Saturday, August 22, 2026

UX Lessons / Opinion Piece - Why Extensive "Setup Wizards" and "First Start Tours / Onboarding Experiences" Suck

Last night I had to help Dad set up a new laptop. It was most enlightening and entertaining / heartening watching him ranting and seething about how Microsoft's new signup flow for Windows 11 was so Anti-User, with particular highlights being:

  * "I do NOT want to set up this machine like my previous one!  I want each one to be a separate / different experience!  Why do you try to force me to link them together?!"

  * "Why does it say, 'Welcome back?!'  This is a new machine!!!"

  * "I do not like how they try to scare and bully you into do things their way" (i.e. in reference to the repeated and scarily-worded prompts about enabling OneDrive sync by default to 'not lose your data')"

  * "Do I have to give it my phone number?  I don't want to give them that"

  * "Link my phone?  Whatever... I don't want that!" 

  * "Where's my internet browser?" 

  * "Argh... Where did I write down that pin again?  The one they forced me to create..." 

 

But of most relevance to today's blog post: 

  * "Why do I have to answer so many questions and sign in so many times just so that I can see what my computer looks like+ check that it's all working!"

 

That last point brings into clear view one of the things that has bothered me for many years: That is, why extensive "Setup Wizards" and "First Start / Onboarding Tour Flows" are problematic.

 

(And, to get this out of the way first:  I did offer to Dad that he could use something "much better" if "he ever got annoyed with what Microsoft were doing"... The main issue in his case is he currently does still need to do a lot of stuff where maintaining compatibility with MsOffice files is important, so I didn't want to force the matter... Otherwise, I'd strongly recommend not even touching Windows 11 at all.)

 

The problem with forcing users to make a whole bunch of setup + configuration decisions up front, before they get to interact with the product at all, is that doing all of that is usually adding a whole bunch of extra steps in their way that they DO NOT CARE ABOUT RIGHT NOW!

 

In this respect, the Linux Live USB model (and also that of the "try live demo before signing up for service" models for SAAS offerings) are generally superior for anything where you first have to create another bloody account + setup payment details, all before you have even decided whether you want to trust that company or not yet (as it's not clear whether their offerings serve your needs yet or not)

 

Sure, going that other route now poses a serious bunch of "switching cost" problems: 

  1)  When do you then prompt the user to actually set things up properly then?

  2)  How do you prevent accidental data loss (i.e. user has actually done a bit of work / stuff they care about, and then, through either pausing the setup process, or the nature of how the setup works, this state gets lost)

  3) How do you nudge users to realise that there are alternative ways to set up their environment to better suit their preferred way of working, when that is usually one of the major early steps you choose in the onboarding flow?

 

I can't claim to have any good solutions to any of those 3 problems yet. But, at the very least, I think it's worth trying to find some good ways to "solve" these, to give everyone the computing experiences they really deserve! 

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