Learning Jira Cloud

My new Learning Jira Cloud course is coming soon! Complete the form below to get notified when it’s available.

By learning Jira you’ll be able to easily manage your own daily tasks and help your organization plan their strategic initiatives. In this course, you’ll learn all about navigating Jira, working with projects and issues, and creating filters, dashboards, and boards.  I’ll show you everything you need to know so you can get started right away.

Notify Me
Enter your email address and we'll notify you when there are book updates, new materials, training opportunities, etc.

Easily Deliver Company-wide Atlassian Product Training

What is your Atlassian product training strategy? You know you need to train your Jira, Jira Service Desk and Confluence users, but organizing training can be daunting and finding a time that works for everyone’s busy schedule is a challenge. How will you educate everyone, encourage adoption, and deliver information on a continual basis? How will you train new users when they join the organization? Training could easily turn into a full time job for application admins and burden an already busy training department.

Many companies either don’t have product-specific training or want training but can’t implement it. Others gather everyone in a room for a marathon training session that doesn’t provide an optimal learning experience. The content is not tailored to different user roles and everyone forgets what the instructor said by the end of the day.  Employees who missed the “training day” don’t get the help they need and new hires won’t get a training opportunity for a long time.

When users don’t understand the software, or when admins don’t have enough experience, the applications won’t work as well as they should. As a result companies spend time and money cleaning up the mess caused by prior mistakes. I saw this first hand. With no training, I became an application administrator! I built things badly and eventually realized I’d copied the mistakes of others and added to the overall mess.

Let Us Handle Your Training

We know training departments don’t always have the time or expertise to create product-specific training. We do and we’re good at it. Let us deliver company-wide training though our efficient, 30-minute, online, skill or topic-based courses.

Our courses are self-paced and include video lessons, homework, and a quiz to test and reinforce understanding.  There’s even a course certificate for your employee’s portfolio or resume!  Users self-enroll and leadership can view enrollment, progress, and completion at any time.

Please complete the form or share it with your training coordinator so we can recommend courses, presentations, and materials.

How can we help with your training needs?

Role Based Jira, Jira Service Desk, and Confluence Training Strategy

When considering your Atlassian product training strategy, select content that’s specific to each user’s role and delivered in manageable pieces. Different types of users need different information, different levels of detail, and need it delivered at different times. It’s tempting to gather everyone in a big room for a marathon training class. But it’s much smarter to offer role-specific information in small, digestible, and progressive pieces.

Progressive, Role-based Training

Intro to Jira Cloud Agenda

In the beginning, a brand new user just needs to know the basics.  Answer questions like:  “What is this application?”, “How do I use it?”, and “How do I access it?” Take a look at the agenda in our 30 minute “Intro to Jira Cloud” online course, for example. It’s short and specifically designed not to overwhelm new users. The goal is to get them feeling comfortable in the application immediately. Consider that some employees may have used Atlassian applications before. Their previous experience, version, use, and expectations could differ from what’s expected in your organization.

As part of initial training, give new users a simple homework assignment. Here’s an example: (1) to log into the application, (2) bookmark it in the browser, and (3) create a Jira issue, a Confluence page, or a Jira Service Desk request. You can test whether their creation meets the needs of the organization. This is a great time to catch problems before they turn into bad habits. Look for future trouble like missing an important issue field, creating a page in the wrong global space, or providing vague request details.

Once the user understands the basics start adding additional content. Select new content based on user role, how they’ll use the software, and skills they’ll need to do their regular job. Time the content delivery so they can learn little by little without impacting their other work.

User Types and Roles

Here are some additional user types and content recommendations:

  • The regular or occasional user needs info about sharing and organizing their data, creating filter subscriptions, linking, and logging time.
  • The power user wants information about basic & advanced search, JQL, and bulk changes.
  • Team leads, project managers, and scrum masters want to know about views like dashboards, boards, and reports.
  • Service Desk Agents want to understand service level agreements (SLAs) and how to use JSD features to support their customers.
  • Application admins want information about configuration, performance, effective workflows, best practices, mistakes, and certification.

