Ep -
297
38 min
Why Your Managers Keep Asking You What To Do
You promoted your best producer, and now they ask you what to do three times a day. Perry Holley explains why that is a development gap rather than a hiring mistake, and what it takes to build people who think for themselves.
Being great at running a contracting business doesn't automatically make you great at leading people.
As your company grows, your role needs to evolve. You can't keep managing every job, solving every problem and making every decision if you want to scale.
But stepping back isn't always easy, especially when you've spent years building your business from the ground up.
In this episode of Contractor Evolution, host Danny Kerr sits down with leadership expert Perry Holley of Maxwell Leadership to discuss how contractors can transition from doing everything themselves to developing leaders who can run the business without constant oversight.

Five Key Takeaways:
1. Stop being the Doer and start being the Leader
The skills that made you a successful contractor aren't necessarily the ones that will make you a successful leader.
As Perry explains, there's a big difference between being a great individual contributor and leading a team of people to achieve results. When you continue stepping in to solve every problem, you limit your team's growth and your company's ability to scale.
The goal is to shift your focus from working in the business to working on the business.
2. Empowerment requires more than delegation
Handing someone responsibility doesn't automatically mean they're ready to handle it.
Perry outlines a seven-step process for developing empowered employees:
- Recruit the right people.
- Position them in the right roles.
- Model what success looks like.
- Equip them with the necessary skills.
- Develop their personal and leadership abilities.
- Empower them to take ownership.
- Measure their progress.
Skipping these steps can leave employees dependent on you, even after you've delegated the work.
3. Develop people, not just their job skills
Training someone to estimate jobs, manage crews or close sales is important. But technical skills alone don't make someone a great leader.
Perry emphasizes developing the personal disciplines that help employees succeed, including time management, prioritization, emotional management and resilience.
Investing in these areas helps create managers who can make decisions and lead their teams independently.
4. Become a leader who asks better questions
When an employee comes to you with a problem, your first instinct might be to provide the answer.
But constantly solving problems for your team prevents them from developing their own judgment.
Instead, Perry encourages leaders to ask questions like:
- What do you think?
- How would you handle this?
- What's your perspective?
Understanding how employees think allows you to coach them more effectively while building their confidence.
5. Build accountability through ownership
Accountability isn't about micromanaging or assigning blame when something goes wrong. It's about creating a culture where employees take responsibility for their results, overcome obstacles and bring solutions instead of excuses.
When managers understand what they own and feel empowered to solve problems, you can spend less time putting out fires.
Build a Business That Doesn't Depend on You
Developing strong leaders takes time, but it's essential if you want your contracting business to grow beyond your personal capacity.
Watch the full episode of Contractor Evolution to hear Perry's practical advice on developing managers, empowering employees and creating a culture of accountability.
And if you're ready to build a team that can run your business without you being involved in every decision, book a complimentary discovery call with Breakthrough Academy to explore how better leadership and management systems can help you scale.



