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Question Obsession: The Silent Sales Killer

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Have you counted how many questions you ask in your typical client meeting? Do you find yourself carefully crafting the “perfect” question sequence before every sales call? Are your meeting notes filled with question frameworks rather than real insights?

If so, you may be suffering from Question Obsession—a condition that’s quietly sabotaging your client relationships and sales results.

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We all know the sacred rule of consultative selling: “Ask before you tell.” This foundational principle has been drilled into us through countless sales trainings, books, and mentoring sessions. And for good reason—clients don’t want to be lectured or sold to without first being understood.

But somewhere along the way, this valuable principle morphed into an unhealthy fixation. What started as “ask good questions” became “the question is everything.” This is Question Obsession, and it’s time we addressed it.

The Question Addiction Cycle

The addiction starts innocently enough. Early in our careers, we witness the power of a well-placed question. A client lights up, barriers come down, and suddenly we’re having a real conversation instead of delivering a pitch. It feels magical.

So we seek more of that magic. We collect questions like trophies. We categorize them, sequence them, and practice them in the mirror. Sales methodologies feed this addiction with ever more sophisticated question taxonomies:

  • Discovery questions vs. qualification questions
  • Pain questions vs. implication questions
  • Strategic questions vs. tactical questions

Soon, our preparation becomes dominated by question planning. We walk into meetings armed with questions for every conceivable scenario. We become so focused on delivering these questions that we’re barely present for the answers.

Does this sound familiar?

  • Have you ever asked a follow-up question without fully processing the answer to your first question?
  • Do you feel panic when the client gives an answer for which you don’t have a follow-up question prepared?
  • Do you evaluate meeting success by how many of your prepared questions you managed to ask?

It’s easy to believe the hype that, with the right questions, you can unlock any deal.

No, you can’t.

This obsession manifests in what I call “question choreography”—the belief that if we can just sequence our questions perfectly, the client will inevitably arrive at our desired conclusion. It’s mechanical. It’s manipulative. And clients can sense it a mile away.

The Dangers of Question Obsession

Question Obsession creates three significant problems:

  1. It makes conversations feel like interrogations. When you’re focused on your next question rather than truly listening, the client experiences the interaction as transactional rather than collaborative. They feel processed rather than understood.
  2. It elevates technique over authentic curiosity. True value comes from genuine interest in the client’s situation—not from methodically working through your question checklist. Question Obsession replaces real curiosity with procedural questioning.
  3. It creates artificial conversation. Natural human dialogue involves a balanced exchange of questions, observations, ideas, and reactions. Question Obsession produces stilted, one-sided conversations that never develop the rhythm of trusted partnership.

Beyond Question Addiction

To break free from Question Obsession, we must remember that questions are means, not ends. They’re tools for creating three outcomes:

Genuine insight: The best questions aren’t clever traps that lead clients to your predetermined conclusion. They’re invitations to joint discovery. When you ask a question, be genuinely open to having your own understanding expanded. Ask yourself: “Am I asking this to confirm what I already believe, or am I truly curious about the answer?”

Deeper connection: Questions should build bridges, not just extract information. Listen for emotional content in answers, not just facts. A simple “How did that impact you personally?” can transform a clinical discussion into a meaningful exchange. The goal isn’t to collect data points but to understand the human experience behind them.

Client empowerment: Questions should leave clients feeling more capable, not more dependent. Great questions help clients articulate thoughts they couldn’t previously express, see patterns they hadn’t noticed, and imagine possibilities they hadn’t considered. They should walk away feeling smarter, not just more thoroughly analyzed.

Remember, it’s not about asking the perfect question; it’s about creating the right conversation. The quality of your attention matters more than the cleverness of your questions. Presence beats preparation. Genuine curiosity trumps question choreography.

Break free from Question Obsession and discover what lies beyond: the authentic dialogue that builds lasting client relationships and drives meaningful change.

 

Trust-Based Resources to Maximize Your Team’s Potential:

I used AI to support researching and writing this blog series.

