"If you are a 'yes' person, you may not be stepping on anyone's toes, but you will never rise to the challenge and grow as an employee either.
"Challenging your boss can be very difficult, and often confronting. Done poorly, there may be negative consequences. But if you do it well, that's where the magic happens. It can transform you into an exciting and forward-thinking employee who adds exceptional value."
Gillam said poor leaders don't want to be challenged by their employees - and can't handle being wrong - but great leaders encouraged and promoted people to challenge one another.
Psychologist Stephanie Thompson, from Insight Matters, said people with a great boss would find challenging his or her ideas relatively easy compared to people with a difficult or touchy boss.
"It doesn't feel right to always be tiptoeing or kow-towing to your boss, but in some situations, people must really think carefully about approaching certain personalities," Thompson said.
"There's one technique that stands out above all others when you find yourself dealing with a tricky work situation, and that is to be positive, sincere and respectful. You can get away with saying almost anything, provided it's said with love.
"When your intention is positive, you will find your tone of voice and your choice of words mean confrontation is avoided and your boss is more likely to listen openly to what you are saying."
So how and when do you challenge your leader in a smart and effective way?
Prepare and anticipate
Get all the facts and anticipate your boss's counter-argument. Gather resources and data to back up your case and make it more credible. You'll be able to stand out for the right reasons, making yourself a valuable part of the team.
Know your boss
Understand your boss' personality before diving in, and don't choose a busy or stressful time to approach him or her with your ideas. Know your boss' triggers, and choose a time and space when there's mental clarity, calm emotions and privacy.
Right forum, right circumstances and the right way
Challenging your boss in front of others, particularly his or her superiors is not a wise move. Things rarely end well for the challenger when employees make demands and embarrass their boss. Asking for a one-on-one meeting, or putting constructive ideas forward at a team meeting is the best approach.
Stop being a 'yes' person
If you simply go along with every decision your boss makes, you're known as the "yes" employee who lacks real leadership qualities. If you're an ambitious and emerging leader, you need to do more than fall in line behind someone else.
Don't sweat on the small stuff
Try not to approach your boss about trivial matters. You risk gaining a reputation for losing sight of the big picture, which can portray a lack of initiative and vision. Stay calm, focused, clear and to the point.
Pick your battles wisely
Let your peers fight their own battles and talk for themselves, and respect your superior's decision if he or she refuses to see your argument. Try to keep negative emotions in check. How you respond might even lead them to reconsider their decision later, or to seek out your input on another matter.
Know when to walk away
There are some bosses and work situations that can cause mental stress and anguish. If your boss uses bullying tactics, or is doing something immoral or illegal, then leaving may be your only option.
"There's a limit to the value of exposing yourself to an intolerable situation, if staying in that situation is having a long-term impact on your life, then consider walking away," Thompson said.
