How to Ask Better Training Questions

The time has come to once again to discuss the art of, “How to ask better training questions.”

(This post ran originally on my blog site for Litmos in January 2018. The content here has been updated.)

Picture this: 

Director of Well-Meaning Stuff enters your space with a training request. We want people to do “better”, and we want you to create training so the masses do “better”.

Cue: Head, Bang, Wall.

Been there done that, bought the t-shirt…

We’ve all been there, done that, created training programs that do not have a snowball’s chance in hell of being successful. We all know it’s not our fault, or theirs, but a combination. There are more than enough blaming fingers to go around for failed training.

The question at hand is, “How can we help the organization make better decisions that lead to stronger impact”?

Often, I’m presented with this question: How can I make the training sponsor understand their training is CRAP? My response: You can’t make them understand anything. You have greater odds of success by leading them to their own epiphany. This requires better upfront training questions.

Better questioning required!

This is key: Do we REALLY understand what problem the business is trying to solve? Does the business understand the real problem? Is the problem really a training issue?

Most times the simple answer is no. Most organizational problems cannot be solved by training alone. Training is part of a larger, more holistic solution. Participation in one training program does not change behaviors, and it’s only the beginning of improving skills.

Toward this end, before we agree to develop any training program – it’s time to ask some meaningful, relevant training questions. I have broken the types of questions into four groups:

  1. Understanding Context
  2. Understand the People
  3. Understand the Challenge around the Problem
  4. Understand the Results

Understand Context

Here’s an example: “For Christmas, Sally received a bracelet.”

What happens if we phrase the questions this way? “For Christmas, Sally received a bracelet from her dying grandmother.”

Now, we are intrigued. We want to know the story. What is the grandmother dying from? How much time does she have to spend with her family? Does the bracelet have a history? Having this context helps frame the remainder of the conversation.

When thinking about context, think these training questions:

  1. What root-cause problem are we trying to solve?
  2. How is this problem impacting business?
  3. Where is the problem happening?
  4. Who is involved?
  5. What is the situation around the problem?
  6. What is happening when the problem presents itself?
  7. Is this a training, process, procedure, cultural or management issue?

Understand the People

Typically, we think of the people who are participating in training as “learners”. What would happen if we thought of learners as simply humans? Humans who are having training targeted at them, for not necessarily the right reasons. Therefore, it’s imperative we target the right audience. The blanket approach to training simply does not work, it has NEVER worked. When you target everyone, no one learns.

Questions to ask about the humans who are potential participants: 

  1. Who is the exact target audience?
  2. Why does this training matter to the people?
  3. Where/How will they be expected to use any training resources on the job?
  4. Do they have the needed knowledge prerequisites to make this training successful?
  5. How will this training help this particular group of people do their jobs better, faster and more efficiently?


Understand the Challenge around the Problem

Many times we get a training request and we smile and nod, runoff and develop a solution. The issue is we not fully realize the scope of the problem and the effect the problem is having on the business. Do we know the barriers to success? Why isn’t good happening NOW?

Example: We need more sales training to improve sales. They aren’t making the budget.

That great – but the REAL question at hand is…why aren’t salespeople producing revenue according to the budget NOW? What are the REAL barriers to success? I guarantee it ain’t all training related.

Ask these questions to uncover the challenges: 

  1. What will good performance look like?
  2. Why aren’t people behaving the way we need them to behave or performing at the levels required? (lack of motivation, missing knowledge, missing skills)
  3. How will success manifest itself?
  4. What are the environmental issues surrounding the problem?
  5. What are the organizational issues that preventing success from happening?
  6. What is the process and procedure around the problem?

Know the Expected Results

Begin with the end in mind.

Know what success is supposed to look like BEFORE you start. Then understand the consequences of failure to the business. If you cannot get a straight answer here, do not proceed. You are setting yourself up for failure and the humans in your organization for frustration.

These questions will help guide you.

  1. What are the consequences if this problem isn’t solved?
  2. How do those consequences impact people?
  3. How do those consequences impact the business?
  4. Are the consequences big enough to warrant a training intervention?
  5. What are success indicators?
  6. What will be happening if training is successful?
  7. How will people start (or stop) behaving?
  8. What demonstrative skills will be observable?

What will success look like to the BUSINESS? Not as a learning objective, but as a business result?

Let’s wrap this up:

Write these four types of questions down. Put them somewhere you will see them. Better yet, somewhere other people can see them.

This is your credo, your manifesto…make a promise that you will strive to ask better questions. By asking better questions you will be a strong advocate for the humans in your organization. They need you to help them, and it starts with not forcing them to participate in training that doesn’t matter.

Just “say no” to training that doesn’t solve a problem. 

One thing to point out before I conclude: I’m not saying you need meet with leadership and present them with all the questions right now. Remember, you are trying to lead them to their own epiphany. Pick the high impact questions that will help you get the answers you need to produce the desired results.

Answers that will help you provide training that matters. 

I’d love to know what types of questions make your list? What best practices can you share with the Learning Rebel community? Share in the comment section below.


Learn more about how Learning Rebels can help you design the microlearning process to make your training stick!


Shannon Tipton

Shannon Tipton

As Owner of Learning Rebels, Shannon Tipton is a skilled learning strategist, content developer and International speaker. Shannon has over 20 years of leadership experience developing successful learning strategies and infrastructures for training departments within organizations in North America, Europe and Korea.

Shannon works with people and organizations to develop learning solutions that brings actual business results. Recognized as bringing real-world expertise into the learning field, Shannon integrates technologies and social learning tools to strengthen workplace alignment, enhance collaboration and increase learning connectivity.

As author of “Disruptive Learning” Shannon frequently speaking at conferences across North America and Europe and ranks as one of the top 100 L&D influencers on Twitter (@stipton).

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