In This Section

Building a Better Software Implementation Relationship

May 18, 2023
Photo of a person on a laptop computer with various icons surrounding

An interview with Dave Caldwell, director of Cloud ERP, Leaf Software Solutions

I recently sat down with Dave Caldwell to talk about the software implementation methodology at Leaf. Deciding to implement a new accounting software package does not come easily. Let’s set aside the thoughts of business disruption for a moment and instead focus on dissolving years of knowledge and habits (good and bad) using the current software that runs the back-office accounting processes within the business. Learning a new system can be daunting, and the fear of change can be the source of delaying this decision for years, potentially leaving the business at risk.


What mistakes do most accounting departments make when implementing new software?

It is natural for companies to be convinced they do not need specialized advisory services to implement accounting software. They don’t understand the heartache and headaches that are certainly going to come their way when they try to get the software up and running. When they realize they lacked the understanding, foresight and strategy, it is often too late.

You must be strategic in how you set up software in your business. The planning and building of the foundation of any ERP accounting system is critical during the setup stage. You must incorporate the vision for your organization into the structure of your system. Indeed, your accounting system must scale to the needs of your business.

Unfortunately, accounting departments learn about this too late. They either try to fix what they’ve done, which can make it worse, or they simply give up and say, “I’ve learned my lesson.”


When do you personally become involved in a client’s journey?

I get involved during the sales process. I call it an informative dialog, where what is known about the client is shared. We make sure to understand the client’s goals and be transparent enough to let them know if the software they’re looking at is going to work for them — or not. If not, we must be strong enough to turn away from that opportunity.

It’s a very good sign when a potential client can articulate what they’re trying to accomplish. This is one of the first of many steps toward building a partnership with a client. During this process, we’re asking a potential client to establish a level of trust with us first. Once that is evident, the software becomes secondary.


How would you describe your onboarding methodology?

We have a defined and dynamic method. Our goal is to maintain the fundamentals, the consistency and the focus through every client.

We combine training and implementation, using client data, with an understanding there are milestones that must be crossed and dependencies that must be met before next steps of training can continue.

This is the non-negotiable part of our implementation methodology. A client can’t expect to go live in a matter of a few days — we have certain things we need to have met within the software to proceed.


How does the project kickoff meeting work?

We begin the kickoff meeting by making sure the client has a clear understanding of why they’re here. I let them know they are responsible for taking notes, and to come prepared with as many questions as they can to help us understand their business, which ultimately leads to the most successful implementation.

As the client walks us through “a day in the life of the accounting department,” we use the whiteboard to document their business processes. This becomes a mini-business review as we gain further understanding of how work is done within other departments. We also identify any pain points missed during discovery.

After the business process review, we start talking about their current Chart of Accounts and introduce them to the concept of dimensions. We also use this time to introduce the multi-entity intercompany transactional environment.

We are intentional about surfacing surprises. We want anything that affects the project to be out of the way as early as possible. We talk about scheduling and how we conduct our subsequent meetings. We reinforce that it is an educational process, define what the client can expect from us and what we expect from the client as we complete the implementation.

We introduce them to the concept of the Valley of Despair which states that during this change, there will be a time when you’re not in control and you’ll feel unstable and uncomfortable. We deal with this phase in a healthy and positive way. We assure them they’ll come out of the Valley of Despair with success to follow.

We minimize dependencies by training people to be self-sufficient with the software.

How is your approach to Implementation unique?

A software company comes to a prospective client either selling software or selling a relationship. We leave the software at the door.

We do work towards holding a common and long-term relationship with our clients. Over time, we have taken facts and experiences and put it all together to decide the best approach. We have inherited clients who are on other software platforms, and we find the majority are not knowledgeable enough to use their software. This goes back to training.

We minimize dependencies by training people to be self-sufficient with the software. Because our clients are part of the building process (we don’t go out and build an accounting platform for them, then give them the “keys” at the end), we tell them this is your system — it’s not ours.

You are building what you are going to own. We are going to advise you, and we are going to educate you on what you need to know so you can make better decisions. But those decisions are ultimately yours, not ours.

For a deeper dive into the topic of technology solutions, don’t miss Leaf Software Solution’s session at our Corporate Finance Forum on June 20 called Modernization—What It Means for Your Organization. Learn more and register at

INCPAS Strategic Partner


Leaf logo

Leaf Software Solutions

Leaf Software Solutions has been delivering mission critical business solutions for over 34 years. From cloud-based accounting, custom software, and CRM, their consultative approach results in custom-tailored solutions that create value for your business. Learn more.

Load more comments
Thank you for the comment! Your comment must be approved first
New code