Delivering information progressively, and based on roles, lets you quickly and effectively train users. They can put the info into practice immediately and won’t forget everything they learned by the end of the day.

Let Us Handle Your Training

We know admins don’t always have the time or expertise to train users. We do and we’re good at it. Let us deliver your company-wide training though our efficient, 30-minute, online, skill or topic-based courses.

Please complete the form, or share it with your training coordinator, so we can recommend courses, presentations, and materials.

How can we help with your training needs?

Training Your Jira, Jira Service Desk & Confluence Users

The job of an Atlassian administrator is never done. Your list of responsibilities is endless. You’re making sure your applications are up and running so work can get done. You’re weighing the benefits and long-term impacts of customization and add-on requests. You’re assisting users with access, permissions, and restrictions. You’re helping teams get the most out of the applications. And some of you are doing all of this while performing other tasks or managing other software. With all the demands on an Atlassian administrator, where does user training fall on your to do list? If you’re like most admins, it’s probably at the very bottom.

Continue reading “Training Your Jira, Jira Service Desk & Confluence Users”


We help companies of all types and sizes choose, set up, clean up, and maintain Atlassian applications.  Need help managing your Jira issues, Jira Service Desk support requests, Confluence content, or Crowd users?  Let’s chat!

Areas of Expertise

  • Choosing Atlassian products and deployment types
  • Strategy, setting standards, and governance
  • Onboarding users and teams
  • Set up and configuration
  • Maintenance, upgrades, and clean up
  • Choosing add-ons, integrations, and connections
  • Training end users, power users, and administrators
  • Designing and improving Jira workflows
  • Creating views with Jira filters, dashboards, and boards
  • Cleaning up Jira custom fields, issue types, and permissions
  • Optimizing Jira Service Desk request types and forms
  • Organizing Confluence content

Recent Projects

  • Helped a large health services company launch Jira, Jira Service Desk, and Confluence
  • Helped a mid-size IT company clean up and consolidate projects in their 1 million issue Jira application
  • Merged two 10-year-old Confluence server instances
  • Helped Atlassian’s Community Team use their own Jira product to combine multiple data sources and track their user group program
  • Worked with a team to improve their Jira workflows, planning, and prioritization process
  • Helped a non-profit transition from Google Docs and Spreadsheets to a community license of Confluence, Jira, and Crowd
  • Was a featured speaker at Atlassian Summit and 25 world-wide user groups

Have Atlassian questions?  Need help managing your applications?  Get help

About Rachel Wright

Rachel Speaking at Atlassian Summit

Rachel Wright is an entrepreneur, process engineer, and Atlassian Certified Jira Administrator.

She started using Jira and Confluence in 2011, became an administrator in 2013, and was certified in 2016.  She’s the author of the Jira Strategy Admin Workbook and a frequent speaker at Atlassian events, like the Summit annual user conference.

Rachel jokes that “Jira and I are in a long-term relationship and Confluence is a close friend.

Certified Expertise

Rachel Wright is an Atlassian certified Jira Administrator

Rachel Wright named “Teacher to Watch”

Skillshare, an online learning community for design, business, and tech has named Rachel Wright a “Teacher to Watch“!  This distinction is for instructors who consistently create high-quality content, continuously grow and innovate, and find new ways to further engage with students.

Rachel has created three courses for Jira administrators on workflow building, custom fields, and admin mistakes to avoid.  The 30 minute courses also include a quiz and sample project to complete.

She’s also created an introduction course for Jira users and one for Confluence users.  The intro courses help new users become comfortable with the software so they can get started creating issues and pages immediately.

Additional classes are on the way!  Have a topic request?  Add it in the “Comments” section below.

