How to communicate big changes in product when these changes have some benefits but require a big effort from your customers to enjoy them?

Welcome to the fun world of Enablement! And there are internal + external aspects of this.

• External
• Message x Value & benefits: What's in it for your users? Migration is a pain in the ass. Before you get to the logistics, you have to sell them on the why
• Transition plan: What's the step-by-step guide? Is it one size fits all, or does it require different approaches for different types of users? These need to be documented and clearly laid out. 
• Timing & cadence: Give your customers enough time to make the changes. I'll leave the communications format, channels, and cadence up to you (but this is never a one-and-done exercise). For example, don't expect one email to the entire database to yield good results or high customer satisfaction.
• Internal
• Is an Enablement team in place at your company? If so, great! Loop them in early on customer enablement plans and they'll be able to position that for your internal folks. If not...
• Message x Value & benefits: Why is this change important to communicate and will it help your team sell more & better? Sell the change internally.
• Transition plan: Leverage what's built for customers and share it widely internally so that every customer-facing team is aware. Roadshow it in team meetings, mention it at all hands, set up office hours to give your colleagues the opportunity to ask questions and poke holes.
• Timing & cadenece: Keep internal teams updated on the customer comms plan. In B2B sales, give your CSM team the opportunity to send 1:1 messages while marking takes care of the 1:many.

My initial reaction to this question was - why would you do this? :D If you are asking a customer to make a big effort, your overall benefits should far outweigh the work needed to achieve it. So instead of "some benefits, big effort" you're really targeting "some effort, big benefits."

But I think what this question is actually asking is about a breaking change, such as a forced migration or a deprecation. These are hard but necessary situations and the approach to take is to overcommunicate, reduce friction, and be empathetic.

Overcommunicate: If you are issuing a change - perhaps an upgrade to a new API with a plan to deprecate the existing one - make sure you harness channels and a cadence that makes your customers extremely aware of the value of the move, and the time they have to make it. Issue a service announcement via email, put it in the product itself, communicate it via social and your blog, etc. The last thing you want is for a customer to be surprised and then have a negative reaction to you and your brand.

Reduce friction: This is going to take real work from your customer. Is there anything you can do to help make it easier? Examples include creating technical guides that help your customer's team know, step-by-step, what they need to do. Or perhaps even working with service partners to create packages that could help a customer make the change without needing to use their own team.

Be empathetic: To the fullest extent possible, be an advocate for your customer internally and in your narratives. If you're able to build out a longer timeline that would help your customers adapt to the change, do it. If you're able to identify key features that your customers would appreciate that require minimal resourcing internally to execute, try to advocate for them to happen. Tip the scales towards as much benefit as you can and tell that story in a compelling way while not sugarcoating the amount of effort required. Your customers are smart and should be treated as such.

• Make it as easy as possible for your customers. Cannot emphasize enough that every decision you make should be prioritizing the customer journey and imagining how it will affect them. If it feels impossible, or as difficult as switching to a competitor, figure out how to fix it. No matter how exciting the benefits are, they may not outweigh the perceived “cost of switching.”

  • Research: Do customer research to deeply understand how the customer will approach what you’re asking them to do. Can they truly do it on their own? Is it too onerous or complicated? Lots of migration plans make perfect sense on a planning document and then hit roadblocks in practice. Pilot the migration with a few friendly and understanding customers. Update your plan with the learnings.

  • Phase the rollout: Complete the rollout in tranches so that you’re resourced to support each set of customers.

  • Ease the burden: Find ways to automate the transition and mitigate the manual work you’re asking them to do. It may be "less expensive" in the long run for your Relationship Managers or Engineers to help customers reconnect their setup or rebuild their dashboards for them, instead of asking customers to do the work themselves.

  • Social proof and benefits: Make a case study with the customers from your pilot program. Showing the business impact of being on the new API can help offset the perceived “cost of switching” for other customers you're convincing to migrate.

• Make communication as clear and straightforward as possible. No one likes to be surprised or feel confused. They also need to understand timelines, the support they can expect to receive, and whether this migration is required or not (i.e., are you sunsetting the old API? If so, create a thoughtful deprecation plan with a reasonable/generous timeline).

• Set goals that are tied to a smooth transition. In addition to whatever business goal is driving the move, set goals to measure the success of a smooth transition. For example, less than x% increase in customer support tickets; churn below a threshold of x%; x% increase in NPS for migrated customers within the first 3 months.

The first step is defining the customer journey and making sure your key functiona teams understand that journey. Then, recognizing that there may be stop gaps that need to be implemented to ensure customers can take advantage of the feature. What needs to happen on the delivery side of the house so CS and technical teams are enabled? How can we over communicate and document docs and materials for our teams and customers?

What kinds of enablement efforts do we need to account for to make sure customers understand the benefits?