Trust in the Time of the COVID-19 Pandemic (Episode 38)Trust Matters,The Podcast

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Welcome to the newest episode of Trust Matters, The Podcast. Listeners submit their personal questions about professional relationships, trust, and business situations to our in-house expert Charles H. Green, CEO, Trusted Advisor Associates and co-author of The Trusted Advisor.

A leader in a consulting firm writes in desperately trying to figure out how to manage business development and clients during the COVID-19 pandemic. She asks “Do you have any ideas about how to build trust with potential clients in a time of crisis like this?”

Do you want to send your questions to Charlie & Trust Matters, The Podcast?

We’ll answer almost ANY question about confusing, complicated or awkward business situations with clients, management, and colleagues. Email us: [email protected]

Should I Start Consulting Or Stay In-House? (Episode 28) Trust Matters, The Podcast

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This is the newest of Trust Matters, The Podcast. Listeners submit their personal questions about professional relationships, trust, and business situations to our in-house expert Charles H. Green, CEO, Trusted Advisor Associates.

An experienced B2B, technology Product Leader asks, “Should I break out and become a SME Consultant, starting my own practice or should I continue working at bigger companies? What do I need to know about starting my own consulting business?”

Do you want to send your questions to Charlie & Trust Matters, The Podcast?

We’ll answer almost ANY question about confusing, complicated or awkward business situations with clients, management, and colleagues.

Email: [email protected]

We’ll be posting new episodes every other week.
Subscribe to get the latest episodes

Trust Matters, The Podcast: Building Trust When Industry Spirals Into Cutthroat Pricing (Episode 13)

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Trust Matters, The Podcast: Competing on Competitors’ Lower Rates (Episode 12)

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If I Were You…

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Mike O. explains how he came to understand what it means to be a trusted advisor.

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Getting It Right

I had been a consultant for many years. I had a good sense of what client service meant – that I should pursue the right thing for my client, rather than just what I thought was the coolest idea.

I had learned the importance of communication. You had to be clear on your thinking in the first place, then be articulate about getting points across. I knew about body language, about using graphics and not just data, and about dramatic presentations.

I knew all this was hard work and that even with good effort and skill, it was still not an easy task to persuade clients of what I knew to be in their best interest.

Then one day something happened.

Getting It Inside Out

I’d gotten to know Manuel reasonably well. We had spent time together “thinking aloud” and had gained respect for each other as thinkers.

We were talking about some business issue, I honestly don’t recall what. Toward the end he asked me what I thought he should do about a particular angle.

At that moment I was completely at ease. The job was going well. He and I got along nicely. It was a sunny day.

I knew the issue inside out. I knew what Manuel was good at and not good at, what he liked and didn’t like, and how he was likely to respond to the particular situation.

In that moment I could envision exactly what would work for him – while still from my perspective as an outsider. It was like being him, but without any attachment to either his limitations, or to my ego. I knew what would be exactly right for him to do.

“If I were you,” I began – and suddenly everything changed.

He leaned in toward me, relaxed, but focused and intent on what I was going to tell him.  He really wanted to hear what I would say next – and I knew he was going to do exactly what I suggested.

Now, I know how to read body language. I realized this had not happened before. Every other time I gave advice to clients, they leaned back or sat up straight; they stiffened their back, rather than relaxing. Their eyes narrowed, rather than opening up; they were preparing to evaluate what I had to say.

But Manuel wasn’t in evaluation mode; he was going to accept exactly what I said, and we both knew it.

If I Were You…

I realized later those words both triggered and expressed a new perspective. Until then, I had always thought of consulting as telling the client what I thought they should do. I was the expert, they were paying me to get my expert advice. I packaged my advice to maximize the chances they’d do the right thing.

But it was always me, advising them. With Manuel, for the first time, I’d gotten outside myself. I’d realized what I would do if I were him.

I no longer had to be me, telling my clients what to do. I could tap into being them, imagining what it was like, what would work, and what wouldn’t. All I had to do was imagine putting myself in their shoes.

