How to Handle Employee Raise Requests in a Landscaping Business

Somebody on the crew asks for more money mid-season. By Friday three more people are lined up. You have jobs sold at locked prices, weather eating days, and no clean answer that does not feel like either a bribe or a fight.

That is what happens when raises are handled as one-off negotiations instead of a system.

This guide pulls from When Employees Ask for Raises with George Urvari of KTC on the How to Hardscape Podcast (episode 372). George is co-founder of Oriole Landscaping in Toronto and Knowledge Tree Consulting. He has spent decades in landscaping operations and now helps landscape and hardscape companies across the US and Canada fix the people and process problems that show up as constant wage drama.

Why Employees Ask for Raises Mid-Season

George’s starting point is blunt: people ask mid-year because you never told them when raises happen.

If onboarding never said “we review pay once a year after the budget, after staff reviews, on a new employment contract,” then every inflation spike, every new responsibility, and every cooler conversation becomes a personal ask aimed at you.

Strategy first, tactics second. Fix the annual system so next year is not another Ferris wheel of ad hoc negotiations. Then handle the asks already in front of you without letting the tail wag the dog.

Build an Annual Raise System Before the Next Ask

A workable landscaping raise process looks like this:

1. Budget first. Raises come out of a plan, not guilt or surprise.
2. Two staff reviews in the cycle so performance and responsibility changes are documented, not argued from memory.
3. One rem window. New contracts (or clear pay letters) go out on a set date after budget review.
4. Slow-season timing. The contract window does not have to match your fiscal year-end. Put one-on-ones in the quieter stretch when you can actually think.
5. COLA baseline. Even small companies without a full pay scale can promise inflationary / cost-of-living movement so nobody goes three years with zero and then demands a massive catch-up.

George’s consulting example: a client who skipped raises for years then faced a huge hourly ask. Doing the compounding inflation math and rationing increases into the budget is cleaner than swinging between nothing and panic.

If you are truly underpaying someone relative to the role and market, fix it. Waiting because it is awkward usually costs more later in turnover and leverage.

Onboarding is where you lock the rule. Hard on policy, soft on people. Explain that constant renegotiation distracts you from selling and producing the work that pays everyone. Ask if they object. Get the policy initialed. When someone tries mid-year later, you are not inventing a story — you are pointing at the agreement.

Know Who You Are Paying: Dependent, Autonomous, Teacher

Before you talk dollars, George sorts people into three levels:

• Dependent — someone always has to worry about them.
• Autonomous — they run without babysitting.
• Teacher — rare; they make the people around them better.

The goal is not a shop full of dependents arguing for raises. You want autonomous operators and the few teachers who raise the whole crew.

He also uses an HR balance sheet with clients: list top assets and real liabilities on both office and production sides. For liabilities, score chance of reform (high / medium / low). High reform chance usually means management failed to set standards. Low chance means exit. Ask whether a replacement is even required — if not, delaying a bad fit rarely helps. Set a timeline instead of the default “wait and see.”

Severance and contract wording matter, especially in Canada. George’s Oriole lesson from the episode: time-limited employment contracts plus probation language can get challenged; a settlement followed, and the company moved to open-ended contracts. HR mistakes are expensive energy. Treat them like that.

What to Say When Raise Requests Start Stacking

Once one person asks, the line forms. George recommends addressing the company once instead of negotiating twenty private deals.

The message in plain terms:

• There are no ad hoc raises this year.
• You are putting (or restoring) reviews and a budget-driven cycle in place.
• Next year’s pay is where negotiation belongs.
• Customer prices and sold contracts are already set — you cannot randomly raise every job midstream to fund random wage bumps.

That does not mean you ignore unfair pay. It means you stop running the business from the hallway. Owners who fear their employees stay stuck. Owners who turn crews into allies explain the why: you need focus on better work, safer schedules, and a payroll environment that does not feel random.

Culture is the retention buffer. People stay for peers, equipment, respect, and the work — not only the hourly rate. A star who leaves unhappy can take others with them. Process is how you reduce that risk before money talks get emotional.

Mid-Year Exceptions Without Breaking the System

What if responsibilities really did grow mid-season?

George’s answer is yes, exceptions exist — the question is how. Handing out a permanent raise the day someone asks trains the whole company to leverage you.

A cleaner conversation:

• Agree that performance so far looks like it may deserve more.
• Note that the year is not finished (peak heat, wet weather, the hard months still ahead).
• Confirm that everyone gets a cost-of-living move.
• Commit to equalize any shortfall at the annual window with more than COLA, often as a bonus rather than locking a higher base now — especially if a soft year would hurt.

That uses trust without setting a precedent that every role creep becomes an emergency raise. Leadership still decides. The employee does not run rem policy from the truck.

When an A-Player Says “Raise or I Leave for a Competitor”

Pay people what they are worth. Do not accept being leveraged on a loop.

