BEST WM Show Migration planning missteps

“What are some migration planning missteps (and how do I avoid them)? Find out on this episode of Appfire Presents: The BEST Work Management Show by Appfire. Jira expert Rachel Wright joins Emily Peet-Lukes to answer some key migration questions, including: What are the worst migration mistakes? What is the biggest migration misconception? How can you manage risk during the migration process?

Use insider knowledge and industry best practices to guide your migrations. Grab your copy of “The essential workbook for planning Jira migrations.”

About the guest

Rachel Wright is an entrepreneur, process engineer, and Atlassian Certified Jira Administrator. She wrote “The Jira Strategy Admin Workbook,” and “The Ultimate Guide to Jira Migrations: How to Migrate from Jira Server to Data Center or Cloud”. She’s also a speaker, an Atlassian Community Leader and author of courses for new and advanced Jira admins and users. She started using Jira and Confluence in 2011, became an administrator in 2013, and was certified in 2016 (the first year you could actually get certified). She’s the owner and founder of Industry Templates, LLC, which helps companies grow, get organized, and develop their processes.

About the show

The BEST Work Management Show by Appfire features smart leaders sharing their secrets for optimizing business processes and increasing productivity. Get the goods on how they handle everything from setting up workflows to automating processes. Every episode is 10 minutes or less, packed with insights you can use right away to supercharge your team’s productivity.

For your convenience, here is the transcript of this episode:

What are some migration planning missteps (and how do I avoid them)?

Emily:  Today we’ll be talking about migration planning and preparation with Atlassian expert and Jira rockstar Rachel Wright. Coming up, Rachel shares her inside knowledge on the best ways to manage your organization’s migration process. Stick around for 10 minutes of migration advice.

Hey, Rachel. Thanks for joining us today.

Rachel:  Thank you for having me.

Emily:  Of course. Always. We’re going to be talking about migration planning and preparation. I’m sure that a lot of people have that top of mind right now with everything going on with Atlassian, and also migrations are kind of going to be a forever part of our lives now.

Rachel:  Absolutely. As more Cloud adoption occurs and as old hardware starts to stale and go away. It’s not like this is going to be the only migration in most people’s IT life.

Emily:  That makes sense. Today we are talking about migration planning and prep, and we have a couple of questions. Let’s jump right to it.

What are the worst migration mistakes that people can make? 

Rachel:  I know I harp on this all the time, but not planning. It sounds so simple, but sometimes people think this is like a one-click upgrade that you login, you click migrate, and it’s done. That’s really not the case, especially for those people who have very big instances with a lot of data, a lot of apps, a lot of users. Proper planning is always the best thing you can do.

Next is lack of testing. I’m surprised at how many people just kind of throw it into production and see how it goes. I have no risk tolerance whatsoever. It’s worth the time to stand up a sandbox, a test environment, and really go through your plan. See what you missed. Test everything out. Do not go to production until everything is perfect.

Emily:  That makes a lot of sense. In planning and preparation, it’s not just a click and go or a throw it up kind of thing. There’s a reason why taking that time to put together a proper plan, test, and troubleshoot any problems that arise is what sets people up for success.

Rachel:  Absolutely. You don’t want to just wing it, especially when people are relying on this software. They don’t want to come to work on Monday morning and they can’t login, they can’t find their work, they can’t do their work.

Emily:  Right. 

Rachel:  I like to avoid those nightmares where possible.

Emily:  That makes total sense. Let’s jump into the next question. What are some of the biggest migration misconceptions?

Rachel:  That this is a simple, easy one-click upgrade kind of situation. I know some software is like that, but even when I use one-click software, I make sure that I test it. 

You’ll learn things that you probably didn’t know about your application. It might even make you a better administrator, to be honest. Most of us don’t dig into certain parts of the configuration very often. We’re creating new projects for people when they request it, we’re managing customizations, but there’s a lot of areas to consider that you don’t go to on a day to day basis. You want to have a plan so you don’t forget about that stuff.

Emily:  There’s kind of something passive about the idea of a click and it’s done type of thing. With migrations, especially dealing with such important stuff like data and users and customers, you really want to make sure that you have your hands on all of it. Being able to really dig in and do that is important, to be able to touch all points. Then you can see if anything happens.

Rachel:  Yes. It’s also important to know what changes will be made, because there is a little bit of data translation going on here. 

I’ll use a very simple example. The priorities in Jira Server used to be, I don’t remember, to be honest, but in Cloud these days it’s different wording. It’s highest, high, medium, lowest. That was not the default when I started working with Jira Server. Of course, we made customizations, so I had extras. Critical blocker and somebody else can answer, I don’t remember what the others are.

The point is if they’re not exactly the same, the values on both applications, you’re going to need to do something, you’re going to need to handle that. You want to retain that data, but that data might look different, so there are implications there. There are implications for when you’re testing the environment to make sure that mapping and translation was done as desired. 

Then, of course, your users are going to come in the next day and have different values. Priority is such a small example, but extrapolate that out to all the things that Jira does, and it’s potentially a lot to consider. 

Emily:  Right. That makes a lot of sense, and it flows in great with what we’re talking about. How can you manage risk during the migration process? We talked about planning, we talked about the importance of prep, and some of the misconceptions. How do you manage the risk that is potentially inevitable?

Rachel:  First, just realize that there are risks and understand what they are. They’re going to be a little bit different for every organization. 

For me, the very worst thing is downtime, or unplanned downtime, or interruption of people’s ability to do their work. What is an acceptable amount of downtime at your organization? When can you plan this execution so it’s a time that most people aren’t relying on the system? That’s certainly something that’s smart to do when planning.

I always like to focus on security. You want to make sure that what people could access before is the same as what they can access now, and definitely more by mistake. 

Of course, use tools and get help. You are not alone in this. So many of us are doing the same thing, and we’ll continue to do this over the years for all of the software. You don’t need to reinvent the wheel. There’s lots of expert information out there available. Don’t go it yourself.

Emily:  That makes a lot of sense. There are a lot of solution partners, a lot of people who are there to answer your questions and help get you through it. 

Do you have a couple of apps that you think are really helpful in mitigating risk or even just enhancing the migration process to make it a little easier for people?

Rachel:  Absolutely. I think the first thing you can do is to clean up what you have so the scope of your migration is much smaller. That just makes it easier. Also, why migrate broken stuff or old strategies, or rust sometimes they call it? Tools that help you clean up that information to find out where things are used and which things can maybe be left behind or removed are super helpful. 

I encourage everybody to do absolutely everything you can to clean it up before you move. Cleaning up after rarely happens because there are new priorities. It’s much harder to do afterward. You might even have a little bit of clean up afterward because of the migration. Do it up front as much as you can. 

Emily:  That makes a lot of sense. Great. Thank you so much, Rachel. This has been super informative. I’m sure a lot of people feel much more at ease hearing some of this advice about their planning and preparation of any migration that they are going to find themselves in. I just want to thank you for joining us.

This has been Appfire Presents The Best Work Management Show by Appfire. Follow the link below to get Appfire’s newest workbook and watch more episodes of The Best Work Management Show at Thanks again for tuning in. We’ll see you next time.

Last updated: 2023-03-21

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