By George B. Thomas, HubSpot Certified Trainer and Founder of Sidekick Strategies
Let me ask you a question. When was the last time your business asked why?
Why do customers really choose you? Why do they leave? Why do they stay?
I've spent over 15 years in the HubSpot ecosystem, working inside hundreds of portals, coaching teams through onboarding, migrations, and full-blown RevOps overhauls. And here's what I've learned: the brands that stop being curious are the ones that stop growing.
Curiosity isn't just a personality trait. It's a business strategy. In the video below, I lay out why curiosity is the competitive edge most companies are leaving on the table.
Why Most Businesses Get This Wrong
Too many businesses assume they already know their customers. "We've been in this industry for years. We know what works." I hear it constantly.
Then the market shifts. A competitor rises. Customers drift away. And the leadership team is shocked.
I've seen this play out dozens of times during HubSpot CRM implementations. A company comes to us convinced their sales process is dialed in. But when we actually dig into their portal data, ask their frontline humans the right questions, and look at where deals stall, the real picture is completely different from what leadership assumed.
The brands that endure are the ones that keep asking questions. They stay curious about humans, not just data. They dig deeper than demographics and uncover real motivations, struggles, and even dreams.
Three Truths About Curiosity in Business
After years of coaching teams and building systems inside HubSpot, I've landed on three truths about curiosity that I keep coming back to.
Truth 1: Curiosity Sparks Innovation
Every breakthrough product, service, or experience started with a question. What if we tried this? Why isn't anyone solving that?
When teams stay curious, they notice unmet needs. They explore new solutions. They challenge assumptions. And that's where innovation lives.
Here's a real example. We were doing a portal audit for a mid-size SaaS company. Instead of just looking at workflows and data hygiene, I asked their customer success team one question: "What do customers complain about that isn't in any ticket or survey?" That single question uncovered a pain point around onboarding timing that their product team had no visibility into. They adjusted their onboarding sequence, and churn dropped 18% in the following quarter.
Without curiosity, businesses stagnate. With it, they evolve.
Put this into practice: For the next 30 days, end every team stand-up with one question: "What did we learn about the customer yesterday that should change how we work today?" Document the answers. Act on one insight per week.
Truth 2: Curiosity Builds Loyalty
Discounts are fine. Feeling seen is better.
When you stay curious about your humans, asking questions, listening deeply, and actually adapting, you make them feel valued. And everybody loves to feel valued.
I've seen this work inside HubSpot specifically. One of our clients replaced their generic NPS survey with three targeted questions:
- What's the hardest part of your day that we could help solve?
- What almost made you leave us this month?
- What would make you say "wow" next time you use our product?
They built a HubSpot workflow to route those responses to the right teams automatically. Within six months, their renewal rate climbed by 12 points. Not because they ran a discount campaign. Because they listened and their customers noticed.
According to Harvard Business Review's research on workplace curiosity, organizations that foster curiosity see measurable improvements in innovation, employee engagement, and adaptability. Loyalty isn't built on discounts alone. It's built on curiosity that says, "Tell me who you are and I'll keep serving you better."
Truth 3: Curiosity Strengthens Connection
This one is close to my heart because I've seen it transform our own team at Sidekick Strategies.
Curious leaders ask their teams, "What do you think? What am I missing? How would you solve this?" That simple posture unlocks better thinking, deeper engagement, and more effective outcomes.
When we built our FEAM (our mix of human team members and AI agents), the whole model is rooted in curiosity. Every weekly sync starts with questions, not status updates. "What surprised you this week? Where did we create friction for a client? What's one thing we could stop doing?"
When humans feel like their perspective matters, they bring their best. And they stay. Curiosity doesn't just connect brands to customers. It connects leaders to the humans they're leading.
"We Don't Have Time for Curiosity" and Other Myths
I know what some of you are thinking. Here's the shift.
Myth: Curiosity slows us down.
Reality: It saves time by preventing rework. You move faster when you stop building things nobody wants. I've watched teams spend months on a feature rollout that one round of customer interviews would have killed in week one.
Myth: We already know our customers.
Reality: Markets shift. Competitors rise. New expectations appear. Curiosity keeps your knowledge current and your offers relevant. HubSpot's own research shows that customer expectations evolve faster than most companies can keep up with.
