Signing the contract is the easy part. The real test of an advising software implementation happens in the eight to twelve weeks after, when your team is trying to migrate years of student data, learn a new system, and keep serving students at the same time.
Most implementations don't fail because the software is wrong. They stall because nobody planned for the predictable friction points. I've watched enough of these rollouts to know the roadblocks tend to repeat themselves. Here are the six I'd tell any leader to plan for.
Your student records aren't sitting in one clean file. They're likely spread across spreadsheets, old case notes, a legacy system nobody trusts anymore, and probably a few personal folders that live only in someone's inbox (or filing cabinet!).
Migrating all of that data into a new system means deciding what's worth keeping, what's outdated, and what format it needs to be in. That decision-making eats more time than the actual data transfer. Build in real time for data cleanup before migration starts, not after you've already hit a wall.
Advisors are busy. If a new tool or software system feels like extra data entry with no obvious payoff, they'll route around it and keep working the old way, quietly, in the background.
Adoption sticks when advisors can see what they get back: less time on manual tracking, one place to find a student's full history, an actual early-warning signal instead of guessing who's at risk. Lead your conversation about upgrading to a new platform with that value proposition, not with just a feature tour.
Connecting a new system to your student information system and identity provider involves real technical work. It usually requires someone from your IT team at the table early, not looped in the week before go-live.
If your CIO or Director of IT hasn't been part of the implementation conversation yet, that's worth fixing now. They're not trying to slow you down. They're the ones accountable for security and uptime after launch, so bringing them in early tends to prevent unnecessary stress that otherwise shows up right when you’re trying to go live on the new software.
This is the roadblock nobody puts on the project plan. A lot of what your team knows about individual students, including who's on a leave of absence, who needed a check-in last semester, or who's been flagged before, lives in someone's head or their personal inbox.
If that person leaves themselves, the knowledge goes with them. Part of implementation should be a deliberate effort to get that context into the shared system, not just the data fields that migrate cleanly from platform to platform.
Getting budget approval is a win. But if the leader who championed the purchase goes quiet once it's signed, momentum drops fast, and advisors notice.
Ask your champion to stay visible through go-live: a kickoff email, a check-in at a staff meeting, a nudge when adoption dips. Advising software implementation isn't just an IT project. It's a change in how a team works day to day, and it needs someone senior reinforcing why that change matters and fielding questions from team members as they get used to the new system.
A lot of teams get deep into implementation before realizing they've never actually agreed on what "at-risk" means for their program. Is it two missed advising appointments? A GPA drop? Both? Something else entirely?
If you wait until the system is live to have that conversation, you'll end up with either a flood of alerts nobody acts on, or a signal so narrow it misses students who needed help. Take the time to discuss and define your criteria before launch, and plan to revisit them after a semester of real data is populated.
None of these roadblocks are permanent. They're predictable, which means you can plan for them ahead of time! Before your next meeting, I'd pull your team together and walk through these six challenges, not as a warning, but as a checklist.
The programs that avoid the mid-rollout scramble often had this conversation early and planned accordingly.