So you meet that one person who is your ideal mentor. Savvy, funny and incredibly successful. You sent an email introducing yourself and thanking that person for speaking with you after (insert any event/ place you met this one shining star) but now what? You are super excited and ready to pick their brain, for any and all information they have to offer. You have everything ready but you don’t know what questions you should be asking. Here are 5 questions you should ask your mentor or industry insider while out for coffee. 

One question to start off the convo with is

 “what were your first 5 years like when you started out at the company you’re at the top of now?”

Everyone has a different first 5 years but hearing their stories will help you structure a path to success.

Don’t be afraid to ask about your resume and cover letter. Even better, bring your cover letter and resume as a print out so that you can take a few moments during the interview to discuss what could be better on it. It is your first impression in paper form after all! They will tell you what they like to see and what they don’t like to see. That is information that not everyone has and it’s one simple edit closer to the success you want- plus, you look engaged and ready to land your dream job without having to say you are. 

Ask your mentor about their strongest and weakest interviews. The stories they give can be invaluable. You will hear about their mistakes and triumphs in one of the most crucial areas of job hunting. Their stories could possibly illuminate mistakes you have made in the past, highlight things you do well, and keep you from repeating the mistakes of others.

If you are struggling with any personal mental health issues, you can ask your new mentor if they too have struggled with any. I often find comfort in knowing someone I admire has also struggled with many of what I’ve endured in my personal life. 

The last question you should ask is if they know anyone searching for an assistant or need a position filled. This question might not amount to anything BUT it could lead to job.  Be sure to save this topic for the end of the conversation. If you ask it any earlier you risk looking like you are only meeting this person to get a job. More often than not your mentor is already going to be prepared to answer this question since you aren’t meeting with them to talk about what they’re having for dinner! Everyone likes to feel appreciated so be sure to ask lots of questions and develop a connection.

My final word of advice is to remember you can say no. If you are meeting with a mentor that means your career is only just starting. Just because you’re sitting with a powerful person doesn’t mean you have to jump and immediately say YES! You may even find yourself leaving your introductory meeting realizing that this mentor is not the person for you. This is your career and your reputation. You have final say on what you do or do not do. 

In conclusion, have fun with it. You are out to coffee with your mentor or insider, this is something not many people get to do. It’s a privilege you have earned and should be proud of. You are on your way to a fearless future now!