In sales, there’s often pressure to move quickly; qualify hard, pitch early, close fast. Interestingly, the most consistent, long-term wins don’t come from those who rush to be heard.
They come from those who take the time to understand.
That’s the thinking behind the Understand principle in the HUMBLE sales philosophy.
It’s about more than asking questions. It’s about deeply exploring client needs, taking genuine interest and using that understanding to guide the sales process with more confidence and less friction.
If the Honour principle helps you define how you want to sell, Understand helps you earn the right to do so.
The Confidence to Be Curious
Salespeople often hold back from asking deeper questions.
This isn’t because they don’t care, often simply that they’re not sure they’ve earned the right to dig.
They might fear looking unprepared or feel the client will be impatient. What’s missed is that real confidence in sales doesn’t come from slick pitches or fast answers. It comes from slowing down, staying curious and being more interested in the client than in your own solution.
Buyers can feel when someone is genuinely invested in understanding them. That creates trust which in turn moves deals.
Why Discovery is So Often Rushed
Many sales teams treat discovery like a gate: something to pass through quickly so they can pitch.
In reality, discovery is the foundation of the entire sales process.
If you’re skipping through it, you’re likely doing one of three things:
- Making assumptions
- Asking the wrong people
- Guessing what will matter in the pitch
None of these build credibility.
You could argue this means some sellers lack the intent to understand. That’s unfair.
It’s that the environment they’re in (think targets, tools, process) sometimes makes real conversation feel like a luxury rather than a necessity.
A Better Approach to Understanding
Sellers should operate more like investigative journalists than product experts. Being curious, prepared and thoughtful. Avoiding launching into qualification. Gently opening doors.
Here’s how they could do it:
- Start wide, then narrow: Ask about context, goals, and priorities before honing in on specifics. “What’s changing in your business this year?” can be more revealing than “What’s the timeline for this project?”
- Link every question to care, not control: Avoid asking for the sake of your CRM. Ask because you’re trying to understand the bigger picture and help.
- Don’t just listen, reflect back: This shows you’ve heard them properly. “So it sounds like you’re trying to reduce operational risk while still innovating, is that fair?”
- Embrace silence: Give space. Some of the most useful insights come just after the client finishes talking.
The Power of Conversation
Conversations don’t follow funnels and people don’t speak in neatly qualified bullet points.
This is where confidence meets humility. You need the skill to guide but the patience to follow. To know your framework, adopted methodology or documented sales process, but not be bound by it.
That’s why at The Humble Sale, we spend so much time on conversation skills, not just processes.
A confident salesperson is the one who knows what to do when the conversation doesn’t go to plan.
Three Practical Ways to Build the Understand Habit
If you want your team to improve here, it won’t happen through telling them to “ask better questions”.
It happens through rhythm and reinforcement.
1. Add a “depth question” review to your pipeline sessions
Ask: “What do we know about their internal challenges that the competition doesn’t?” If the answer is vague, it’s a signal to revisit discovery.
2. Run peer coaching on real-world curiosity
Get small groups to practise opening 5-minute conversations, with one person playing the buyer. Focus on tone, not just the questions. Feedback should include how it felt to be asked those questions.
3. Build curiosity into the culture
Celebrate examples of great discovery, not just signed deals. Share the story of a conversation that unlocked insight. Make it normal to be curious, not pushy.
A Note for Sales Leaders
The Understand principle is where coaching matters most. This is because if the early conversations in a new sales process are shallow, everything that follows becomes harder.
Encourage your team to ask the next question. Give them language to stay curious. Most importantly, create an environment where taking time to understand is seen as skilful, not slow.
When a salesperson says, “I don’t know enough yet to move this forward,” see that as a strength. That’s what real confidence sounds like.
Final Thought
Understanding isn’t passive. It’s active. It takes time, skill, and presence.
When salespeople understand their clients better than anyone else, everything else becomes easier: positioning, pricing, proposals and progress.
So next time you’re reviewing a deal, start by asking: “Do we really understand what’s going on here?” Because if you don’t, the deal might move but it may not move towards you.
Key Takeaways on Using Curiosity, Empathy & Conversation as Sales Tools
– The best salespeople focus on understanding before being understood
– Curiosity signals confidence and creates trust in conversations
– Rushed discovery leads to assumptions, misalignment and weaker outcomes
– Real progress comes from depth of insight, not speed of movement
– Taking time to understand is not slow, it’s skilful
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