Always be Leading

Lately, I’ve noticed a surge in LinkedIn posts promoting the mantra, “Always be helping.” It’s a warm, people-centric counter to the more traditional sales adage, “Always be closing.” At face value, it’s a noble idea—and one that resonates well beyond the world of business. Being helpful is universally appreciated, and building trust through service is undoubtedly part of effective relationship-building.

However, in the context of sales, “Always be helping” needs a caveat.

The best salespeople are, indeed, helpful—but they are not people-pleasers. There’s a big difference.

Great sales professionals do not help indiscriminately or endlessly. Instead, they are strategic and intentional. They offer value, but they also know the value of their time, their expertise, and their product or service. Helping, for them, is part of a structured exchange, not a one-way street.

On the other hand, people-pleasers often fall into a trap. They focus so much on being liked or being seen as helpful that they forget why they’re in the room in the first place—to guide a deal to a successful close. In their eagerness to assist, they frequently give too much without getting anything in return. They provide resources, time, ideas, and support—but without setting boundaries or expectations. The result? The buyer often goes silent, or worse, gives their business to a more assertive competitor.

So what separates the high-performing sellers from the well-meaning, underperforming ones?

Leadership.

Top-tier salespeople behave like leaders throughout the sales process. They aren’t just there to take orders or play the role of a helpful assistant. They take charge of the conversation. They set the agenda. They ask thoughtful questions. And when they help, they do so with intention—help that moves the deal forward, not sideways.

This doesn’t mean being aggressive or manipulative. Leadership in sales is about earning respect, building credibility, and guiding the prospect toward a decision. It’s about giving help, yes—but only in ways that are mutually beneficial. They might offer a demo, a custom proposal, or insider insight—but they do so with a clear understanding of what comes next. “I’m happy to provide X, but in return, I’d like to schedule a decision meeting,” is a common example of how a skilled salesperson ensures an exchange of value.

Ultimately, “Always be helping” only works if you also know how—and when—to lead. Without leadership, helping becomes a time sink. With leadership, helping becomes a powerful tool to build trust, demonstrate expertise, and ultimately, close deals.

So by all means, help your prospects. Be generous. Be thoughtful. But never forget: your job isn’t just to serve—it’s to sell. And to do that effectively, you must lead.