I realized they really did want my advice – if I was a steward about it, really reflecting their take on things.  I became more careful about giving my advice, waiting until I not only had the facts and the problem straight, but had a chance to empathize with the client as well.  That way, when the time came, I knew I could sincerely say, “If I were you…”

Consulting began to get a lot easier. I still had to do the leg work, the thinking, the presenting. But I no longer felt it was a struggle. I now know, my best advising comes when I’m able to put myself in the other guy’s shoes.

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Thanks, Mike, eloquently said.

Announcing eConsulting and eCoaching

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Starting today, I am offering a direct consulting/coaching service – one-on-one with me personally, via email – to a limited number of people.

Read more about the program at trustedadvisor.com/econsulting

All the detail is contained at trustedavisor.com/econsulting, but here are a few FAQs:

FAQs

Q. How does it work?

A. Up to one email interchange per day between you personally, and me, Charlie Green, for 8 weeks.

Q. What do you mean, you, personally? Doesn’t your team develop the answers?

A. Oh no. I mean me, Charlie Green, 100%, personally, individually, writing every email response with my own key-tapping fingers. Me. No one else.

Q. Is this a replacement for your existing coaching offerings?

A. No. We continue to offer excellent traditional coaching services through Stewart Hirsch. This is via email, more concentrated, more transactional, more action-based; read the full eConsulting page for more insight.

Q. Who is it for?

A. People who want very fast, very practical, very personalized advice on specific situations from me personally. Got a key client meeting or sales call coming up in two days? That’s what this is for. It’s all in the full eConsulting page.

Q. How many openings are there?

A. A one-digit number of slots; this will take time, and I’m not giving up my day job.

Q. How much does it cost?

A. Read through the full eConsulting page; it’s there, I promise you.

Accenture CEO Bill Green: What Leading from Principle Sounds Like

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A few years ago, I watched Bill Green, Chairman and CEO of Accenture, as he addressed a very senior leadership group at the end of a 2-day offsite meeting. Relaxed, he sat on a stage chair on a small platform and took questions from the 75-80 people in the room.

About halfway in, someone asked about a recently announced organizational shift. 

“Bill,” the person asked, “how do we know that the incentives are rightly aligned with the new global roles; that if I ask my colleague in Eastern Europe or Australia for help, they’ll be incented to do the right thing?”

Green quickly stood up, visibly tensing at the question. 

“Let me—well–,” he sputtered, “OK, I guess I’m glad you asked that question. Because I want to tell you—I don’t want to hear that question again!

“Here’s what I mean. And I expect every one in this room to get this; moreover, I expect everyone in this room to make sure you teach everyone back in your offices too.

“Here’s the thing. When there’s a conflict between the incentives and the right thing: you do the right thing, and then fix the incentives later. Understand? This is critical.

“We must be a values-driven organization before we are an incentives-driven organization. You design incentives to reinforce and reward behavior—you don’t design them to drive behavior. Values are what we need to drive behavior. If there’s a mismatch: you fix the incentives. After you do the right thing.

“And just to be clear: the right thing is almost always defined in terms of the client—not in terms of our internal P&L distribution.

“Now—am I being clear enough? Thanks for the question. And I don’t want to hear it again.”

Bill Green was plenty clear that day about what was important.  When he said "the right thing," he meant principles like client focus, taking a longer term perspective, and collaboration.  And he was clear that principles, not incentives, were the way to establish a values-driven organization.

For my part, when people ask me to name a big company that does trust well, Accenture is one of the few names I mention. Every company is far from perfect, but some are less so than others. Accenture is a lot better than most, and I think it’s because of the kind of leadership Bill Green demonstrated so clearly in this situation.

That’s what leading from principle sounds like.

You Too Can Be a Strategy Consultant: Three Secret Tools Revealed

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You always suspected it, and I’m here to tell you it’s true.

The art of general management and strategic consulting lies in the mastery of a few simple tools. Now, despite the inevitable threats against my person made by parties who do not want to see the Truth revealed, I am about to share with you, Trust Matters readers, the Three Strategic Secret Sauces. Guard them carefully.

Secret Sauce One: The Rule of the Axes.

