Be Bold… When The Time Is Right

“What’s the harm in asking? The worst thing they could say is ‘no’.” How many times have you said that? I’ve said it a 1000 times, as I’ve asked for improbable things. I’ve also been on the receiving end of somebody asking for something when they know the answer will be “no.” I think we need to be judicious with our asks. Sometimes, go for it, other times you may want to consider the long-term impact of the ask.

I was talking with somebody recently, and they bragged to me that they had asked a large well-known foundation for a gift of $1,000,000. He laughed as he said it, following it up with “what’s the harm in asking.” I laughed and responded “you’re crazy.” He then said, “yeah, I told them I don’t want their typical low interest loan, I want you to give me $1,000,000.” “How did they respond?” I asked. “They laughed.” As I picture the scene, I see an uncomfortable laugh, as they all think to themselves “NO, you’re not getting $1,000,000.” I appreciate my friend’s boldness, but I’m not sure this was the time or the place. There are plenty of other places for them to invest money and if I were in that foundation’s place I’d be thinking “you’re greedy, we’ll invest our funds elsewhere.”

I think boldness and asking for big and unreasonable things is great, when you actually have nothing to lose. When you’re in a relationship, or trying to build a relationship, those bold asks can come across as greedy, selfish, self-serving, or entitled. The person being asked can get the sense that they are only good for the service or money they are providing. If you’re buying a used car, by all means get crazy with the ask, you’re not in “relationship building mode,” you’re in “get the best deal possible mode.” In that scenario, the worst thing that happens is a “no.”

Let me tell you another story about boldness that seems to be a pretty good use of the “what do I have to lose” theory. In the 1950’s, my grandfather was driving across the Golden Gate bridge and saw a group of police officers trying to talk somebody off the ledge. My grandfather stopped and boldly walked up to the police officer in charge and said he wanted to talk to the jumper. The police officer blew him off, but my grandfather was not going to be dissuaded. After some back and forth, and persistence, they allowed my grandfather to speak with this man (I know… it was the 50’s, that would never happen today). He then told the officers to step back 100 yards so he could have privacy, tell me that’s not bold. I don’t know how he got away with it, but he did. In the next 15 minutes, he successfully (and boldly I might add) talked the man off the ledge, a life was saved that day. If you have the ability to help, that is absolutely the right time to step in, ask boldly and bring your abilities to a situation. The worst thing that happens is they put you in a cop car and scold you down at the station, the best thing that happens is that you save a life.

Let’s be bold and do huge things. Ask for crazy things. Sometimes though we have to be aware of what we’re trying to accomplish and use our asks judiciously. There are times we only get because we ask, if we stay silent we get nothing at all. Some circumstances are different though, and we’ll get our chance to ask but right now isn’t the right time. Our focus needs to be on building relationships and trust and down the road we’ll have our opportunity, and when we make the ask it will be from a position of strength and trust. Our ability to know when to be bold, and when to hold-back and play the long game may make all the difference in getting where we’re headed.

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