Take Rachel’s courses on Skillshare or at training.jirastrategy.com.   Need training for your entire team?  Contact info@jirastrategy.com.

9 Ways to Learn Jira Administration

I’m asked the same question all the time:  How do I learn more about Jira administration so I can be a great admin?  There are a ton of resources available;  you just have to know where to look, to seek them out, and be willing to put in a little time and effort.  Like anything in life, the more you put in, the more you get back.

Here are some ways to increase your Jira admin knowledge:

1. Seek out new opportunities
You’re never finished learning.  I’ve used Jira since 2011 and there’s still plenty I don’t know and new things to learn.   Every time I think I know it all, I humble myself very quickly by reviewing the unanswered questions on the Atlassian Community website.  Look for opportunities to strengthen your knowledge, or learn something new, by trying something new.


  • Pick an unanswered question, research the answer, and document the solution
  • Identify a problem Jira can solve and create a proof of concept
    • Example:  Who’s tracking information in email or spreadsheets?  Show them how to do it better in Jira.
  • Do a side by side comparison of changes between two versions
  • Install an add-on and learn everything you can about how it works
  • Get read only access to the database and learn how information is stored
  • Help a team adopt Jira or improve their processes
  • Set up Jira for a non-profit
  • Try to break Jira (Not in production, of course!)
  • Hold info share sessions and teach others how to solve common problems
  • Thoroughly document a feature
  • Use Jira in different ways
  • Download the Atlassian Plugin SDK and experiment with a plugin tutorial
  • Learn a related skill, like agile principles or server administration

Opportunities are everywhere.  The goal is to stretch your exposure and do different things then you’re already doing.  I’m no DBA but I learned a lot by experimenting with the database!

2. Install your own test environment
Even if your company already has an official test environment, I recommend you have your own personal one.  You need a place to experiment, play, and make mistakes, without impacting others.  It doesn’t have to be expensive or complex.  A $10 instance installed on an old laptop is sufficient.  You’ll stretch your skills and learn a lot by installing, using, maintaining, and upgrading it.

3. Join your local Atlassian User Group
Atlassian Users Groups are where users meet, learn, network, and share best practices.  Members are newbies and veterans who like to “talk shop” about Atlassian software, about Agile development, and about related business topics.  You can network with your peers, share solutions, meet Expert Partners, get special content from Atlassian, and enjoy a beer.  Find a user group near you (or start one) at:  aug.atlassian.com.

I’m an introvert and was new to Jira, but I took a deep breath and started a group.  It helped me learn new things, meet people, and become a contributor in the Atlassian community.

4. Read a book
There are a number of Jira books written by fellow administrators.  My book, the Jira Strategy Admin Workbook helps you set up, clean up, and maintain Jira.  It’s about strategy – not documentation and it’s not version specific.  Check it out and all the companion Jira offerings on Amazon.

5. Take an online training course
I’ve developed quick, 30 minute, online training courses for:  cleaning up custom fields, building workflows for business teams, admin mistakes, and other topics.  Take the courses and earn a certificate to add to your portfolio or resume at:  training.jirastrategy.com.

Atlassian also provides live online training, recorded training, and hands-on team training through Atlassian University.

6. Join the Atlassian Community
The Atlassian online Community is where you find answers, support, and inspiration from other users.  Join with your Atlassian ID at: community.atlassian.com.  Post your question or start a discussion.

There are also a plethora of Jira-themed support and networking groups.  Check out the Strategy for Jira® group on LinkedIn or Facebook.

7. Attend the user conference
Summit is the grand Atlassian event of the year.  With the palpable enthusiasm of the employees, the knowledge of the presenters, and the immense networking opportunities, this is the place to experience all that is Atlassian.  Add the next annual event to your calendar now.  Visit summit.atlassian.com for details.

