. A write-up on its own tells him he is in trouble, and it does not tell him what done looks like. Porter describes something different: a plan you build with him, checked at 30 days, with a wider review at 60 to 90.
One Friday it becomes too much, and you do it fast to get it over with. The EOS piece does say that if he does not get the job, want it or have the ability to do it, and no role exists where he could succeed, removing him is for the good of the company. It also says to act soon and sit down with him face to face first. When he gets no warning, the team watches a man who stayed all those years find out last, and they remember it.
Picture the job you gave him. It was six people and a few trucks, and he was the best you had. Today the same title means running other people through forty jobs, watching a budget and answering to customers who want a report on Friday. Nobody sat him down and said so, because it grew a month at a time. In our judgment, that is what has happened most of the time when a loyal man stops getting it done. The job grew and nobody told him.
Loyalty is what he gave you. It is real, and you owe him something for it. It is not the same as doing today's job, and owners get stuck when they let his loyalty make up for the work that is not getting done.
Before you say anything to him, you need to know how he compares with the rest of your team, and right now you do not know. You have been comparing him with the man he was ten years ago, or with how you feel about him. You have never put him next to the others on the same questions. Until you do, you cannot tell whether he is the only one short of what his job needs, or just the one you feel worst about. That is the fair way to start, because you will say things in that room that you cannot take back.
Then tell him. Respect means telling him the truth early about what changed and what done looks like now, and giving him a fair shot at it. Do not hide it from him until it blows up.
We see three fair ways this can end. He rises to it, he moves to work he can do and the company really needs, or he leaves with dignity. Do not make up a job for him.
The assessment shows your own answers about your own people. It cannot tell you why someone is falling short, and it does not decide for you.
This page is not legal advice. Talk to an employment lawyer before you let a long-time person go.
If he is only one of the reasons everything lands on you, read Why Everything Still Comes Back to You, Even With a Team.
B10M works on the seven parts of a company that make it grow: leadership, focus, hiring, marketing, sales, accountability and innovation. You work on one at a time, never all seven.
The way of choosing which one is called The One-Play Method, and it has three steps: find the lowest one, move it up one level, repeat.
Here the lowest one is a job that has changed without anyone saying so out loud, and it falls under accountability. Moving it up one level is small on purpose. The job gets written down as it is today, he hears it from you, and you both know what done looks like. You do not reorganize the company around him. Once that is working, you look at what is lowest next.
You have one man in your head right now. Put him next to everyone else who reports to you, and see where he lands when you answer the same questions about all of them.
See where he landsHere is each road by what it fixes, what it leaves undone and who pays for what it leaves.
| Option | What it fixes | What it leaves | Who still pays |
|---|---|---|---|
| Waiting and hoping | Nothing, though it spares you a hard talk this week | The same work undone, and him still not told | You, and whoever picks up the slack |
| Hinting and dropping comments | Your feeling that you said something | A clear standard he could actually meet | Him, because he does not know what you meant |
| Working around him | The work gets done this week | A job that no longer matches what he does | You with your hours, and whoever took his work |
| Hiring someone over him or beside him | Some of the missing work gets done | What his job is now, and who answers for what | The new hire, him and your payroll |
| A new title or a made-up role | The awkward moment, and his pride for a while | Work nobody really needs, at the same pay | The company, and him when he works it out |
| A write-up with nothing behind it | You have a record of the problem | What done looks like, and any plan to get there | Him, because he gets a warning and no real shot |
| Letting him go with no warning | The job is open, and the waiting stops | Who keeps what he knows, and what the team makes of what you did | Him first, then the team's trust in you |
| See him against the team, then tell him the truth (B10M) | You see where he stands, and you say so early with a fair shot | Why it happened, and the decision itself, because the list is only your own answers. It can still end with him leaving | You, in the hard talk you have put off, and him, who finally hears it |
Waiting and hoping fixes nothing, though it spares you a hard talk this week. It leaves the same work undone and him still not told, and you and whoever picks up the slack pay for it. Hinting and dropping comments fixes your feeling that you said something. It leaves out a clear standard he could actually meet, and he pays, because he does not know what you meant. Working around him gets the work done this week. It leaves a job that no longer matches what he does, and you pay with your hours, along with whoever took his work. Hiring someone over him or beside him gets some of the missing work done. It leaves open what his job is now and who answers for what, and the new hire, he and your payroll all pay. A new title or a made-up role fixes the awkward moment and saves his pride for a while. It leaves work nobody really needs at the same pay, and the company pays, then he does when he works it out. A write-up with nothing behind it gives you a record of the problem. It leaves out what done looks like and any plan to get there, and he pays, because he gets a warning and no real shot. Letting him go with no warning opens the job and stops the waiting. It leaves open who keeps what he knows and what the team makes of what you did, and he pays first, then the team's trust in you does. Seeing him against the team and then telling him the truth means you see where he stands and say so early, with a fair shot. It leaves open why it happened and the decision itself, because the list is only your own answers, and it can still end with him leaving. You pay in the hard talk you have put off, and he pays when he finally hears it.
