Originally aired January 28, 2026 on Extropy On AIr.
Finance transformation goes best when people are brought along, not pushed through. In this episode, Mike Jasper and Extropy Project Manager Maira Correia share how clear communication, strong project structure and hands-on support take the stress out of finance digital transformation, and what to do at the three moments when stress peaks: kickoff, testing and go-live.
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Key takeaways
- People are doing the project on top of their day jobs. Structure, a steady meeting rhythm and real support make that manageable.
- Start with a current state demo so the whole extended team understands where you are starting from.
- Tie every change to a purpose. People accept change when they understand why it matters to them.
- At kickoff, acknowledge how big the change is, bring an executive to explain the why, and share time commitments by role.
- Turn your most critical testers into champions, and use metrics during hypercare to show the system is working.
Why do finance transformations stress people out?
Finance digital transformations can be long and complex, and the people involved still have their day jobs. As Maira puts it, you have to meet people where they are and address their concerns rather than brushing them off. Many are comfortable in their current process, even an outdated one, and change feels like it uproots their whole routine. Some team members have been in the same process for 20 years or more.
There is also a real fear of becoming obsolete. When people hear digital transformation, they often think automation is coming for their job. Mike’s experience is the opposite. Transformations usually let teams do more strategic work, or help the company grow without doubling the team. The people who embrace the change and become experts in it tend to find the work more fulfilling than repeating the same ten keystrokes.
How do you keep people grounded throughout a project?
It starts with how the team is structured. A project manager owns the timeline and is the main point of contact, while solution consultants understand both the client’s needs and the new platform well enough to answer questions with confidence. From kickoff through hypercare, a set weekly schedule gives people dedicated time to work through testing and training together, without being buried in technical jargon.
Mike recommends a current state demo for the entire extended team, including consultants, the software implementation team and other business areas, so everyone understands where things are starting from and how big the change will be for day-to-day users.
He also reminds teams that digital transformation is about more than the digital part. There are people changes, process changes and technology changes, all driven by purpose. Linking each change to a clear why, like more strategic work, lower audit risk or room to expand into new regions, shows people the change isn’t just change for its own sake.
What should happen at a project kickoff?
Kickoff is often the first time the people who run the process day to day see the project. The decision makers who signed the contract usually aren’t in the daily work. Maira typically sees three groups in that first call: people who are excited and tech forward, people who are confused or worried it will add work, and people who are resistant because the current way works for them. Spotting who is who early shapes how you engage each person.
Three things help most:
- Acknowledge the change. Don’t be flippant because you’ve done many implementations. Make it clear you are one team, and that the goal is to make the system fit them, not force them to fit the system.
- Bring an executive. When a CFO, CIO or CTO explains in their own words why the project matters and what pain it will remove, like overtime and late nights, users feel heard. Often this is a team whose spreadsheets and workarounds have been ignored for years.
- Share the time commitment. Lay out phases, milestones and how much time each role will need at each stage, so people can plan around month-end close instead of being told a week before training to clear 20 hours.
Maira shared how one of Extropy’s project managers built a multi-region timeline around the fact that August is a vacation month in much of Europe, shifting focus to another region that month. Teams could see their way of working was being respected from the start.
How do you manage stress during testing?
Testing is long and detailed. Teams check that workflows move as designed, that invoices flow through the process and that limits and tolerances are set correctly. It can mean several multi-hour sessions a week, and people start to worry whether the system will really work for them. Some testers go in looking for what is wrong, often the same people who were most resistant at kickoff.
Mike’s advice is to keep the wider team informed about design decisions made between kickoff and testing, and to ask for their input on things like workflows and access rights before testing begins. It helps people feel part of the project and catches issues earlier.
He also recommends finding the most vocal and critical testers and working closely with them. They are usually the ones thinking hardest about the impact of the change. As Maira notes, the most knowledgeable people have the most questions because they are ten steps ahead, thinking about rare scenarios. Address their concerns and they become your champions and the power users everyone goes to after go-live.
What makes go-live and hypercare successful?
In testing you know what the outcome should be. On day one of go-live, real transactions arrive at full volume, and when something stops, people have to figure out whether it is supposed to. Maira compares it to theater: you nail the dress rehearsal, and then it’s opening night with a full crowd. Hypercare is when the team stays by the client’s side to diagnose issues, fix them and improve the process so it works better next time.
Mike tracks key metrics during hypercare. Bottlenecks point to where more training, a configuration change or a process rethink is needed. He also watches that work coming in and work going out start to run parallel, a sign the team is keeping up with volume. With modern reporting and dashboards, it is easy to see in real time where things are stuck, and clients can keep using those same tools to make decisions long after the project team steps back.
In their words
We’re not throwing change at you just for the sake of change.
Mike Jasper, Extropy Advisors
I’m not going to tell you to not feel how you feel, but we’re going to work through it together.
Maira Correia, Extropy Advisors
About the speakers
Mike Jasper is VP of Finance Transformation at Extropy Advisors, where he leads digital transformation and client success, working hands-on with clients to set success criteria, optimize their people, process and technology, and measure the results.
Maira Correia is a Project Manager at Extropy Advisors, guiding clients through finance transformation from kickoff to hypercare.
FAQ
Why are finance transformation projects so stressful for teams?
Finance teams are asked to take on a large, complex project on top of their day jobs, and the business doesn’t stop. People worry about the unknown, about how the change will affect their routines, and in some cases about whether automation will make their role obsolete. Stress peaks at kickoff, testing and go-live.
How do you reduce stress at a project kickoff?
Acknowledge that the change is a big deal, have an executive explain in their own words why the project matters, and share a project outline with phases, milestones and how much time each role will need to commit, so people can plan ahead.
What happens during hypercare after go-live?
Hypercare is the hands-on support period right after go-live. The implementation team stays alongside users to troubleshoot issues in production, tracks key metrics to spot bottlenecks or backlogs, and adjusts training, configuration or process until the team is confident running the system on its own.
Keep exploring
- More episodes of Extropy On AIr
- Previous episode with show notes: Unlocking Intelligent Invoice Lifecycle Management with Basware
- Next episode with show notes: The Hidden Cost of Organizational Entropy
- Related: The Execution Gap: Why Great Strategies Fall Apart
- Why Extropy
Planning a finance transformation and want your team to feel confident through it? Book a discovery call with our team.
