Letting someone go is one of the least glamorous parts of leadership. It’s uncomfortable, emotional, and if you’re anything like me in my early years, you’ve probably kept at least one person around six months longer than you should have. Not because they were performing. Not because they were improving. But because you liked them and the thought of firing staff made you want to crawl into the void.
But if you want a high performing team, especially when you’re working with remote staff or a Virtual Assistant through LinkedVA, you have to get good at difficult conversations. You have to get good at making decisions that protect your business, not just your feelings.
And sometimes the bravest thing you can do as a leader is admit when someone is no longer a fit.
Why We Keep the Wrong People Too Long
Founders don’t hang on to bad fits because they’re clueless. They hang on because they’re tired, overwhelmed, or emotionally attached. You think you can coach them into being the person you need. You don’t want to hurt their feelings. You dread rehiring. Or you worry that if they fail, it means you failed too.
I’ve been there. I’ve had people on my team who drained my energy for months because I refused to call it. I convinced myself things would improve. Spoiler: they didn’t.
Keeping the wrong person will always cost you more than replacing them. It hits your time, your team culture, and your sanity. And your good people feel it long before you do.
So how do you know when it’s truly time to let someone go?
You use a checklist. A real one. Not your dramatic founder gut that fires someone on Monday and forgives them by Wednesday.
The Checklist
Before you even think about firing staff, you need to answer three questions honestly.
1. What is their attitude like?
Skills can be trained. Systems can be taught.
But a bad attitude? That is a long road and most people never come back from it.
Attitude shows up in the small moments. The defensiveness when you give feedback. The excuses. The blame shifting. The way their energy tanks a whole meeting. The way they make the rest of your team shrink rather than rise.
I once had a VA who checked every technical box. Fast. Accurate. Showed up. But the vibe was awful. Every piece of feedback was met with stiffness or silence. Every mistake was someone else’s fault. On paper she was fine. In practice she made everyone miserable.
Compare that with someone who genuinely wants to improve. I once hired a woman who barely knew the tools we used, but she tracked her own learning in a spreadsheet because she wanted to get better faster. She asked for feedback. She implemented it immediately. That is leadership gold.
If someone’s attitude is consistently draining and nothing changes after repeated feedback, that’s your first red flag.
2. Have you actually set expectations?
Most performance problems don’t come from bad employees. They come from unclear leaders.
Expectations live in your head until you put them in writing. How fast should they reply? How do you want tasks prioritised? What quality looks like? What you consider urgent?
I’ve watched so many founders get frustrated with a Virtual Assistant because they didn’t reply instantly or didn’t finish something “quickly enough,” yet they never communicated what response times mattered, what deadlines existed, or what urgency even meant in their business.
If you haven’t clearly set and reinforced expectations, you can’t judge someone for missing them. This is leadership responsibility, not their failure.
3. Have you trained them properly?
This is the part most founders skip, especially when they’re onboarding through LinkedVA or bringing in someone to reduce their workload fast.
Did you give them actual training, or a handful of Loom videos and a prayer?
Did you show them your style, your standards, your reasoning?
Did you give feedback early and follow up on it?
Did you explain how to improve, not just what was wrong?
Even experts still need context. A CRM specialist doesn’t magically know your tagging system. A designer isn’t born knowing your brand rules. Lack of training masquerades as incompetence when really it’s just missing information.
If someone has never been trained properly, you haven’t given them a fair chance.
So When Is It Time to Let Them Go?
If you’ve genuinely done all three:
- assessed their attitude
- set expectations clearly
- provided real training and feedback
and they are still not improving, still draining your energy, and still not meeting the mark, it’s time.
This doesn’t make you heartless. It makes you responsible. You cannot sacrifice your team performance because you like someone. You cannot hold onto someone who is costing the business more than they are contributing. And you definitely cannot keep hoping that next month will magically fix what has not changed in six.
Letting someone go is not unkind. Keeping someone in a job where they are failing is.
Final Thoughts
If reading this made you think of someone on your team, that’s not an accident. Every founder has that one person they’ve been carrying out of guilt, fear, or misplaced optimism.
But now you have a checklist. Now you can make decisions with clarity, not emotion. And now you can protect the team you’re trying so hard to build.
If you’ve been venting to your business bestie about someone for months without taking action, send this to them too. You’re not the only one who needs it.
