A Practical Planning Lens for Leadership Development in 2026

Questions HR Leaders Should Be Asking

If you’re building your 2026 leadership development plan right now, you’re not alone. Many HR leaders are balancing engagement and retention concerns, rising expectations, and real capacity constraints.

The good news is you don’t need to predict everything that will happen next year. You can create momentum by refining your focus—asking better questions upfront before you commit budget, time, and energy.

The Questions HR Leaders Should Be Asking Right Now

Before you choose programs, speakers, or a calendar of offerings for 2026, it helps to start one level higher. Because what you’re really trying to design isn’t “more training.”

You’re designing better leadership habits, stronger teams, and more consistency in how work gets done. Think of these questions as a quick audit. They help you spot where your agenda may be overbuilt with content, or underbuilt for the real moments where leaders need support.

Where Is Leadership Strain Showing Up Most Right Now?

Not in theory. In your organization. Where are you seeing the most friction: burnout and overload, slower decisions, tension between teams, a drop in accountability, performance issues landing on HR’s desk, or trust starting to thin?

This question matters because strain is a signal. It tells you where leaders may need clearer expectations, stronger coaching habits, or better support navigating change—before the strain becomes turnover or disengagement.

What Do Leaders Need to Do Differently in the Next 6–12 Months?

This is where planning gets clearer. Instead of starting with a long list of competencies, ask: what behaviors would make the biggest difference if they became more consistent across leaders?

For example: coaching instead of rescuing, giving feedback sooner, making decisions with imperfect information, setting clearer priorities, or creating space for people to speak up early.

When you name the behavior shift, you get out of “program shopping” mode and into practical design. You’re no longer building for learning. You’re building for application.

Who Needs Development the Most—and What Kind?

Not everyone needs the same thing, and that’s okay. Some leaders need foundational support because they’re new to management. Others are experienced but stretched thin. Some teams need trust and alignment. Others need execution rhythms, faster decisions, or more effective collaboration across distance.

When development is segmented by role and leadership moment, it becomes easier for leaders to engage, easier for HR to reinforce, and more likely to translate into real change.

What Should Scale Across the Organization—and What Should Stay Targeted?

It’s tempting to push everything enterprise-wide, especially when time is limited.

But in many cases, the smartest move is to scale a few core behaviors broadly—then go deeper where the need is greatest.

That might look like consistent expectations for coaching and feedback across all managers, paired with targeted support for the leaders who translate strategy into action every day. (If that layer struggles, execution stalls—no matter how strong the strategy is.)

How Will You Reinforce Learning After the Session Ends?

This is one of the most important planning questions, and it’s often the one that gets skipped.

It’s not enough for leaders to agree with the content in the moment. They need support to apply it when they’re back in real life: conflict, hard conversations, performance issues, AI-related change, and tight deadlines.

Reinforcement can be simple, but it needs to be intentional: short follow-ups, peer accountability, practical tools, and check-ins that help leaders practice in real time—not just remember what they heard.

What Impact Do You Need to See by This Time Next Year?

You don’t need perfect metrics. But you do need clarity. When you know what success looks like, it’s easier to make trade-offs and tell a clear story internally about why you’re investing where you are.

That might be improved retention, stronger engagement, more ready-now leaders, stronger bench strength, or more consistent leadership behaviors that teams can actually feel.

The goal is to move from activity to impact—development that changes behavior and makes a measurable difference.

A Thoughtful Next Step for Your 2026 Plan

If you’re building your 2026 leadership development plan right now, you don’t need more noise. You need a clearer lens: A chance to step back, compare what you’re seeing internally with what research is showing across organizations, and refine your agenda in a way that creates momentum—without slipping into hustle or overbuilding your plan.

That’s exactly what we’ll explore in FlashPoint’s 2026 Trends Webinar: the trends shaping leadership development in 2026, FlashPoint’s “hot takes” on what organizations must do differently, and practical ideas you can use to evolve your agenda for the year ahead. If it would help to have that perspective as you plan, we’d love to have you join us.

This is Part 2 of our 2-part series on leadership development planning for 2026.
If you missed it, read Part 1: The 2026 Leadership Landscape and the Shifts HR Leaders Should Watch