Delegation & Hiring for a Maintenance-Heavy Landscaping Company Trying to Scale
I’ve been looking into accountability charts and delegation after listening to the Jobber podcast where they talked about this, but I’m not sure where to begin. Right now I’m still heavily involved in day-to-day residential maintenance landscaping operations—quoting, scheduling, managing crews, and even some marketing—which makes it hard to step back and focus on growing into larger/higher earning project work beyond maintenance. For those who’ve gone through this at a similar stage, what responsibilities did you delegate first—and to whom? Also, what was your first key hire that really helped free up your time to focus on growth? Any practical guidance would be great.Transitioning from Landscape Maintenance to Higher Earning / Project Work
For those who started in maintenance, how did you transition into larger projects like hardscaping and design? Did you train your existing crew or build a separate team? I’m trying to figure out the best path forward without disrupting our current operations. Any advice from those who’ve made that shift would be really helpful.
How do you handle unreliable employees in a home service business?
Hello! I run a Home Remodeling & Handyman business, and we're excited to share that we've recently expanded to include a Cleaning Division. We've noticed that in our area, many folks are eager for jobs but sometimes lack the commitment to follow through. How do you navigate this challenge? We've already offered competitive pay, which is quite high for our area, yet issues like poor communication, missed appointments, and subpar work still pop up. I'm curious to hear how others have managed similar situations and what strategies you've found effective—whether it's offering career growth opportunities, enforcing strict communication policies, or even increasing wages further. Any advice or ideas would be greatly appreciated!How do you balance kindness and strict standards as a business owner?
My personal values are very important to me as a business owner. Being a person of faith I care deeply about people. For years I have struggled to find this balance between kindness and compassion and strict standards. For those of you that have hearts for people and want to be kind and compassionate...how do you help your team rise to the occasion without having to seem heartless and only care about the bottom line?When to hire a General Manager?
I am a painting company. Have any of you hired a general manager and stepped away from the day to day operations of your business? How did you go about it? Was there a revenue metric you aimed for? Break it down for me in detail? Did it help you grow and go to the next level? How did you find your general manager? What did you set as the pay/salary? Bonus structure?Who Was Your First Hire?
I’ll never forget mine! My first hire was a foreman. I needed someone who could run the job while I focused on running and growing the business. That was the moment it stopped being just me and started becoming something bigger. Scary? Of course. Exciting? Absolutely. That first hire teaches you the hard stuff. How to train. How to lead. How to TRUST someone with your name and your clients. You don’t always get it right, but that’s how you grow. What I learned: Hire sooner than you think you’re ready Character beats skill every time Being a boss is a completely different trade than doing the work So let me ask you… who was your first hire, and what did they teach you?What Features Would Be Helpful for Dealing with Subcontractors on Your Team?
Subcontractors can be a powerful way to grow your service business—but managing them smoothly takes the right tools. From scheduling to paperwork to payments, things can get complicated fast if you're relying on spreadsheets or text threads. Here are a few key ideas to kick off the conversation: Insurance Certificate Tracking + Expiration Reminders Making sure your subcontractors are insured is a no-brainer—but keeping track of their certificates and renewal dates can be a hassle. A built-in feature that stores insurance docs and sends automatic reminders before they expire would help keep your business protected and organized. Built-in Payment Processing for Subcontractors Paying subs quickly and clearly is essential for maintaining good relationships. Imagine being able to approve their invoices and process payments right through Jobber—no more chasing emails or juggling payment apps. Subcontractor Availability Scheduling Knowing when your subs are available is half the battle. A shared calendar where subcontractors can input their availability would make job assignment way easier and help avoid scheduling conflicts before they happen. What would you like to see added to help manage subcontractors better? Drop your ideas in the comments—👇
Feeling Stuck in the Busy-But-Broke Zone – How Did You Break Through?
Hey folks, I’m hoping to get some insight from those of you who’ve already muscled through this phase of business. I’m currently in that painful zone where the jobs are coming in steady—so much so that I’m completely maxed out—but the numbers aren’t quite adding up to confidently bring someone else on board. I’ve got the workflow, the drive, and the service quality dialed in, but when it comes to scaling by hiring help, I feel like I’m staring at a wall I can’t quite climb. The catch-22 is real: can’t afford help without more time, and can’t get more time without help. For those of you who made it past this threshold: - What did you do to shift the equation? - How did you find the confidence (or capital) to invest in that first team member? - Any creative pricing or scheduling tactics that helped balance the load in the meantime? Appreciate any stories, hard-learned lessons, or nuggets of advice. Trying to work smarter, not just harder.Do You Train Your Team to Think or Just Work?
Every Monday, we hold a short training session with our team. We train on communication. leadership. & mindset. The reason being most tradespeople aren’t struggling because they can’t do the work. They’re struggling because they were never taught how to: Speak with clarity Handle conflict Lead a crew Represent the business professionally These tend to be the issues I see bottling up, either from our exit interviews or customer feed back or when things are misunderstood. Thats why I'm curious: Do you train soft skills with your crew?Everyone Wants to HIRE the “3–5 Year Guy” — But Why?
Once again, contractors are falling into the same pattern. I keep seeing posts on Instagram that say: “Must have 3–5 years experience.”What do you guys think about this? Here’s my take: It’s because most people want someone they can toss straight into the field. No training. No culture building. Just go-go-go. But that’s how we end up with more bad hires than good ones. Here’s the truth: Hiring talent doesn’t fix broken systems. If you don’t know what problem you’re solving — even the “perfect” hire won’t help. So I made this visual graphic to help. This is how I think through hiring when I know I’m ready to grow. What are your thoughts?