Sample
Carla, Gene and everyone else on this list are made up. They are not clients, and nothing here is a result.
Carla owns an electrical contracting company, and four people report to her. One of them is Gene, her operations manager, who has been with her fifteen years. She typed in four first names and roles, answered the questions about each person, and this is the order she got:
Carla came to this thinking about one man. The list shows what she could not see with only Gene in her head. Tess is short of what her job needs too, and Carla is covering the difference in both jobs. Gene's grade is the same as Tess's. What sets him apart is how far the job has moved and that Carla hesitated.
None of the questions ask how long he has been there, and Carla still knows it. The order is a starting order, and she can move anyone up or down, because she knows things the questions did not ask.
The list does not tell her why, and it does not choose for her. She still has to decide whether the job gets smaller, and she still has to sit down with Gene and tell him what the job needs now.
To see your own list, type the first names and roles of the people who report to you. It takes about two minutes a person, and your list stays in your browser unless you ask for the emailed version.
See where he landsThe method is proven over 30 years in business and 17 years helping small companies.
Max Koz is the man behind B10M. Here is his record with clients, in his words: 45 of 50 had significant positive movement.
Those results are those owners' results. They are not a forecast for your company, and we are not promising them.
We wrote this for two reasons. The first is to be useful even if we never talk: put him next to the others, write down what his job needs today, and tell him. The second is to show you where to go if you want help. Run the Team Assessment first. If you want help after that, apply for a 15-minute call with Max.
Yes, and that is why this page exists. What you owe him is the truth while he can still do something with it, a clear picture of what the job needs today, and a fair shot at it. If it comes to that, you also owe him a dignified way out. You do not owe him years of being worked around without knowing it.
That is a real risk, and the assessment asks about it for each person: if this person quit on Friday, what happens? A serious answer there says more about how the work is set up than about him. Get what he knows written down whichever way this goes, and ask him to help, because he is the one who knows it.
The team already knows he is not getting it done, and they have known for a while. What they do not know yet is what you do about it. They will watch whether you let it slide, and they will watch how you treat a man who stayed. Telling him straight and treating him well answers both.
Sometimes, if the work is real. The EOS piece says to look for a role where he could succeed, and Entrepreneur's writers warn that a sideways move at the same pay usually drains money and leaves everyone uncomfortable. Our test is simple. If he left tomorrow, would you hire someone to do that work? If the answer is no, you are making up a job.
The assessment takes about two minutes a person, and ten people is about twenty minutes. You already spend more than that on his work every week, fixing what comes back. What takes real time is the talk and what follows it, and you will have to give him that time whether you start now or next year.
Nothing here says EOS is wrong. Its own piece on this man gives much of the same advice: do not wait, and sit down face to face. In our judgment, a whole-company program can stall when the owner has to run all of it. This asks for one thing: tell him out loud what the job he holds needs now. If that works, you look at what is lowest next.
If two or three people report to you and he is one of them, this matters more, because one person is a big share of your company and everyone can see it. The assessment works for a short list too, and it does not ask for anything you need to look up. List the people who report to you, not the whole payroll.
If you end up hiring for the job, read Why a Great Interview Turns Into a Bad Hire.
Checked November 4, 2026. Facts about other companies come from their own pages and are in our words. This page is not legal advice. Everything else on this page is our judgment.
Waiting for a long-time employee to improve is not a good plan. Sit down face to face, look for a role he could do, and if none exists, removing him is for the good of the company.
Owners keep long-time people who no longer add value to avoid disruption. There is never a convenient time, and moving someone sideways without cutting pay usually costs money and leaves everyone uncomfortable.
Say the problem and what you expect to his face, build a plan with him, check it at 30 days and again at 60 to 90.
Federal age law protects people 40 and older, covers employers with 20 or more employees, and reaches firing.