Industries We Serve

Ask This Before You Sign Your ERP Deal

The right questions before you sign separate partners who deliver from ones who disappear after go-live.

A gold pen rests on a signed contract next to an authorized signature line.

Signing an ERP contract feels like the finish line. It isn't. It's the starting point for a relationship that will shape how your business runs for the next decade, and most executives sign it without asking the questions that actually matter.

That's not a knock on anyone's judgment. ERP contracts are dense, the sales process moves fast, and vendors are very good at making everyone in the room feel confident. But confidence isn't the same as clarity, and by the time a company realizes it picked the wrong partner, the money is spent, the timeline has slipped and the relationship everyone hoped would last for years has already gone sideways.

The good news is that the warning signs are visible before you sign anything. You just have to know what to ask.

The people in your sales meetings are almost never the people who implement your system. That's standard practice across the industry and it isn't automatically a problem, but you need to know who is walking in the door once the contract is signed.

Ask for the names, backgrounds and experience level of the actual implementation team, not the sales team. Ask how many similar projects that team has delivered in your industry. Ask whether the consultants on your project are employees or subcontractors, because staffing models vary widely and you deserve to know who is doing the work. If a vendor gets vague or defensive about answering these questions, treat that as useful information. A partner confident in their team will answer without hesitation.

Every ERP project hits turbulence. Requirements shift, timelines slip and unexpected issues surface once you get into the details of your actual business processes. What separates a good partner from a bad one isn't whether problems happen. It's what happens next.

Ask how the vendor handles scope changes and who decides what counts as in scope versus a new charge. Ask what their escalation process looks like when a project falls behind schedule. Ask for a specific example of a project that ran into serious trouble and how they resolved it. Any partner who claims every project they've ever run went perfectly is either new to the business or not being straight with you, and neither one is reassuring.

Many companies discover, right around go-live, that "support" meant something very different to the vendor than it did to them. This is one of the most common and most expensive misunderstandings in ERP contracts, and it's entirely avoidable if you ask the right questions upfront.

Get specific about what post-go-live support includes and for how long. Ask whether the same team that built your system will be the one supporting it, or whether you'll be handed off to a separate support desk that has to relearn your configuration from scratch. Ask what response times look like when something breaks during your first month live, when things are most fragile and the stakes are highest. Get all of this in writing. A verbal assurance from a salesperson means nothing once the contract is signed and that salesperson has moved on to their next deal.

This question gets skipped more often than any other, and it can trap a company for years. Ask explicitly what happens to your data, your customizations and your system configuration if you ever want to leave the vendor or switch partners. Some vendors build systems in ways that make an exit deliberately painful, whether through proprietary customizations, undocumented configurations or licensing structures that penalize you for leaving.

You want a partner who builds your system in a way that keeps you in control of your own data and your own future, not one who profits from making you feel stuck. Ask for documentation standards. Ask whether your team will have full visibility into how the system is configured, or whether that knowledge stays locked inside the vendor's team.

Reference calls get treated as a formality, and that's a mistake, because they're one of the only chances you get to hear directly from someone who has lived through what you're about to sign up for. Ask for references from companies in your industry and at your revenue size, not just whichever client relationship the vendor happens to feel good about that quarter.

When you get on those calls, ask pointed questions. Ask what surprised them during implementation. Ask what they wish they had known before signing. Ask whether the team that sold them the project is the same team that supported them a year later. The answers to these questions tell you far more than any proposal document ever will.

The initial contract price is only part of the story. Ask for a clear breakdown of ongoing licensing costs, support fees and what happens to pricing at renewal. Ask whether the quote includes every module and integration your business actually needs, or whether critical pieces are positioned as add-ons you'll discover later. Vendors that build their margin on surprise fees after year one are common enough that this deserves direct, specific questions rather than a general assurance that "pricing is transparent."

An ERP contract is not just a purchase order for software. It's a commitment to a partner who will be inside your business, touching your data and your processes, for years. The companies that get this right treat contract negotiation as due diligence, not paperwork, and they ask the uncomfortable questions before signing rather than after something has already gone wrong.

At Hoalani Group, we've built our business on being the partner that answers these questions clearly, before you sign anything. We implement Microsoft Dynamics 365 Finance, Supply Chain Management, Business Central and the Power Platform for mid-market companies across the US, Spain, Portugal, Ghana and Canada, and we'd rather earn your trust with a straight answer than a polished pitch.

If you're evaluating ERP partners and want a second opinion on a contract sitting in front of you, or a list of the questions specific to your industry, reach out. Visit https://www.hoalani.com or email info@hoalani.com.