Cutting Through The Fear And Finding My Dream Mentor

Cutting Through The Fear And Finding My Dream Mentor | Career | The Chronicles of Carly

Cutting Through The Fear And Finding My Dream Mentor

Finding a career mentor is something I have wanted/needed to do for quite some time but I have been putting it off. It was living in the ‘too hard basket’ until recently when I decided to procrastinate no more and reach out to my ideal woman. I share my full experience, from start to finish, including a cold-email template based off what I sent and a list of questions to ask!

Mentoring. Something we all should do as part of our ongoing professional development, but many don’t. Why? Well, if you are like me there is a number of contributing factors; fear of rejection, fear of failure, fear of putting yourself out there, fear of reaching out to a complete stranger, fear of having coffee with a complete stranger… the list could go on but at the core of it is FEAR.

Finding a mentor (or mentors) is something I have wanted/needed to do for quite some time but I have been putting it off. It was living in the ‘too hard basket’ until one night at work I decided to procrastinate no more and reach out to my ideal woman.

The woman I reached out to was the mentor of all mentors; my best case scenario. Her career has had showtime on the international stage, she has a long list of awards and an even longer list of boards she serves on. This person is highly respected in her field all while she has managed to create a family. And yes, she is a woman. Sign me up!

I won’t tell you the name of this woman because a) it doesn’t matter, this article is about YOU finding YOUR dream mentor and b) I want to respect her right to not be named.

Reaching out to my dream mentor:

Thursday night I sent out an email, a cold-email may I add. She had never heard of me and we had never met. I was literally a stranger to her.

Friday morning, no freaking joke, I had a reply! How simple was that?! I aimed high and got a slam dunk first go.

She put me onto her assistant and boom, coffee catch-up booked in.

Why do I think I got so lucky?

  • I did my homework
  • I wrote a very personal email. There was no way this email could have been mistaken for a generic template that I was sending out to 10 different people.
  • I made the email about her! At the heart of it, we are all humans. We all want to feel special, appreciated, noticed and valued.
  • I appreciated the importance of your time - there is nothing I hate more than people asking for something with no appreciation of the gravity of the request.
  • I asked what I could do in return - even if she never takes me up on the offer, I have demonstrated that I am not the type of person to take, take, take. I want to give back. I want this relationship to be a two-way street.

If you want to see the email I sent, scroll to the bottom of this page.

Preparing for the meeting:

“By failing to prepare, you are preparing to fail” - Benjamin Franklin

If you are thinking ‘pssssshhttttt, preparation schmeparation’ think again. This (presumably kick-ass) person has agreed to meet with you, the least you can freaking do is walk into that meeting prepared.

Some key things I did in preparation:

  • Did my research on the person: yes, I already knew a lot about her but I could always learn more.
  • Made sure I knew how to pronounce her surname: the devil is in the details.
  • Prepared some talking points and questions: I never really used them but they were there as back up if the conversation wasn’t flowing. Prepping questions also helped me flesh out what I wanted to know, making sure I would get the most out of the meeting and I wasn't wasting her time.

The day of the meeting:

The day of the meeting I was a clammy ball of nerves; I felt like I was interviewing for a job. So if that happens to you too, do not stress… you are in good company.

Here are a few things I did:

