Have hard conversations

Tough talks are necessary to lead your landscaping business. Here are some common pitfalls preventing your business from flourishing amidst those conversations.

Two stick figures having conversation through thought bubbles

Illustration © Yutthana Gaetgeaw | istockphoto.com

There’s a problem that costs the U.S. economy $9.6 trillion every year — and it’s a problem that’s obvious to diagnose but difficult to address.

Wilson360’s Sheila Matthews told the audience at the Wilson 360 Thought Leaders Retreat that Gallup studies confirm disengaged employees are one of the most difficult issues plaguing workplaces across every industry. “The presence of just one toxic employee can reduce team output by 30- to 40% due to conflict, confusion or distraction,” she says, adding that the one toxic employee increases the chance of other employees quitting by 54%.

Matthews asked attendees if they had disengaged workers at their respective companies. Nearly every hand in the crowd went up. This confirms the study Matthews cited that indicated employee engagement is at an all-time low with just 21% engaged.

But addressing those problems becomes an unspoken issue around the office quickly. “The problems we’re encountering in our businesses persist because we’re not offering feedback or hard truths,” Matthews says, adding that a lot of times, employees who have been on board for years are the ones who need more feedback. Those employees then circumvent policies and procedures that are in place to make the workplace better. “Have you ever heard someone say, ‘They’re rolling out a new system … let me show you how to really do it.’”

Matthews offered attendees three mental traps they face when looking at disengaged employees, then a few tips on how to give those folks feedback. “I’ve got a black belt in keepin’ it real,” Matthews jokes. “I’ll cut to the chase and say the thing that needs to be said.”

Trap No. 1 Someone’s lying because I’m right.

Matthews told TLR attendees that she had just seen this very trap come up with a non-landscaping client. The client placed an executive assistant in charge of implementing new human resources procedures, but the issue was that the assistant had never managed something so complex.

One major issue immediately arose: The assistant and the owner didn’t communicate about who would release an announcement to the team. The assistant also reached out to the operations manager who wanted to review the announcement to ensure it tied in strategic values.

So, when Friday rolled around and employees still hadn’t heard about the new HR support program, the operator and the assistant both showed up at the owner’s office with proof that they weren’t in charge of releasing the announcement.

Sheila Matthews told TLR attendees how even one toxic employee can reduce company output by 30%.
Photo: Jimmy Miller

But technically, nobody ever claimed responsibility for releasing the announcement to the full team. It’s important to address the fact that the communication to the team got missed, not trying to assign a winner and loser in the conflict.

“They’re both right. That’s what the bias is here,” Matthews says. “The trap is, ‘Only one of us is right so you must be lying.”

Trap No. 2 “You did this…on purpose!”

Matthews says egos often interfere with productive work. For example, if someone points out a mistake you made in a meeting, it looks to you like they’re trying to make it seem that you don’t know what you’re doing. She adds that we see this outside the office, too: When someone cuts you off in traffic, you automatically assume they did it on purpose.

So, Matthews says it’s important to address problems when they arise. But there’s a powerful way to reframe issues when they feel personal. She recommends making the core of the conversation all about the impact it had on the business. They may not have had malintent in the first place, and it’s not important anyway.

“When you have something happen to you and it doesn’t feel good, you still have to have those conversations at work,” Matthews says. “Don’t worry about why they said or did the thing. You won’t move the conversation forward making those types of accusations, even if the connection is obvious to you.”

Trap No. 3 “I blame you!”

Matthews says language around negative feedback can often come across as combative. If a customer calls unhappy about service and a crew lead needs to talk to his team about the feedback, it could easily come across as though he’s blaming them for the frustrated client. The crew lead might say things like “you forgot to shut the gate in the backyard” and the crew member might hear “you didn’t do this right.”

Matthews says this type of framing is a mistake. After all, the crew lead is responsible for the entire crew and could’ve just as easily shut the gate. She suggests a powerful reframe in addressing the behavior, using phrases like, “Hey, we both contributed to this outcome. Let’s fix it.”

Other TLR sessions included Joe Kujawa (far left) interviewing Bruce Wilson, and Andrew Bray (right) talking politics.
Photos: Jimmy Miller

She also says clearly and objectively describing the specific behavior is important. For example, if an owner notices a crew lead isn’t teaching a new field employee how to use the company’s software, it’s important to approach the crew lead without accusatory language. Phrases like “how many times have I told you?” or “you’re not doing enough” won’t help. Instead, she suggests plainly labeling the mistake and then pointing out its impact.

“Connect the behavior to its effects on the team, project, or overall business,” Matthews suggests.

Final words of wisdom

Matthews admits tough conversations can be difficult for business owners. Despite this, she says it’s important not to rush through them. Offering feedback — positive and negative — requires time for the other person to contribute to the conversation.

“Invite the other person to share their thoughts or provide their point of view,” Matthews says. “(Say something like), ‘What do you think?’ Do not speak anymore. Give this person several moments of silence to think and respond thoughtfully.”

Matthews suggests practicing by setting a timer and letting yourself feel what 30 seconds of silence feels like. “You came into this conversation knowing what you’d be talking about. Maybe they didn’t. You have to be patient. Do not rush this part.”

And, above all, Matthews says couching feedback in the reason why it’s important, helps neutralize negative emotions. Employees who’ve been in the business for so long might need to be told something like, “Because you’ve been in the business so long, I have more expectations for you, not less.”

“We have to say, ‘Because I care about you, we have to have this conversation,’” Matthews says.

The author is digital editor with Lawn & Landscape.

November 2025
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