The Hardest Goodbye, Best Lemon Pasta, & Smartest TV
For many, firing someone is the hardest thing a manager has to do. It shows up that way in movies and television — the sweaty palms, the closed door, the box of belongings. That reputation is earned, and folks will go to extraordinary lengths to avoid it.
What's less often said is why it's so hard — and what we do instead.
We keep someone on longer than we should, telling ourselves it'll improve. We absorb the impact of their underperformance rather than address it. We avoid the conversation until the situation has become so untenable that the ending, when it finally comes, is messier and more painful than it ever needed to be. (Am I also talking about my love life? Not no.)
And unlike client relationships, where the power dynamic is relatively clear, relationships with contractors and employees carry a particular kind of weight. You are responsible, at least in part, for someone's livelihood. That's a heavy thing. But it can become a reason to stay stuck — and a reason to deprive someone of feedback they genuinely needed and deserved.
This is Part 3 of our four-part series on ending business relationships well. We previously discussed how to know when it’s time to end a client relationship and what to do about it. This week: how to know when it's time to part ways with a contractor or employee — and why getting there sooner, and more honestly, is usually the kinder choice.
🧠 Why we stay too long
The reasons we linger in contractor and employee relationships that aren't working are different from the reasons we stay with clients. A few worth naming:
The livelihood weight. When you're responsible for someone's income — even partially — ending the relationship feels higher stakes. That's real. It's also worth examining, because it can tip from compassion into avoidance.
The power dynamic confusion. Contractors occupy a strange middle ground: they run their own businesses, often have more experience in their specific domain than you do, and yet are accountable to you for deliverables. Many of us aren't sure how much authority we have, how much feedback is appropriate, or whether we're even allowed to have standards. (You are.)
The personal connection. Sometimes the contractor isn't just a professional contact — they're a friend's referral, a colleague's recommendation, or even a family friend. Ending that relationship can feel like a referendum on the personal connection, even when it isn't. Here's what's true: it's okay for someone your network loves not to be the right fit for you or a particular project. One example we heard recently: your family accountant may simply not have the small business expertise. But you wouldn't hold it against a colleague if their referral didn't work out. And you don't owe anyone a professional relationship that isn't serving either of you.
The guilt of external circumstances. Sometimes it has nothing to do with performance at all. Cash flow dries up. A client reduces scope. The political or economic landscape shifts in ways that directly impact your business — government contracts disappear, companies pull back on initiatives that drove your revenue, consumers tighten their belts, funding sources evaporate. These things happen, and they have real consequences for the people working with you. That guilt is understandable. It isn't a reason to avoid the conversation — it's a reason to have it with extra care and clarity.
🤝 Start here: did you set them up to succeed?
Before you get to the question of whether it's time to part ways, there's a prior question worth sitting with honestly: did you give this person what they needed to do the work well?
Clear expectations upfront — deliverables, deadlines, approval structure, the parts of your approach that are specific to how you work versus general industry standard — aren't just good management. They're the foundation that makes honest feedback possible. If you haven't articulated what you need, you don't have much to point back to when it isn't being met.
Different contractors and employees will need different levels of direction. Someone experienced in their domain may need only a brief and then space to execute. Others will need more step-by-step guidance. Everyone needs to be read in on whatever is particular to how you work. That's not hand-holding. That's setup.
When the work isn't landing the way you hoped, ask yourself honestly:
Did I communicate my expectations clearly — and specifically enough for them to act on?
Did I give feedback early enough for them to adjust?
Is the quality poor, or just different from the way I would do it? (If this one's hitting close to home, our newsletter on delegation is worth a reread.)
Did I give them a real opportunity to meet the bar before deciding they couldn't?
If the answer to any of these is no, the first move isn't ending the relationship. It's resetting it — having an honest conversation about what's not working, what you need, and whether you can get there together. Sometimes that conversation changes everything. Sometimes it clarifies that the fit isn't there. Either way, you'll have done right by both of you.
The absence of feedback isn't neutrality. It's its own kind of harm. The conversation at the end should never be the first honest conversation you've had.
🚩 If it can't be reset — signs it might be time
💸 The economics have changed
The budget that supported this role or engagement no longer exists — or no longer makes sense. This isn't a performance issue. It's math. The kindest thing you can do is name it clearly and quickly, so the person can make decisions about their own business or job search without delay.
🔁 You're getting the same results after giving feedback
You've communicated what you need. You've given them the opportunity to adjust. The work hasn't changed. At some point, continued feedback without action stops being generative and starts being a loop.
😶 You're working around them
You've started doing their work yourself, routing deliverables around them, or quietly absorbing their responsibilities rather than addressing the gap. This is avoidance dressed up as efficiency.
🎯 The fit was never quite right
The skills looked right on paper, but in practice the working style, level of output, or approach isn't what you needed. Sometimes this becomes clear early. Sometimes it takes longer. Either way, it's useful information — for you and for them.
🔋 The relationship requires more management than the work
If you're spending more time correcting, clarifying, or compensating for someone than you are benefiting from their contribution, that's a signal worth taking seriously.
🌱 They may have outgrown what you can offer
Sometimes the person doing the work is ready for more than your engagement can give them — more scope, more seniority, more creative challenge. Before you assume they'd rather move on, ask. They might love the brain break your work provides, or they might want to collaborate on winning bigger work together. You won't know unless you have the conversation. What you should not do is quietly decide for them that they'd be better off elsewhere — you might also be draining their bank account.
➡️ Next week: Once you know it's time — how do you actually do it? We'll cover the conversation itself, what you're legally required versus what's simply good practice for employees and contractors, and how to part in a way that leaves both of you with your dignity intact.
These conversations are hard, but they get easier with experience. Don’t have a ton of your own? Borrow ours! Our *final* Signature Dinner is on June 9th.
🪢 Laura & Lauren
Things We Loved This Week
LaurA’s Things
🤯 Pedro Pascal + puppies
😬 I fear this is the life I deserve…
🍋 Trying this asap.
Lauren’s Things
💊 How have I not done this yet? We know I have the supplies.
🏀 Is he?
📺 “I just think it’s so smart what CBS is doing.”
