Booking meetings with Chief Information Officers (CIOs) or Chief Information Security Officers (CISOs) takes a bold, new approach strategy these days. The best source to learn how to get the job done is right from their mouths. That's what I've assembled for you in this post.

Chief executives are telling sales reps and small business owners how to sell to them. But are you listening?

Robert Neill, CIO at Weaver, gets ten cold calls in thirty minutes. Thirty per day. Thousands of unread emails. And countless scripted sales pitches pretending to be conversations.

“I just want to see sales done right and not be a disruptive endeavor,” Robert wrote in a LinkedIn post. “I’m placing vendors on a mental 'do not buy list' that keep doing it poorly.”

He’s not being dramatic. He’s being generous. Generous with time, with patience — and guidance.

To salespeople and marketers supporting them.

This article breaks down his advice. Because Robert’s not just venting — he’s explaining what good looks like. And how to earn time, rather than burn it.

Don't focus on personas (UCPs)

Wait. What? Avoid focusing on Unique Customer Profiles? Yup. Best to focus on High Probability Suspects.

Suspects are defined as "higher than average likely" to engage. Call ONLY on these contacts. Maximize your precious time.

Knowing what triggered current customers to buy is the way to find new suspects. Interview current customers to get this insight. Their answers are your High Probability Suspect selection criteria!

The idea is to understand — what caused existing CISO or CIO customers to move from considering to WANTING change.

So go ahead. Try and persuade the masses, earn fewer conversations. Or, instead, call on the RIGHT contacts using "high status" language to earn attract meetings to you. Help them feel an urge to ask.

Want the conversation. But you don’t NEED it.

You can either look like a needy salesperson — or a confident provocateur. Because confidence is the foundation of provocation.

Read that again.

Remember: Call on suspects. People most likely to be in market OR will be soon. Then, use words and tonality matching their status — help them feel like someone of equal status is speaking.

Then, help them convince themselves to chat. Avoid persuasion.

Back to Robert.

Robert’s not a fan of cold calls. Not because he’s too important to take them, but because they’re a mismatch with how real decisions get made. But there's more...

Be careful about 'calling high'

Those ended up in the team locking in on that option and not  looking at others. This resulted in bad purchases.

I make sure the relevant manager and team understand the business need, the timeframe we are working in, and some general budgetary boundaries and then let them go research and reach out to potential vendors to do some initial viability assessments. Getting me onboard first does not increase the chances of winning the deal.

Having the best value proposition does."

Robert has seven direct reports and says he does not want first contact calls. Yikes! 

"My IT Managers/Directors understand our needs, what we are prioritizing and where we are headed with our tech strategy. They are all well experienced, have extensive professional networks and know how to gain knowledge of potential solutions.

My preference is to be engaged once that level has done some evaluations and are ready to take deeper dives on front runners. In the end, my biggest weight will be put on my team’s recommendation when making a decision. My interactions with tech sales teams play only a small factor."

And watch out. Artificial Intelligence (AI) agents are already here — on the BUYER'S side, not yours!

"What if reps, instead, pitched to your AI agent via voice or video call on Zoom?" Santosh Sharan, a CEO at ZeerAI asked Robert.

"It takes 5 minutes one time to train the agent on what you care about, Robert. Your agent qualifies them on the initial call, and only if it recommends a follow-up, you can decide whether to engage with them in future."

Robert bit in his LinkedIn post comments. I'm not surprised.

Stop persuading — start provoking 

One of the most telling moments in Robert’s post was his reaction to the phrase, “This is not a sales call.”

“A cold call is a sales call,” Robert wrote. “Own it.”

Pretending otherwise? That’s persuasion in disguise. And buyers — especially experienced ones — sense it immediately.

Seller: “This isn’t a sales call…”

Me: “Then we have an existing business relationship where you invoice me and I pay you?”

Them: “Well, no, I just want to see if we can partner with you to help your business…”

Me: “And once we partner up, I send you money?”

Them: “We help businesses like yours with…”

Me: “And then they pay you?”

Them: “Yes."

Me: “Sounds like a sales call to me. And since the call started with the world’s most obvious lie, I’m not interested in doing business with you.”

