"Successful people ask better questions, and as a result, they get better answers."

Tony Robbins

Isn't this such a simple but powerful quote to help get us started this week?

Successful sales professionals shift the focus from easy conversations to courageous ones.

The average sales rep asks conventional questions that solicit expected answers, confirming the status quo and leading to average results.

A true professional who sells from the heart crafts better questions, questions born of genuine care and a deep desire to help the client see their own business clearly.

These questions bring with them some levels of friction, forcing the client out of their comfort zone to articulate the hidden costs of inaction or the specific fear holding them back.

The result is that these sales professionals receive better answers, answers rooted not in surface-level data, but in trust and emotional honesty.

Intentional curiosity is the engine of authentic sales success.

Our focus together is quite simple... The quality of the questions you ask is the direct measure of the value you intend to deliver.

You cannot get to any of those things if you’re too afraid to ask the hard questions.

Every stalled opportunity, every think it over, every ghosted follow-up, every discount request, and every proposal that dies in committee has a root cause.

Most salespeople never find it, not because clients hide it, but because salespeople never ask the kind of courageous, heart-led, trust-building questions that reveal it.

This is where Selling from the Heart separates real professionals from empty suits.

Empty suits stay surface-level, authentic sales professionals go deep.

Deepening the conversation requires courage.

It requires curiosity, heart, and massive amounts of discipline.

You will struggle to build trust unless you’re willing to ask the uncomfortable questions that uncover the truth your clients or future clients rarely volunteer on their own.

Allow our time together to be your mirror. Hold it up and most of all, be honest with yourself.

Most Salespeople Avoid Hard Questions

The issue isn’t that you don’t know what to ask, it’s that you’re afraid of the answers.

Hard questions create tension, and most salespeople avoid tension at all costs.

However, in a business world devoid of trust, where competition is intense, and buyers are overwhelmed, the only way to stand out is to lean into tension, not away from it.

Let's call out some of the fears that hold salespeople back...

Fear of losing the deal

Salespeople worry uncomfortable questions will make people retreat. Reality, most will pull back when they don’t feel understood, not when you ask questions that show you care.

Fear of seeming intrusive

Salespeople don’t want to look pushy. Authentic selling isn’t interrogation, it’s genuine curiosity. Asking meaningful questions signal professionalism, empathy, and seriousness.

Fear of slowing the sales cycle

Salespeople think asking why will derail momentum. Truth be told, hard questions bring clarity and clarity speeds up decision making.

Fear of uncovering the real problem

Once salespeople hear it, they're responsible for addressing it. Many sellers would rather pitch features than face a buyer’s true pain.

Hard questions prevent no decision more than any tactic ever will.

Hard Questions Build Trust

Trust is not a tactic, I believe it’s a byproduct of how you show up by...

• Building Authentic Relationships

• Delivering Meaningful Value

• Creating Inspirational Experiences

• Maintaining Disciplined Habits

Every one of those pillars is deepened, strengthened, and accelerated when you ask the questions most salespeople avoid.

Your clients and future clients trust salespeople who...

• Ask what others never think to ask

• Seek to truly understand

• Slow down enough to explore root causes

• Have the courage to challenge assumptions

• Bring clarity instead of complexity

This is not only true at the first meeting, it’s true throughout the entire journey and in ongoing client management.

The harder questions you ask, the deeper the trust. The deeper the trust, the better the outcomes.

Surface-Level Questions Create Surface-Level Trust

If your meetings sound something like this...

• What’s your biggest challenge?

• What are your goals this year?

• What criteria will you use to decide?

Then you sound exactly like the five reps who came before you.

These questions aren’t wrong, they’re simply not enough.

Surface questions don’t...

• Differentiate you

• Build credibility

• Reveal urgency

• Uncover internal friction

• Create emotional connection

People leave meetings with you thinking... Nice person but nothing new, nothing deeper.

Inside this post-trust world, nice loses while depth, insight and courage win out.

Depth comes from courage

Real differentiation happens when you’re willing to ask the questions sales reps avoid...

• What’s the impact if nothing changes this quarter?

