The Four Greatest Challenges of Mentoring!

Mentoring is very much in the “spotlight” these days, though for entrepreneurs it never really went out of style.

There are numerous mentoring initiatives happening today, and more people are taking on the challenge of becoming a mentor; individuals from every discipline, with varied expertise. Many professionals who previously never thought of mentoring are now eager to help others achieve their goals, some with an eye to ‘giving back’, and helping ‘restart’ the economy through individual achievement rather than government assistance.

The greatest reward of course for being a mentor is the success of your mentee, so nearly all obstacles or challenges are well worth understanding, and overcoming.

So what are the four most frequent challenges that I hear about from those who are new to mentoring?mentorcasudi

1 – Time: How to manage my time mentoring, so it does not become a major time suck?

First, define the amount of time you are wiling to contribute at the very beginning of the mentoring relationship, and if and when it gets out of hand the first time, put your foot down, or you’re already on that ‘slippery slope’.

Emergencies may warrant more of my time on occasions, however if emergencies become a “way of life” with the entrepreneur I mentor, it needs strong controls Define what time & attention you are willing to give, and the communication channels you are willing to use outside the scheduled sessions, and I do mean scheduled…that’s one sure way to keep things in hand.

I usually do email follow up Q&A between the scheduled sessions on Skype, by phone, or in real life meetings. Be aware though, email can get out of hand also and become a big time suck. You should see some of the lengthy rants I’ve received by email! So keeping the mentee on track with short, to the point communications via email or even IM from the get-go is definitely a requirement.

2 – Focus: How do I keep things focused on the “task at hand” so that irrelevancies are not drawn into the mentoring sessions?

Just the same way you control the mentoring time, you control the focus, keeping the mentee focused! With clear direction from the start of your relationship, and as you progress!

Of course everyone is different, so if I see things getting out of hand, and find myself listening to marital problems rather than how to grow the business (although yes, they can be related!), I first question the motives of the mentee, does he want a marriage councilor or a business mentor? And if the real issue is the former…I’m outta there!

You will find that if a mentee is committed to their purpose they will work hard to get the most benefit out of your valuable time, and not head off in irrelevant directions. A couple of clear reminders should be all it will take to get things back on track, and if not …guess what…bye for now!

3 – Goals: How do you set mutual goals for mentoring when the mentee doesn’t know where they are going?

The mentee wants help but they don’t know where they are going or what they want to do! The mentor is set on defining the parameters, and setting the goals for the mentoring journey…. but without a roadmap…how far can you get?

This can either turn into a disaster or a great opportunity…. An opportunity for the person you are mentoring to really discover who and what they are, and understand their strongest assets, which can be channeled into new interesting, and perhaps very lucrative focus on something they are passionate about. I have seen this “discovery” take some time, but it’s always a very rewarding part of mentoring for me, to guide someone on their own journey of discovery, to a point where they know where they are and can set realistic goals for their start up, small business or future path.

4 – Advice: How much advice should I give, as opposed to asking questions that guide the mentee to find the answers?

It’s a fine line between telling someone what to do and advising them how to figure it out. My personal mentoring style has always been via asking questions, so in essence the person I am mentoring finds their own path by discovering the answers to my questions, and ditto answers to their own questions!

I know mentors who tell stories about their own experiences as a way of guiding others, to take or not take a similar path ~ this is teaching or mentoring by example, when it’s done well.

When I hear the complaints of “he/she didn’t listen to my advice”…..I have to wonder if this is mentoring or something else? My father was an expert in giving me advice, but cleverly getting me to think it was my idea; and that is the way I hope those I mentor feel, that they did it all by themselves!

Mentoring isn’t always as smooth as we would like it to be; often there are hard decisions to be made by both parties, things rather not faced by those we mentor; however being there as a resource, a questioner, a sounding board, or just an available presence, could make the difference between failure and success.



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




  • October 1, 2013


    DrYadavalli Thank you for sharing this piece. #bealeader is at the forefront of mentoring as well as #AIMW2013 CASUDI

  • October 1, 2013


    The 4 Greatest Challenges of Mentoring! by CASUDI via gingerconsult #bealeader

  • October 1, 2013


    DebbieLaskeyMBA TYSM for the share ~ greatly appreciated ~ any challenges to add to the post? gingerconsult

  • October 1, 2013


    JohnAguiar CASUDI Thanks, John. Appreciate you sharing. #bealeader

  • October 1, 2013


    aj_waso Oh, very helpful I think…thanks!

  • October 1, 2013


    SusanMazza what do U think ~ can U add to my Mentoring challenges? gingerconsult TYSM 4 the RT

  • October 4, 2013


    TanveerNaseer Enjoy the weekend, Tanveer. Cheers CASUDI #bealeader

  • October 8, 2013


    DeniseWakeman TYSM for the share ~ really appreciate gingerconsult #BeAleader