Mentoring Our Younger Self To Be A Leader

I am pretty certain that mentoring my ‘younger self’ on how to lead would have been a difficult and thankless task!

Like most of my peers, I was idealistic, optimistic, strong willed, and thought I had all the answers. I was convinced that I only had to implement an organized, logical plan in order to lead others. All well and good when things go well, but what if…?mentoringyourself1

In addition to the usual Leadership advice we give to those coming up through the ranks, there are three things I would tell my younger self which certainly could have enabled me to lead more effectively sooner, if I had known them then.

The second focus on my list below was explained at great length by one of my first mentors, but I really didn’t get it until several years later. Perhaps I should add “learn to listen, hear, and process the information to where it becomes actionable…..” but that has to be on everyone’s mentoring their younger self list already!

In mentoring my younger self in how to lead effectively, these are the areas I would recommend my younger self pay special attention to:


This means expectations based of what I should expect from others, not expectations based on what I can and would do.

I often fell into the trap of expecting others to do what I was capable of doing. It’s not that I was super woman or anything like that, but I was driven; for example I would work all night to get something done. Realistically I should not have expected others to do this, as some people need sleep to function, and after a good night’s sleep can work at double speed to get the job completed, maybe a bit later, but definitely in better shape!

Setting expectations of others on this basis may often set oneself up for a loss or disappointment every time others don’t behave as one expects in any given situation.

I also have blanked out the weaknesses of a team member (because I didn’t have those same issues), and consequently assigned them a totally inappropriate and unrealistic task, which resulted in a big lose for everyone, including my small company. Had I judged the person on their own merits (and they had many) they would have been assigned quite different tasks and we all would have succeeded!

This was a difficult and expensive learning lesson I have had to learn more than once!

2. Step back

Step back and let others do their thing.

What my mentor pointed out to me after observing how I led a group of people was that I took responsibility, maybe “obsessive” responsibility, for everyone on the team (was that really so bad?).

I infused myself into every action and reaction and made sure that everyone did well and looked good! My mentor continued to point out that this would give me a distorted view of the people around me and what they were actually capable of. People need guidance, but they need to stand on their own feet and take responsibility for their own actions; otherwise he pointed out it will be as though you are looking in the mirror at yourself and the recommendations you give others as they move on may be false.

This did in fact happen to me when I introduced a former employee to a new job in a different company where I knew the management. In my opinion they were an exceptional team member, but the feedback I received made me really think about what my mentor had told me earlier. Apparently in the new work environment, with minimal structure, my former team member was unable to motivate himself or take any initiative or contribute meaningfully!

Today we call this micro-managing, and it’s where you don’t allow others to take initiative, learn and grow!

A very basic and integral part of leadership is growing other leaders, and how can you do this if you are continually infusing yourself into others to make them do and look good!

3. Let others fail

As a mentor, leader, and especially a parent, this is the very hardest thing to do, as we all spend most of our time in business and life helping people to be successful.

“Those who don’t let you fail” was the very powerful unofficial theme of the amazing Sobcon conference in Portland I attended, which added a new dimension to what does it mean to let others fail?

Those who have had to deal with an alcoholic friend or family member realize that you have to allow the person with a severe drinking problem to hit rock bottom before they themselves realize they need help and will in fact accept help. So if/when you let others fail, stand by and be very ready to assist.

It’s a fine line for leaders, mentors, and especially for parents, to discriminate as to when to help prevent failure and when to allow it to happen. Allowing a fail to happen can be one of life’s many important lessons.


When looking back at your younger self, would you have benefited from being mentored in any or all of these three areas? Or if you are starting out have you encountered any of this in yourself?

The common thread in mentoring my younger self would appear to be having a “realistic” view of others, letting them learn and grow, and taking myself (some would call it ego) and parking it more in the background!

If you found this post helpful, please check my two #bealeader posts on mentoring – Connect With A Mentor and Five Questions To Ask Your Mentor

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




  • July 1, 2014


    gingerconsult great start to the day Jen appreciated the read

  • July 1, 2014


    ManageAmericans Thank you so much. I’m so glad you liked it CASUDI #bealeader

  • July 1, 2014


    jmeucci Thanks, Jason. Cheers cc: CASUDI #bealeader

  • July 1, 2014


    CNNJulie Thanks, Julie. Appreciate it greatly. #bealeader cc CASUDI jmeucci

  • July 2, 2014


    RT MeghanMBiro: Mentoring Our Younger Self To Be A Leader via be_aleader #leadership