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Why Entrepreneurs Should Never Hire a Yes-Man (or Woman)


Who’s familiar with the old story, “The Emperor’s New Clothes”? Here’s a short recap: An emperor thinks he’s wearing a new suit, but he’s really just naked. When he parades around in his “new suit,” the people are too scared to tell him that he isn’t wearing anything, so nobody does for a while.

Folks, this is exactly the kind of thing you want to avoid in business. Do you want to be the naked emperor who thinks he’s wearing a magnificent suit? No. So don’t be the entrepreneur whose dumb ideas are applauded. Be the entrepreneur whose employees (or coworkers, as I like to call them) have the courage to say No, your ideas are crap.

I don’t know about you, but I need my coworkers to save me from myself. Sure, I have plenty of experience and great ideas. But, I also know that sometimes my ideas may be a little out there. And when I’m out in the cornfield again, pursuing some goofy idea, I need coworkers who are willing to tell me and reel me in.

That’s why I cannot hire a yes-man (or woman). Trust me when I say that you do not want to hire yes-people if you want to grow your small business.

Where’s Waldo? Spotting the yes-man

It’s easy to spot the yes-man . . . if you’re watching a TV show or movie. But when it’s happening in your business, finding the yes-men and women might not be so easy.

Here are some things that might indicate you’re dealing with a yes-person or people:

  • You feel good about your business ideas all the time (aka, your ego is huge).
  • There’s never any pushback.
  • You only hire like-minded employees.
  • Nobody takes responsibility because nobody else is accountable.
  • Your company culture creates and rewards yes-men and women.
  • An employee tells you your ideas are good but tells others they’re bad.
  • Your business is plateauing.
  • You say something crazy and your employees agree.

Looking for a yes-man might be tricky at first. But as you start to pick up on more signs, it will get easier.

Why you should hire the nope-guy or gal instead

Some of your business ideas are going to be crazy. You’re an entrepreneur—you sometimes fly by the seat of your pants. But that’s OK! For as many good and creative ideas you have, you’re bound to have a few that are a little out there (or some that aren’t out there enough).

And when you inevitably come up with something that could end up hurting your business, you don’t want someone kissing up to you and agreeing with your horrible idea. You don’t need an enabler. Entrepreneurs need people to say Nope, not a good idea or Nope, here’s how we can do it better. We need nope-guys and gals.

So when it comes time to hire or promote someone in your business, you need to look past the yes-men and women and find the nope-guys and gals. Don’t believe me? Here are a few reasons why you need to say no to the yes-man.

1. The yes-man squashes innovation and growth

Businesses need innovation to grow—true or false? Companies need growth to stay in business—true or false? True and true.

I’m sure we all know that innovation and growth are the goals in business ownership. And I bet we all know that our coworkers and support systems can help us reach those goals. But if we hire the yes-man, we’ll be getting a lot of the same thing, and it’s not the things we need for innovation and growth.

A nope-guy or gal will challenge you, build on good ideas to make them better, and get you thinking about the flip side of an idea. On the other hand, the yes-person will nod along, squashing innovation and growth.

The nope-person doesn’t have all the answers. But by looking at things from a different light, they can point out things you might have missed.

2. The yes-man substitutes honesty with what you want to hear

There’s no way I could have gotten this far in business without my wife. Not only are her ideas brilliant, but she is also honest with me—and that includes saying no to some of my business ideas.

Honesty is critical for relationships to succeed. Shouldn’t the same go for your business relationships?

When it comes to yes-people, one thing’s for sure—they aren’t upfront with you. They might tell you one thing then go off and whisper something different to a coworker.

Think about it. Do you really want to surround yourself day in and day out with workers who aren’t honest with you? I sure don’t. Not only is this going to get really old really fast, but it’s going to cultivate a toxic, gossipy work environment.

Some of your employees may have trouble telling you something they think you don’t want to hear. And the truth is, you might not always want to hear it. Who wants to hear people doubt their “brilliant” ideas? But one thing’s for certain: you won’t be doubting their integrity, courage, or honesty.

3. The yes-man is good for a limited time only

The yes-man is like a ticking time bomb. Sure, you might feel comfortable talking to the yes-man for a time. You may feel like your strategies are perfect for a time. But here’s the important part: that feeling is fleeting.

Eventually, you’ll discover that the lack of pushback and creative ideas is stifling your business’s potential. And that’s when you’ll begin to question why nobody said anything sooner.

The yes-person plays it safe to save their own hide. But in business, you need to do a risk analysis and take calculated risks for long-term success. That’s why you need workers who question the status quo.

4. The yes-man inflates your ego

Being confident in business is oh-so-important. However, there’s a fine line between believing in yourself and believing in only yourself. You have to keep your ego in check when you run your own company. You’ve done an amazing thing that only a fraction of the population does. But if you want your business to grow, you need to keep a sense of humility.

When you have employees agreeing with everything you say, your ego might start to get pretty big. That’s why I invite being wrong. I can’t let my ego get in the way of my business.

Here’s another tip: You have to be humble enough to say sorry. And sometimes, it takes a nope-guy or gal to point out that you messed up and owe someone an apology.

A few years ago, I had a meeting with a few of my coworkers. I was so sure that I was right about something in the meeting. But when it was over, one of my quiet, laid-back coworkers came to my office. He adamantly told me I was wrong and owed another coworker an apology. Well, that hadn’t even occurred to me until he spoke up!  I quickly apologized to my coworker.

You need to opt for hiring people who keep you humble by pointing out the things you haven’t seen. Not only can the nope-guys and gals teach you new things, but they can remind you of the importance of staying grounded.

Another word of advice . . .

Just because you hire people who are willing to give you other ideas doesn’t mean you always have to listen to them. Sometimes, you need to listen to yourself. If you think you have a winning idea worth pursuing even after your employees give you blank stares and counter ideas, you don’t have to take their advice.

I always listen to my coworkers and hear them out. And much of the time, I do take their advice. But sometimes, despite their counter ideas, I stick to my guns.

Does that mean I wish they had agreed with my winning idea? Nope, never. It just means that if you still like an idea after some pushback, you may just have to go with it.


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