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We can all agree that there are tasks out there that aren’t fun at all, such as filing taxes, paying bills, creating a will, etc. When it comes to designing UX for an unpleasant task, the first thing to accept (and remind oneself throughout) is that the task itself sucks because it just does, and that the UX professional should do as much as possible to not make it suck more. From UXMatters.com comes a FANTASTIC piece discussing design strategies for unpleasant tasks, starting with:

Accept That You Can’t Make Some Tasks Pleasant
A positive user experience can help minimize the pain and avoids adding more unpleasantness, but it’s not going to completely take the pain away. As UX designers, our job is to help people get through their unpleasant tasks smoothly, without piling on more difficulty. Ease of use and efficiency are especially important in easing the way through unpleasant situations.

Stay Out of the Way
Ensure that the UI you design doesn’t get in the way or cause more problems. Remove unnecessary features, distractions, questions, and interruptions so users can focus on their icky tasks.

Be Careful What You Say
When writing messages and other text relating to unpleasant tasks, it’s best for the tone of the content to remain neutral or perhaps mildly encouraging. Being cute or irreverent is not going to go over well.

Avoid Overwhelming People
Too much information or too many options can easily overwhelm people who are already stressed, anxious, fed up and pissed off. Keep in mind the following techniques:

Ease into Things
Dashboards present an overview that eases users into complex information by presenting a simplified view first before they dive into the details. This approach may be more appropriate than dumping a user into complicated screen right away.

Show What’s Coming Up
Another way to ease into a process is by telling users what to expect. People are more likely to begin and complete a process if you give them a reason to do so and show them what’s involved. Consider a quick text overview before a new section to better set expectations, or a progress indicator like those used in a check out process in e-commerce transactions.

Focus on One Step at a Time
How do you eat an elephant? Exactly. For some activities it’s best to break the task into smaller, more manageable “bites.” This makes the overall task feel less overwhelming and allows the user focus better on requirements.

Use Progressive Disclosure
Provide only the information and options users need to see in order to accomplish the tasks they’re dealing with now.

Hide Complexity
Don’t expose users to information they don’t need to see. Duh, right?

Minimize the Need to Read (when appropriate)
It’s widely accepted that people don’t like to read online instructions. Under normal circumstances, they’ll skim just the content they need to get through. When people are stressed out, this is even more true. So for stressed out users, do them a favor and keep the content concise and make it easy to scan with headings, bullet points, and format text that needs to be emphasized.

Automate Actions
Automate frequent, repetitive actions, or make it easy for the user to set an automated preference. Then make it obvious that it’s been completed in case the user wants to undo the action.

Provide Common Defaults
Provide time-saving defaults to users so they don’t have to input the values themselves.

Avoid Surprises
Enough said. Keep users informed and set proper expectations.

Give Users Control
Give users a sense of control by providing them with options instead of constraining them to a specific path. Advanced, knowledgeable users will appreciate skipping the screens and information they’ve seen before. Also, in the same vein:

Provide Options For Different Audiences
E.g, Novice vs Advanced users.

Give a Sense of Progression to Encourage Users
“Are we there yet?” Not knowing makes just about everyone nuts. Especially in the midst of an unpleasant task. So let users see how their progressing to remind them that relief is in sight.

Provide Various Levels of Help
Instructional text, tool tips, contextual help, live chat access, call center access, email, contact us, progressive disclosure tips.

Help Users Make Difficult Decisions
Provide information, suggestion and recommendations. Especially when tasks and/or subjects may be unfamiliar or infrequent.

Oh yeah, avoid being annoying. “Clippy” anyone?

Read the complete article with relevant examples at UX Matters:
“Designing Solutions for Unpleasant Tasks”