George’s counters from the episode (paraphrased):

• Ask whether this will happen again next year.
• Ask what is driving it — locker-room talk, market rumors, or pressure from home. Spouses and partners often push the ask; you may be arguing with a story that did not start on your job site.
• Change the dynamic: “Are you really that unhappy here?” Force the why.
• Make crew economics visible. If dead weight on the crew is real, put the productivity math on the table so the raise conversation is about production, not a hostage note.

You can still choose to pay a premium for a true star. The line you protect is that threats do not become the company’s raise calendar.

Pay Gossip, Market Rates, and Signing Bonuses

A common fight: two employees compare pay. The newer hire makes more because you hired into a post-shortage market. The longer-tenure person got COLA but started from a pre-spike base.

In a large company, confidentiality breach may have teeth. In a small landscaping shop, people have leverage and will talk. George’s practical path: explain the market reality, commit to equalization over time, and do not instantly jump the whole payroll by several dollars an hour if your sold work cannot carry it.

When you need a scarce foreman, talk to the company before the rumor mill does. George described addressing a crew about a hiring package with a staged signing bonus and asking whether they preferred staying short-handed or bringing in production that raises the bar. Offer referral money if someone helps land the hire. Frame it as capacity and standards — not money stolen from their pocket.

Benefits, Bonuses, and Small Frequent Raises

Cash is not the only lever, but “extra vacation” is not free. Opportunity cost shows up when winter work windows open and nobody is available. Oriole learned that stacking days off can backfire when the season stretches. Cumulative sick banks can also turn into expensive exits. Benefits are still a negotiation — keep them on terms you can staff.

For stars you need to keep, George often prefers bonus over permanent wage when optics and flexibility matter. A bonus can recognize value without locking every future year to a panic number.

What about tiny raises every few months (for example, frequent small hourly bumps)? In some lower-wage, short-horizon labor markets that can work if it is strategic and automated. It also creates bookkeeper admin and debates about who did not deserve the bump. George’s bias: less admin. One annual system beats a drip of exceptions.

Superstars, Career Paths, and Honest “No Path” Talks

If you have a measured superstar — clean sites, raving clients, people want to work with them — losing them over pay is usually the expensive choice. George frames business currencies as time, grief, and money. Taking a hit on money to keep time and grief under control for a few more years is often rational, especially in a tight talent market.

Pay excellent foremen enough that you need less middle management. At Oriole, strong field leads who order their own materials and run without babysitting can outproduce a stack of supervisors that only exist because processes are weak. Prefer better process and technology plus higher pay for real producers over another layer of checking.

Ambition still needs honesty. Few people volunteer for foreman when the pay bump is small and the responsibility jump is huge. Many want to become designers — while designer ads flood with applicants and good foreman ads barely draw. If someone wants a role they will not succeed in (people skills, sales presence, craft), say so. Desire is not the same as fit.

Staff review opener George uses: Are you happy? A qualified yes is a no — dig in. If there is one designer seat and a tenured person is not leaving, do not fake a path. Offer a strong recommendation when it is time, ask for real notice, and leave the door clean. People who leave Oriole the right way have been referred work, leased older equipment, bought material, and rented yard space. That is culture too.

Training That Supports Pay Conversations

Small multi-hat owners rarely have a corporate training department. George’s practical version:

• Once a year, list the highest-ROI skill gaps (equipment, cutting, specific field skills).
• Run paid Saturday sessions with a foreman for a few weeks.
• Set availability expectations at onboarding so training dates are not a surprise.
• Use on-the-job training only with leaders who will teach — impatience and pure schedule panic kill development.
• Accept that some trained people leave (CDL / license examples). Budget for that; keep enough trained people that logistics do not collapse.

Software and videos help. They do not replace doing the work.

For a highly paid foreman who will not take on full admin or communication duties, money alone will not create desire. Split the role: do or delegate. Put a lead hand who thinks and admin on the paperwork. Use scoreboards and performance bonuses for communication standards the team agrees to (response windows the crew sets together). Hire for the seven traits of a complete lead when you can — communicate, administer, organize, read the work, execute, teach — and stop pretending every great craftsman is that person.

How to Start This Week

1. Write the raise rule in one paragraph: once a year, after budget, after reviews, on a set contract date in your slow season.
2. Put that rule into onboarding and next season’s kickoff so everybody hears the same story.
3. Build a simple HR balance sheet: assets, liabilities, reform chance, replace or not, exit timeline.
4. If asks are already stacking, hold one company meeting. Freeze ad hoc raises. Point everyone to the next cycle. Fix true underpayment on purpose, not under hallway pressure.
5. For A-players, separate “worth more” from “leveraging me.” Use bonus or next-cycle equalization when you need flexibility.
6. Explain market-rate new hires and equalization over time before gossip does it for you.
7. Pay to keep real superstars; be honest when there is no next seat; train for skill gaps you can actually staff.

If you want the full conversation, listen to When Employees Ask for Raises with George Urvari of KTC on the How to Hardscape Podcast. For consulting, George is at ktc.biz (george@ktc.biz).