8. Get certified
Taking an exam or extending your Atlassian Certification is a great way to show your existing skills and learn more through the study process.  I learned things I simply didn’t know and explored parts of the application I hadn’t touched in a while.  The certification experience made me a better Jira Administrator.  I learned so much valuable information earning the “Email in Jira” Skills Badge.

9. Read the documentation
Official product documentation is available at:  jirastrategy.com/link/official-docs.  The documentation includes information for end users and a guide specifically for administrators.  The documentation is categorized up by application type (e.g. Server or Cloud) and also by version.  Make sure you’re reading the correct version!

Watch “The Users’ Community: Your Hidden Treasure and Best Ally” from Fabian Lopez.  Originally given at Summit, this presentation includes all the ways to get involved in the Atlassian community and even specific users to follow!  Lots of fellow users continually post helpful tips, answers, and discussions.

What are other ways to learn more about Jira?  Add your ideas to the “Comments” section below.

Learn About Jira on Skillshare

Where can you learn about Jira, improve your coding skills, and grow your business all in one place?  At Skillshare!  Skillshare is an online learning community with thousands of classes on design, business, technology – and now, Jira!  It’s the Netflix of learning.

Rachel Wright teamed up with Skillshare to create “Jira Workflows for Business Teamsto help you build smart workflows that your business teams will actually use!

This course is available now to all Skillshare members!  Don’t have an account?  Sign up to enroll in Rachel’s class, access all the other classes, and receive a one-month free trial.

Five Steps to a Successful Jira Upgrade

For most Jira Server users, an upgrade is a major activity that requires careful planning.  What is your upgrade plan?  How will you prepare?  How will you ensure success?  How often will you upgrade?

I approach upgrades as five high level steps:

Step 1:  Research

Conduct all pre-upgrade “what changed” and compatibility research

This very important first step can determine the success of your upgrade.  Start by reviewing the retrospective from the last upgrade so you can improve the upgrade process and plan for issues encountered in the last event.   Also, it’s a good time to make sure your emergency rollback plan is still accurate.

Next, read all of Atlassian’s “Release Notes” and “Upgrade Notes” for every version between yours and the one you’re upgrading too.

Look for changes that might impact the application, users, or user behavior.  Look for bugs you’ve been waiting for fixes for.

Also read the Security Advisories, End of Support announcements, and End of Life policy.

Ask your REST API and database users to read the Atlassian documentation too, so they can prepare for any changes needed in their applications.

After, verify the compatibility of your hardware, operating system, database,  java version, add-ons, and any internally developed customizations.  Resources:  Jira Requirements, Supported Platforms, and Checking Add-On Compatibility

Finally, double-check that your license is valid through the upgrade testing period and you are not about to reach your license limit.   You don’t want license issues to delay your upgrade.

Step 2:  Pre-Upgrade Tasks (Test Environment)

Copy all production data to lower environments, update plugins, upgrade and test

Don’t have a test environment?  Remedy that issue first!  Ideally you’ll have a secondary server instance but if that’s not possible at least create a local instance on your personal computer.  Make sure the resources powering your test environment match your production environment as much as possible.  Make sure the software version and configuration are an exact copy of production.

Before upgrading your test environment, be sure to copy all of your production data to the environment.  It’s not enough to test an upgrade on a vanilla instance; you need to test it with your specific configuration data!

By now you should know which version you’re able to upgrade to.  Download the installer file, stop the application, and run the binary.  Document the installation process, so you can repeat the steps in production.  Review all configuration files, paths, custom files, and settings for accuracy.  Also check the logs for major problems.

If all is well on startup, it’s time to update the Universal Plugin Manager, other add-ons, and re-index.  After the re-index, start your regression testing.  Make sure all basic application functions and new features are working as expected.

