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How to Ask Bold Questions and Get Bold Action

How to Ask Bold Questions and Get Bold Action

By: Katelyn Kriesel

What a great topic. It conjures up feelings of bravery, courage, and grit. It speaks to strategy and a mechanism for success and achievement. It is centered in cause and effect. If we understand how to properly use the art form of asking bold questions, it will lead to the end result we’re looking for: bold action.

As it turns out, I do the opposite. Allow me to explain…

Are you free to meet next week for coffee?

Now, this question doesn’t sound very bold, but the act of asking it was. Why? This question appeared at the end of an email to someone I had never met. I had no connection to this person, and there was no one making an introduction. I went in totally cold.

So, how did I ask my bold question? It’s simple.

I asked the question.

We all know how to do this! You hit send. You mail the letter. You pick up the phone and call. Be polite. Say please, thank you, and use a question mark. We’ve all done this! It doesn’t matter how big, or bold, or important the question is, the how is the same.

You just have to ask.

Onto the next component: the bold question. What did I ask for? To meet for coffee. This is not a particularly bold request. I could have asked them to become my client. That would have been very bold! They also would have said, no. So, I start with a very simple request. Are you free next week to meet for coffee? This is easy to say yes to! So, the best way to ask a bold question? Never ask a bold question.

Step three: Bold action. We’re meeting for coffee, and now is my chance, right? Take a deep breath, go all in, and get some big, bold action step?

Nope. I do the literal opposite. I have no action in mind that I would like to achieve, whatsoever.

I wanted to meet this individual in person and get to know them. By leaving the meeting open ended, I have nothing to lose and everything to gain. I don’t have to worry about gearing up for my ulterior motive. The boldness of this entire meeting is that I have no predetermined, desired action. Instead, I get to see where the conversation leads.

So, if all I’ve ever done is ask not bold questions, and not aim for bold action, how am I successful?

Over the last several years, I have had dozens of meetings like the one I just described. I end the meetings with something like, It was lovely to have met you and to learn more about what you do! Thank you for taking the time to get together with me. Would you mind if I followed up with you on the project that you mentioned? I think I can help with that.

See what I did there? Another not so bold question. With another not so bold action. Before you know it, we’re talking about how I can help them with their work, and they’ve become a client.

The boldest part about all of this was sending the email in the first place, and having the audacity to ask for a meeting. We’re so afraid of rejection and what the other person might think of us. I don’t know about you, but if anyone ever emailed me and said, Katelyn - We haven’t had the opportunity to meet yet, but I’ve been reading about all the work that you do, and I’m really interested in learning more. Are you free next week sometime to get coffee?

I would say, “Yes!” And who knows where that conversation would lead?

A lot of these conversations didn’t become lead to client relationship. They led to other things like a business opportunity, a referral, a speaking engagement, or someone to chat with at an event. Or, my favorite, we became friends.

So, in summary, how can you ask a bold question and get bold action?

Simply by asking your question at all.

Katelyn is a Financial Advisor for Hansen's Advisory Services, a socially responsible investment firm located in Fayetteville, NY. The team at Hansen's works with clients to create an investment portfolio that reflects their values, allowing them to do well by doing good. She is also the president of the Reinvestment Alliance, a not-for-profit organization based in Syracuse, NY with a mission to raise community awareness regarding economic sustainability and empowerment.

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