You're smart enough to avoid starting cold B2B outreach with "How are you?" or "I’ve heard great things about your company." But I'll bet you're still in a persuasive mindset -- when conducting cold sales outreach, seeking new client conversations. It’s time to change your strategy. 

Because modern buyers are smarter and more skeptical than ever before. They’ve seen all the tricks, they’ve heard the pitches, and they’ve grown immune to what’s become tired, overused jargon. Not to mention automated personalization and artificial intelligence-written fakery.

Let’s take a closer look at five commonly suggested strategies. They're popular but aren’t doing you any favors. I'll introduce a better approach—sparking genuine curiosity and starting meaningful conversations.

#1: Question your questions

"How are you?"

You know better than that one, right? This question is like saying, "Hey, how’s the weather?" before launching into a sales pitch. People brush it off because it’s a non-question; they know what's coming next.

The Suggested ‘Better’ Approach:
"What are some of the biggest challenges your team is facing right now?"

You might think this is a good question—it’s specific, it’s relevant. But here’s the catch: it assumes the prospect is motivated enough and ready to dive deep into their problems with someone they barely know.

The Real Winner – Facilitative Questions:
So, what works? Facilitative Questions. This flavor of question is unique. Because it's NOT designed to lead the person being asked to answers we, or they, anticipate. Instead, FQ's are asked to open the door for deep self-reflection.

The goal isn’t to fish for an answer; rather, to get someone thinking, exploring, and re-evaluating their situation.

It’s a question bringing value to them, not you. Value through the process of contemplating a potential answer.

Thus, we ask not to receive information from them; rather, for them to reflect. Deeply. Even to the point of confusion.

For example:
"How would you describe your current challenges with [specific process]?"

Remember: You don't ask with seeking information in mind. In fact, the best FQs cannot be answered by you... and may not be answerable by the customer either! They may be questions customers should ask themselves, but avoid it. (out of fear)

That’s the kind of question that invites a conversation. It provokes.

It encourages them to think about a process or situation—or lack thereof! Or something they’ve been putting off thinking about. (but at their own peril)

It’s not about asking in seek of a solution; rather, inviting them to open up (to themselves) about their own experience (with you as a witness).

Challenging the status quo works better than you think.

As CEO at TitanX, Joey Gilkey puts it: “If you’re not challenging the status quo, what are you really doing? Clients respect the ones who make them think.”

#2: Personalize

"I’ve heard good things about your company."

Sound familiar? You may think a compliment is the ticket to engaging a prospect. LOTS of 'experts' recommend this tactic. Wrongfully. It’s not enough. It’s just another version of "I’m trying to get on your good side." It lacks substance, and prospects can see through it—especially when everyone (yes, everyone) on the planet has been using this tactic for decades.

Yes, decades.

The Suggested ‘Innovative’ Approach to Start B2B Conversations:
"I’ve been reading about your innovative approach to [specific industry trend], and I’m really impressed. Out of curiosity, tell me more about that?"

This might seem more personalized, but it has that underlying agenda of "I did my homework, now give me your attention." And in a world where AI is doing the homework for us, even the appearance of research can come off as automated or insincere.

Lately, I'm studying how most expressions of curiosity are coming across as insincere by potential customers. (and what to do instead)

Customers know the source of our curiosity: A need to sell. They detect it instantly. We all do. Because we are offered insincere curiosity daily by lazy marketers. Yet as a seller ourselves we are told to BE curious. And EXPRESS this.

"Saying 'I'm Curious' and actually being curious. These are two very different things," says John Juhasz, who sells hydraulic systems.

Think about it. The intent you perceive in my curiosity (about you) may offend, confuse or annoy. You may not answer at all. Because you know my curiosity is false -- a gimmick to start a sales conversation. 

Compare this with my asking a question which shocks you.

A question you should be asking yourself -- but are not.

A painful one.

Example: What is your understanding of how asking a question 'out of curiosity...' can backfire when reaching out?

This question is less restrictive; more open, less suggestive.

It's not seeking information to access your thoughts. It's Facilitative.

It's challenging you. Do you understand your own potential weakness?

The Real Winner – Insights:
What works instead? Insights. Not just superficial observations—real, thoughtful insights that you’ve pieced together from your own research. Insights show that you’re not merely reading (auto-scraping) a prospect’s LinkedIn profile; you’re engaging with their world.

You’re not saying, “I noticed that you’re [hiring, expanding, launching something new],” you’re saying, “I’ve been following these trends, and here’s what they could mean for your company.” (in hyper-specific terms)

#3: Earn trust, offer help

While the intent behind offering help may seem kind, it is often perceived as condescending or passive-aggressive. The act of offering help can make the prospect feel like they are being "sold" help, rather than invited into a collaborative conversation.

