Why You Have to Get Better at Saying 'No' If your people-pleasing ways are hurting your business and productivity, it's time to rethink your strategy.

A while back, I met with an employee to do an interim performance review. I was excited because I was about to surprise her with a significant pay increase in recognition of extra responsibilities she had taken on. At the end of the review I told her what her new salary would be, and the entirety of her expressionless response was: "I thought this would come much sooner."

You know that "wah, waah, waaah" cartoon sound when something ends in excruciating disappointment? Yeah, that.

Then there was the supplier who asked if we could pay him a month early for a big production run "just this one time." Having been on the other side of that situation a few times myself—and given that this was a friend, not to mention our key supplier, whose terms were a critical part of our inventory turnover and cash flow—I obliged.

When he asked for the third time, I initially told him that while I appreciated his situation, we couldn't make another exception. He promised a super-rush shipment. What could I do? In fact, the shipment came two months late, which, when added to my prepayment, meant a cash hit lasting a full quarter.

Shame on me for putting my desire not to disappoint ahead of my responsibility to my business. Lesson learned? Nah, I still do stuff like that all the time. I'm bad at saying no—a terrible problem to have in business.

Making people happy has always been among my highest priorities, a point of pride. I don't do it to be a hero; I don't even do it for gratitude. I do it because I think it's right and good. But one of the hardest lessons I've learned in more than 20 years of running businesses is that the need to please can be a real handicap, and that it is, in fact, possible to care too much.

Don't get me wrong: I will never stop believing that a desire to make customers, employees and stakeholders insanely happy—and building a culture that facilitates that—is the highest calling of business ownership and the richest soil for growing a successful company. But the nuances here are desire vs. need, as well as the differences between happiness, satisfaction and approval.

The trouble starts when you feel that you must make someone happy or satisfy whatever wish or need they may have or, worst of all, elicit approval of your actions. Good leadership puts a priority on making the right (or at least best possible) decisions and accepting that they might not make everyone happy, much less win everyone's approval. When possible, you should try to please—perhaps even bending the rules a bit to do so, as you would when trying to satisfy a customer—but never at the expense of doing what you know to be best for the company overall. If you believe an action will hurt the company, just say, "No."

Those who don't like it, well, won't like it. Allow for that and move on.