#sales leadership Tag

The Wolf, the Eagle, and the Sheep: What Does It Have to Do with Sales? In the 2001 movie Training Day, the lead character, Alonzo Harris, a Los Angeles police officer played by Denzel Washington, makes these memorable statements: “You got to decide whether you’re a wolf… or a sheep” “A wolf doesn’t concern himself with the opinion of sheep.” Although the character who delivers the line is hardly a model of integrity, the quote itself has an interesting message about confidence, independence, and conviction. The basic idea is that people who are confident in their abilities and committed to a particular mission should...

18 August, 2026

What Surprised Me Most About Sales I have been asked this question many times over the years, and it has never been easy to answer. After more than three decades in enterprise sales, sales leadership, and executive management, I have learned countless lessons. But because the question asks what surprised me most, one experience stands above the rest. I entered sales in an unconventional way. I was an accountant for a major hotel chain and had recently passed the Certified Public Accountant (CPA) examination. My career path seemed well defined, and I had no intention of leaving the accounting profession. Then an unexpected...

05 August, 2026

So, Who Exactly is the Key Decision Maker, aka Economic Buyer? While many use the term “key decision maker,” I prefer the term “economic buyer,” as popularized by sales trainers and authors Robert Miller and Stephen Heiman.1 There is always one person—or sometimes a small group—who fulfills this role for a given sales opportunity. They possess both influence and authority. They can approve a deal when others cannot, and just as easily veto a decision that others support. While they may not attend every meeting, they are typically present when a final recommendation or proposal is presented. In recent years, particularly in enterprise...

12 May, 2026

The Myth of “Anything’s Possible” Can an amateur golfer sink a 50-foot putt while blindfolded? Sure. It’s also possible to survive going over Niagara Falls—and a small number of people actually have.1 But in both cases, the keyword is possible, not probable. A professional golfer sinks a 50-foot putt only about 3 percent of the time.2 What do you think the odds are for an amateur to do it blindfolded? Slim to none. And that’s where sales is different. Sales Is Not a Game of Luck In enterprise sales, “anything’s possible” is not a strategy. Success is not random, and it certainly isn’t accidental. In my experience, sales...

06 May, 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

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

The Myth of Uniqueness: Understanding Buyer Perceptions of Uniqueness When selling accounting systems to mid- and large-sized corporations, I made it a point to start every engagement with a conversation—not a presentation. My goal wasn’t to sell features; it was to understand how the buyer’s business operated, what challenges they faced, and how they measured success. These early discovery sessions were invaluable. I would begin by asking a series of probing, open-ended questions, such as: What type of business do you operate, and what’s your typical transaction volume? How many people are involved in your accounting processes? What are your biggest challenges...

01 December, 2025
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