ERP. CRM. WMS. PLM. HRMS. EMR.

Pick your acronym. Add a polished demo. Stir in some magical thinking and a pint of unrealistic expectations. Marinate in a six or seven-figure budget. Sprinkle on an arbitrary go-live date. Bake in a 550-degree pressure cooker for 12-18 months.

And prepare to wipe the mess off the ceiling at launch.

Here’s the uncomfortable truth: most large software initiatives don’t fail because of the software. They fail because of talent gaps (internal and external), insufficient change resources, unrealistic expectations, and well-worn pitfalls during the project (see McKinsey research.)

Do I really want you to cancel? No. But do take the time to get ready before you start.

 

Get the Best People

We often carve up projects into people, process, technology, and data. Each is vitally important. As is often the case, even in today’s age of AI, people matter the most. Strong teams make better decisions and make them faster. That means less rework, less schedule disruption, lower costs, and better outcomes. Mic drop.

Large software projects often staff teams based on seniority or availability rather than deep knowledge and peer credibility. It’s like that old joke about looking for your keys under the streetlight even though you dropped them elsewhere in the dark: convenient but not effective.

 

Choose an Excellent Vendor

Organizations spend lots of time and energy selecting software and often comparatively little selecting the vendor who will implement it. In a mature software market, choosing the implementation vendor matters at least as much as the system… maybe more.

Take the time to assess the implementation vendor, and take the time to interview the staff your vendor wants to assign to your project. You’d never make an internal hire without an interview. Don’t accept external resources sight unseen.

 

Develop an Actual Team

Once you have all the talent you need, internal and external, remember to do intentional team-building: facilitated conversations and exercises that help team members build trust, set norms, and understand how they will actually work together under pressure.

If your organization uses a tool like Strengthsfinder, Predictive Index, DISC, etc. I highly recommend you give the assessment to the external team members. Use the results for team building and team management throughout the project. If someone new joins the team from inside or the vendor, take the time to do another team-building session.

 

Define Key Roles

On successful projects, the following roles are clearly defined and actively staffed. They don’t all need to be full-time, and they don’t always need to be ten different people, but they do need to be explicitly named and owned, even in small organizations.

● Project Manager

● Executive Sponsor

● Testing Manager

● Training Manager

● Change Manager

● Integration Lead

● Data Lead

● Reporting / Analytics Lead

● Roles & Security Lead

● System Administrator

Ideally they sit on your side of the table and come from inside your org. Bringing in expertise and capacity from outside is OK too, to augment the team or just coach. But tread carefully if using your implementation vendor for any of these roles. And never let the implementer be the sole project manager.

 

“Governance” and “Decision Rights” are Not Bureaucracy

Deciding who can decide may sound like corporate speak, but it’s incredibly valuable to increase speed and avoid problems. I highly recommend a facilitated session to develop a responsibility matrix of some kind – RACI, LPD, MOCHA, etc.

When decision rights are clear, teams spend less time escalating, second-guessing, or waiting for approval and more time moving the work forward. Clear ownership also helps escalate risks appropriately to the Sponsor or Steering Committee while there’s still time to act and resolve.

 

In Closing

Large software projects are difficult even when they go well. And each project is different. To steal a phrase from a fellow musician, they’re “never the same way once.” One thing these projects have in common: they rarely succeed or fail solely because of technology.

Successful organizations take the time to free up the best internal talent, acquire valuable outside help, select an excellent implementation vendor, and put them all together in a high-functioning team with clear expectations and the conditions for high-quality decisions consistently over time. When teams are strong, roles are clear, and decision rights are explicit, problems surface earlier and are cheaper to fix.

If you don’t run projects like this often, it’s worth slowing down at the start. Get ready before you go fast. That preparation may include outside perspective to help you see blind spots, challenge assumptions, and de-risk the effort along the way. Done well, that pause can be the recipe for a successful go-live that delivers the results you invested in rather than an explosive mess you’re scraping off the ceiling.

 

61 Keys is a business advisory firm focused on helping organizations navigate complexity, strengthen leadership, and execute meaningful change. Through strategic guidance and hands-on support, the team works with leaders to improve decision-making, align people and processes, and build sustainable operational momentum.