Let’s face it. Many owners and managers in the green industry have one thing in common: they try to do too much.
In the early days, it was necessary. You were the crew, the salesperson, the bookkeeper, and the admin all rolled into one. But as your company grows, that same DIY mindset starts to hold you back.
If you’re feeling stretched thin, constantly chasing after loose ends, or unsure why your team can’t seem to keep up, here’s something to consider.
Delegation is not a luxury. It’s a leadership requirement.
And most managers don’t do it well, not because they don’t care but because they don’t understand the process behind it. Delegation is a skill. Just like pruning, planting, or estimating, it requires a method, some coaching, and a commitment to doing it right.
Why Most Delegation Fails
Too often, delegation is treated like a handoff at a sprint. Managers say, “Here, take this,” and walk away assuming the job will be done just like they would have done it themselves.
But delegation isn’t a relay race. It’s a communication loop. And when it breaks down, the results are missed deadlines, dropped balls, and the worst outcome of all are tasks that end up back on your desk.
If you’ve ever felt like delegating makes more work for you instead of less, the problem isn’t the people…it’s the process.
The 6 Steps to Delegation That Actually Works
Here’s the truth: good delegation doesn’t just free up your time. It trains your team to think, act, and lead with more independence. It creates future crew leaders. It builds trust.
But it only works when you follow a few essential steps.
1. Prepare Before You Assign
Before you can delegate a task, you need to understand it yourself. That means mapping out the outcome you want, any constraints or parameters (like timing, cost, or materials), and any background knowledge they’ll need to succeed.
Many managers skip this part. They delegate an idea instead of a clear task. The result? Confusion and subpar results. Clarity upfront prevents cleanup later.
2. Communicate with Intention
When assigning the task, be specific. Describe what needs to happen, when it’s due, what “done” looks like, and why it matters.
Don’t assume your team knows the background. Don’t skip the “why.” Giving context shows that the task has purpose, and people are much more likely to take ownership when they understand how their work connects to the bigger picture.
3. Check for Understanding
Here’s where most delegation falls apart. The manager explains the task, the employee nods, and off they go. Later, you discover they misunderstood something critical.
It takes only two minutes to ask, “Can you walk me through how you’re thinking about tackling this?” It’s not a quiz, it’s a checkpoint. It clears up confusion and prevents costly do-overs.
4. Confirm Buy-In
Delegation isn’t just about assigning work. It’s about transferring ownership.
Once the task has been explained, ask, “Are you good with this?” or “Is this something you feel confident taking on?” This moment of mutual agreement is like handing off the baton in a relay, and it should be just as intentional.
When someone commits out loud, they are more likely to take the task seriously and deliver.
5. Don’t Take It Back
We’ve all done it. A team member runs into a roadblock, asks for help, and the next thing you know, you’re doing it yourself again.
That’s not delegation. That’s “reverse delegation.”
Instead, coach through the challenge. Offer guidance. Provide a resource or a second opinion. But keep the responsibility where it belongs—with them. That’s how learning and leadership develop.
6. Create a Culture of Accountability
Delegation without follow-up is just wishful thinking.
Set regular check-ins for larger projects or quick verbal updates for smaller tasks. Ask questions like:
→ “How’s progress going?”
→ “What’s your plan to finish it on time?”
→ “What do you need from me to keep moving forward?”
Accountability doesn’t mean hovering. It means staying connected. That way, if things go off track, you can redirect before it becomes a crisis.
Why This Matters More in Our Industry
In landscaping, tree care, and lawn services, delegation is the only way to scale without sacrificing quality. You can’t be on every job site. You can’t inspect every mow line, plant install, or safety procedure.
Delegation builds people. It turns helpers into crew leaders, and crew leaders into managers. When done right, it becomes part of your company’s growth engine.
Delegation Becomes Easier Over Time
At first, learning to delegate might feel awkward. You might worry about giving up control or about things not getting done right.
But with each successful handoff, your confidence builds, and so does theirs.
Eventually, delegation becomes second nature. It’s no longer about offloading tasks. It’s about investing in your team and multiplying your impact.
And the better you get, the more your business grows. It’s that simple.
Want to Learn How Accountability and Delegation Work Together?
If this message hits home, there’s a powerful next step you can take.
Join me for an upcoming leadership training that connects the dots between personal accountability and smart delegation. When you put those two things together, your team gets stronger, faster, and more confident.
Live Webinar: Using Delegation to Optimize Results
In this 90-minute masterclass, I will walk you through the mindset, mechanics, and methods of smart delegation. This isn’t about dumping tasks. It’s about building a business that runs better, grows faster, and frees you up to lead more effectively.
Whether you’re trying to level up your leadership team or simply stop being the bottleneck, this session will equip you with practical tools to delegate with confidence and purpose.
What You Will Learn
✔ Why Delegation Feels Hard – And How to Get Over It
✔ The Six Steps to Delegating Effectively (Without Micromanaging)
✔ How to Match the Right Tasks to the Right People
✔ Common Delegation Mistakes That Hurt Growth and Morale
✔ How to Use Delegation to Develop Leaders and Improve Accountability
April 22, 2025 | 1:00 – 2:30 PM EST
Be well, do good work, and keep in touch.
Fred Haskett
TrueWinds Consulting
