How To Remedy the Curse of Knowledge

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What is the easiest way to remain cognizant of the curse of knowledge and make sure your content will be understood by any audience? Imagine stopping any random stranger on the street with the goal of relating with them and catching their interest. You would only use common language and simple messaging you are sure every adult would understand. That is how you take any complex subject (such as self-management) and talk about it in a way that doesn't deter or confuse your audience.
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A Complex Subject
There are countless subjects out there which are inherently complex. Purely for the sake of example, I'll be talking out my field of work: self-management and self-organization. However, the lessons within this article are applicable to any field.
If you search for information about any especially complex topic, you are bound to come across explanations that you find to be vague or complicated. For example, my first several introductions to self-management, self-organization, and Holacracy involved the same two metaphors over and over:
City infrastructure and urban planning logistics
Biology and evolution
Every reference to these concepts was accurate and understandable, but only if you could follow it. Literally every individual I know of who "just got it" when someone first explained Holacracy to them is, admittedly, an incredibly intelligent entrepreneur and software developer. Granted, those same individuals were all also completely out of touch with the day-to-day struggles of their peers who didn't immediately grasp it. There was no empathy for the lack of understanding and it was treated as an unwillingness to learn rather than an inability to.
For the majority, the concepts like this are already complex. Unsurprisingly, trying to explain it with science and engineering often proves to be counter-productive, even if the reasoning is factually sound. So how do we take a complex subject and explain it in a way that anyone and everyone can easily comprehend?
The Curse of Knowledge
First and foremost, you must be painfully aware of the curse of knowledge. That is, knowing when you might have more knowledge than other people in the room and will thus need to consciously control what you talk about and how so that it makes sense to those listening. This is a skill that immediately sets you apart as more than just smart, but truly knowledgeable. There are plenty of genius astrophysicists, but understanding astrophysics well enough to explain it simply to a child is an entirely different skillset. That's why we typically only know the names of astrophysicists who are able to talk in a way that the general public can understand.
As a teacher/consultant/presenter, the burden of understanding is not on your audience, it is on you. It is your responsibility to talk in a way so as to be understood.
Being asked to be consciously aware of how easily you understand something that somebody else doesn't is no easy ask, but it's a necessary skill when trying to teach a new concept. That, and it's always valuable to acknowledge that no matter how smart you are, there are things others perfectly understand that you don't.
So how do you combat the curse of knowledge?
Know Your Audience
If you are presenting to a room full of urban developers, then talking about city infrastructure is perfectly fine because, chances are, everyone in that room has a relevant background. This allows then to easily follow along and make connections between the topic and your chosen metaphors. Presenting to only those with Master's Degrees? Use any level of knowledge that is typically obtained during those several years of schooling.
Additionally, knowing your audience will allow you to personalize your material further and connect with them on a deeper level. Jokes that only make sense within a given industry are a great way to make an audience laugh. Pointing to examples you know they specifically struggle with can make them feel like you understand their challenges.
Of course, there will be times when you can't know your audience ahead of time. Additionally, there are plenty of times when the audience is a diverse mix of backgrounds and education levels. What do you do when you can't know your audience?
Present To The Least Common Denominator
With respect to my previous advice, even the above title of this section may not be a term that everyone is familiar with. In that case, what I mean is this: consider the lowest level of education and most unrelated background someone in your audience could possibly have and build your content for them.
If you don't explicitly know the base line for your audience's knowledge, assume they've never heard of the topic before. Assume they have no higher than grade-school level knowledge, they don't have the same hobbies or interests as you, and they've never worked in the same industry as you. This helps you to approach audiences on a level that almost everyone can meet you at.
What if you are used to always talking about city infrastructure, but you've gotten feedback that not everyone understands? Why not instead talk about traffic? Most people have been in and experienced the stresses and woes of traffic, even if they haven't themselves driven in it. Nearly ever person understands the dangers of a car running a red light, whether they've experienced it in a car, as a pedestrian or cyclist, or even from watching a YouTube video.
Inevitably, no matter how much you prepare, there is always a chance that someone won't understand. This too is not a lost cause.
Be Proactive
There are several different ways to proactively address particularly confusing parts of your content. The more you present your content, the better you will get at recognizing which areas tend to be the hardest for audience members to grasp. If you take questions, you may notice you get the same few questions every time.
Ideally, you will tweak your content to address those points going forward. For the things you can't change, you can call it out ahead of time so nobody feels alienated. Here are a few methods which can help you do this without disrupting the flow of your presentation.
Call it out at the beginning. At the very start of your session, when going over any logistics and what they can expect, be forthcoming about the complexity of the subject. Let them know you will do your best to keep it simple, but if anyone is still lost, give them a clear path for how they can get answers. That path depends on the nature of how you're presenting. If you are working with a small group, ask them to raise their hand so you can pause the session and answer it right then and there. With a larger audience, tell them to write down their questions and tell them you will address it during Q&A time at the end. If that isn't an option, let them know how to get in touch with you after the presentation - be it mingling in-person after the event or via your email address.
Give yourself extra time during difficult sections. If you have built out your presentation and know roughly how long every section will take, carve out an extra 5-10 minutes after the very difficult sections. This time will let you dive in deeper, answer more questions right then, and make sure everyone understands before moving on.
Ask for feedback. After you have completed your presentation, consider asking attendees to provide feedback. You can do this in-person for those willing to share, or send a link to a survey form later. Getting feedback to critical to discovering what worked and what didn't. If people regularly tell you the same part is confusing, it would be in your best interest to figure out how to simplify your message.
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Have you heard explanations of complex subjects that were too hard to follow? What have been the simplest explanations you've heard to help you understand a complex subject? We would love for you to share them with us!