During testing, I discovered one of my heavily used plugins wasn’t compatible with the upgrade version and had moved from free to paid.  I clicked the “Buy Now” button on the “Manage add-ons” page, assuming it would take me to a shopping cart with pricing information.  Instead, it immediately installed an unlicensed version of the new plugin code!  All of our workflows broke and I was inundated by reports of license errors from users.  I had to quickly generate a free trial code to restore functionality and sheepishly contact the purchasing department to secure emergency funding for the new plugin.  I did all this in production!  #facepalm

Finally, contact your REST API and database users so they can verify all is well with their applications.  Also, compile any “new features” documentation to share with end users.  Conduct an end user and project-level admin demo if UI or feature changes are substantial.

Step 3:  Upgrade Preparation

Line up support resources, schedule production upgrade activities, and announce plans

At this point, you are confident in the stability of your test environment and ready to schedule the production event.  Start by identifying an upgrade team.  Who will execute the upgrade?  Who will “smoke test” the major functions?  Who can you contact if there’s emergency?

After you have your team assembled, pick an upgrade time outside of peak use hours.  Communicate the upgrade date, time, and expected duration to users and any support teams, like the company help desk or network operations center.  Don’t surprise these teams with “Jira is down!” reports during the upgrade window!

Use Jira’s announcement banner function to communicate upgrade plans.

Sample Code:
<div style=”border: 1px solid #9e1c1c; background-color: #fff; padding: 10px;”>Upgrade Outage
The upgrade will start on [day], [date] at [time] [timezone] and conclude before the start of business on [day], [date].  During the upgrade window: (1) you WILL NOT be able to login to JIRA, (2) any changes attempted WILL NOT be retained, (3) API calls will fail, and (4) issue creation via email will fail.  For a list of new features and fixes, see our JIRA Upgrade notes.

Download sample wording for your entire upgrade process from the Strategy for Jira store.

Step 4:  Upgrade Tasks (Production)

Backup production data, update add-ons, upgrade and test

Hopefully you’re already taking regular (automated) backups of your database and file system.  But when’s the last time you verified that your most recent backup occurred and is actually usable?  Do that before proceeding.

At last, you’ve planned as much as possible, know what to expect, and are ready for the upgrade event!  It’s time to repeat the installation steps you practiced in your test environment including:  installation, add-on updates, and regression testing.  Use the notes you took in step 2 and be sure to address any differences that exist in the production environment.

Step 5:  Communication

Announce upgrade and communicate changes and benefits to user base

Finally, it’s time to announce the upgrade to users and complete post-upgrade steps.

Use Jira’s announcement banner function to communicate the upgrade is complete.  Include a link to the “new features” documentation you compiled in step 2.

Review any previous trouble reports, in case the upgrade remedied them, and be ready to respond to new reports.  Check in with your REST API and database users, to make sure all is well with their apps.

Finish any outstanding tasks, compile your retrospective, and make any needed plan updates in preparation for the next upgrade.  Also be sure to thank your upgrade team!

Detailed Upgrade Plan

Jira Detailed Upgrade Plan

A well-crafted plan can help ensure upgrade success.  Download the sample upgrade plan worksheet.  Customize it to fit your needs and environment.  This worksheet may contain more or fewer steps than necessary for your situation, but it gives you a great starting point.  Don’t forget to update and improve the plan after each upgrade.

A test instance and a healthy application are the foundation of a successful upgrade event.  You’ll want to upgrade often for the newest features, fixes, and performance improvements.  Happy upgrading!

“Jira Admin Mistakes” Now Online!

Did you hear about the company with 132 Jira Administrators?  How about the company plagued with 134 Issue Types?  Have you ever accidentally broken workflows and everyone’s filters?  Join Rachel Wright as she recounts the top 20 Jira admin mistakes she’s made and seen.  Hopefully you can avoid these mistakes and keep your application out of the Jira swamp!  Get started at: training.jirastrategy.com

Presentation Preview

This presentation is for Jira Administrators and is based on the mistakes and examples in the Jira Strategy Admin Workbook.  This presentation is self-paced so you can review the material you want, in the order that makes sense for you.

View the presentation!