There are many different techniques used for user research. But when it comes to value over effort, there's few as effective as simply sitting down with your users and talking with them.
Research is often made out out be a big, expensive endeavor. But it doesn't have to be. It can be as simple as getting a bunch of $10 Starbucks gift cards and asking people for 20 minutes of their time.
On many of the projects I work on, I try to make it a point to spend some time talking to users in addition to other research techniques being used. And when possible, I bring along a member of the team that's actively involved in the project so they can see for themselves, often for the first time, how real people use their software.
If you've ever tried interviewing people, you'd find it's not always easy. Even people that enjoy talking with strangers can sometimes walk away from an interview having little to show for it.
So without further introduction, here's a few ways you can get more out of conversations with your users.
Figure out what you want to learn
Before you begin, take some time to ask what you would like to get out of the conversation. Are you trying to learn how they use your software? How they make purchasing decisions? How a new feature is being used or why it's not being used? Decide on the most important things you'd like to figure out and write them on the top of your notes for reference. Knowing beforehand what you want to get out of the conversation helps with guiding the conversation and making sure you get the most out of it.
Figuring out what you want to learn not only helps with guiding the conversation, but also who you should be having conversations with. If you want to make your software more enticing for people to subscribe, talk to whoever makes the purchasing decisions, not the employee who uses it to track their projects. If you want to know what features are most important, talk to the employees that use it, not the manager who got it for them.
Start with an overview question
Starting with an overview question is a great way to kick off the conversation and help the interviewee feel more comfortable talking. Asking the interviewee about their typical workday is a good place to start because it can clear up assumptions you might have had about their role and gives you plenty of topics you can dive into next or come back to later.
Don't do: "How do you use our software?"
Instead: "Tell me about your typical workday."
Treat it like a conversation, not a survey
One of the best parts of talking with your users is not having to hold to a predetermined script. Although it can sometimes be comforting knowing what you're going to say next, oftentimes there's a lot of great insights that are missed because you wouldn't have thought to ask. Allow the conversation to flow and gently reign it in when it's clear it's going off topic. There's been several times I've had a conversation go on longer than I thought would be useful, only to have the person share something that became pivotal later in the project.
Don't do: Interviewer: "Question #12: On a scale of 1-5, how satisfied are you with X?"
Instead: Interviewer: "That's interesting. Tell me more about that."
Avoid leading questions
Asking someone if they would like a potential new feature will often result in a yes. Not necessarily because it's sorely missed in your software, but because humans are social and we'll more often say we agree, even when we don't. Not only that, but we're really bad at predicting our own behavior. So better for you to ask what they currently do, and figure out whether adding that feature would be of value than to ask them to predict it themselves.
Don't do: "Would you find this feature useful?"
Instead: "What features are important to you?"
Don't do: Interviewer: "Would you use this feature if it was added?" Interviewee: "Uh, yeah I think so." Interviewer: "Nice! I had no idea so many people wanted bagel toasting in their financial software."
Instead: Interviewer: "Is there anything you think is missing?" Interviewee: "Yeah, now that you mention it, I wish there was a way to do X, it would really save me a lot of time."
Have them show you
Often having users show you how they use software can be much more informative than talking about it. If you have the opportunity to sit down in person, ask if they could show you how they use your software.
When people learn how to use software, they often stop learning just after they've mastered the basics. Sometimes the solutions they came up with while learning are very indirect and unexpected. Observing users will reveal the seemingly odd ways they use your software and could reveal opportunities for improvement.
I once asked a user how they log in to the software I was researching. I watched in horror as they opened Internet Explorer, entered "google" into the Bing search bar, searched, clicked on the first result for google.com, entered "[software name] sign in" in the Google search bar, searched, and clicked on the first result to finally get to the sign in page. I nearly bit my finger off.
Extra Tip: When someone is showing you how they use your software, fight the urge to correct them. How they use it can often be indicators to ways you can improve your learning process, simplify flow, or clarify copy. If you have to correct them, wait until after the interview is over to show them a different way.
Listen for problems, not solutions
People will often frame their feedback in the form of what they think you should do, rather than the actual problem they have.
Instead, try to understand why they're making the suggestions they're making. Ask for clarification why they think that would be helpful. Sometimes it can be difficult for people who aren't familiar with software to articulate what they would like it to do so they make suggestions based on what they've seen elsewhere.
Ask what they would like to accomplish after using your software
This is probably the best shortcut to figuring out what you should be focusing on with your software. By asking what users would like to accomplish as a result of your software, you can start to understand the motivation of why they use your software.
Closing and Further Reading
Interviewing people is a skill. When you first start out, it may take a few interviews for you to keep the conversation flowing or know what you should be listening for.
If you're interested in reading more about successful interviewing, I recommend reading Learning From Strangers by Robert S. Weiss. It contains a lot a great information about preparing for an interview, how to keep the conversation on track, and how to interpret data afterward.