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Case Study: Your customers are using a 10-year-old version of your software. What do you do?

Say you are a product manager for desktop-app.  This is a very old product.  Within the preferences setting of the product, there is an option for auto-update. 

 

A) Automatically install updates ( Recommended)

B) Ask me to install every time there is an update. 

 

Now as a result of giving this option there are some sets of people, who are still using a very old version. Some are even on a 10-year-old version. 

 

Problem 1: Your engineering team hates this, for them its overhead to keep supporting such an old version.

Problem 2: Users are also missing important security and performance updates, they are also missing on a lot of cool features. 

 

Q: How often product checks for updates? 

Ans: The product is checking for the updates every 24 hrs. 

 

Q: What message does the user see when there is an update? 

Ans: New version ApppName is available, would you like to update? Yes/No

 

Q: If the user selects No, will the user get a notification again for this update?

Ans: Yes user would continue to get this message for once every 24 hours.

 

Q: How often the product makes release?

Ans: The product makes release every month end.

 

Q: Does the product any SLA? 

Ans: Yes product has an SLA of 99.99 of availability.  

 

 

I would like to see how different people will approach this problem. 

Feel free to ask more clarification questions.

For all clarification questions asked, I will add them to the end of the original post itself. 

 

I have two solutions in mind and I will answer after 2 days :).

 

 
Asked at Slack
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Answers (1)
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Assumption:  These customers are the ones who want to get notified about whenever an update is available and they kept on declining the updates for the past 10 years.

Approach:

Step 1) First send an email to all customers talking to benefits, deadline and not supporting etc.

Lets assume the conversion rate was merely 20-25%.

Step 2) Break it down the reamaining customers into three revenue generation categories and also check CLV(customer lifetime value)

1) High revenue

2) Medium Revenue

3) Low revenue

For Low revenue customers, I would just push the updates automatically because I am assuming that business may have to take some loss in revenue for doing this.

For High revenue, I would use Account exec and personal customer support to work on the update as they are high paying and company dont want to loose their account to rival.

For medium revenue, I would use mix of automatic updates for few and remaining ones to be supported by customer support.

And check week over week the progress of the strategy and if it is not working then we may need to do a different strategy.
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Get access to 2,346 pm interview questions and answers to give yourself a strong edge against other candidates that are interviewing for the same position
Get access to over 238 hours of video material containing an interview prep course, recorded mock interviews by expert PMs, group practice sessions, and QAs with expert PMs
Boost your confidence in PM interviews by attending peer to peer mock interview practices, group practices, and QA sessions with expert PMs