Senior association leadership often has high-level goals tied to professional development (board-driven or otherwise), and those expectations are not always clearly articulated. At times, they may also have missing pieces, such as market research or data to back up larger goals. Despite these gaps, PD professionals must ensure the output we produce aligns with broader strategic objectives. As we face these conversations with senior leadership in real time, the challenge isn’t just asking the right questions — it’s also about interpreting responses, positioning ourselves as thought leaders rather than order takers, and anticipating future roadblocks before they arise.

Reframing the Conversation: From Execution to Strategy

Too often, PD teams are seen as implementers rather than strategic contributors. Instead of waiting for leadership to define our role and our deliverables, we need to actively shape the conversation. This means going beyond “What do you want us to offer?” and instead asking, “What impact are we trying to create?”

When engaging in real-time conversations, consider leading with questions that uncover your underlying goals:

• What impact do you want our professional development programs to have over the next 12 to 18 months?
• What is the definition of success for this product/service in the first 12 to 18 months?
• What is the data to support this initiative/product/service? Do we need other data points to fully support the initiative and resource allocation?

These questions shift the conversation from tactics to strategy, helping leadership articulate expectations in terms of outcomes rather than just deliverables.

Real-Time Responsiveness: Navigating the Conversation

In live conversations, we won’t always have all the answers. The key is being adaptable while guiding leadership toward achievable, strategic outcomes. Here are a few techniques to keep the conversation productive:

• Clarify vague expectations by asking for specific goals: E.g., “When you say we need XYZ from this product/service, what does that look like in practice?”
• Reframe challenges as opportunities: For example, if there’s concern about declining attendance, position it as a chance to explore new delivery methods, new training partners, or audience segmentation.
• Propose quick wins to build momentum: If leadership is hesitant about major change, suggest pilot programs or repurposing existing or partner content that can demonstrate immediate value.

Anticipate and Communicate Future Hiccups

If there’s one major lesson that I’ve implemented over the last few years, it is to expect the target to shift without your input or to have massive changes to how things operate. These hiccups include training partnerships evaporating overnight, enrollments shrinking unexpectedly, or board strategy adjustments occurring behind closed doors. By being up front with your leadership from the start and identifying potential obstacles in the future, you may find creative ways to identify them now, rather than as they’re happening.

Asking questions in advance allows you to adapt your strategy for attacking the goals and communicating the deliverables to your teams, all with the “why” behind them, rather than having ambiguous reasons, at best, delivered from the top. Transparency and open communication create more successful projects and productive teams, while allowing for continued dialogue to align with your organization’s mission.