Nonprofit talent development host shares 10 questions strategic learning leaders ask when they start a project

In this episode of Learning for Good, I share 10 questions strategic learning leaders can ask to move beyond content creation and into real organizational impact, using learning and development strategies rooted in behavior change and performance.

Most nonprofit L&D professionals know that training alone does not create change. But without the right questions, it is easy to build solutions that miss the mark, overlook the real barriers, or fail to connect to organizational strategy. The gap between a training that checks a box and one that actually shifts behavior often comes down to what you asked, and what you did not.

▶️ Key Points:

00:00 Why the Best L&D Tool You Have Is a Question

04:07 10 Questions Strategic Learning Leaders Ask

12:29 Why Questions Alone Are Not Enough

Why Questions Matter More than Answers in Learning and Development

Before we get into the list of questions you can ask, I want to share my thoughts around this episode: one of the most strategic things you can do in a stakeholder conversation isn’t to have all the answers. It’s to ask the right questions.

Being strategic in L&D doesn’t mean having a polished solution ready before the meeting ends. It means slowing down long enough to understand what’s actually going on. We have to uncover the real problem, the real barriers, and the real vision of success. When we do that, what we build actually works. We create change. We create impact. And as strategic L&D leaders, we get invited back to the table again and again.

The questions I share on episode 192 of the Learning for Good podcast are tools for exactly that.

10 Questions Strategic Learning Leaders Ask

So what are the questions we should ask as learning leaders? I’m sharing 10 today. Think of these like a menu. You may not need all of them, depending on what your stakeholders approach you with. And think of them like a living document as well. There are other questions you might need to add to your “menu” for specific projects or stakeholders.

Training Solves a Problem

What problem are we trying to solve?

This is the foundation. When someone approaches you with a training request, your first job is not to figure out what format to use or how long it should be. It’s to understand the underlying pain point.

What’s not working? What’s the sticking point? What outcome are they hoping a training will create? Getting clear on the problem before you design anything is what separates a reactive order-taker from a trusted strategic partner.

Training Changes Behavior

What behavior needs to change?

A lot of training requests come wrapped in knowledge. Stakeholders say things like: “they need to know the policy,” “they need to understand the process.” But knowledge transfer alone rarely creates change. What needs to actually shift in how people show up, what they do, or how they make decisions?

Focusing on behavior gets you closer to designing for real change.

Strategic Learning Designers Diagnose the Root Cause

Why is this happening (or not happening)?

This is where you start diagnosing the root cause. Is the behavior missing because people don’t know what to do? Because they lack confidence? Because the systems around them don’t support it? Because their manager doesn’t reinforce it?

There’s a big difference between a skills gap and a systems problem. Understanding why something is or isn’t happening tells you what kind of solution will actually move the needle.

Strategic Learning Designers Understand the Environment

What barriers exist?

Even the best training can fail if the environment around it doesn’t support the change. This question helps you surface what’s working against you before you invest in building a solution.

Are there managers who will undermine the message? Processes that make the new behavior harder than the old one? Cultural norms that haven’t shifted? Naming these barriers early means you can either address them directly or build them into your design.

Learning and Behavior Change Require Motivation

What would motivate someone to do this?

Motivation is often the missing piece in L&D design. You can give someone the knowledge and the skill, but if there’s no reason to change—no clear benefit, no built-in reinforcement—the behavior won’t stick.

Think about what drives the specific audience you’re designing for. What would make this feel worthwhile to them? What does success look like from their perspective, not just the organization’s?

Nonprofit Stakeholders Agree on a Picture of Success

What does success look like?

This question does double duty. It helps align everyone involved to a shared picture of what you’'re working toward, and it gives you a benchmark for measurement later.

Try pushing it further: What does success sound like? What does it feel like?

Example: A manager who’s truly improved their communication skills sounds like someone who’s coaching, asking questions, and giving feedback in real time.

The more vivid and specific you can make that picture together, the more focused your design becomes.

Learning Strategy Aligns to Organizational Strategy

How does this connect to organizational strategy?

This one is non-negotiable if you want to be taken seriously as a strategic partner.

Manager communication skills are worth developing. But why now? Is there a retention problem tied to poor management? Is the organization scaling and managers are struggling to lead at a new level? Is there a strategic priority around culture change?

Connecting the learning initiative to the broader strategy doesn’t just give you context, it gives your work credibility. It also sets you up to measure impact in a way that leadership actually cares about.

Strategic Learning Leaders Identify Key Stakeholders

Who needs to be involved?

Here’s a reality that every L&D professional has run into: the stakeholder you didn’t know about until the final review cycle…the one who appears at the last minute with a list of changes that throw off your timeline and your design.

This question helps you surface those secret stakeholders before they surface themselves. Think beyond the obvious—who needs to approve it, who has input, who is being designed for, and who supervises or influences the people you’re designing for. Getting everyone into the room early is how you protect the integrity of the project and your timeline.

Strategic Learning Leaders Consider Available Resources

What support is needed and available?

Consider this from two angles.

First, project support: Do you have the resources, access, and bandwidth to build this well? If not, what needs to shift?

Second, learner support: What does the person going through this training need to actually apply what they’ve learned when they get back to their desk? Peer accountability? Manager check-ins? Job aids? Practice opportunities?

The support question is where good design starts to bridge into sustained change.

Workplace Behavior Change Must Be Sustainable

How will we sustain the change?

Change doesn’t happen in a single learning event. People return to the same environment, the same team, the same pressures, and without intentional reinforcement, even the best training fades.

This question puts you in the role of a true change architect, not just a content creator. What mechanisms will be in place to remind, reinforce, and support the behavior over time? How do you help people build the habit, not just acquire the knowledge?

The Mindset Shift for Nonprofit Learning Leaders

Being strategic requires more than a set of questions. You could take this list into your next stakeholder meeting and still not feel like a strategic partner.

That’s not because the questions don’t work. It’s because strategy is more than a set of tools. It’s a mindset shift—from seeing yourself as someone who executes requests to someone who shapes outcomes. From waiting to be brought in to bringing yourself to the table. From tracking completions to tracking change.

The 10 questions above are part of how you make that shift visible to the people around you. When you slow a conversation down, ask the harder questions, and push toward a shared definition of success, you’re not just being thorough. You’re modeling what strategic partnership looks like in action.

To learn more about these 10 questions, tune into episode 192 of the Learning for Good podcast.

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