• What truth about this situation isn’t being talked about but should be?

• What has made solving this a priority now, when it wasn’t three or six months ago?

These questions signal preparation, confidence, and genuine care, the core of Selling from the Heart.

They begin to trust you not because you’re polished, but because you’re present. Not because you’re smart, but because you’re real. Not because you’re different, but because you’re authentic.

You don’t earn trust by being impressive. You earn trust by being invested.

What Hard Questions Sound Like

Hard questions aren’t sharp, they’re deep. They don’t challenge the person; they challenge the problem. A huge difference.

Might sound like some of these examples...

Root-Cause Questions

Why do you believe this issue keeps resurfacing?

What’s made it difficult to resolve before now?

If nothing changes, what does this cost you over the next 12–18 months?

Impact Questions

How is this affecting your team’s performance, confidence, or capacity?

Who else inside the organization is carrying the weight of this problem?

Alignment Questions

What internal conversations are happening that I haven’t heard yet?

Where do others see the situation differently?

Accountability Questions

In what ways has your current process unintentionally contributed to this?

What part of this is in your control and what isn’t?

These aren’t easy questions, as they require heart, courage, and trust.

These are the questions that move deals forward, that deepen relationships and that elevate you from vendor to trusted advisor.

Hard Questions Change the Entire Sales Conversation

Your clients don’t want product experts; they want clarity experts.

Hard questions position you as a strategic partner, not a sales rep.

Salespeople win more when they understand what value means to each decision maker, which you cannot learn without deeper questions.

Hard questions reveal internal misalignment, as most deals die not because your solution is wrong but because the buying team doesn't agree internally.

Hard questions surface tension early, while you can still influence it.

Hard questions uncover motivation, not just information, as people make buying decisions emotionally, then justify logically.

When you dig deep enough, you will uncover the emotional motivators behind the business case.

Hard questions build authentic relationships.

You demonstrate authenticity when you ask the questions that show you care.

Hard Questions Require Disciplined Habits

Inside the Trust Formula, disciplined habits are the force multiplier. They’re what separate sellers who create trust from those who simply hope for it.

Nobody starts asking courageous, business-impacting questions by accident. It’s intentional, thoughtful and practiced.

Disciplined professionals...

• Prepare meaningful, value-focused questions before every meeting

• Research each decision maker’s personal goals and business priorities

• Build time into their calendar to reflect after every conversation

• Debrief with peers or leaders to sharpen their approach

• Continuously refine how they show up

Undisciplined sales reps, on the other hand, rely on winging it, which leads to...

• Surface-level conversations

• Being ghosted

• Stalled deals

• Proposals that miss the mark

• No-decisions that waste everyone’s time

Hard questions demand preparation. Preparation builds confidence, and confidence builds trust.

Hard Questions Require Heart

Authenticity is the ultimate competitive advantage.

Hard questions come from the heart...

• A heart that cares enough to dig deeper

• A heart that seeks truth over convenience

• A heart that focuses on serving, not selling

• A heart that sees people, not prospects

Trust and authenticity aren’t soft; they’re strategic assets that yield hard dollars when applied consistently.

If you want to sell from the heart, you must also question from the heart.

Hard questions also reveal your willingness to slow down and truly see people, not just the problems they’re trying to solve.

When you ask questions that go beneath the surface, questions rooted in curiosity, care, and courage, you signal that you’re committed to understanding their world, not manipulating it.

This is where authentic relationships begin to deepen. Trust is built when your intentions are transparent and your care is unmistakable.

Hard questions show you’re not chasing a transaction; you’re pursuing truth, clarity, and partnership.

Here’s Your Challenge

Every meeting you have this week, every single one, ask at least one question that makes you uncomfortable.

Not to create awkwardness but to create clarity.

Clarity for you, clarity for the other person and clarity for the path forward.

You owe your clients the truth. You owe yourself the truth, and you owe your pipeline the truth.

Hard questions deliver it.

Because those who ask the hard questions are those who earn the deep trust.

Originally published on Larry Levine's LinkedIn.