Is there any friendly way to ensure that an older demographic understands a modern toggle sidebar nytimes-esque type of navigation?
We currently have a sidebar with endless links and the web resembles a 1998 design.
Any tips or ideas?
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Lawyers (especially older ones) have years of experience and models of how the legal world is organized.
You may discover patterns of how people categorize information conceptually which will help ensure your users understand the website you're building.
A classic mistake is to structure the information space based on how you view the content — which often results in different subsites for each of your company's departments or information providers.
Card sorting is a method used to help design or evaluate the information architecture of a site. In a card sorting session, participants organize topics into categories that make sense to them and they may also help you label these groups. To conduct a card sort, you can use actual cards, pieces of paper, or one of several online card-sorting software tools.
Another advantage of this research is that for your case, your users will feel comfortable with simple pen and paper, so there's no technology barriers for them to give meaningful input.
You can start with your proposed category names, then list out all the links, each on their own card. Allow the users to organize them according to how they see the world. Also ask them if the category names even make sense, and if some items belong in a new category.
Older people have primarily the following problems uses digital tools:
The above issues boil down to the following:
Understand their conceptual model of organizing information.
Big and spaced font and font sizes
Working on information architecture (grouping into categories and subcategories). A good example would be Yellow Pages and Dictionary/Thesaurus or index in books which are excellent examples of information chunking and categorizing patterns.
Attention to contrasts and colour sensitivity.
High affordance - making it clear that there is something more. The best way would be to have avoid a 'hamburger type menu'.
Seniors keep a list of steps and instructions about how to use websites they need or often visit.
If there is an existing pattern it is probably best to retain it or make it more accessible or even expose it completely.
NN Group did a Seniors as Web Users research and one of their conclusions was:
Pull-down menus, hierarchically walking menus, and other moving interface elements are problematic for seniors
So, the answer to your question is: plenty of them will have troubles using toggle sidebar navigation.
In that same article NN Group also advises to
Avoid Navigation Changes
so you should be very careful about changing the site's navigation structure.