“I want to create a place where these guys can have a second chance.”

William was describing his approach to employment. I loved this about him and his businesses. Like most of my clients, he recognized how transformative the work environment can be on someone. He was leaning into it.

However, not long after, came this conversation:
“I don’t know how to make this work! We just had our garage broken into, and $50,000 worth of equipment was stolen. Cameras show us it was one of the guys we were trying to help.”

He was surprised. I wasn’t.

Over half of his crew had criminal histories. Most of them were addicts—heroin was the drug of choice. Yes, they had “gotten clean” while in jail. But… hiring risky employees comes with challenges that must be addressed.

How to Manage Risky Employees Effectively

It’s not always as simple as saying, “Just don’t hire those kinds of people.”

Some employers, like William, choose to work with risky employees. Many others find their applicant pool leans heavily toward “risky.” You can’t always choose your hiring pool, but you can create a workplace where both your business and your employees succeed.

Three Tools to Make It Work: Culture, Structure, and Mentoring

1. Culture

Use the power of what academics call “normative pressure.” Most people try to go along to get along. We want to be liked and accepted, so we mimic who we are around.

This is true at work. Use it to your advantage. Develop a very clear culture based on your values and vision. The clearer and better articulated this is, the easier it is for people to follow.

Protect your ratios: At a minimum, each risky employee should be surrounded by at least six “healthy” examples of your culture. For example, if your values include punctuality, professionalism, and teamwork, ensure the majority of your team models these behaviors daily. Your risky hire will be marinated in relationships that demonstrate how you do things.

2. Structure

Risky employees, almost by definition, need more structure. They usually have a harder time with self-management. Clearly defined roles, responsibilities, and processes go a long way to helping them succeed.

For example: Set up written agreements that outline expectations for attendance, work performance, and behavior. These agreements should include a plan for consequences if expectations aren’t met. This keeps everything transparent and fair.

You’ll also need to step up security and safety precautions. Without creating a sense of, “We don’t trust you,” set up a visible alarm system with cameras. Lock up valuable tools. Ensure passwords are updated regularly.

You’re not assuming someone will do something wrong—you’re setting up a system that helps keep honest people honest while also maintaining a secure environment for risky employees to thrive.

3. Mentoring

Along with culture, train several of your more respected employees to be mentors. Mentoring is an intentional relationship intended to produce growth.

Keep it simple: Effective mentoring doesn’t have to be complicated. Teach mentors to check in regularly, listen well, and ask thoughtful questions. They don’t need to become a risky employee’s best friend but can provide a steady, intentional presence of accountability and support.

Put Your Oxygen Mask on First

I’m sure you’ve heard the instruction on the airplane:

“In the event of an emergency, a mask will fall from the ceiling. Please put your mask on first before helping fellow travelers.”

The logic is simple: you’re no good to anyone if you’re not taken care of. But once you are, you can help others.

If you hire risky employees, ensure that you and the healthy members of your team are supported and equipped. If you don’t, you won’t have the resources or resilience to help others.

Conclusion

If you combine Culture, Structure, and Mentoring, you’ll go a long way toward creating a workplace where risky employees—and your business—can thrive.

Of those three: Culture, Structure, and Mentoring – which is the most important area for you to focus on right now? What one change can you make that will make the biggest difference?