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Two Week Tech Trial

29 April, 2021

You've got two weeks to make the most of it. It could be, like Charles Dickens put it, the best of times and the worst of times. Either way, it’s the free trial time most tech programs allow for you to decide whether you want to move forward from there. How do you make it the best of times? We asked some contractors and tech providers for advice on how to use your free fortnight.

All the Right Questions

First off, you need to know what you’re getting into and what you’re getting out of it. Make sure you have your goals and processes before you start looking. Everyone we consulted recommends trying out customer support. If you don’t get help during the “dating phase,” it won’t be any better during the “marriage,” so make sure you ask about response time and charges, for example, and are comfortable with the answers.

Jonathan Weinberg, Builder Prime

  • Why is this software the best fit for my workflow and the way that I do business?
  • How will this help my business grow, and what other software applications will I need to manage and grow the business?

Sale Team, Company Cam:

  • How compatible is this software with other tools? Does it integrate well?
  • What is the ROI (return on investment) from the technology for your business? Does this provider add value to your company or solve any problems?

Tom Droste, Estimate Rocket:

  • How can your software solve my main problem? Be specific and focus on the top-priority issue for your company.
  • Who typically is the primary customer for your software? Is it sales?
  • Employees? What size company do you typically service?
  • What does your software have in place specifically for painters and painting contractors?

Shawn Cadeau, Jobber:

How will this solution help me win more jobs and grow my bottom line? [Can’t get a better question than this one!] Check that the solution you’re considering has features that can help you deliver a better experience. 

Use your trial to make sure your software helps you organize your business and offers convenient electronic options such as online booking, digital quotes and online payments. For example, automated appointment reminders and two-way text messaging can also make businesses more accessible to your customers.

What other software can your solution be integrated with? There will be times with any software that you need to integrate your data with
another product or service. It’s important to know that other third party products will integrate with your chosen solution.

All the Right Answers

Now, turn it on and … USE IT! That might be the best way to get your questions answered. Here are some recommendations as to how to best utilize your free trial period.

Jeff Wraley, Groundwork:

Two weeks is a very short amount of time. That trial period can go by quickly if you aren't careful, then you’re stuck trying to figure out if you want to pay for the tool even though you aren’t sure how it works. I would ask the following:

How does this program integrate with the other technology solutions I have in place, and are those integrations available during the trial?
• What can I do to get the most out of the trial? Your vendor rep should be able to give you tips so you can learn enough to make a good decision after the trial ends.

Michael Henry, Cork CRM:

Run a few real customers through the basic workflow of the software to evaluate how well this compares to your desired workflow.

Builder Prime

Start using the tool with real customers and real data.  Don’t worry so much about historical data, and instead focus on getting your new leads through the workflow or whatever is the main process for the software being evaluated.

Don’t worry about using and evaluating every single feature and function that the software has to offer. Make sure that the main functions add value and increase usage of all the other features as you get more comfortable.

Keep an open mind as to how the software can further improve and automate your process rather than just doing a lift and shift of existing manual processes.


Use the app as if you've already committed to paying for it.

Add your team to the app. Our reps are paid to tell you how awesome the app is, but your crew is not! Adding your team as users will allow for honest feedback about app's functionality and user experience.

Get stumped? Ask. Particularly during the two-week trial, take time to chat with support or call your rep if you have questions. You may run into issues that are solved by a simple setting switch. Communicating with your software company can provide helpful feedback to improve the app not only for you but for all their customers!

Estimate Rocket

Prioritize the issues you want to solve with the software, and design a testing plan around those issues. If you define the top three to five issues that you want to solve, that will give you success criteria to measure your trial against. (Keep in mind that no software package
will solve every problem you have in your business exactly as you would like.)

Walk several small projects through the system end to end, if it’s possible, to see how it feels. A trial is not an implementation; it’s a chance to discover whether the software is a general fit. Measure it against the success criteria you found in step one.

Determine how helpful your vendor is during the trial. You’re looking for a long-term partner, so be sure this is a company that you can work with over time.


Use the product to ensure you understand all its features and you can maximize the solution to meet the needs of your business. Think about how the software could help your business look more professional, become better organized and grow in the future. The right solution can give a real-time snapshot of booking trends, invoicing, expenses, team efficiency and more—it allows you to build accurate reports based on real-time insights.

Make sure that the software you’re testing can be accessed on computers, tablets and smartphones so that you can run day-to-day operations from the field. Being able to track time spent on jobs and adjust schedules while on the go helps the team stay organized and
adjust to last-minute changes.

Focus on how intuitive the software is to use—not only for you but also for your crews. It should be easy to learn for new and existing crew members of all ages and skill sets, or they will try and work around it. If it’s intuitive, using the software and its features will become second nature for you and all your team members.

Contractors ... on trial

What do contractors look for in a free trial period? Andrew Chisena of Gables and Grove Painting in Coral Gables, Florida, wants to see if a new program makes his life easier. “The main thing is how many things can it take off my plate,” he says. Since there isn’t one program that does it all, Chisena looks to see how this new technology goes with what he has already. Will it take the place of two or three things he has now? Will it integrate? “Once it’s set up, it should make for less work, not more,” he says.

Next, go for the gold. Many tech companies offer different tiers of service, so don’t just look at the bottom rung. “I want to see the levels of service up front because at some point you're going to want the best out of that program. There's no way you’re going to just settle with the middle. I want cutting edge,” he says.

Kennedy Painting does a lot of research up front, so the two-week trial is more of a confirmation than an exploration. The program has to make a definitive difference, says Sean Kennedy, owner of this St. Louis-based painting company. “The opportunity to change has to outweigh the pain of not changing,” he says. “If it takes 10 steps to do something now, and we get a new software that still takes 10 steps, it’s really not doing any good.”

Timeliness of support is also important. If you have a question about an estimating program, for example, too much delay in response opens a window for your competition to snatch the job away from you.

Finally, ask around! Kennedy, as part of Nolan Consulting’s Summit Group, networks with other contractors to find out what’s successful for them, to kick off his research.

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If cost and liability were not an issue, what's your one must-have at the company picnic?

Paintball Feld
Axe Throwing
10-Foot Nacho Trough
Potato Salad

Dang it's hot! Does your work vehicle have an orange water cooler?

It's not orange

Did you work for a painting contractor prior to owning your company?


Why haven't you hired a business coach?

Not worth the money
Too difficult to find a good one
I don't need one
I did hire one!

Has OSHA ever inspected your jobsite?


Who Buys the Paint Brushes?

We do...the company
Our painters buy their own

What's the most paint you've ever spilled?

5 Gallons
An Ungodly Amount

Did you take a week-long (or longer) vacation this summer?

Not yet, but I'm gonna

If you had to rename your company one of the following, which would it be?

Flapjack Painting
Porkchop Painting
Half Slab Painting
Whole Hog Painting

You meet someone new, and they ask what you do. What do you say?

I'm a painter
I'm a contractor
I'm a painting contractor
I own a painting business

On the job site, my painters mostly listen to...

Classic Rock
Hip Hop
Who knows. They got headphones

Which social media platform is most effective for marketing your business?

I don't use one

What do you drive for work?

Pickup Truck

How long ago did you redesign your company hat?


Do you have a spray booth?


If you've bought a used sprayer, was it a good decision?


Will your crews be working the week between Christmas and New Years?


Do you accept credit card payments from customers?


Will you be giving end-of-year bonuses (not gifts) this year?


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