Ask questions like a support analyst

At Esri Canada’s Customer Support, we solve problems with asking questions. In this blog, we'll share the types of questions we ask to understand an issue, identify potential causes, and guide investigations. These same techniques can help you troubleshoot your own challenges and maybe even earn a reputation as the go-to problem solver on your team.

Ever feel like your support case has turned into a game of twenty questions? While it might seem that way, every question serves a purpose. Our Customer Support analysts learn to approach problems methodically, gathering clues about the software, data, environment, workflow and users involved. The more complete the picture, the faster we can narrow in on the root cause.

In this blog, we will share with you the type of questions we ask to help our customers resolve their cases. You can use these types of questions to help resolve your own cases or even be the troubleshooting star in your organization by assisting your colleagues. 
If you are looking for tips on how to resolve your Customer Support case quickly, I highly recommend reading 8 ways to more quickly resolve your technical support case. 

The problem with "It's not working" 

We’ve all had someone approach us and say something vague along the lines of: 

• “I can’t get this to work”
• "Publishing isn't working."
• "The application is slow."
• "I got an error."
• “It crashed” 
  

I can almost hear the collective eye roll as you think back to these familiar, yet frustratingly ambiguous statements. These types of questions have little context and now we must start investigative questioning.  

1. Start with the software 

Before investigating an issue, it's important to understand the software involved. 
Some useful questions include: 

• What product is being used?
• What version is installed?
• Are there any extensions, add-ins or custom tools involved?
• What error message is being returned?
• Have the log files been reviewed? 
  

These questions establish the technical foundation needed for further investigation. A known issue in one version may not exist in another and customizations can introduce variables that aren't immediately obvious.  

2. Understand the data 

Data is often a contributing factor, especially when a workflow works successfully for one dataset but fails for another. 

Consider asking: 

• Where did the data come from?
• Can the issue be reproduced using sample data?
• Are there special characters in field names or values? 
• How complex is the dataset?
• Is this data the output of another workflow? 

These questions help determine whether the problem originates from the software itself or from the information being processed.  

3. Examine the environment 

Technology rarely operates in isolation. 

A GIS workflow may depend on: 

• Operating systems
• Servers
• Databases
• Cloud resources
• Firewalls
• Security software
• Available hardware resources 
  

Questions worth asking include:

• What operating system is being used?
• Is there sufficient memory and disk space?
• Is the software running locally, virtually or in the cloud?
• Could antivirus or firewall rules interfere?
• Are there any relevant architecture diagrams available? 
  

Sometimes an issue that appears to be software-related is caused by environmental factors such as resource constraints or network communication issues.  

4. Focus on the workflow

One of the most powerful troubleshooting questions is:

"What are you ultimately trying to accomplish?" 

Understanding the goal can be just as important as understanding the problem. 

Additional questions may include: 

• What steps are being performed?
• When does the issue occur?
• Has this workflow ever worked successfully?
• Where did the workflow originate?
• Is there an alternative way to achieve the same result? 
  

Sometimes the solution isn't fixing the workflow. Sometimes it's identifying a better workflow that achieves the same business objective.  

5. Don't forget about the users 

Technical problems don't always affect everyone equally. 
Questions about users often reveal valuable clues: 

• Does the issue affect one user or multiple users?
• What permissions have been assigned?
• Are users authenticated differently?
• Does the issue occur on another workstation or network?
• Are there organizational policies affecting access? 
  

If only one person is impacted, the investigation may focus on permissions, profiles or workstation settings. If everyone is affected, the issue is more likely related to configuration or infrastructure.  

The clues are usually in the logs 

Good troubleshooting isn't just about asking questions. It's also about gathering evidence. Logs can often provide the context needed to understand why an issue is occurring. 

Useful sources include: 

• Application logs
• Operating system event logs
• Error messages
• Screenshots
• Diagnostic reports 
  

Providing this information early can significantly reduce the time spent gathering details and allow more time to focus on finding a solution.  

The most important question of all 

If I had to pick one question that consistently leads to answers, it would be: 

“What changed?” 

Changes might include: 

• Software upgrades
• Security updates
• New hardware
• Configuration modifications 
  
• Data updates 
  
• Permission changes 
  

Understanding what changed provides valuable context and often points directly toward the root cause.  

Final thoughts 

The next time you're faced with a technical issue, resist the temptation to expect an obvious quick fix. Complex problems often require a deeper look before the right solution becomes clear. Instead, take a step back and focus on understanding the problem first. By asking thoughtful questions about the software, data, environment, workflow and users involved, you'll gather the context needed to troubleshoot more effectively. The best troubleshooters aren't the people with all the answers. They're the people who know which questions to ask.

If you're still in a troubleshooting rut, our Customer Support team is always here to help. Share what you've learned, what you've tested and any clues you've uncovered along the way. A second set of eyes can often spot something you've overlooked or help connect the dots.