Asking great questions

This is the second post in our 14-week journey through the 4 Questions and 10 Rules of Strategic Doing, first outlined in this October 2023 blog post. Each week, we’re unpacking one question or rule in more depth. If you haven’t yet read Rule #1: Create a Safe Space for Deep, Focused Conversations, you may want to start there; it lays the foundation for everything that follows.

Asking great questions is a skill that’s never asked about on a job interview, but can make an enormous difference in your ability to lead effectively (or follow, for that matter). You’ve probably observed it in action, and there are some people who just seem naturally gifted at it.

Good news! You don’t have to be born with the ability to ask great questions. You can develop it if you 1) know some of the secrets to powerful questions and 2) practice. In this post, we’ll unpack that first one. The second is, like all habits, on you.

What makes a question great? Three (maybe four) keys

Strong questions move a conversation forward. That might mean pushing the group to take action. In earlier stages of a group’s work, they might not yet be at the point of doing that, but they are open to thinking more creatively or expansively about their work. Either way, one characteristic of a really good question is that it’s framed positively – it doesn’t dwell on a problem; it focuses instead on an opportunity. David Cooperrider’s work on appreciative inquiry is foundational here; he says that “we move in the direction of our questions.” Questions that are problem-based tend to end up in a discussion (or argument) about the root causes of the issue. That might work and even be valuable for a single session, but over time it drags the group down. If your question starts with “why,” it probably fails the positivity test.

Great questions also paint a picture of a future that isn’t here yet (and, in keeping with the first point, it’s a desirable future). That usually means tapping into people’s deep desires and values, not just giving a fact that will be true. They also, as appropriate, are tailored to the sphere that you want a group to focus on. If you want a group to focus on community health, for example, leave out information about education (even though it’s true that education levels are often tied to health outcomes). Go for a long horizon to really inspire people – at least a few years out.

You should also go for short and punchy. Less is definitely more when it comes to powerful questions – resist the temptation to pack a lot in. Pick one aspect that will really resonate with the audience and lean into it. This is especially a pitfall for groups that are working off of a strategic plan: it’s easy to craft a question that’s something like, “What if by 2035 our organization was known as a group that did (strategic goal #1), (strategic goal #2), (strategic goal #3), (strategic goal #4), and (strategic goal #5)? Do you want to achieve those things? Of course. But that is not a question that will ever move a group. When you find yourself doing that, ask yourself about the bigger “why” that those goals were built on, and then craft your question around that. 25 words or less is a good goal – or to put it another way, no longer than you can remember without having to check your notes.

Finally, here’s a “maybe” guideline: consider perspective. You can often choose between a question that’s focused on the organization’s actions and one that’s focused on customers’/clients’/residents’ experience. The latter is often a stronger question than the former (it’s usually connected to that “why” for the organization’s existence). However, if part of what you’re trying to do is to reset culture within an organization, focus internally. Here the “why” becomes the internal motivation of the employees, not the “why” of the entire organization.

What about practice?

The fact is, most people are not born good at this skill. It takes practice. For me, improving how I worded questions was easy, but ridding myself of my often “glass half empty” habit of viewing the world took a lot longer (it’s still a work in progress!). Hundreds of questions later, I’m pretty skilled at it – although I’m still in awe of those for whom it’s instinctual. If you’ve got an important gathering coming up and don’t have enough time to build your skills, think about getting help from the Lab or the greater agile leadership community.

Some examples

Here are a few of the really good questions I’ve encountered:

• A group working on disaster recovery: Imagine that the next time our city is in the NY Times, is it because we’re known for the compassionate/rapid response way we handled this crisis?
• A Chamber of Commerce: Imagine that “the business of doing business” in our town was simple. What would that look like?
• A research lab: What would it look like to be a vibrant research community that unlocks potential for out-of-the-box ideas?

Want more? Attend a Strategic Doing practitioner training – you also get access to a large online resource library, including examples of questions.

Action step: what’s the next meeting or gathering you’re leading? Try crafting a strong question to get the group started. Bonus hint: work on the question with someone else; the synergy of working together usually makes for better questions.

Learn more: Strategic Doing: Ten Skills for Agile Leadership has a whole chapter on questions (and several members of the Lab team were co-authors).