Mastering the Art of Asking Questions

Episode Transcript

Hello, everybody. Today, we are talking about something deceptively simple, something that every marketer does, but few of us master: asking really good questions. Now, in Agile marketing, we talk a lot about systems and ceremonies and work visualization and OKRs and experimentation. You're reducing waste and everything else that's in the Agile marketing operating system that we explore all throughout this show, but the glue that holds all of that together, the thing that keeps the operating system from silently rotting underneath us, is the quality of our questions.

Now, if you've listened to some recent episodes, you might have noticed a pattern. Teams struggle with psychological safety because no one asks the right clarifying questions that reveal hidden misalignment. AI pilots fail because leaders ask, "Where's the ROI?" instead of, "What do we need to learn first?" Scaling collapses because we never stop to ask, "Is this customization solving a real need, or is it protecting the status quo?" Waste accumulates because teams don't ask, "What problem is this asset solving?" before they build 27 versions of it. Dependencies blow up campaigns because nobody asked, "Who else needs to know about this?" before they started building it.

Questions shape culture. Culture shapes decisions. Decisions shape outcomes. So, today, we are going to explore five types of strategic questions, which I have taken from a recent HBR framework and mapped directly to the Agile marketing operating system, because if there is one skill that every Agile marketer needs right now, especially in the age of AI and volatility and constant change, it is how to ask the right question at the right moment. So let's get into it.

Welcome to The Agile Marketing Edge, the first podcast dedicated to turning Agile theory into real-world marketing breakthroughs. I'm Andrea Fryrear, CEO of Agile Sherpas and your guide on this climb to smarter, faster, outcome-driven marketing. Every week, we unpack the what, who, and how behind Agile marketing, from building high-velocity workflows and slashing waste to measuring what really matters and scaling success across teams. You'll hear quick-hit strategies that you can deploy today, plus candid stories from marketers who have traded chaos for clarity and never looked back. Hit Follow wherever you listen, and let's carve the next switchback together.

All right, so as I mentioned, the question types that we are talking about today come from The Art of Asking Smarter Questions from the Harvard Business Review. The article originally came out in May of 2024, if you wanna go and find it and read the original article itself. Now, that article outlined five types of questions, and we're gonna be going into those questions one by one and seeing where they fit in our Agile marketing operating system. So let's figure out what those types are first.

Up first, we have investigative questions. That's basically, what do we know? And we ask these questions when we're facing a problem or an opportunity, and the best decision-makers are gonna start by, of course, clarifying their purpose with these kinds of questions, asking themselves what they want to achieve and what they need to learn to do so.

Our second question type is speculative, and these are "what if" questions. They help us consider the situation at hand more broadly, reframing the problem and exploring more out-of-the-box solutions.

Our third question type is productive. These are "now what" type questions. These help us assess the availability of talent, capabilities, time, and all the other stuff that's ultimately available to help us determine the right course of action.

Fourth question type is interpretive. These are "so what" questions. They're kind of natural follow-up questions to help us continually refine and redefine a core issue. They're gonna help us go beneath the surface and draw out the implications of an observation or an idea.

Our fifth and final question type is subjective, or "what's unsaid." Now, this question is gonna deal with things like personal reservations, frustrations, tensions, and hidden agendas that could be pushing our decision-making off-course.

But knowing what kinds of questions are possible is a good starting point, but really, we're just at the beginning here. We also have to know when it's appropriate to use each type of question. So, our next step is to map these to the components of the Agile marketing operating system, so we have an actually complete toolkit of questions to pull from at the right time.

So let's start with our investigative questions. These are our what do we know questions, and these are great to use in the following parts of the operating system: planning, data, and customer centricity. These questions are gonna help us do things like clarify our purpose, eliminate ambiguity, and ground our decisions in reality instead of assumptions.

There are a lot of echoes of the Agile Manifesto in here, right? We are really staying close to those original values here, and Agile marketers are gonna get in a lot of trouble if we skip over this question type. So don't fall into the trap of thinking that this is too simple or that you can just breeze right past these questions. Remember back in episode 12, we talked about how traditional planning can basically be political theater because it is built on unchallenged assumptions and outdated information. Investigative questions are one way to stop that runaway train before it plows into the side of the mountain.

