Inspect What You Expect: The Weekly Discipline Behind Great CEOs with Tom Barrett

Overview: What if your sales problem isn’t really a sales problem?

Tom Barrett has spent 30 years as a CEO, chairman, investor, and operator learning what actually drives sustainable revenue growth.

As a first-time CEO, he walked into a family business losing approximately $12 million a year and helped turn it into one generating $10 million in annual profit. He later built a software company from zero to $15 million in recurring revenue and has been involved in exits ranging from approximately 5x to 21x.

Today, Tom is a coach at CEO Coaching International, where he brings decades of operating, investing, and sales experience to CEOs working to grow and scale their businesses.

During his conversation with Mark Moses on the Make BIG Happen Podcast, Tom shared why CEOs need to inspect the business more frequently, what sales activity can tell you months before revenue changes, how to know whether your pipeline is real, what buyers look for in high-quality revenue, and why the people decisions you delay are often the ones costing you the most.

Your Sales Problem May Actually Be a People Problem

When Tom became a first-time CEO, he walked into a large, complicated organization.

The company had approximately $120 million in revenue, thousands of employees, and dozens of locations across multiple states.

It was also losing roughly $1 million a month.

One of the biggest challenges was enrollment.

In an education business, enrollment was effectively sales. But the people responsible for delivering the product didn’t necessarily see themselves as salespeople.

Tom had to help them understand the larger equation.

More students meant more resources. More resources meant better technology, programs, and educational opportunities.

The revenue problem wasn’t simply about generating more demand.

It was about getting the organization to understand how the business actually worked.

Key Takeaway: When revenue slows, don’t assume you have a sales problem. Find out whether you really have a people, process, or alignment problem.

Monthly Reporting Is Too Late

Before Tom arrived, enrollment numbers were reported monthly.

By the time he saw the number, the month was already over.

So he changed the cadence.

For the first six months, Tom and his team held quick daily calls with principals.

What happened yesterday?

Who is here today?

What is getting in the way?

Those conversations exposed problems that would have remained hidden inside a monthly report.

Tom calls it:

Inspect what you expect.

When Mark asked what every CEO should inspect weekly, Tom’s answer was straightforward:

Cash.

Revenue.

Expenses.

But knowing the numbers isn’t enough. CEOs need to understand what sits underneath them.

At one company, the team was preparing to spend approximately $1.4 million replacing computers while the business was losing roughly $1 million a month.

Tom went into the locations himself and discovered they didn’t need nearly as many computers as projected.

Ultimately, he said they spent roughly $50,000 instead of $1.4 million while still giving students the technology they needed.

Key Takeaway: Know your numbers, but don’t manage exclusively from them. Inspect frequently enough that you still have time to change the outcome.

Today’s Sales Activity Tells You What Revenue Will Look Like Months From Now

Tom leans heavily on sales KPIs.

Calls.

Emails.

Appointments.

Proposals.

Bookings.

And the conversion rate from one stage to the next.

Once you understand those numbers, you can begin predicting what revenue will look like one, two, or three months from now.

If activity drops today, revenue may look fine for a while because the existing pipeline hides the problem.

Three or four months later, the impact shows up.

That’s also why Tom believes prospecting has to remain consistent.

Prospecting is often the first thing salespeople stop doing because it’s hard. Once they have active opportunities, it’s much easier to focus on proposals, relationships, and closing deals.

But that creates a cycle of intense prospecting followed by an empty pipeline.

Tom would rather see consistent activity than occasional heroic months.

He also encourages sales teams to develop multiple channels for finding new opportunities, including partnerships, speaking engagements, trade shows, cold outreach, and marketing.

Key Takeaway: Don’t wait for revenue to tell you sales has slowed. Measure the activities creating tomorrow’s revenue today.

The CEO Should Be in the Pipeline Review

Tom believes CEOs should be intimately involved in pipeline reviews.

That doesn’t mean micromanaging.

It means understanding whether the pipeline is real.

A salesperson may say a deal is committed.

Tom wants to know:

Who actually committed?

What needs to happen before the contract is signed?

Does legal need to review it?

Who else needs to approve it?

What could still stop the deal?

In one case, Tom joined a salesperson for lunch with a prospect who was supposedly about to sign.

Tom asked what still needed to happen.

The customer explained that the contract first had to go through outside legal counsel, which typically took several weeks.

The deal wasn’t about to close.

The process was about to begin.

That distinction matters when CEOs are making hiring, spending, and investment decisions based on the forecast.

Key Takeaway: Don’t manage from the forecast your sales team hopes will happen. Ask enough questions to understand the forecast you actually believe will happen.

Build a Company a Buyer Will Want Before You’re Ready to Sell

Tom has seen businesses exit at multiples ranging from approximately 5x to 21x.

What separates the more valuable businesses?

Recurring revenue.

A large addressable market.

A strong management team.

A product customers truly need.

Revenue that is difficult to displace.

And consistent, repeatable growth.

If a CEO wants to sell three years from now, Tom believes the work needs to start now.

Build a history of predictable growth.

Put the right people, products, and processes in place.

Organize your data.

And build a business that doesn’t depend on the CEO personally touching every major deal.

Key Takeaway: Build your company as though a buyer could inspect it at any time. One day, someone probably will.

Don’t Wait on the People Decision You Already Know You Need to Make

Tom has seen CEOs wait too long to replace someone they already know isn’t right for the role.

Replacing someone is difficult.

The conversation is uncomfortable.

So leaders wait.

But Tom believes the waiting is usually far more expensive.

He also sees another common people mistake in sales: promoting the best salesperson into management.

Being great at selling doesn’t necessarily make someone great at leading salespeople.

The best sales leaders, in Tom’s experience, lead from the front. They’re in the field, coaching their people, helping prepare for important meetings, and getting involved in the biggest deals.

Tom also believes CEOs should always be recruiting.

His philosophy:

Dig your well before you’re thirsty.

Someone will leave. Someone will get promoted. The business will grow.

If you meet an A-player before you have an opening, build the relationship anyway.

Key Takeaway: Don’t wait until you desperately need the right person to start looking for them — and don’t wait too long to make a change when you already know you have the wrong one.

Don’t Overcomplicate AI

Tom sees CEOs trying to make AI too big too quickly.

Instead of looking for one massive transformation, he recommends starting with smaller wins and learning as you go.

Tom shared an example where AI was used to compare quotes, purchase orders, invoices, and changes.

The process still required human verification, but Tom estimated the solution eliminated close to 80 hours of work per week.

That allowed the company to continue growing without immediately adding more administrative staff.

In sales, Tom sees pipeline and forecast management as one of the easiest places to start.

AI can analyze activity, notes, follow-ups, and deal criteria to help determine whether an opportunity really belongs in commit or should be considered best case.

Key Takeaway: Don’t wait for the perfect AI transformation. Find a real problem, create a small win, learn from it, and keep going.

Final Thought

At the end of their conversation, Mark asked Tom for one thing a CEO could do the following week.

Tom’s answer:

Visit your top three prospects with your sales rep. In person.

You’ll learn something you didn’t know.

You’ll get closer to the truth about your pipeline.

And you’ll show your salesperson you’re willing to get in the field and help them win.

Sustainable sales growth is built through consistent activity, disciplined inspection, and staying close enough to the business to see what’s really happening.

Inspect what you expect.

Listen to the full Make BIG Happen Podcast episode with Tom Barrett.