Myth: Asking questions makes us look unsure.
Reality: Asking questions signals confidence, humility, and a commitment to better answers. Customers respect that. Your humans respect that.
A Weekly Curiosity Cadence You Can Start This Monday
You don't need a giant transformation. You need a simple rhythm you can repeat.
Monday: Question of the Week. Pick one. "Why did customers choose us last quarter?" or "Where did we create friction in our onboarding?" One question. Write it on the whiteboard.
Tuesday: Listen Without Defensiveness. Review 10 real customer interactions. Read complaints. Watch call recordings. Scan chat threads. Ask "Tell me more" before you explain anything.
Wednesday: Decide One Small Test. Turn the best insight into a quick experiment. Define success in plain language. No 40-page test plan required.
Thursday: Ship the Change. Run the test. Inform the team. Notify affected customers when it's relevant.
Friday: Share What You Learned. A short Loom or Slack note. What we tried. What changed. What's next.
Repeat. Curiosity is not a workshop. It's a weekly habit.
The Curiosity Question Bank
Use these prompts across sales, marketing, product, and service. I've personally used every one of these in client engagements.
- What were you trying to accomplish today, and where did it become challenging?
- What almost stopped you from making a purchase or booking?
- If we disappeared tomorrow, what would you miss the most?
- Where are we adding steps that don't add value?
- What's the smallest change that would create the biggest win for you?
Pro tip: Collect answers in a simple "voice of customer" library inside your HubSpot CRM. Tag by theme. Pull those phrases into your copy, onboarding, and product roadmap. The best marketing copy comes straight from your customers' mouths.
Close the Loop or Lose Their Trust
Curiosity without action frustrates humans. When customers and teammates take time to answer your questions, show them it mattered.
- Share back the patterns you heard.
- Ship one visible change quickly.
- Explain why you prioritized it.
- Thank them for the nudge.
This cycle turns curiosity into momentum. Humans lean in because they see progress, not just promises.
What to Measure
You don't need a dashboard that looks like a spaceship cockpit. Track a short list that ties back to value.
- Time to first response for support and sales
- Activation rate for new customers
- Repeat purchase or renewal rate
- Qualitative "moments of delight" logged each week
- Number of customer insights turned into shipped changes
If a metric doesn't benefit your customers or your team, it's noise.
The Heart of It
Here's the beauty of curiosity. It keeps you humble. It reminds you that you don't have all the answers. And guess what? That's okay. You don't have to have all the answers.
Curiosity keeps you human. It keeps you learning. And it keeps your brand alive in the hearts of the humans you're actually serving.
If you want a business that lasts, build a culture that never stops asking better questions and turning those answers into better experiences.
Frequently Asked Questions
How does curiosity improve business growth?
Curiosity drives growth by helping teams identify unmet customer needs before competitors do, reduce churn through deeper understanding of customer frustrations, and build loyalty that discounts alone can't create. Companies that build systematic curiosity practices (like regular customer interviews and feedback loops) consistently outperform those that rely on assumptions.
What's the difference between being curious and just asking questions?
Asking questions is the first step. Real business curiosity means listening without defensiveness, acting on what you learn, and closing the loop with the humans who gave you their input. A survey that goes nowhere is worse than no survey at all. Curiosity is a discipline: ask, listen, act, report back.
How do you build a culture of curiosity in a team?
Start with leadership. When leaders regularly ask "What am I missing?" and "How would you solve this?", it signals that curiosity is safe and valued. Then build a weekly rhythm: one question on Monday, active listening on Tuesday, a small test by Thursday, and a shared learning by Friday. Consistency matters more than grand initiatives.
Can curiosity actually be measured?
Not directly, but its outcomes can. Track metrics like customer renewal rates, time to first response, activation rates, and the number of customer insights that became shipped changes. Over time, teams that practice curiosity systematically will see measurable improvement in all of these areas.
Your move: What's one question you'll ask your customers or your team this week? Write it down. Ask it. Share what you learned with your humans.
If you're ready to build your business with purpose, passion, persistence, and the curiosity to keep growing, start a conversation with Sidekick Strategies. Let's help more humans flourish, one honest question at a time.
Last updated: April 2026