All right, so here's some examples of good and effective investigative questions. What problem are we actually trying to solve? Go and ask this to five people on your team, and you're gonna be amazed at how different their answers are. Another good question here is, what do we already know about customer behavior? Now this one you're gonna need to ask a lot these days because it is changing and changing fast. So keep this one at the ready all the time.

Next good investigative question is, what data don't we trust yet? Great follow-ups include: how might we make our data more trustworthy, what could we do with more accurate data, and what dangers are hiding in our less-than-accurate data? There are many, many meetings that need to happen around all of those conversations.

Last investigative question model here: what would success look like here, not sound like? Really try to get visceral and descriptive answers to this question. Try to get beyond KPIs and get people calling out as many senses as you can. We really know things in a lot of ways that are not just intellectual, so try to tap into those when you get people to answer that question.

And of course there are more investigative questions than these, but these are great starting points for things like backlog refining, scope tightening, and busting the assumptions that can derail your best laid plans. The reason they matter particularly for Agile marketing is they can help prevent waste before it happens. Remember that waste includes things like rework, handoffs, overproduction, delays, and underutilized talent. So if we're asking questions about work before it starts, that's one of the best ways to eliminate or at least cut down on all of these kinds of waste before they infiltrate your processes.

All right, second question type is speculative, so these are our what if questions. They play very nicely in the experiment, mindset, innovation, and people areas of the Agile marketing operating system. Speculative questions are where the creativity and courage of Agile teams really, really shines, because these kinds of questions let us explore possibilities, not just probabilities.

You definitely have a psychological safety problem that needs to be addressed before you start worrying about things like, when should we be asking these questions? Okay, back to the speculative questions. Here's why they really matter in the context of Agile marketing. It's because these kinds of questions help us create optionality, and that is crucial to agility. We need to know what our options are so that we can choose, and pivot, and react, and respond appropriately.

All right, question type number three is productive questions. This is where we ask, now what? And this connects to the Agile marketing operating system in the areas of things like capacity management, WIP limits, work visualization, and dependencies. And this is where we're gonna get into transforming our ideas into action. Now, if you remember back in episode eight when we covered the theory of constraints, we talked about how improving anywhere except the bottleneck is gonna make the whole system worse. Now, productive questions help us spot that bottleneck and elevate it before it buries the whole system.

These questions are gonna help us stay grounded in the reality of what our teams can actually do. So, here's some examples. Given our capacity and constraints, what's the next highest value thing that we might do? What can we stop doing to make this possible?

Okay, this one right here. If you don't do anything else from this episode, this is the question, this one right here. What can we stop doing to make this possible? Put it on a big giant piece of paper and put it behind your computer so you see it, and any time a big new ask comes in, ask this question. What can we stop doing to make this possible? Your new mantra, ask it all the time.

All right, next one. Who needs to collaborate with us to avoid downstream delays? Because marketing teams are deeply interconnected, so just because you can move fast does not mean that you fixed everything. Bring everybody on board sooner and everything goes smoother. How will this impact the system, not just our team? Remember our episode with Kamal Hans about the marketing campaign that was so successful that it crushed the fulfillment department? This question really, really matters.

And on a bigger level, why these kinds of questions matter in general is because without productive what now questions, marketing is basically like living inside a fantasy novel where we have lots of imagination and no plot coherence. Productive questions connect our amazing ambition to real tactical execution.

All right, our fourth question type is interpretive. These are our so what questions. We want to bring these out in the following areas of the Agile marketing operating system: reviews, retros, really any moment of continuous improvement opportunities, and times we're talking about customer value and customer centricity. Because interpretive questions help us to uncover meaning and implications and root causes, and they're gonna help us get beyond just our surface observations. If you remember back to the episode on scaling, we saw behaviors like teams arguing about who's doing Agile right, instead of asking why adaptations existed or whether they delivered better outcomes. Those are the kinds of things that happen when we do not ask interpretive so what questions.

