There used to be sales people and then the rest of us. But… regardless of our vocation or influence, we all carry out some form of sales every day. The key to success is knowing how and when to pitch.

I came across an interpersonal story about an event planner who was invited by a philanthropist to lead a charitable fundraiser.

He was reputable, dependable and committed, but, from the start, he knew that the job was going to be a challenge.

The philanthropist was not in the least an event planner, but was used to being everything to everyone. He had difficulty stepping back and giving the event planner room to breathe.

Recognizing that he couldn’t produce his best work feeling like he was being micromanaged; he expressed his feelings to the philanthropist.

What do you think happened?

“Experts say regularly challenging your superiors could be good for your career – provided you are smart about it.” So, unless you are a ‘yes’ person, you’re going to want to do more than just bite your tongue and fall in line. The question is, how do you challenge your leader without damaging the relationship?

A Connie Clarke article in The Daily Telegraph shared these tips on how to challenge your leader in a smart and effective manner:

Know your boss’ personality and triggers. Be considerate of his/her time.

Gather resources and data to back up your case and make it more credible.

• Use the right forum, choose the right circumstance to challenge and do it in the right way.
• Don’t sweat the small stuff. You risk gaining a reputation as a troublemaker.
• Pick your battles wisely.
• Know when to walk away.

… Oh, the philanthropist thanked the event planner for his time and severed the relationship, but with the right approach you can be a champion.

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