The Price of Trying to Please Everyone

Last Updated Jul 12, 2011 12:43 PM EDT

A very close relative -- a person I respect and consider a trusted advisor -- recently told me that I was holding myself and my business back by trying too hard to please everyone. He used a phrase that I thought was excellent, and it has stuck with me: "You need to be more presidential."

The truth is, he's right. I do try way too hard to please everyone and I am keenly aware of it. But my rationale has always been that a) it has generally served me well over 20 years in business; I am proud of my reputation, relationships, and my company. And b) it beats the alternative -- I'd rather risk being too nice, too generous, even too eager to please, than to risk the slippery slope of moving in the opposite direction. When I explained this to my relative, he said, "There's a whole lot of distance between those two extremes. Why don't you try something in the middle... take it back a notch and be more presidential."

Easier said than done. It is my nature to want to make people happy, and I know for sure it is good business. But sometimes it can work to my own detriment. Business may be good, but maybe it would be even better if I spent less time obsessing about pleasing everyone. So I would like to find a middle ground. As I see it, there are three categories of opposing forces that I have to reckon with in order to try to do so:

Familiarity vs. Detachment: Most agree that good leaders don't get too emotional about business, and some people believe that extends to maintaining some degree of interpersonal detachment. I have always had a hard time with that, as I see leadership (especially in a small business) as being all about personal attachment.

Yet I admire people who don't "give it all away;" leaders who strike the perfect balance between being fully engaged while still, somehow, playing it close to the vest and keeping themselves from getting too attached to any situation or relationship. I love being close to my colleagues, customers, and suppliers, but that closeness can make it difficult to deal with certain situations or make hard or unpopular decisions. Where are the boundaries? How do you nurture precious, critical relationships while you run a business free of emotional obstacles?

Generosity vs. "Business first": I don't like stingy people. So once again, I have always gone to the opposite extreme, whether it's giving away product that perhaps didn't need to be given away, selling a thing or two at a loss (I don't believe in profiting off friends and family, for example), or giving an employee a raise despite performance shortfalls. This has most certainly cost me meaningful money over the years, and I have always written it off to karma (though some might say there's a degree of insecurity involved). My loyal general manager gets on my case because she thinks I sometimes let people take advantage of my generosity, and my response is always: "The value of making that person happy -- even if he's taking advantage of us -- far outweighs the cost."

Most of the time I do think it's true, but I know sometimes I'm just giving money away when it's neither expected nor justified. So, how do you avoid being stingy or short-sighted without crossing the line of doing what's best for your business financially?

Pleasing everyone vs. accepting that you can't please everyone: This is probably the net/net of the whole thing. Can you please everyone? Probably not. Should you please everyone? Probably not. But if you are trying to run a good, healthy, well-regarded, and "happy" business, should you try to please everyone? Again, the answer is still probably not. So it seems to me that being presidential means knowing when to try, when not to, and how to do either and get the desired results.

Here's your chance to be generous and do some free consulting and coaching. I'd like to know your thoughts: Where do you fall on this spectrum of pleasing others? Do you think that there is meaning and value to being presidential, and if so, how do you define it? What do you believe is the most effective and productive way for a company leader to embody it? All opinions welcome... because I don't want anyone to be unhappy.

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Flickr image by Marion Doss
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    Michael is an entrepreneur who has launched businesses including Skooba Design and Hotdog Yoga Gear travel bag brands, as well as Journeyware Travel Outfitters. Michael sold his company in 2014 and is now focused on writing, speaking and consulting. Learn more about his ventures at