Short form: Draw two axes.  Now decide what to label them.

You’ve seen this rule before, though perhaps you never noticed it for what it was. Consider:

  • • The Laffer Curve: tax rates by governmental revenue
  • • The classic Business Barnyard Matrix: market share by growth rate of a business
  • • Newspaper headline font levels on disaster stories by distance between the paper’s home town and the location of the disaster
  • • New York Magazine’s Approval Matrix (highbrow/lowbrow by brilliant/despicable)

Why is the Rule of the Axes such a hit? Because it simplifies complexity, immediately giving the axes-author the appearance of wisdom.
(Close cousins: Occam’s razor, and the rule of “always use 3-4 bullet points”)

Secret Sauce Two: The 80-20 Rule.

Short form: Look for concentration—in anything.

Classic formulations of the 80-20 rule include:

  • • 80% of the revenue/profit comes from 20% of the clients
  • • 80% of the taxes are paid by 20% of the citizens
  • • 80% of the crimes are committed by 20% of the population
  • • 80% of the Ivy League admissions come from 20% of the population

The 80-20 rule works because it forces the mind toward points of leverage. A good strategist always looks for maximum effect with minimum resources—just like a military general, or a change manager.  (Note: it doesn’t have to actually be 80/20, in fact it rarely is.  Anywhere above 60/40 can work.)

Secret Sauce Three: Vicious and Virtuous Circles.

Short form: Find what works, or doesn’t; add a few interim steps, draw them in a circle to make it appear permanent.

Here are some examples:

  • • Parental abuse drives fear, which drives aggression, which drives pre-emptive defense, which drives abuse
  • • US auto companies give up low-margin segment, which drives market share for low-margin Asian competitors, which increases their volume, which lowers price, which lowers margins, which causes US auto companies to give up the next-lower margin segment
  • • You empower what you fear
  • • The fastest way to make a man trustworthy is to trust him.

The Circles are powerful because they force us out of traditional linear models, and because they make sense of what often appears contradictory. The Circles offer a narrative, and usually suggest points at which to intervene to change the narrative. They also sound amazingly like rules and laws of nature, even when they’re bogus.

So there you have it. And guess what:

  • • If you chart usage of these three tools against business success, you’ll find a clear correlation;
  • • In fact, 80% of general management and strategic consulting goes to the 20% who have mastered these three tools;
  • • The more these three tools get used, the better known they get, the more clients learn to recognize excellent tool mastery on the part of consultants, the more they get hired for excellent use of these three tools, and the more they get used.

Now you too can be quoted, command high rates, and gain that aura of the oracle that surrounds the Great Strategists. Just use the three tools.

Your financial tokens of gratitude for this revelation may be sent to me at trustedadvisor.com. Credit cards and PayPal are accepted. You’re welcome.
 

Consulting and the Art of Self-deprecation

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According to Wikipedia, comedians use self-deprecating humor “to avoid seeming arrogant or pompous and to help the audience identify with them.” Sounds like a good strategy for anyone looking to build trust and rapport with another human being. Sounds like an especially good strategy for anyone in the consulting profession.

Ask any client who has worked with consultants over the years – they’ll have at least a few horror stories to tell about the Big Important Expert they hired. That creates messes we are all left to clean up.

Self-deprecation is an art that should be routinely practiced by anyone who claims the title “consultant.”

Here’s some material for your toolkit (original author unknown):

Top Ten Things You’ll Never Hear from a Consultant

1. You’re right; we’re billing way too much for this

2. Bet you I can go a week without saying “synergy” or “value-added”

3. How about paying us based on the success of the project?

4. This whole strategy is based on a Harvard business case I read

5. Actually, the only difference is that we charge more than they do

6. I don’t know enough to speak intelligently about that

7. Implementation? I only care about writing long reports

8. I can’t take the credit. It was Ed in your marketing department

9. The problem is, you have too much work for too few people

10. Everything looks okay to me

Share this with your clients. They’ll enjoy laughing at your expense. And they’ll appreciate your ability to laugh at yourself!