Congratulations! You have connected with a mentor…Now what?

August 8th, 2013 by CASUDI

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!

You can't eliminate storms, only learn to navigate better ©CASUDI

You can’t eliminate storms, only learn to navigate better ©CASUDI

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.

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?



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!



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……



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!



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.



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


CASUDI Creator of Entrepreneurs Questions #EQlist





8 Responses to “Congratulations! You have connected with a mentor…Now what?”

  1. Brian Driggs Says:

    I love the idea of mentoring and wish I had more time for it, personally – on both sides of the table. I know I’m stubborn with my quasi-Utopian business ideals, but you can’t build bridges until you get a clear view of the other side of the gap.

    Expectations and goals are a function of honesty and deep self-reflection. Nobody really wants to be a carbon copy of their mentor, and no mentor wants to build an army of rote copycats. (Shills and sadists aside, of course.)

    I think the ideal mentoring situation is going to feel natural, frictionless. Could it happen without structure or, necessarily, intent? I’m still not sure. Here’s to hoping I can make it happen before too long.

    Hope all is well at your end, Casudi. :)

  2. CASUDI (Caroline Di Diego) Says:

    ACTUALLY I do think mentoring can happen with out structure and intent. Sometimes you just fall into it but then you intend to help…however the mentoring can remain quite without structure and as and when needed (and I don’t mean when situations become dire by this!)

    Generally I like to start with structure especially with someone I don’t know well and is new to being mentored, however this can evolve to something less structured and more improvised. It comes down to whatever works, and please mentor the person in front of you, not someone else you imagine or hope it is! I used to be more set on structure (lists for everything) but now I am more set on what works best.

    Thanks for commenting Brian… I’ve learned a lot from your comments through the years…you would make an excellent mentor as you know the right questions to ask!

  3. Brian Driggs Says:

    No problem, Casudi.

    What are your thoughts on someone being a mentor without their direct involvement? Example, I consider the following people mentors, though I’ve never formally asked and they’ve never formally offered. Fortunately, they are public individuals, sharing a lot of insight and advice, which has stayed with me over time.

    Valeria Maltoni – Conversation Agent
    She inspires me to connect people and ideas, to talk about things that matter to my audience, and how I can build my business on a rock solid foundation by making meaningful promises – and keeping them. I consider myself a conversation agent in training.

    Olivier Blanchard – The Brand Builder
    I can smell Social Media ROI bullshit a mile away now. And I can explain WHY it’s bullshit. This is some of the most dangerous information I possess. Maybe I should change my Twitter bio to something like “Be glad I’m not disrupting your industry.”

    And, of course, the one and only Casudi!
    “Building bridges to success.” You’ve got an international curiosity, diverse interests, but there’s a common thread throughout – design. From that first double espresso of the day, to the charity helping people secure fresh water, to smart interior/exterior/business/life design, to the last sunset picture of the day, you kinda cover it all, and with aplomb.

    In a formal mentoring arrangement, I’d say structure isn’t required, but it certainly helps to define the ways success will be measured. Progress begets progress – especially when we can see we’re MAKING progress!

  4. CASUDI (Caroline Di Diego) Says:

    +Saul Fleischman asked on G+:
    My big question on mentors: how do you know that they are not in it – to rob you blind. In fact, the one person who was introduced to me, the one guy who threw me a thought or two, after I asked for advice on getting the RiteTag project started – turned around, applied for a patent for one of my idea, and then told me that I may not use it. Yes. Kind of makes me “gun-shy” about letting people who come off as mentors know what I plan to do.

    So, since I would like advice, how to you evaluate people who present themselves as mentors? How do you be sure they are not thieves?

    I answered:
    Ask questions and listen and watch the answers… I bet at some level if you had asked the right questions you might have spotted what this “so called mentor ” was.

    Often we are so eager to get the “advice” ,sometimes desperate for it (it’s free) that we don’t do the due diligence we should.

    Even what we think of as trusted recommendations may not be so trusted…. so consider developing your people assessment skills. What questions should you have asked this person that would have revealed what you later found out?

  5. CASUDI (Caroline Di Diego) Says:

    Brian, we probably need to pick nits between Mentor, influenecer and friend. IMO there is probably some two-way required in mentoring. Mentor ~ Mentee relationships can be very short term… maybe just one situation or longer term for life or a business situation. I think it’s possible to have a very informal relationship for a lunch or several emails online and mentor someone through a challenge or issue. Or maybe that’s what we do as an influencer or friend?

  6. Brian Driggs Says:

    Ah, but are we not engaging in the two-way right here? What’s the difference between an hour a week for lunch or email over the course of, say, three months, and three years of time-shifted conversation in blog comments and social posts?

    /devil’s advocate

    I find it interesting to see how application of a label can constrain thinking. That’s both a good AND bad thing.

  7. CASUDI (Caroline Di Diego) Says:

    Well it must be by consent: If you think I am mentoring you and if I think so also, then we are in an “informal” mentoring relationship. Cheers.

  8. #beamentor Resources | A Listly List Says:

    […] Congratulations! You have connected with a mentor…Now what? […]

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