How Do I Prepare a Customer for Their First Software Training?
To prepare a customer for software training, settle scope with them before anyone sits down. Get five answers agreed and written. What the tool replaces, what stays the same, what happens to work in progress and data, who decides the daily workflow, and when the old way turns off.
The kickoff went fine and the training is booked. The users have been told what the tool does and why leadership bought it. Nobody has told them what happens to the report they build every Wednesday.
Why Do Users Arrive at Software Training Unprepared?
The announcement they received explained the purchase. It said what the tool does, why it was chosen, and when it goes live. It didn't say which of their current steps go away or whether their saved work survives the switch.
Each user carries their own version of those questions into the session. Does my weekly report still work? Where do my open items go? Who do I ask when the new setup doesn't fit how we do things? When do I have to stop using the old system?
A training session can't answer any of them, because the answers are decisions the customer hasn't made yet. Prosci, describing the awareness stage of its ADKAR model, reports that the reason people most often give for pushing back on a change is that nobody explained why it was happening or what it meant for them.
Michael Ginzberg, in a 1981 longitudinal study in Management Science, measured users' expectations of a new information system before it was implemented, then followed the project. Users whose expectations were realistic beforehand were more satisfied with the system later and used it more. He noted that the decisions shaping what users will see, such as goals and scope, are made early, which makes expectations at that point an early warning. The five written answers are where those expectations get set.
The sponsor who wrote the announcement doesn't have each user's week in mind. You have run this rollout at other accounts and know which questions come up, so you are in a position to get them answered first.
What Should a Customer Decide before Software Training?
Send these five questions to the sponsor with a name next to each.
1. What does the tool replace, and what happens to the old one? Owner: the sponsor or the internal project lead. Prevents: two systems running side by side for months, with users doing the same work in both.
2. What stays the same? Owner: the same person. Prevents: users assuming everything is changing and bracing for all of it at once.
3. What happens to work in progress and to data? Owner: the admin or IT contact handling the migration. Prevents: users arriving unsure whether their open items and saved work carry over, and raising it in the session with no answer ready.
4. Who decides how the team uses the tool day to day? Owner: the manager of the team whose work changes. Prevents: setup questions with nowhere to go, and a configuration nobody on the team chose.
5. When does the old way turn off? Owner: the sponsor or project lead, with a date. Prevents: an open-ended transition. If there is no date yet, write that down. It tells you the rollout has no end point.
Why Tell Users What Isn't Changing?
Sponsors can skip question two, because the announcement was written to make the change sound important. Users who read it that way can expect more to change than will.
Ming Hsu and colleagues, in a 2005 study in Science, found the brain's threat-detection circuit responding more to choices with unknown odds than to choices with known odds. A short list of what isn't changing turns part of the unknown into something known, before the feature tour starts.
How Do I Get Workflow Problems Raised before Setup Is Final?
Ask the manager from question four for two or three real cases, in writing. A report the team produces every week and the inputs it needs. A handoff between two people that the old tool handled.
Your implementation team can check each case against the setup while it can still change, and the manager has a hand in how it's configured. If the manager can't produce cases in writing, sit in on one working session with the team, write the cases yourself, and send them to the manager to confirm.
Jon Hartwick and Henri Barki, in a 1994 field study of information system projects in Management Science, found that user participation raised users' involvement with the system, and involvement in turn carried the link to system use. The part of participation that counted most was overall responsibility. Their study measured the participation of the users themselves, so ask the manager to gather the cases from the people on the team who will use the tool.
What if the Customer Can't Answer the Questions Yet?
A missing answer is useful information. It shows you which decision the customer hasn't made, and it shows you before twenty people are in a session waiting for it.
Book a 30-minute scope call with the sponsor and the owner of each open question. Bring the questions with the gaps marked. Leave with a name and a date next to each open answer, even if the date is a week away.
If the cutover date is the open one, ask for a target and label it as a target. Users can plan around a target month for the old system to go read-only.
How Do I Use the Five Answers in the Training?
Open the session with what stays the same, read from the list the sponsor agreed to. Then show what the tool replaces and when the old way turns off.
Build the rest of the session on the manager's written cases. Teach the product by producing the team's own weekly report in it, with their own inputs. Users see their Wednesday task done in the new tool before they leave the room, and questions about data and work in progress already have answers you can point to.
Don't confirm the training date until at least three of the five questions have answers on paper.
If the customer bought the product and usage still isn't moving, Unstick the Account walks you through who the rollout is stuck on, person by person, and what to do about each one.
If you're the founder still doing customer success yourself, or the sales lead who just got handed it, I do two-week consulting stretches on exactly this kind of thing. All async, no calls. Here's how that works.
References & Related Reading
- Awareness: The Prosci ADKAR Model, Tim Creasey, Prosci, 2018 (updated 2026).
- Neural Systems Responding to Degrees of Uncertainty in Human Decision-Making, Ming Hsu, Meghana Bhatt, Ralph Adolphs, Daniel Tranel, and Colin F. Camerer, Science, 2005.
- Early Diagnosis of MIS Implementation Failure: Promising Results and Unanswered Questions, Michael J. Ginzberg, Management Science, 1981.
- Explaining the Role of User Participation in Information System Use, Jon Hartwick and Henri Barki, Management Science, 1994.
- Convincing Employees to Use New Technology, Didier Bonnet, Harvard Business Review, 2014.