  • Woke up early to pay a little extra attention to my appearance: first impressions matter and like it or not, your appearance is a big part of that! It is also just another way you can demonstrate you value their time (i.e. you have made sure you are presentable and not looking sloppy).
  • Arrived at the area of the meeting with plenty of spare time: I then sat in a cafe with a sparkling water reviewing my notes and questions ahead of the meeting. It really helped to calm the nerves, feel prepared and informed and leaving nothing to chance. I was not going to be running in their complaining about how the traffic held me up, or that parking was sh*t, or that I couldn’t find the building. I was going to sashay in their calm and confident (and not sweaty because I was running late).
  • Arrived at the actual meeting destination 10 minutes early. Again, this shows you value their time and that you are an organised and measured person; a person worth investing their time in. In my case, we met at her offices.
  • Ensured I was polite and engaged with EVERYONE I came into contact with. You never know who you are talking to. If you are at a cafe, that could be your future-mentors local cafe. Be nice to the barista or they will tell your dream mentor that you are a crappy person. Trust me, regular customers have really great and trusting relationships with their barista. If it is an office, and I can’t believe I have to say this, but be nice to the receptionist.
  • Did NOT touch my phone while waiting. I am right on the line of Gen Y and Gen Z. Both generations have pretty crappy reputations that we need to work against. Acting entitled and/or glued to your phone fuels that crappy reputation. Be engaged, assess the environment your meeting will be taking place in, look at your surroundings, take in the vibe; all these things will help you.
  • Gave a strong handshake with eye contact. Eye contact is my arch nemesis, but it is something that is required in a good handshake. It shows strength, presence, and respect. And the handshake is one of the first things you do. Again, you want to make that first impression a bloody good one.
  • Did not fiddle, or slouch, or lose focus. During the hour I was in the meeting I was p.r.e.s.e.n.t. I made it a point to ensure my attention did not waver. You are probably sick of me saying this but it shows respect; for the person, their knowledge and their time. Plus, you only have a finite amount of time with this person, wouldn’t you want to get the absolute most out of it?
  • At the meeting’s conclusion, I a) asked where I could take my dirty dishes because I do not think I am above anybody (and neither should you) and b) gave another strong handshake with good eye contact. If all things went well, you probably want to meet this person again so make sure you make a strong, last impression.

After the meeting:

The meeting finished, I was on an absolute high. Not only had this kick-ass woman agreed to meet with me but we had a good connection, great dialogue and I took away I lot.

After the meeting I:

  • Hopped into the lift and did a happy dance. Disclaimer: I was the only one in the lift, which made it easier. I am slowly but surely learning to celebrate wins and it feels good.
  • Ordered a bunch of flowers to be sent to her as I walked back to my car. Anyone can send a ‘thank you email’ but this person (who is worth a lot of $$$ per hour) deserves something a little bit more thoughtful; plus I am a sucker for personal touches. Give me a handwritten card over an email any day!
    Brisbane go-getters, I use Flour and Bloom whenever a need flowers. They are fairly priced and always deliver beautiful bouquets on time!
  • Took action! In the meeting, the person gave me quite a lot of tips, things to check out and other actions to take. The day of the meeting is when you are going to feel most motivated so action as many things as you can!
  • That’s it, folks! The chronicles of my first mentor meeting. I am feeling really positive about it all and have my fingers and toes crossed that this can turn into a lasting and mutually beneficial relationship… only time will tell.

I hope that this has inspired you to reach out to your dream mentor. I promise it isn’t as scary as you are making it out to be in your head.

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As always thank you so much for reading. It means a lot to have you on this journey with me,
Carly xx

Rather than sharing the email with you, I will share the ‘recipe’ of my email. Hopefully, this helps you to reach out to your dream mentor!

SUBJECT: What is your coffee of choice?

Hi [name],

[Compliment them - everyone loves to feel special and valued]

[Introducing yourself - Who are you? Where do you work?]

I am aware that you are busy, to say the least. I am also aware that requesting your time is no small favour but I’d love to hear your story and learn more about your career path. Could I ask for 30 minutes of your time over coffee?

If there’s anything I can do to help in return, please let me know - I never shy away from putting in the hard work.

Thank you in advance and I look forward to speaking soon,
[your name]

My preplanned questions were: 

  1. What does a day in the life of you look like?
  2. Is this where you thought you would end up?
  3. How would you describe your personal style? Side note: management/career not fashion
  4. What’s the most effective daily habit you possess?
  5. What are you best at? How did you become competent in this area?
  6. What were some of your former weaknesses? How did you overcome them?
  7. What are some lessons you've learned the hard way?
  8. Was there ever a job position you were given or task that you received that you felt you weren’t 100% qualified for?
  9. Have you set goals for 2019? How are you working to achieve them?
  10. Do you have any quick tips for re-energizing a team?
  11. How do you keep your feelings separate from your decision making?
  12. What positive thing do you see in me that I need to focus on developing?
  13. Do you have any books you would suggest I read?
  14. I am incredibly grateful for your time, what can I do for you?

I then highlighted my five favourite questions in case we were short on time. Plus it made the VIP questions easier to read if I quickly ran my eyes over it mid-meeting.