Updated July 2026. Expanded from a short answer into the full one, including the part underneath it that I had left out.
The question, more or less as it was sent to me: how do you drive adoption for something people know they need but would rather be hit in the head with a hammer than deal with, without being scary about it?
Compliance software. Data hygiene. Security. Anything that solves a problem the customer genuinely has and genuinely does not want to think about. The work is not exciting. It is necessary. And they are dragging their feet.
Before the tactics, the thing underneath the question.
You Are Not Here to Make Your Customers Happy
The reluctance to bring up consequences is almost never about tactics. It comes from a belief that the job is to keep the customer feeling good.
When I say we are not here to make customers happy, people hear that I want customers unhappy. Not what I said. I said happiness is not the thing we can solve for. We solve for the customer achieving what they came to achieve, and sometimes getting there requires pushing someone to do a thing they would rather not do. That will occasionally leave them less than delighted with you on a Tuesday. That is acceptable.
Hold that belief the other way around and you will avoid every conversation that carries any friction, which happens to be every conversation that matters.
Naming the Downside Is Not a Scare Tactic
Think about what the customer already knows. They bought compliance software. They understand there is a rule. They understand what happens if they are not compliant by the deadline. That understanding is the entire reason they are a customer.
And we want to avoid mentioning it.
Avoiding the reason someone became your customer is not sensitivity. It is a strange kind of self-sabotage.
Saying plainly that a deadline exists and that missing it carries consequences is not manufacturing fear. It is describing the situation the customer bought you to resolve. A scare tactic is inventing a threat or inflating one. Restating the actual stakes is just accuracy.
This is not only a compliance thing. Say a customer bought your platform to add a specific amount of new revenue this quarter, and you can see they are not on track because they are not doing what you jointly agreed they would do. If you notice that and choose not to say anything, you are not doing customer success. I am not saying you are not working hard. I am saying whatever that work is, it is something else.
There Is No Such Thing as a Difficult Conversation
Count how many times in a week you or someone on your team describes an upcoming customer conversation as difficult. Or challenging. Or tough.
Now notice which conversations get that label. It is the one where you tell them they are off track. The one about the deadline they are going to miss. In other words, the most important conversations you will have all quarter, pre-labeled as unpleasant.
A conversation you have framed as difficult is a conversation that slips. It gets scheduled late, or shortened, or quietly dropped. The label does the avoiding for you.
There are no difficult conversations. There are conversations. Some carry news the customer would rather not hear, and having them promptly is most of the job.
If you lead a team, this one is yours specifically. I have watched heads of Customer Success run a weekly standup asking who had a difficult conversation this week, treating it as a badge of honor. That is a culture being built on purpose, and what it builds is hesitation. Your team will not have those conversations faster than you make it normal to have them.
The Person Doing the Work Did Not Buy Your Product
Here is the structural piece, and it explains most foot-dragging that gets misread as attitude.
An executive understood the requirement, evaluated options, and signed. Then the work was handed to someone else. That person did not attend the demo. They were not consulted. They found out they now own a new top priority, on top of the priorities they already could not finish.
They are not resistant. They were blindsided, and the two look identical from where you are standing.
Two things fix it, one upstream and one immediate.
Upstream: get your sales team to bring the execution team into the buying process. Not to approve the purchase, just to be in the room, ask questions, and hear what the first ninety days look like. The pitch to the prospect is easy, because it is true: in our experience, having the people who will actually run this involved early makes the rollout go significantly better. It costs one meeting and it buys you ownership instead of ambush.
Immediate, for every customer already past that point: when you meet the person doing the work, start by learning what else is on their plate. Then build the plan around that reality rather than around your onboarding template. Fifteen focused minutes a day, in this order, done by this date. Something a human with an existing job could actually do.
There Is Peace in the Plan
I heard an interview with a pediatric neurosurgeon that reframed this for me.
When they deliver a diagnosis to parents, everything in the room becomes fear and chaos. The instinct is to let it settle before discussing what happens next. What they found is that it never settles. So they give the diagnosis and lay out the plan immediately. Here is what we do first, then this, then this, over this timeline.
The plan does not make the situation less frightening. It makes it less unknown, and a great deal of the fear was the unknown.
I am not comparing onboarding to brain surgery. The common factor is that both involve a human being handed something overwhelming. A person who has just been told they are behind and given no path forward will avoid you. The same person, handed a specific sequence with dates, has something to do on Monday.
Three Things to Do
Involve the execution team before the deal closes, so the people doing the work are never surprised by it.
Build the plan for the person actually doing it, around the rest of their job, and say out loud that you know this landed on top of everything else.
And stop calling them difficult conversations. They are conversations, they are the important ones, and the sooner you have them the smaller they get.