Eric Berne’s Transactional Analysis teaches us, this dynamic reflects a "Parent-Child" interaction where the seller positions themselves as the helper (Parent), and the prospect is cast as the helpless (Child) figure. This is not a balanced conversation and undermines the potential for an equal, respectful dialogue. Your ulterior motive is revealed! (even when you don't have one)

The Suggested ‘Better’ Approach:
"I’ve noticed your company is facing [specific challenge]. I’ve worked on similar issues before, and I'd be happy to share some insights or strategies that could be helpful."

While this feels more “genuine,” it still assumes that the prospect is open to your advice. It positions you as the expert, but the problem is, you might not have earned that position yet.

Also, too much kindness, especially when it drains your energy, isn’t virtuous—it’s harmful. Stoicism teaches the value of balanced generosity, which ensures while we help others, we don’t lose ourselves in the process.

Tom Manning of Pathway Academy, and sales trainer, Benjamin Dennehy echo this sentiment by emphasizing that salespeople need to stop trying to "save everyone." Manning advises salespeople to disqualify prospects who aren’t serious, rather than assuming that everyone deserves help. This ensures that your generosity (in the form of time, effort, or advice) is given only where it will make a difference.

By giving away too much of your expertise without any commitment, you risk being exploited by prospects who have no intention of buying, or worse, by competitors masquerading as prospects.

"I learned the hard way that over-educating a prospect only helps them—especially if they aren’t going to pay for it," says Mike McKenna of Core Scientific. 

The Real Winner – Balanced Generosity:
Rather than offering help freely, think about balanced generosity. This is a Stoic principle: be generous, but not to the point of depletion. As Tom Manning wisely advises: “Teach your salespeople to disqualify prospects rather than assume everyone deserves help. Disqualify as much as you qualify. Too many salespeople think everyone deserves help, but that's not true. Help should be earned."

Real-World Example:
Many salespeople fall into the trap of over-educating their prospects in an effort to demonstrate value. But as Benjamin Dennehy puts it: “Educating a prospect is not a sales tactic but a weakness.” Instead, engage with prospects by asking the right questions and drawing insights from them, rather than offering advice right off the bat.

#4: Demonstrate research

"Impressive to see on LinkedIn that your company has grown 27% in the past year."

"Really cool that you worked at Microsoft for 3 years... and Apple before."

The above are all part of a clearly defined, decades-long spam pattern.

What?! Yes. Just when you thought saying, "I know this about you" to prospects was a way to show them you're not spamming templates -- the concept itself has become targeted by humans and anti-spam software.

I'm not saying don't do it. There are no absolutes. Only tradeoffs. It depends on your situation. It depends on what you're selling and to whom. Overall, recipients are on to the ruse.

What works instead? Provocation.

By challenging the status quo, you can shake up the prospect’s thinking and make them stop and reflect. Powerful, high status decision-makers respect those who can challenge them in a constructive way. It’s not about being combative—it’s about thoughtful disruption.

Provocation opens the door for curiosity to take root.

Real-World Example:
As Josh Braun puts it: "Salespeople who provoke thinking are the ones who stay at the top. The ones who just regurgitate info? They get ignored."

#5: Complement, flatter them

"I really love what you’re doing at [company]."

Sounds like an attempt to gain favor. Again -- HUGE spam pattern. For decades now. Plus, compliments are often seen as insincere and can make prospects feel like they’re being used as a stepping stone to something else.

The Suggested ‘Better’ Approach:
"I’ve been following your recent initiatives, especially in [specific area], and I’m curious about the challenges you’ve faced in executing them."

While this is more specific, it still carries the same underlying purpose: to set up a conversation that benefits you. Instead of complimenting, focus on engaging them in a discussion about their real needs.

"Curiosity doesn’t say 'I am curious,' says John Juhasz. "It makes curiosity, manifestly, obvious by action. The same as you don’t 'check in' by saying 'I’m checking in.'

You don’t add value by saying 'we add value."

Your actions provide evidence of a value and somebody detects or assigns what the value is FOR THEM."

The Real Winner – Expertise Over Compliment:
Stop with the compliments and focus on genuine expertise.

Jake Dunlap, CEO, says it best: “If you want to book more meetings with C-levels, cut the compliments, become an expert at what CEOs are facing right now, and tell me how you can help.”

CEOs don’t want compliments—they want to hear from someone who understands their challenges and can offer insights that move the needle.

Provoke curiosity 

Common strategies like asking surface-level questions, giving empty compliments, or offering unsolicited help don’t cut it anymore. What works is sparking curiosity and provoking a deep (perplexing, if not terrifying) thought in a way that’s genuinely helpful to the prospect.

Activating a thought which was already there. Not implanting. Activating.  

By challenging assumptions and offering meaningful insights, you open the door to start trustting... and set the stage for a deeper, more productive conversation.

Start experimenting with these high-status approaches today. Ask more provocative questions, challenge your prospects' thinking, and stop relying on cheap hooks. Real engagement begins when you focus on the prospect’s needs, not yours.