10 Questions to ask your girl boss idol

Girl Boss Idols

//My girl boss idols? Hayley Barna & Katia Beauchamp, Founders of Birchbox //

//Photo Courtesy: referralcandy.com//

I’ve always loved the security question: “If you could have coffee with anyone who would it be?”

Let me guess: Your answer is someone who’s life you’re either in awe of, or want to assimilate to?

I know, I must have ESPN or something.

For me, the notion of meeting someone I admire or aspire to be like has me thinking about one tiny little detail: What the hell would I talk to them about?

Kind of an important question huh?

There are many people in my present reality who I’d love to grab coffee with. In fact over the past few years I’ve had the unique opportunity to meet and talk with many girl bosses I admire.  And what I’ve realized more than anything with each meeting is the importance of using that time wisely, and asking questions that really matter.

So whether you have a meeting scheduled with an alumni mentor or an opportunity for some one-on-one time with your company’s CEO, here are my top 10 need-to-ask-questions for your girl boss idol:

1. What were you doing when you were my age? 

Tip: Important – Their answer is not supposed to make you feel inadequate. More often than not, I’m surprised to learn what my girl boss idols were doing at my age. Some of them weren’t even in the industry yet. Still, it’s helpful to compare my own career progression to someone else’s. Asking this question gives me a reference point. 

2. What was your “aha!” moment? 

Tip: One of my favorite things to learn from those I admire is how they decided to do what they do. It’s what I like to call an “Aha!” moment. These stories always inspire me to consider my own “Aha!” moments, or if I haven’t had one yet, to know what to look for. 

3. Did you ever consider or experience a career change?

Tip: Rarely does anyone go through life not ever considering changing careers. It’s quite possible your mentor or boss didn’t initially plan on doing what they do now. If you haven’t felt an “itch for a switch” yet, don’t worry it’s coming. Either way, it’s helpful to have a reference of someone who’s gone through it. 

4. What was the best advice a manager or mentor gave you?

Tip: Your girl boss idol probably had her own, and they probably had some badass advice as well. Can you say, two for one deal?

5. When was time you felt completely discouraged and how did you push through it?

Tip: This question came from my blogger gal pal Paige Mariah, and I LOVE it. Remember it’s less about the actual obstacles you face, and more about how you deal with them. Understanding how someone else overcame a frustrating circumstance can help you anticipate dealing with your own. 

6. When you’re hiring someone, what’s the number one thing you look for? 

Tip: Your girl boss has probably hired one or two (or 10!) people, so here’s your chance to get some insider information. Use it wisely! 

7. What, in your opinion, is a realistic goal to set for myself at work? 

Tip: Goal setting is HUGE. So why not advise someone who knows what their doing to weigh in on your goals? Paint the picture of you current career situation and where you’d like to be in five years. They can help you identify firm realistic goals to focus on over the next few years. 

8. What should be keeping me up a night? 

Tip: Do you ever find yourself constantly worrying about work? The crazy part is, you’re probably worrying about things that don’t even matter in the big picture. Trust the experts on this one. Ask your girl boss what SHE thinks should keep you up in the wee hours of the night. 

9. Who else should I connect with? 

Tip: Always ask forward-thinking questions. Your girl boss is probably connected to other badass men and women, and through her, you suddenly have access to them. Ask politely for an introduction and you’re off to the races. 

10. Would you be willing to meet up again, or stay in touch via email or phone? 

Tip: Again, forward-thinking questions. If the conversation goes well (which it obviously will because you’re incredible!), then be sure to keep the lines of communication open. 

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