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We have all seen cartoons of a dog chasing the garbage truck down the street.  What happens when the truck stops and the dog catches it? Frequently, the dog is left uncertain, unsure of what to do next, and simply barks in confusion. A similar scenario often unfolds in enterprise sales. A sales pro invests significant effort in developing a lead into a qualified prospect. After persistently pursuing an in-person meeting, the contact finally agrees. At this pivotal moment, what should the sales pro do next? Once the contact confirms an in-person meeting, the sales pro’s role should transition from pursuit to purposeful...

20 April, 2026

Lessons From Bad Managers Over the course of my career, I’ve worked for more than a few poor managers—enough that choosing just one as the worst would be nearly impossible. Instead, I’ve narrowed it down to three who left the deepest impression. Ironically, I’ve also been fortunate to work for some truly exceptional leaders, whom I’ll write about separately. The contrast couldn’t be sharper: the best managers elevated my career, respected me as a person, and recognized my strengths. The three below did exactly the opposite. Richard I joined Richard’s petrochemical construction company as a Budget Manager after being referred by the Controller of...

13 April, 2026

Think about the last time you attended a meeting where a seller utilized PowerPoint slides to present their offerings. Did the presentation effectively persuade you to give more serious consideration to their company? Many have bored me to fight to stay awake. This is probably because the seller utilized the company’s PowerPoint deck. Stop Letting Your Sales Deck Sabotage You Most companies arm their sales teams with a standard PowerPoint deck—polished by marketing, visually appealing, and packed with content. On the surface, it looks impressive. In reality, it often works against you. What’s Typically in These Decks? A standard sales presentation usually includes: Title slide Presenter...

07 April, 2026

Reasonably accurate sales forecasting has been a persistent challenge in every sales organization I’ve encountered throughout my career. The question is simple: why can’t sales pros forecast their deals to close this month and next month with even 60% accuracy? On the surface, it should be straightforward. In reality, it is anything but. The data confirms this is not an isolated issue—it is systemic. According to Gartner CSO Insights (2020), only 45% of sales leaders are confident in their forecast accuracy.1 More recently, Forbes reported that 67% of sales operations leaders believe forecasting has become more difficult in just the past...

19 March, 2026

Why use the Player/Coach Model? This hybrid approach combines hands-on contribution (Player) with team management and mentorship (Coach). It is common in startups and agile organizations. The model offers leaders who both do the work and shape strategy.  It can be deployed in sales and non-sales positions. Rethinking the Player/Coach Model in Sales Leadership Late in my career, I held a role as a sales manager while also carrying an individual sales quota. Although I achieved considerable success in that position, it was also one of the most stressful periods of my professional life. Looking back, I am convinced that my team would...

19 March, 2026

Can a sales pro with little formal training—and only a limited understanding of the enterprise sales cycle—consistently exceed quota? Most sales leaders would probably say no. After all, today’s complex selling environments demand structured methodologies, disciplined qualification, and carefully managed sales processes. Yet during my career, I encountered a salesperson who seemed to defy that logic. I'm not talking about seasoned sales pros who, thanks to years of experience, have reached the point of unconscious competence—that is, selling comes as naturally to them as breathing. Experts often describe this as the highest stage of sales mastery, marking the progression from unconscious incompetence to...

12 March, 2026

Demonstrations Don’t Always Go as Planned—Here’s How to Recover Have you ever experienced a product demonstration going awry in front of a prospect? Perhaps the internet connection failed, a technical glitch appeared at the worst possible moment, or a critical feature didn’t perform as expected. Maybe some attendees struggled to join the video conference—or worse, you couldn’t access the platform at all, bringing the entire presentation to a halt. In today’s remote and hybrid selling environment—accelerated by the reliance on videoconferencing—these situations have become increasingly common. Unfortunately, when technology fails, the product you confidently described as “easy to use” can suddenly appear complicated...

27 February, 2026

Have you ever worked on a prospect who did everything right? They showed genuine interest. They gave you access to decision-makers. They confirmed they had the budget. They returned your calls promptly. On paper, they were the perfect opportunity. They checked every box of a “qualified prospect.” They even matched your ideal customer profile. And yet… they never bought. Each time you follow up, they tell you they’re “still considering” your proposal. No objections. No pushback on price. No budget concerns. Just polite delay. Meanwhile, your sales manager is asking the uncomfortable question: Is this ever going to close? Early in my sales career,...

17 February, 2026

The first—and most important—piece of good news is this: you recognize that you are a Quota Sloth. Self-awareness is the starting point for improvement. A Quota Sloth is not lazy. In fact, most Quota Sloths are very busy. They spend their time working deals that are already in motion, responding to emails, attending internal meetings, and trying to close enough business to keep their manager satisfied and the commission checks coming. Some even ease off the gas because they are ahead of quota—for now. The problem is not effort. The problem is focus. You already know the law of the mathematics of the sales...

20 January, 2026

When I ask salespeople who their toughest competitor is, they usually name four or five competitors they see in the marketplace.  Sometimes they get emotional about a competitor who has caused them recent losses.  Then I tell them these companies are not their toughest competitor.  It is “do nothing,” or sticking with the status quo. The most expensive decision a business can make isn’t choosing the wrong solution—it’s choosing nothing at all. Doing nothing feels safe, rational, and low risk. In reality, it often carries the highest cost, quietly draining value while no one is looking. Is choosing not to act—or remaining with...

14 January, 2026
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