Effective Questioning: Uncovering Root Causes

Here’s the truth: Stakeholders aren’t L&D pros, and they don’t think like we do. They’re focused on outcomes, fast fixes, and they probably see training as a straightforward solution. But effective L&D isn’t about checking boxes—it’s about solving real business problems.

The challenge? We can’t coach stakeholders to tell us what’s really going on, at least not directly. What we can do, though, is use a toolkit of open-ended questions that naturally reveal the truth. Over time, this process will subtly shift how stakeholders approach us with their needs (or perceived needs) —but don’t hold your breath for them to fully adopt an L&D mindset. It’s likely never to happen, and it’s really not their job. Instead, we need to lead with targeted questions that uncover the real need beneath the noise.

Tool 1: Frame Conversations Around Curiosity, Not Compliance

Start with open-ended questions that keep the conversation authentic and in their language.

Questions like:

“What’s happening in your team that brought us together today?”

“When you picture the end result, what are you hoping to see?”

Open-ended questions might seem a little loose and there’s a potential worry that the stakeholder might think that you’re not being specific, but they keep things informal and conversational while allowing them to expand on the context of the situation. They will, however, help you get more specific than you would have without using open-ended questions. Right from the start you will set the stage for uncovering the real need.

Tool 2: Lead with ‘Why’ Questions That Get to the Heart of It

Here’s where you move from information-gathering to unearthing real insights. Questions that start with “why” take the conversation from reactive to reflective:

“Why do you think this problem is coming up right now?”

“Why is this training a top priority for your team at this point?”

These types of questions guide the stakeholder away from “we need training now” and into “here’s the bigger picture”—and suddenly, you’re talking about factors beyond training that contribute to the issue at hand.

Tool 3: Follow Up for Clarity, -Every Single Time

Are you still getting somewhat vague answers? Push for more. Your job is to follow up and drill down. Not in a mean way, but your solution won’t be what it should without the right level of information. In the end they’ll thank you for your work.

The questions:

“Tell me more about the daily impact this has on your team.”

“If a change doesn’t happen, what’s the worst thing that could happen?”

Clarity here is critical. Stakeholders who can describe the impact help you understand the stakes, allowing you to build a solution that actually targets the core issue.

Think of This as a Long-Term Investment

Ok so this isn’t really a tool, per say. But here’s the best part: these open-ended questions don’t take much more time to ask, but they bring exponential benefits. When a stakeholder feels genuinely heard and understood, you build trust, plain and simple. They walk away from the conversation feeling like a partner in the solution—and the next time training opportunities come up, they’ll be more eager and open to work with you (and you specifically).

This isn’t about transforming their mindset into that of an L&D professional. It’s about making them allies in the analysis, one conversation at a time.

How to Get Real with Effective Questioning

Using these questioning tools isn’t about making stakeholders L&D experts; it’s about partnering with them to get to the core of the need. Here’s how to get real when applying these strategies:

Set the Stage with Context: 

Before you dive into questions, give a quick reality check on how the process works. Explain that your goal is to understand their true end-result and current challenges, not to “interrogate” or add extra steps. Let them know these questions are a way to ensure the training (or whatever solution is being discussed) actually meets their goals. This preps them to be open and honest, knowing you’re genuinely there to help, not to add complexity.

Avoid Jargon and Stay Conversational: 

Stakeholders might shut down if they feel like they’re being talked to in “L&D speak.” Drop any jargon and keep it natural. For example, instead of saying, “Let’s assess performance gaps,” try, “What’s making things tough for your team right now?” The more you sound like a partner, the more they’ll be willing to open up and share specifics.

Drill Down Without Overwhelming: 

Asking open-ended questions and following up for clarity is critical, but balance is key. When you feel you’re getting close to the root issue, resist the urge to ask “just one more thing” if it risks stalling the conversation. Know when to stop and take time to reflect on what you’ve learned so far. You can always return to unresolved points in a follow-up conversation.

Follow Up and Circle Back: 

Effective questioning is a long-term game. After your initial conversation, recap what you heard and any next steps to keep them engaged. Not only does this reinforce their commitment to the process, but it also shows that you’re paying attention to the details and making them a priority.

Be Ready to Share Your Value: 

If you sense a stakeholder’s hesitancy or doubt, remind them that this deeper dive is what sets L&D apart from simply delivering content. Tell them, “The more we understand what’s really happening, the more targeted—and valuable—the solution will be.” Sometimes, a little reassurance goes a long way in building the trust you need to get to the truth.

These steps aren’t about getting fancy with analysis; they’re about keeping it real so you can deliver results that matter. The more honest and straightforward you are, the more stakeholders will feel like true partners in the process, and that’s where the best results happen.