How to Ask Better Questions in Customer Advisory Board Meetings
The questions we ask in advisory board meetings shape not just what executives answer, but what they feel safe enough to say. Rene Almeling’s recent article, The Power of Asking ‘How?’ got us thinking about the questions we encounter daily in advisory board meeting facilitation, and why the distinction between ‘how’ and ‘why’ matters more than it might seem.
Dr. Almeling offers a deceptively simple yet powerful insight: when exploring human behavior and complex organizational challenges, asking ‘how’ rather than ‘why’ unlocks richer, more actionable understanding. While ‘why’ questions tend to elicit singular, rationalized answers that can shut down exploration, ‘how’ questions invite storytelling that reveals the interplay of individual decisions, organizational dynamics, and broader market forces.
“It’s a simple switch of one three-letter word for another when you ask a question, and yet it produces a powerful shift in thinking.”
Why the Shift from 'Why' to 'How' Matters for Advisory Boards
We’ve written before about why structuring advisory board sessions around questions beats structuring around topics. The grammar of your questions shapes what executives feel safe sharing.
Facilitators leading executive-level advisory discussions are trying to uncover the hidden processes, relationships, and leverage points that shape complex, strategic decision-making at the highest levels.
This is the very sort of complexity that Dr. Almeling argues is better explored via storytelling (how) than explanation (why). If ‘why’ triggers defensiveness, we may inadvertently cut that exploration short.
It's worth noting: ‘how’ questions open things up, which is the goal — but that also means more facilitation work. Richer answers can require more active synthesis and more skill in redirecting. Crafting ‘how’ questions isn’t a shortcut; it’s a practice.
Reminder: Focus First on Question Discovery, Not Just Phrasing
Even a beautifully phrased ‘how’ lands hollow if you haven’t first clarified what you’re actually trying to learn or test.
In our Executive's Guide to Customer Advisory Board Discussions, we walk through the prep work: starting with two foundational questions — What are we facing? and How can the board help? — to get clarity on your hypothesis before you ever phrase a question.
The question reframes in this post only work once you've done that discovery. That’s the foundation. What follows assumes you have that groundwork in place — and shows what opens up when you do.
Many discussion leaders or facilitators skip that prep work, which is exactly why well-intentioned and beautifully worded questions can still fall flat. When you know what you’re trying to surface, reframing from ‘why’ to ‘how’ follows naturally. The examples below show what that shift can look like in real CAB conversations.
Reframing the Questions that Drive Your Advisory Board Meeting
At Farland Group, we’ve found that structuring executive advisory board meeting conversations around 'how' questions transforms the quality of insights we gather.
Here are some examples of questions advisory boards might explore, and how you can rephrase them.
| FROM "WHY..." | TO "HOW..." |
|---|---|
| Why is digital transformation a priority? | How did digital transformation emerge as a strategic imperative? How have you been navigating competing priorities and stakeholder alignment? |
| Why are you concerned about talent retention? | How has your leadership team been approaching workforce challenges over the past year? How have market shifts influenced your strategy? |
| Why are you investing in AI? | How is your leadership team prioritizing its AI initiatives? How are you approaching those that are genuinely strategic vs. those driven by competitive pressure or board expectations? |
| Why is AI governance a concern? | How are you building accountability structures around AI decision-making? How are those conversations landing with your board and teams? |
| Why are you rethinking your operating model? | How have macro pressures — inflation, geopolitical disruption, shifting capital markets — changed the conversations in your organization? How are you translating that into decisions on the ground? |
Well-Framed Questions Leave Room for Uncertainty & Nuance
These reframed questions do more than extract information—they create space for your executives to reflect on the messy reality of their decision-making processes, including the influential relationships, unexpected obstacles, and organizational dynamics that don’t appear in polished board presentations. Understanding these social processes helps us design better strategies, craft more resonant messaging, and identify new partnership opportunities.
This approach not only yields deeper insights but also creates psychological safety — allowing senior leaders to share authentic experiences rather than rehearsed talking points.
“Psychological safety is not about being nice; it’s about giving candid feedback, openly admitting mistakes, and learning from each other. ”
Dr. Edmondson’s distinction on psychological safety applies to these question makeovers: A switch from 'why' to 'how' isn't about softening the conversation — it's about opening it up. The questions that produce the richest exchange rarely demand a verdict; they invite candid perspective sharing.
Questions that Put Executives on the Stand vs. In the Room Where it Happened
When we embrace the complexity that ‘how’ questions reveal, we move beyond surface-level feedback to reveal the multi-layered factors that drive executive behavior and create opportunities for peer learning and genuine strategic exchange.
Asking ‘why’ puts executives on the stand, where asking ‘how’ puts them in the room. While executives are skilled at producing crisp rationales for why they made a decision, polished isn't the same as real or complete.
“Why did you prioritize AI investment?” invites a typical boardroom answer, whereas a simple reframing of, “How has your leadership team been working through the AI investment question?” invites an actual conversation.
What we’ve found is that ‘how’ questions assume process, not just conclusion; they signal you’re interested in the journey including the competing disruptions, false starts, and pivots, not just the outcome. Asking ‘how’ questions also signal curiosity over judgment. In a CAB setting, that peer dynamic amplifies this. It allows executives to say, “We’re still figuring this out”, which is often where the most useful insight lives.
A Shift Worth Practicing, but Not Dictating
Dr. Almeling’s observations about one three-letter word producing a powerful shift in thinking holds up in the customer advisory board meeting room. A simple reframing won’t change what you’re trying to learn, but it can change what executives feel safe enough to share. And in a CAB setting, where the value lives in candid peer exchange, that openness is exactly the point.
That said, CAB meetings are live (and hopefully lively) conversations, subject to twists, turns, and plenty of improvisation. Edgar Schein's baseline concept of humble inquiry is worth keeping in mind.
“[Humble inquiry] is the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in the other person.”
I suspect Dr. Schein would remind us that what matters most is the genuine curiosity behind the question, not its grammatical construction. A ‘why’ asked with real openness — what Dr. Schein would describe as “asking rather than telling” — can do similar work.
Don't let careful scripting get in the way of genuine interest. For executives, whose instinct is often to perform certainty, 'how' tends to signal that curiosity reliably. The shift from ‘why’ to ‘how’ we're describing isn't a rule; it's a default worth practicing.
The preparation matters. The framing matters. And when both are in place, the conversation tends to take care of itself. It’s worth trying in your next session. Notice what changes when executives stop defending decisions and start describing them.