You Have Connected With A Mentor…Now What?

“My life will be easier because my mentor will give me great advice which will solve all the problems impeding my path to success.”  WRONG! 

Committing to a mentor, which means working together to meet known & unknown (and often challenging) objectives or goals, may in many respects make your life harder.


Image by Casudi (Caroline) Di Diego

My experience is that the best mentors ask questions, often difficult ones, and you the mentee will be expected to find the answers…. and then if required, to make the decisions and take the action. Often the decisions or actions are very difficult ones; If the path to success was easy everyone would be successful!

Connecting with a mentor can be a short process, especially if your mentor is assigned or selects you via a mentor/mentee introduction website such as #bealeader, or is an investor in your business or start up. it can also be a slow evolving process which happens as you get to know someone (from anywhere, including online) and you both decide the mentor-mentee relationship will be a good fit for both of you.

A mentor wants to know (as much as one can know going in) that the time invested, the sharing of knowledge and expertise, will create a positive result. The best mentors are busy individuals and they don’t give up their “free” time without expecting that they can make a difference.

So before you set out engaging with a mentor, do a reality check on yourself to see if you are ready to get the most out of being mentored.


Attitude is a key ingredient.  Give yourself the third-degree on your attitude. Do you know it all? Can you accept being wrong? Are you truly willing to learn new and different? How many times can you fail without getting discouraged? Do you have to be perfect?

Expectations and Goals

It’s important to let your mentor understand what your expectations and mentoring goals are at the very beginning of the mentoring relationship. A disparity in expectations can lead to an impasse and big waste of time. Think through both your expectations and goals before the get go and add a heavy dose of “realistic” to the pot.  Keep in mind that finding ones goals and career or purpose path can be a reason to connect and engage with a mentor.

One of the expectations to discuss is if this is potentially a longer term relationship (if things gel between the two of you) or is it to just handle a specific issue. And what if things don’t gel between you…. no hard feelings of course!

Being Honest and Realistic

If you can’t be honest and realistic about situations ~ tell it like it is ~ you will have a difficult time progressing, meeting your challenges and mentoring goals. How can a mentor ask you the right questions to draw out the actionable solutions if you have glossed over a seriously bad situation? Remember, you are not trying to impress your mentor with how fabulous you are……

Time and Attention Commitment

The time and attention you and your mentor are willing to commit to the relationship should be part of the initial discussion. If you expect a mentor to be there for you 24/7, if you are a “time suck” (look in the mirror), then mentoring will most probably not work for you. Would a commitment for an intense one-hour a week meeting or a virtual meeting via Skype, phone or hangout work for you? How about occasional email (or IM) conversations added to the mix when warranted? Mentoring time should be the best use of time possible to resolve the issues at hand, whether it be looking at all options, being asked the right questions or describing something in a ruthlessly honest way. If the commitment is for one or two hours, be on time and work hard. But also work hard and show progress between sessions. It’s the achievement between sessions which will be the payback to you and your mentor.

What I really like as a mentor is when I receive an email 10 minutes after a mentoring session with a list of action items to be implemented by the person I mentor; this is especially meaningful when it is something I have not asked for!

Growing and Evolving

The purpose of mentoring is growing and evolving, and of course being successful; whether resolving a specific issue or generally expanding your horizons. The most successful mentoring relationships are where both learn, the mentor and the mentee.

I am often asked as a mentor what I want in return, and my answer is your success! I love it when I’ve asked you just the right questions which have illuminated an actionable path for you to take, which when taken have made your company fundable or profitable.

Ask The Mentor The Right Questions

So you’ve connected with a possible mentor; it’s okay to check your mentor out by asking questions. What would your questions be?


This post has been republished with permission by Casudi (Caroline) Di Diego

CASUDI aka Caroline Di Diego
Caroline Di Diego aka CASUDI is a Social Media whisperer helping Brands, Communities and individuals find their social voice. She is the creator of the successful Entrepreneurs Questions blog; an effective self-help resource for Entrepreneurs. She is an award winning documentary film-maker, using New-Media to tell people's stories with impact. Esse Group, boutique consultancy has been helping companies move from concept/chaos to fundable and or profitable for over 25 years. INCLINEDESIGN focuses on Architectural Design solutions. She is a Co-Founder of the non-profit BankOnRain, solving the global water crisis with an available resource, THINK RAIN! . She is an avid guest blogger
CASUDI aka Caroline Di Diego
CASUDI aka Caroline Di Diego



1 Comment

  • November 16, 2013


    This is a wonderful lead-in for anyone looking for a mentor to work with. I have been on both sides and now reading this, I see exactly: what I wish I could have been clearer on as a mentee, the difference it made when I grew enough to receive the wisdom and direction and mentoring my own Trainees. 
    I would like to say thank you for this clear post as I will share it with all of my own trainees in the future.