Painting Sales Training: Why New Reps Struggle and What Fixes It
You hired salespeople for the busy season. A few weeks in, the numbers aren’t there, the one-on-ones feel fine but nothing changes, and you start to wonder whether you hired the wrong people. In Episode 39, Micah Stelter, CEO of Paris Painting and sales leader at Aleph Ventures, explains how he ramps up new reps and why the fix is usually in the field, not at your desk.
Episode 39
Why Your New Salespeople Are Struggling
with Micah Stelter
In this episode, Micah Stelter shares expert insights on hiring, onboarding, coaching, and developing sales teams in the painting industry. Discover how we work to accelerate sales performance, avoid common pitfalls, and build a high-performing sales culture.
Micah talked with Haakon Hansen at the end of April, a month into the quarter that decides the year for most residential painting companies. His team had just hired five new reps for the season. What he described isn’t complicated. It takes time on the calendar, and that’s the part most owners skip.
The first 30 days: a training grind with a clear target
Micah’s new reps spend their first two weeks mostly watching. They learn the bidding software, paint and paint failures, and the sales model, and they ride along with the existing team and their sales manager. In week two they start applying what they’ve seen, still under a watchful eye.
The target for those two weeks is specific: estimate within 5% of a skilled estimator on the common homes they’ll see most, like stucco and wood siding at typical sizes. Micah contrasted that with owners he hears about who spend most of a year reviewing a new rep’s bids.
In weeks three and four, reps take a handful of their own estimates, spread out, while they keep observing. Coaches rate them on a scale and decide whether to hold them back on specific skills or hand them a full calendar. After that come what Micah calls “dipstick” moments: quick checks through the week on how reps come across to homeowners, how their bids look and what they’re selling.
Watch one number every week: success ratio
The weekly measure is simple: bids run against jobs sold. Five sold on ten bids is 50%. Micah expects new reps to start low while they build a funnel, then climb into the 30s and past 40% for the year. If someone has had three weeks of their own bids and is sitting around 15 to 25%, they get a one-on-one built on the data and a plan for one to three coaching events in the field, aimed at that number.
He also prioritizes. Reps whose numbers look stable get less of his time that week, and the ones who need help get more. If you don’t yet track how many bids each rep runs, how many they sell and the ratio between the two, Micah’s advice is to start, because that number tells you who needs you.
The real gap: solving sales problems from the desk
Haakon named the pattern he sees in conversations with owners: good leaders who care about their people, trying to solve sales problems from the office without getting in front of customers with their reps. Micah, running a large company, said he had recently been putting 16 or more hours a week into field coaching: prep calls, attending bids, debriefs and written feedback against the sales model, so a rep gets something objective instead of “I feel like you could do better.”
“Getting in the field and watching what is actually happening solves so much pain and time.”
Once you see the appointment, Micah said, the problem is usually plain: the rep isn’t connecting with the homeowner, or didn’t dig deeper to understand the client. For an owner who has sold successfully, the gaps are obvious in person in a way they never are on a dashboard.
“I would say nine times out of ten it’s just simple things that you would have done and they didn’t do.”
Haakon’s self-check for owners is one question: how many of your team’s appointments are you shadowing each week?
Show them, don’t just tell them
Micah’s best coaching moments are demonstrations. He described a rep who kept losing bigger jobs because, when a homeowner said their budget was lower than the bid, he simply held the price. Micah showed him a different response: offer the scope that fits the budget as the base bid and list the rest as options. Homeowners who buy the base job, he said, tend to pick up options later, because they’ve already stopped shopping.
Haakon added a story from a partner who rode along with a rep who only worked inbound leads. The owner modeled a call to a property manager, and it turned into an opportunity. Often, as Haakon put it, the rep had simply never seen it done.
Field time also makes hard decisions easier. If you coach someone, they watch you do it, and they still don’t prepare or follow through, Micah said, you can call it a poor fit with far more confidence than you get from staring at a report.
Make coaching about them, not about judging them
Coaching can feel awkward. The rep thinks the boss is checking up on them. The owner doubts they’re qualified to coach. Or the owner figures that’s what the rep was hired for, which Micah calls delegation. His answer is to set the tone like a personal trainer: the best athletes have the most coaches, and the learner’s job is to get as much value out of the coach as they can.
“This is about you. It’s not about me evaluating you, deciding do you have worth.”
On the worry about not being a skilled coach, he was blunt: there are advanced models you can study later, but the entry point is just going to watch.
“But that’s not the requirement to build painting companies that have skilled salespeople. It’s side-by-side field time.”
He said the same applies to project managers. Systems, playbooks and software help, but in his words they break down without the human work of coaching side by side.
Coaching doesn’t stop after the first year
Micah’s rhythm:
First 30 days: two to three coaching touches a week once reps are running their own estimates.
Roughly the first six months: some form of coaching once a week, using the data to skip a week for someone who doesn’t need it.
Experienced reps: one meaningful connection every 30 days. That might be a ride-along, or lunch and a conversation about where they want to go.
That monthly rhythm is how you catch the veteran whose numbers suddenly drop, whether it’s something at home or a job that went badly and shook their confidence. In Micah’s experience, a good coaching event keeps someone running with the right fix for about four weeks before things start to slip, and the success ratio will show you when.
Key takeaways
Give new reps a defined two-week training window with a clear accuracy target for their estimates.
Track bids, jobs sold and success ratio for every rep, every week, and let the data pick who gets your time.
Put ride-alongs on your calendar. Most problems are simple once you watch the appointment.
Demonstrate the fix in front of the customer, then follow up with written feedback.
Frame coaching as the rep’s development, not your evaluation of them.
Keep coaching experienced reps at least monthly so you catch a slump early.