Why Your Team Won’t Step Up (and What You Can Do to Fix It)

I once had an employee request a surprisingly large budget to redecorate the office bathroom. My first reaction was, Why are we talking about paint colors when we’re buried in client work?

But then I remembered a younger version of myself—an administrative assistant in charge of maintaining the breakroom. I kept everything stocked and spotless, but over time I became strangely fixated on how much coffee everyone drank and what it was costing us. I didn’t realize then that the coffee budget was the smallest piece of what actually keeps a team supported and happy.

What I really wanted was meaningful responsibility. Purpose. A problem to solve that actually mattered. So I took that tiny task and ran way too far with it.

Looking at my employee, I recognized that same drive—the desire to own something, to contribute in a real way, and to be pointed toward work that makes a difference. And it hit me: as their leader, I hadn’t given them the direction or the meaningful responsibility they needed… or that the business needed them to have.

And do you know why? Yes, as a small business leader you are likely guilty of this too:

Holding on instead of letting go. 

I was slowly transferring responsibility to ensure tasks were done to my standards but was still nervous to trust someone other than myself to own the important work, despite my overflowing calendar.

If you have experienced this too, your team focused on the wrong objective that isn’t aligned with your mission or monthly goals, coming to you with the same questions on repeat, shying away from making decisions, then congratulations! You are ready for the next level of your leadership journey.

Common reasons your team isn’t stepping up:

• They don’t know what “good” looks like.
• They don’t feel empowered to make decisions.
• They fear messing up or disappointing you.
• They have been unintentionally trained to rely on you.

These are bottlenecks created early on, intentionally or unintentionally, as you grow your business to create consistency and quality standards. At some point, every leader outgrows this system and we need to transition to a system of trust and shared authority in order to focus on growth, strategy, or get time back; However, we’re usually so buried in the weeds with limited time to dig ourselves out because we didn’t see this milestone coming until it smacks us in the face.

If you find yourself:

• Doing everything yourself because “it’s just faster.”
• Micromanaging or reviewing all projects and deliverables.
• Jumping in the moment things go wrong (like that proposal that needs to go out for the client but an employee is out sick.)

If this sounds familiar, you’re not alone- every strong business owner experiences this. The important thing is not to stay here.

Shift your leadership.

Making the shift from task manager (a.k.a. “boss”) to leader becomes critical to successfully transitioning to the leader your business and your team now needs you to be. It is rooted in clear expectations, outcomes, and what “success” looks like. This shift reduces the need for constant oversight and micromanagement. Rarely do I see a team that isn’t ready for the opportunity to show you what they are capable of. What you need to be teaching now is critical thinking instead of purely task ownership.

Empower your team.

Yes, this step is going to require forethought and planning. No pain, no gain my friend. Share your decision criteria- this likely lives in your head and I don’t know about your employees, but mine have never passed the mind reading class. Fill them in on what you look for when you are reviewing. What decision authority are they trusted with and at what point do they need to kick it up the chain?

Ask “what do you think?” before answering.

I had another employee that was incredible but was not confident in making decisions on her own. I hadn’t given her the freedom to make decisions either, I was still overseeing all of her work to ensure quality control which filled up my calendar needlessly. Because she kept asking, I thought she didn’t know how to handle situations until I gave her the answer but I knew her potential and what she was capable of. I started asking her how she thought she should handle a client situation. Several times she blew me away with her answers! Knowing what was in her head gave us both the confidence for me to step out of her way and let her do the job I hired her to do. I have seen this time and time again with my clients, untapped potential on their teams just waiting for the opportunity to show what they can do. You would be surprised what your employees know if you just listen. 

At the end of the day, most employees genuinely want to contribute at a higher level—they just need clarity, direction, and a leader who believes they’re capable. When you give your team the structure and space to step up, they will surprise you in the best possible way. And you don’t have to figure that out alone. 

Choose one area to focus on this week:

• Clearer expectations
• Better handoffs
• A defined “ownership zone” for each role
• More consistent touchpoints

Change one of those, and you’ll feel relief faster than you expect. And remember, you don’t have to overhaul everything at once. Start with one clarified role, one delegated responsibility, or one conversation that sets expectations. Small shifts build the trust and momentum you’re craving.

If this is the kind of support you’ve been craving—practical steps, a smoother team dynamic, and more space to breathe—my From Boss to Leader cohort walks you through the exact framework to make that shift. It’s designed to help you build a team that steps up with confidence so you can finally step back without chaos.

Learn to lead differently here.