Winning At Mentorship

Hannah Olukoye
3 min readApr 26, 2021


By William Bout

Are you genuinely interested in assisting someone else expecting nothing in return? If yes, then you are on the right track to being an incredible mentor. All it takes is a willingness and desire to devote some time and effort to the mentoring relationship.

A few years ago, I got my first opportunity to mentor. It was a very nerve-wracking experience for me. I knew fully that I had signed up to be vulnerable to a stranger. The thought of guiding another person with life skills was riveting. I thought the only way to make it work would be to hide all of my flaws and only talk about my victories.

This year, I was smarter and more deliberate in my most recent mentorship enrollment. I knew exactly what they expected of me and I was ready to take up the challenge. It impressed me that the Wentors platform provided a guideline/workbook for the mentees and mentors to use throughout the mentorship program. The program organizers also paired the mentees with a mentor who best suits their objectives, which I thought was a great idea because it avoided the awkwardness that would often arise when introducing one another during a mentorship relationship.

I figured it would be helpful to share some tips for both mentors and mentees who are just getting started in their mentorship journey.

To mentors

  1. Be genuine and transparent — Admit to your mentee your past and present failures. This will go a long way towards encouraging honesty throughout the mentorship relationship.
  2. Avoid financial implications at all costs — In some cases, it might be enticing to provide financial help to the mentee, but this may transform the mentorship relationship into a dependency arrangement that can become strenuous.
  3. The mentee is the star of the show — Make the mentee the centre of attention. Let them drive the conversations and the goal setting. I remember, one of my mentees emerged as the best student in her class and this re-affirmed that it truly was about her.
  4. Offer guidance — This isn’t the time to second-guess your choices. Your mentee is looking up to you to assist them in making firm and sensible job decisions. If you’ve made a misjudgement, admit it and apologise.
  5. Ask for feedback — As a mentor, understanding the strengths and things to improve on is crucial. If you made the mentorship partnership transparent from the start, you would only get truthful answers.

To mentees

  1. Tardiness kills the relationship — Imagine your mentor is a busy person (e.g. A manager at Amazon) and they have a tight schedule. It would make all the difference if you arrive on time and keep track of time.
  2. C̶o̶m̶m̶u̶n̶i̶c̶a̶t̶e̶ Over-communicate — Send weekly updates at least. Progress updates show you are really interested in achieving your goals because going silent allows room for doubt and assumption.
  3. Be passionate about your goals — Set sensible goals that are worth your time. Setting unrealistic goals only makes you look bad. Good thing, your mentor will flag unrealistic goals quite early in your mentorship relationship.

Special thanks to my mentees and mentors over the years… You rock!

Thank you so much Hannah Olukoye. You are indeed a fantastic mentor. I’m so grateful for your words of encouragement and mentorship. -Naomi Usman-



Hannah Olukoye

Google Developer Expert— Android