Growth Without Guesswork: The Questions Great Vistage Chairs Ask

After leading more than 150 Vistage workshops, working with hundreds of CEOs navigating growth challenges, and spending more than 10 years as a Vistage member myself, I’ve noticed a consistent pattern in conversations with business leaders. No matter the industry, the symptoms sound familiar.

• “Our pipeline feels softer.”

• “Traffic is down, but we don’t know why.”

• “Sales says marketing isn’t delivering.”

• “Marketing says sales isn’t following up.”

• “We’re spending more and growing less.”

The frustration is real. For many leaders, the first instinct is to search for a quick tactical fix: more lead generation, a new sales leader, a different marketing agency, another CRM investment.

But most of the time, the issue isn’t effort and it is rarely a lack of activity.

It is guesswork.

Today’s market is moving faster than most companies are adapting. Recent B2B research shows that 97% of buyers research online before ever contacting a company, buyers evaluate an average of 7.6 providers before engaging, and in 84% of deals, the first vendor contacted wins.

That means if your member is not showing up early and clearly in the buyer journey, they may never get the opportunity to compete.

At ChairWorld this year, I shared a session called Growth Without Guesswork because I believe this is one of the most important leadership conversations Chairs can help facilitate right now.

The opportunity for Chairs is not to become the sales and marketing expert in the room. It is to help members move from vague frustration to clear decisions by asking better questions.

Because better questions lead to better growth.

The New Buyer Has Changed the Rules

Today’s buyers are more informed, more independent, and more digital than ever before.

They complete most of their research before speaking to sales. They compare multiple providers, rely on peer reviews, check third-party sources, and increasingly use AI tools like ChatGPT, Perplexity, and Google AI Overviews to shape decisions before a company even knows they are in the market.

They want validation, not pitches.

They want proof, not promises.

Buying decisions have also become far more complex. According to Gartner and Forrester, B2B buying committees have grown from five stakeholders to as many as 11 to 13 decision makers in just a few years. At the same time, 65% of B2B buyers are now Millennials and Gen Z, bringing consumer grade expectations for speed, transparency, and self-service into every business purchase.

That means many CEOs are still managing growth based on assumptions that were true three or five years ago, but no longer reflect how buyers actually buy.

This creates hidden revenue leaks.

Leaders often optimize operations well, but fail to reexamine customer behavior, market perception, and where trust is built in a digital-first environment.

This is where Chairs create disproportionate value.

Start with One Question: Where Are the Growth Leaks?

One of the most useful shifts in a Chair conversation is moving from broad frustration to focused diagnosis.

Instead of asking, “How is sales going?” ask:

Where are the growth leaks?

That single question changes the discussion.

It forces members to think beyond symptoms and identify where revenue is actually being lost.

• Is the issue customer focus?

• Do they truly know who they serve best and why customers choose them?

• Is it market insight?

• Are they operating on assumptions instead of recent customer feedback?

• Is it buyer alignment?

• Does their sales and marketing process reflect how buyers want to buy today?

• Is it visibility?

• Are they showing up where buyers are researching, especially in AI-driven search?

• Or is it ROI?

• Are they spending money without a clear understanding of what is creating pipeline and what is not?

A powerful follow up question is:

If we fixed just one sales or marketing issue this quarter, which one would move the needle most on growth?

Most CEOs know the answer. They often just need the discipline and challenge to confront it.

Use the Growth Gears Framework

One of the simplest and most practical tools I use with Vistage members is the Growth Gears Framework.

It helps leaders evaluate growth through three connected areas:

Insights

Do we truly understand customers, competitors, and market shifts?

Strategy

Are we clear on who we serve, how we win, and where we should focus?

Execution

Are sales, marketing, and customer success aligned around the same revenue outcomes?

Healthy growth requires all three gears working together. Weakness in one creates drag across the entire system.

A simple exercise in a 1:1 is to ask members to rate each gear:

Red. Yellow. Green.

Then ask the most important follow up:

Are you thinking this, or do you know it based on actual evidence?

That question often exposes where guesswork is doing the most damage.

It also helps Chairs keep the conversation strategic rather than tactical.

AI Search Is Now a Revenue Issue

Many CEOs still think AI is a future issue.

It is already a growth issue.

Search is no longer just ten blue links. Buyers increasingly get recommendations directly inside AI tools like ChatGPT and Google AI Overviews.

If your member’s company does not show up in those answers, they may never make the shortlist.

And this is not just a visibility issue.

It is a revenue issue.

B2B leads originating from AI search clicks show a 56.3% higher closed won rate compared to leads from traditional search. ChatGPT referrals convert to closed deals at 4.08%, nearly double the Google organic conversion rate of 2.2%.

At the same time, Google AI Overviews are reducing website traffic by an average of 21%, with some companies seeing declines as high as 39%.

That means traditional traffic reports may be hiding a much larger strategic shift.

Visibility is no longer just about rankings.

It is about being cited and trusted.

A practical Chair assignment is simple:

Ask your member to search their company name and primary category.

Then ask an AI assistant:

• Who are the best providers in this space?

• Do they appear?

• If not, who does?

That exercise alone creates immediate strategic urgency.

End with One 90-Day Revenue Commitment

A common opportunity for Chairs is ensuring conversations move beyond insight to action.

Insight creates awareness.

Progress happens when members leave with a specific commitment and next step.

Every conversation should end with one 90-day revenue priority.

Not ten.

One.

It might be improving lead response time, reducing late stage losses, increasing qualified meetings from top accounts, improving visibility in AI search, or fixing one point of friction between sales and marketing.

The discipline is the same:

Who owns it?

By when?

What evidence will tell us it worked?

That is where Chair accountability creates real leverage.

Not in more discussion, but in measurable progress.

The Chair’s Real Role

The goal is not to solve every sales and marketing problem for your members.

The goal is to help them see clearly enough to make the right decisions.

In a market moving this quickly, guesswork is expensive.

The cost of guesswork rarely shows up in one quarter. It appears over time in stalled pipeline, missed market share, longer sales cycles, and competitors owning the buyer conversation before your member even knows an opportunity exists.

Chairs create value by helping members replace assumptions with evidence, and ideas with accountable action.

Better questions.

Better decisions.

Better growth.

That is Chair work.

A Practical Resource for Chairs

To make these conversations easier, I created the Growth Without Guesswork Chair Workbook, a practical companion resource designed specifically for Vistage Chairs.

It includes 1:1 conversation prompts, the Growth Gears diagnostic, Voice of Customer tools, sales and marketing alignment checklists, and a simple 90-day revenue action plan you can use with members immediately.

If you would like a copy of the workbook or if you would like me to present Growth Without Guesswork for your Vistage group or Chair community, please reach out directly.

Because in this market, growth without guesswork is no longer optional.