Starting my first business repairing commercial signs as a naive 23-year-old came with its fair share of challenges. My competitors were considerably older, wiser, and more experienced. It was tough convincing potential clients to choose the new kid on the block over veterans they knew and trusted.

This was nothing compared to the difficulty of hiring guys who were twice my age to work for me. When you're 40, someone in their early 20s seems as green and fresh as a puppy.  This dynamic was especially apparent when one of my employees made a request that I was hesitant to agree to. It was downright awkward. I felt like, as I'd been raised from infancy to respect my elders, who was I to say no?

Well, I was their boss, for one thing. In the words of former British Prime minister Tony Blair, "The art of leadership is saying no, not yes." I've found that to be true. The difficulty of saying no decreased as I gained experience, but I still follow the same six guidelines today that I painstakingly figured out two decades ago:

1. Lay the foundation beforehand. 

Your employees will take a 'no' much easier from you when they believe you appreciate, admire, and respect them. If they're on the fence about that--if you give them mixed messages or ignore them--they' ll take a no as a slap in the face.

Of course, some people are going to take a 'no' as a slap in the face no matter how you treat them. But treating your people well will give you confidence regardless of their response.

2. Don't be everybody's best friend.

At the same time, don't equate being respectful and appreciative with being everybody's best pal. I'm especially susceptible to this mixup; I count many of my colleagues as among my closest friends, and I wouldn't want to go to work if I didn't look forward to spending time with my coworkers.

I've learned the hard way, however, that boundary-setting is a crucial leadership skill. It isn't always easy to walk the line--when you're rubbing shoulders with folks for more than 40 hours a week, it's easy to confuse comradery with deep personal ties--but as long as your relationship is built on a solid, professional foundation, you won't stress about the ramifications of saying no. 

3. Embrace your awkward side. 

Our fear of awkwardness harkens back to grade school. Awkwardness makes us feel vulnerable and dumb, so we avoid it like the plague.

When faced with a particularly bad, face-to-face request, make awkwardness work for you. Give yourself plenty of space before saying no. Even better, wait till the other person breaks the silence--chances are that they'll reconsider what they've asked and simply answer 'no' for themselves. 

4. Use deadpan humor. 

I was once approached by an employee who thought he'd come up with a great idea for some content about my company. I won't go into the gory details; suffice it to say that his enthusiasm had overtaken his reason on the subject.

I didn't want to hurt his feelings, because he was obviously eager for my approval. I thought quickly but couldn't think of anything to say. Then my brain turned off and I spoke automatically: "Uh, how about ... no."

He paused for a moment and then we both burst into laughter. He reworked the idea into something less insane and provided this anecdote with a happy ending. Brutal honesty can be funny, and humor has a tendency to defuse otherwise tense situations.

5. Don't get used.

Every so often, you'll hire someone who's too clever for their own good. Ambitious, smooth, and manipulative, they'll use their dubious gifts to climb the ladder and put their own desires ahead of the team.

As leader of the group, you'll be seen by this sort as a special target. They'll ask you to lunch, say, and then present you with "hypothetical" situations that actually represent real-life conflicts in the office. In this way, they'll try to gain your approval for some move they're planning without actually asking your permission.

Learn to recognize this type and nip their efforts in the bud by saying no to the lunch.

6. Embrace your inner procrastinator. 

If you can't say no on the spot, feel free to put it off until later. Your colleagues know that your time is precious, and won't begrudge you a reasonable request for space to think. 

Use the space to consider the best approach--after all, you now have five great ones to choose from. Broach the topic with them again when you're ready and deliver your judgment. Even if they're disappointed, they'll be happy you gave it some thought before turning it down.