What Makes a “Smarter” Question?
I recently went down a rabbit hole on what actually makes a good question, and it led me to a great Harvard Business Review article (paraphrased here; link in the comments).
The core idea is simple but powerful: smarter questions follow a sequence. They help teams move from ambiguity to clarity, from ideas to action, and from surface-level discussion to real insight.
The 6 Types of Smarter Questions
1. The Unasked Questions
“What don’t we know?”
The questions that cause the most trouble are often the ones we never ask. These are the questions that challenge habits, assumptions, and group dynamics. They may feel uncomfortable or inconvenient, but avoiding them is what gets leaders and teams into trouble.
If a conversation feels oddly “complete” too quickly, that is often a signal that something important has not been surfaced.
2. Investigative Questions: What’s Known?
“What’s actually happening here?”
Strong decision-makers start by clarifying purpose:
What are we trying to achieve?
What do we need to learn?
This stage is about depth, not speed. Techniques like the Five Whys help teams move past symptoms and uncover root causes. The most common mistake is stopping too early and mistaking surface explanations for real understanding.
3. Speculative Questions: What If?
“How might we…?”
Once the problem is well understood, it is time to expand the solution space.
Speculative questions help teams:
Challenge assumptions
Reframe constraints
Generate new possibilities
Using prompts like “How might we…?” encourages creative thinking and prevents teams from defaulting to familiar answers.
4. Productive Questions: Now What?
“How do we make this real?”
These questions turn ideas into execution. They focus on resources, constraints, and coordination:
How can we get this done?
Who needs to be involved?
How will we measure progress?
Where might we get stuck?
Productive questions shape timelines, metrics, ownership, and momentum. They are critical for turning strategy into results.
5. Interpretive Questions: So, What…?
“What does this actually mean?”
Interpretive (or sensemaking) questions help teams synthesize information and insights.
They push conversations deeper by asking:
What is the real issue underneath this?
What are the implications of this insight?
How does this change our understanding or priorities?
These questions help teams avoid activity without insight.
6. Subjective Questions: What’s Unsaid?
“What are we not acknowledging?”
This final category is often the most overlooked and the most powerful.
While the other questions focus on logic and strategy, these address:
Emotions
Tensions
Reservations
Hidden agendas
As the article puts it: “When we fail, it’s often because we haven’t considered the emotional part.” Ignoring this layer can quietly derail even the best plans.
The Takeaway
No one asks all six types of questions equally well, and that is okay.
The key is balance. Know which types you naturally lean into and which you tend to avoid. Before your next big meeting or decision, mentally walk through this framework and ask yourself:
Which category are we missing right now?
Smarter questions do not just lead to better answers. They lead to better outcomes.