The above is a great example from COO, Steve Jordan of SUURV Technologies.

Justen Rosenberg, who calls on CISOs, summed it up:

“It most definitely IS a sales call. Same can be said with LinkedIn... Hate getting connection requests only to immediately be messaged asking for a meeting for something I have no say in or control over.”

The cold outreach isn't offensive. It’s the dishonest framing of it.

Samantha McKenna pointed out, it’s not about the call. It’s about the effort — and the relevance of that effort.

So instead of trying to persuade or pitch, do less. Say less. Create room for curiosity.

As AE, Josh Deanne shared from his own experience:

“I’ve found the best responses are when the voicemail is honest, concise, and open-ended… Here’s who I am, here’s why I’m calling — call me if you’re curious.”

This is the difference between chasing and attracting.

Sales consultant, Ahmed Soliman nailed the concept visually:

Replace questions with facilitations 

Robert says the most maddening cold call tactic is asking, “What is your involvement in technology purchase decisions?” Or worse, “Which of these challenges are you facing?”

These are BANT-style, qualifying questions pretending to be conversation starters. They’re not just insulting — they’re counterproductive.

“And of course the infamous: 'When we’ve been speaking to other business leaders in your industry…'" says Jon Ward who replies, ‘Amazing — who were they and what is it we actually do?’"

This kind of questioning is rooted in the seller’s agenda — not the buyer’s reality.

Facilitative Questions, by contrast, are inward-directed and help the buyer reflect on their status quo. For example:

• “How do your teams typically decide whether a new tool is worth evaluating?”
• “How would you describe the quality of the vendor vetting process?”

These aren’t designed to get answers. They’re designed to provoke self-assessment. They're a starting point for a conversation which might lead to a purchase-focused conversation.

Call only on high probability suspects 

Sellers often treat C-level executives as the ideal target. But as Robert explains, his team drives the buying process — not him.

Samantha McKenna reinforces this: “If we all send the same generic emails and ask for 15 minutes, we’re not standing out. And the buyer isn’t saying yes to 10 emails that ask for that.”

The fix: Focus on relevance over role.

Instead of asking, “How do I get in front of the CIO?” ask yourself, “What is this company already motivated by — and who’s working on it?”

This is what we call targeting high-probability suspects — the people more likely to be receptive because of what they do and how they think, not just title.

Sales is not marketing

Consider: Marketing should earn the call — before sales ever makes it. Robert’s final point might be the most overlooked:

“Have really great websites with superb access to information about your solutions.”

He’s not saying sellers shouldn’t do outreach. He’s saying: marketing has a job to do first. Educate. Demonstrate expertise. Make it easy for the right person to raise their hand.

As Robert explained:

“We focus a lot on content- and knowledge-driven marketing. We provide insights for our current customers and prospects to showcase our experience. We don’t have a sales team cold calling CFOs around the country.”

Marketing earns attention. Sales converts it — when the time is right.

Marketing should earn the call — before sales ever makes it.

Best practices aren't

Robert’s post struck a nerve because it confirmed something many sellers already feel. What they’re being told to do — by sales trainers, software tools, and team leads — doesn’t work. And it never really did.

“It had to be said. And someone on the receiving end had to be the one to say it. This is why cold calling is a problem," says Mike Herberts.

The old playbook isn’t just failing. It’s creating resentment. It’s poisoning the well for thoughtful sellers trying to do it the right way.

Bottom line: Robert Neill doesn’t hate salespeople. In fact, he used to work in tech lead generation himself. He gets it.

But he’s not going to reward spam tactics with his time.

He’s not going to play along with pretend pitches or BANT (Budget, Authority, Need, Timing) scripts. He’s not going to respond to persuasive tricks.

He will respond to relevance backed by research and/or a well-timed message that aligns with his team’s active priorities. 

As he told one rep in the comments:

“Getting me onboard first does not increase the chances of winning the deal — having the best value proposition does.”

And that’s the lesson.

It’s not about getting through to the CIO.

It’s about earning the attention of the team doing the work — by doing yours first. This isn’t anti-sales. It’s what real sales leadership looks like in 2025.

So let’s stop chasing. Let’s start attracting. Cheers!