How to Know If Someone Is a Good Hire (Before It Costs You Money)

In this clip, I break down how I decide if someone is a good hire before bringing them on full-time. Hiring in a small business is always a risk. One wrong person can hurt morale, culture, and reputation. Here’s what I actually look for, how I evaluate character, and why some of the best interviews turn into the worst employees.

If you are trying to figure out how to know if someone is a good hire, especially in a small business, this is how I think about it.

Hiring is always a risk.

When you are small, one wrong hire does not just slow things down. It can hurt morale. It can hurt culture. It can hurt reputation. It can cost real money.

So when I decide to bring someone on full time, I am not just asking if they can do the job.

I am asking if I trust their character.

That matters more than people think.

Why Reputation Matters When Hiring in a Small Business

In a small company, every person represents the brand.

There is no buffer. No layers. No big corporate shield.

If you send someone to a trade show or a client meeting, that person is the company.

I have been in industries where people still talk about things someone did three years ago at an event. Someone drank too much. Said something stupid. Did something reckless. That story sticks.

And it does not just stick to the person. It sticks to the company.

If you run a software company, this matters even more.

I have always thought about a CRM like a bank.

Customers store their data there. Their pipeline. Their revenue. Their communication history.

You need to trust the bank.

You do not want the bank acting reckless. You do not want the bank flexing. You do not want the bank loose with information.

You want it steady.

So when I am hiring, one of the biggest questions in my head is simple.

Is this person steady?

Not flashy. Not chaotic. Not trying to impress everyone.

Steady.

If I know someone is not going to embarrass the company, that is a strong foundation. And if the foundation is strong, it is hard to completely wreck the business.

How to Evaluate Character Before You Hire Someone

You can train skill.

It is much harder to train character.

I can teach someone software.
I can teach systems.
I can teach process.

It is much harder to teach emotional control, discipline, integrity, and long term thinking.

When I decided to hire Kado full time, it was not because of one interview.

It was because I had watched him over time.

At events. In conversations. In how he treated people. In how he handled himself when nothing was at stake.

No ego. No drama. No chaos.

That predictability mattered more than a resume.

If you are trying to know if someone is a good hire, look beyond the job description. Look at their patterns.

How do they live?

How do they act when no one is watching?

That tells you more than an interview ever will.

Why the Best Interviews Often Lead to the Worst Employees

This is something most business owners learn the hard way.

Some of the worst employees I have ever had were incredible in interviews.

They said all the right things.
They mirrored what I was looking for.
They were polished.

Then later, they became toxic.

Hiring has a honeymoon stage. People put their best foot forward. If they figure out what you want, they will try to become that version of themselves for 45 minutes.

That is why you should not tell candidates everything you are looking for.

If you say you need someone organized and great with computers, most people will immediately say they are organized and great with computers.

That is not useful information.

Instead, ask open questions.

What are your strengths?
Describe how you like to work.
Tell me about a time you messed something up.

Then listen carefully.

If someone naturally says they are meticulous and cannot stand when things are out of place, and you did not prompt that, that is real data.

If you ask about strengths and they hesitate and say they just think it is a cool job, that is different.

Not automatically bad. Just different.

The key is to watch how people think, not just what they say.

How to Avoid Hiring the Wrong Employee in a Small Business

Here are a few principles I follow.

First, do not oversell the role.

If you oversell it, you attract people chasing hype instead of responsibility. Be honest about what the job actually is.

Second, talk less in interviews.

The more you talk, the easier it is for them to mirror you. Ask questions and let them do most of the talking.

Third, look for patterns.

Anyone can fake one good conversation. What matters is how they operate over time. How they handle stress. How they treat people. How they show up consistently.

Fourth, accept that hiring is a skill.

A lot of business owners say they are not good at hiring.

That is fine.

It is a skill. And skills improve with repetition.

The more people you hire and fire, the more patterns you see. It becomes easier to spot red flags early. It becomes easier to let someone go when it is not working.

Firing is uncomfortable.

Keeping the wrong person is more expensive.

Hiring a Friend in Business

Hiring a friend is not automatically a mistake.

But you need to be honest with yourself.

Have you observed them in real situations?
Have you seen how they handle pressure?
Are you willing to lose money if it does not work out?

If you are not willing to lose money, you are not taking a calculated risk. You are making an emotional decision.

When I brought Kado on, I knew there was risk.

But I trusted his character because I had seen it over time.

That is very different than hoping someone turns out to be disciplined.

The Question I Always Ask Before Hiring

Before hiring anyone, I ask myself one simple question.

If this person never improves beyond who they are today, would I still trust them representing the company?

If the answer is no, that is a signal.

Skills can grow.

Character usually does not change dramatically.

If you are trying to figure out how to know if someone is a good hire, focus on the foundation.

Protect your reputation.
Protect your culture.
Protect your long term trust.

Once the foundation is solid, everything else gets easier.