Great post, @ellibot! You're absolutely correct in pointing out that familiarity with something often leads us to forget the challenges of learning it for the first time.

Imagine being in a situation where you have to teach someone a board game that you've been playing for years. If you assume they already know the rules, it's likely to result in disappointment and a less enjoyable game night.

To avoid falling into this trap, the secret lies in always remembering that your goal is to help someone learn. This mindset will enable you to be patient and encouraging, transforming you from a mere map of instructions to a guiding presence.

Approaching each customer call with the intention of increasing their understanding becomes a meaningful achievement. It's true that this may be easier said than done, especially during busy onboarding projects when going on autopilot is tempting. However, adopting this approach will undoubtedly lead to more positive outcomes.

Love this. It can be really tough especially in today’s environment of conflicting acronyms, specialization, and cross-national projects resulting in language barriers.

As @emaynez said you have to start with a baseline assuming nothing and grow from there. If you assume your client knows nothing (or the minimum) in a respectful way you can then build a foundation from which to grow.

For example, when I led Work Opportunity Tax Credit implementations we were primarily dealing with HR managers who knew nothing of the program their finance bretheren had purchased. We went in with the assumption that they client needed a primer on the program and asked up front, “what do you know about WOTC?” and built from there. Sometimes we would get people that had used the program before and were very familiar and other times complete newbies.

Another item is to have resources available to help the client through the journey. Slideshows, FAQs, webinars, and other training materials can help set the foundation of a successful project and help build the client’s knowledge to maximize the value of the product implementation and onboarding.

@rondeaul hit the nail on the head. This question is the BEST one to identify where your customers are at:

“What do you know about xyz?” 

Meeting the customers where they’re at is key to taking them where they want to be.

This is something that I deal with a lot when creating training content. The solution is empathy, which comes with practice.

It can be easier to avoid that bias with an advertised training than running an implementation, because I can state the target audience in a course description and tailor what get’s covered from there. However that doesn’t eliminate the need to still practice empathy and placing yourself in the other person’s shoes.

When developing a course, I ask for a lot of feedback throughout the process, not only from Subject Matter Experts, but from new learners as well. I start gathering everything needed to be able to teach the subject to someone who is completely knew to it, from there I then look at my target audience and pare it down to what they would need. This helps me get into the mindset of the learner.

This also means that if I’m doing a live training and I realize that my audience isn’t understanding, I already have thought through how I would teach it to someone who is brand new. By doing as others have suggested and stepping back and identifying where they’re at in their learning journey, I can make sure that I tailor the experience to them.

I imagine that a lot of the same skills used for creating training is applicable to preparing for an onboarding. By creating a plan for someone with no experience before adjusting it for someone with the average amount of experience that you clients have, you have things that you can fall back on if you need to.