Several years ago I hired a vendor that wasn’t a good fit. Try as we might to work together, we didn’t communicate well. Everything was a struggle. After a frustrating few weeks, the owner of the business offered to refund my money and amicably part ways. His company had already done work on our behalf and I didn’t want to lose momentum. I turned him down. That was a mistake. When a small business owner, who needs your business (money), tells you to go elsewhere, listen. We parted ways a few months later in a much more costly and less amicable way.
You don’t want to work with people who don’t want to work with you. The same is true for friends and romantic relationships. Don’t chase people. If they don’t want you, move on. There are lots of other people who will see your value.
There are differing schools of thought on whether or not you should try to retain employees who quit. I’d be interested in seeing statistics on how long employees who quit but are then retained, stay with an organization and how well they perform. I’d let them go. Again, you don’t want people who don’t want you.

The challenge is that most people are afraid to speak up in organizations and relationships (of all kinds) when they’re unhappy. Unhappy employees typically quit versus make requests and give feedback.
The antidote is to create a culture in which employees, vendors, and customers openly make requests and talk about what is and isn’t working. Create a climate of candor in which feedback is exchanged regularly versus just during exit interviews, which is too late.
How to know when to cut bait with unhappy employees and vendors:
- You’ve had several open discussions and can’t meet each others’ needs. If you don’t have a job the employee wants, that’s a good reason to part ways.
- It’s not a good culture fit. You talk and talk but don’t communicate. Issues don’t get resolved. Frustration is the norm. This is also a good reason to end a working (or personal) relationship.
Five steps to create a more candid culture:
- Discuss employees’, customers’, and vendors’ needs and requests at the beginning of working relationships. Agree upon what success and a good job looks like. Ask lots and lots of questions, and listen closely to the answers.
- Ask for feedback regularly. Conduct a weekly plus/delta (a discussion of what is and isn’t working) during which all parties are invited and expected to speak freely. The more you have these discussions, the easier they will be and the more candid people will become.
- Address challenges as they happen.
- Discuss challenges that can’t be fixed.
- If a relationship isn’t working, end it sooner rather than later. Be slow to hire and quick to fire.
There are lots of talented vendors and employees. Find employees and suppliers who are easy to work with (for you) and who can meet your needs, and vice versa. If you can’t meet each others’ needs or the relationship is a constant struggle, those are good reasons to move on. Don’t chase.

Being in the wrong job feels terrible. It’s not unlike being in the wrong romantic relationship, group of friends, or neighborhood. We feel misplaced. Everything is a struggle. Feeling like we don’t fit and can’t be successful is one of the worst feelings in the world.
The ideal situation is for an underperforming employee to decide to move on. But when this doesn’t happen, managers need to help employees make a change.
The first step in helping an underperforming employee move on to something where s/he can be more successful is to accept that giving negative feedback and managing employee performance is not unkind. When managers have an underperforming employee, they often think it isn’t nice to say something. Managers don’t want to hurt employees’ feelings or deal with their defensive reactions. In fact, when we help someone move on to a job that she will enjoy and where she can excel, we do the employee a favor. We set her free from a difficult situation that she was not able to leave out of her own volition.
I get asked the question “How do I know when it’s time to let an employee go?” a lot.
Here’s what I teach managers in our managing employee performance training programs: There are four reasons employees don’t do what they need to do:
- They don’t know how.
- They don’t think they know how.
- They don’t want to.
- They can’t. Even with coaching and training, they don’t have the ability to do what you’re asking.
Numbers one and two are coachable. With the right training and coaching, employees will likely be able to do what you’re asking them to do.
Numbers three and four are less coachable and are likely not trainable.
When you’re confronted with someone who simply can’t do what you need them to do, it’s time to help the person make a change.
The way you discover whether or not someone can do something is to:
- Set clear expectations
- Observe performance
- Train, coach, and give feedback
- Observe performance
- Train, coach and give feedback
- Observe performance
- Train, coach and give feedback
Welcome to management.
After you’ve trained, coached, and given feedback for a period of time, and the person still can’t do what you’re asking her to do, it’s time to make a change.
Making a change does not mean firing someone. You have options:
- Take away responsibilities the person can’t do well and give him other things that he can do well.
- Rotate the person to a different job.
Firing someone is always a last resort.
Sometimes we get too attached to job descriptions. The job description outlines a specific responsibility that the person can’t do. So we fire the person versus considering, who else in the organization can do that task? Be open-minded. If you have a person who is engaged, committed, and able to do most of her job, be flexible and creative. Give away parts of the job to someone who can do them well. I’ve also seen employees who were failing thrive in a different job. Organizations that are flexible survive; organizations that are rigid do not.

Let’s say you’ve stripped away the parts of the job that an underperforming employee can do well, and she still can’t perform effectively. Now it’s time to make a change.
Here are some words to use when having the difficult “it’s time to move on” conversation:
“I really want you on my team and to be successful in our organization. Over the past six months, we’ve had several conversations about the parts of your job that are a struggle. We’ve taken away responsibilities that aren’t a fit for you and have replaced those responsibilities with things that seemed like a better fit. And yet I can see that you are still struggling. I’m very sorry to say that it’s not appropriate for you to continue working here. Today is your last day.” Depending on your organizational culture, can also say, “How do you want to handle this? You can resign or we can let you go. I’ll do whatever feels more comfortable for you.”
This is a difficult conversation that no manager wants to have. Yet I promise you, this conversation feels better to your employee than suffering in a job in which s/he can’t be successful. After you’ve set expectations, observed performance, and coached and given feedback repeatedly, letting someone go is kinder than letting the employee flounder in a job in which he cannot be successful.