So, here's some examples of good interpretive questions. So what does this customer insight mean for our next sprint? So what is this metric telling us about our process? So what should we change based on what we learned? We keep missing our sprint commitments, so what are we gonna do about it? Interpretive questions turn data into decisions. They are really helpful at turning retrospectives from therapy sessions or complaint sessions into actual process transformation engines. So if you feel like your team is stuck in complacency or that job hugging is starting to suck out your team's innovative spirit, some so what questions may be just the jolt that you need to kick yourselves back into gear. They really matter in Agile marketing because if we aren't pausing for interpretation, we might just be getting faster at doing the wrong things.

Okay, fifth and final question here is subjective questions. These are our what's unsaid questions. They map to the Agile marketing operating system in the areas of people, psychological safety, radical candor, and leadership. These are questions where we get down into the nitty-gritty. We are gonna explore emotions, intentions, hidden assumptions, and everybody's favorite, interpersonal dynamics. They are at the heart of the people part of the Agile operating system, which, as we learned across so many episodes, is usually the real blocker to a lot of our goals of improving our ways of working. If you remember from the episode on psychological safety versus radical candor, we saw what happens when unspoken fears can become systemic barriers. We get niceness theater and political back-channeling and indirectness that slows work to a crawl. Subjective questions are what's gonna help us to break those patterns.

But now there's an important warning here. These are the most fraught and dangerous of all five question types. So approach with caution, and only after you feel like you are good at asking questions in general and having challenging conversations overall. Do not jump to question type five immediately. Work your way up to these, okay? And you will see why as we get into these examples. Things like: What feels risky about this approach? What concerns haven't been voiced yet? What's the tension here that we haven't named? If this fails, what are you afraid will happen? I mean, those are big questions. They require skill and safety and maturity to ask and answer well. But when teams are able to go there, they really level up and they can become unstoppable.

So why they matter to Agile marketers in particular is, if we're being honest with ourselves, every Agile team has a second backlog. We've got that emotional one as well, and subjective questions are how we refine and action that backlog alongside our actual marketing execution backlog.

Okay, let's bring it all together here. How can we build a question-driven Agile culture? Because I hate it when we talk about soft skills in Agile, 'cause asking these kinds of questions is really important — a tactical, hard, business-centric skill. So if you wanna look for concrete spots to start practicing these questions, you can actually map the five question types directly to Agile ceremonies. So if you are, for example, going into a visioning or, like, a quarterly planning — more of that long-term view type of planning instance — bring in the investigative and speculative question types. If we're going a little bit more short term and we're doing something like backlog refinement, we can keep the investigative question. Now we can bring in a productive question type as well. When we're getting now even more specific and short term in something like sprint planning, we wanna focus on productive questions.

When we've moved into daily stand-ups and we're actually executing on the work, we're gonna keep those productive questions and blend in subjective questions. As we're having reviews and retrospectives, remember interpretive questions, very useful here. And also in the retrospective, subjective questions can be useful there. So anytime you feel like your particular ceremony is flat or unproductive or kind of staying at that surface level, look at which question type you might be missing, and maybe that's where your dysfunction is hiding, and you can ask the right questions, bring it out into the light, and make that ceremony or meeting work better for you.

Because as we know, Agile is not just a process. It's not just ceremonies or boards or cadences. It is how we think, and asking strategic, thoughtful, and intentional questions is really the thinking engine that's gonna drive our agility.

So if your team wants to move faster, ask better questions. If your team wants less waste in the system, ask better questions. If your team wants to innovate or depoliticize work or reduce dependencies, you guessed it, ask better questions, because, I mean, these days everybody can access the sum total of human knowledge in their pocket. So, answers — commodities. Questions are differentiators.

If you would like help training your teams or leaders on how to use questioning as a strategic lever inside the Agile marketing operating system, of course The Agile Sherpas team is here to help any time. You can visit agilesherpas.com to start the conversation. Until next time, I'm your host, Andrea Fryrear. And remember, the struggle is real, but so is Agile marketing.