Hire smarter. Fire better. Both with AI.

Hire smarter. Fire better. Both with AI.

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In 2019, still running the medical supply business, I needed an operations manager. I was drowning. I posted on Indeed, got 22 resumes, read them on my couch at 11pm on a Tuesday, picked the one with the cleanest resume and the strongest LinkedIn, and hired him within two weeks.

It took 11 weeks and roughly $17,000 to unwind that hire. Severance. A botched supplier migration he half-finished. The cost of re-running the search. The cost of me doing his job for a month while we found his replacement.

Best-looking resume in the stack. Worst hire I've ever made.

Two lessons. First: speed kills in hiring. Second: my pattern-matching at 11pm on a Tuesday is not a reliable instrument. Neither is yours.

The good news is AI is genuinely useful here — on both sides of the equation. Hiring better. And, for the painful conversations every owner postpones for six months too long, firing better. We're going to cover both.

The "fully automated AI hiring" platforms. There are three or four in the wild now — AI reads resumes, AI conducts a text-based first-round interview, AI scores candidates, you get a ranked list. The vendors claim humans don't enter the loop until the final stage.

Skip. Two reasons.

One: AI screening for employment is under active regulatory scrutiny. A small business does not need to be the test case. Two: I sat through a demo of one of these tools last month and the "ranked candidate" list rewarded resumes stuffed with the right keywords over candidates who wrote like actual humans. That is the wrong filter for almost every SMB role.

Use AI to help you screen. Don't use it to replace screening.

Three weeks ago I helped a client of mine — runs an HVAC company, about 40 techs — sort through applicants for a service manager opening. 18 resumes in five days. He called me almost shouting: "I just spent three hours reading these. Three. Why am I doing this in 2026?"

Here's the workflow we used.

Step one: write your filters before you touch a single resume.

Open Claude (the $20/mo Pro plan). Type out what you actually need. Not a job description — your real, embarrassing, specific requirements. The ones you'd say out loud to your spouse but not write in a job post.

For his service manager role, it came out to: "Must have supervised at least five people directly. Must have worked in a service business with physical job sites — not retail, not office. Can't have job-hopped more than twice in the last five years. Nice to have: experience with dispatching or routing software."

Save it. That is your screening prompt for the entire role.

Step two: batch the resumes.

Paste three resumes at a time into Claude with this instruction:

That last sentence matters. Without it, Claude will fill in blanks with assumptions. With it, Claude will say "this resume doesn't specify team size, so I can't confirm the supervised-five-people requirement." That's the kind of disciplined reading I am not capable of at 11pm on a Tuesday.

Eighteen resumes in six batches: about 25 minutes. Manual would have been 90 minutes with worse consistency.

Step three: tailored phone screen questions.

Once you have your shortlist, paste each resume back in with the requirements and ask:

That second clause is mine. I added it years ago after a phone screen where I asked "did you manage a team?" and got a technically-true yes that meant nothing. Don't ask soft questions. Don't accept soft answers.

What didn't work:

He tried a tool called Fetcher — automated AI candidate outreach. $200/month. The AI-generated emails to passive candidates were so generic that two recipients replied asking if it was spam. One turned out to be the second-best candidate in the pile. We recovered, barely. Canceled after one cycle.

This is the part nobody talks about. Every owner I work with has someone in mind right now — an employee whose performance has been slipping for six months, who they should have addressed three months ago, and who they're still avoiding. AI doesn't make the decision. It removes the friction that makes you delay.

Step one: is it a coaching problem or a firing problem?

Open Claude and write out, in plain language, what's actually happening. The behaviors. The dates. The conversations you've already had. Then ask:

The clarifying questions are the value. AI will ask you things like "Has this employee had a documented conversation about this specific behavior?" and "Is the problem skill, will, or fit?" Half the owners I work with realize halfway through this conversation that they already knew the answer and were just avoiding it.

Step two: build the documentation trail you should have been keeping.

If you've decided it's a firing situation but you don't have documentation, you have a problem. Most owners don't. AI can help you reconstruct it from real conversations and observations — not invent it.

Last part is critical. Do not let AI invent incidents. Document only what really happened. The file needs to be real or it's worse than no file at all.

Step three: draft the performance improvement plan (if you're going that route) or the termination letter and conversation script.

If you're giving the employee one more shot, ask Claude to draft a PIP with specific, measurable goals, a clear timeline (usually 30-60-90 days), and explicit consequences. Bring it to your employment lawyer for a 15-minute review before you deliver it. Cheaper than having a PIP that doesn't hold up later.

If you've decided to end the employment, ask Claude to draft three things:

Then bring all three to your employment lawyer. Same 15-minute review. You will walk in prepared instead of paying him to think from scratch.

A real example. A dental practice owner I work with had been postponing a termination for four months. The hygienist was good when she started, but the last six months were a steady decline — chronic lateness, two patient complaints, and an open hostility toward the new front-desk manager. We ran the whole workflow on a Sunday afternoon. By Monday at 3pm she had delivered the conversation. The hygienist actually thanked her on the way out — she'd known it was coming and had been hoping for the clarity. The owner told me afterward she'd lost four months of sleep over a conversation that took 11 minutes to have.

What I'd use for the full hire-and-fire workflow:

Canceled: Fetcher. $200/mo. Automated outreach that read like spam. Not worth the subscription.

The wrong hire costs you a quarter. The wrong hire kept on too long costs you a year. The hard conversation you've been postponing is already costing you — you just can't see the line item.

If you only do one thing this week: write your real must-haves and deal-breakers in plain language for the next role you'll hire for. Don't post a job until you have them on the page.

If you've got 20 minutes more: pick the employee whose name just popped into your head when I described the postponed conversation. Run the "coaching problem or firing problem" prompt above. See what you already know.

— Hank