Mentoring Exercises – 12 Scenarios


Mentoring is here to stay. Here are a selection of mentoring exercises that will help your company practise scenario analysis.

Situation 1:

Your HR Department has just deployed a new member to your team. He is very experienced and knowledgeable in your industry. It seems he was laid-off from a competing company and is quite judgmental about your current company’s operations. You have been assigned to be his mentor.

Describe your response.

Situation 2:

In a business plan competition, you have been assigned to be a mentor for a Startup. However, the Startup has not been very cooperative and does not reflect a need to be mentored in the first place. To your own astonishment, the Startup has even approached another mentor to be in their team!

You decide to break away from them and coincidentally, you discover some information that will help them be more persuasive in their business plan presentation.

Will you inform them?

Situation 3:

You have a friend who has just lost his job in senior management position. His retrenchment has thrown a spanner in the works, especially with regards to sending his only child for further studies overseas.

He approaches you and ask for employment within your Startup – preferably as the Managing Director, so that his bank loans will not be affected. However, you are in a dilemma because you feel that there is a wide generational gap.

How will you resolve this problem?

Situation 4:

You chanced on a blog that was set up by your assigned workplace-mentee, that provides much unfavourable remarks about your current company. Your mentee has been careful not to quote specific names but you are definite that the photos that he has uploaded are taken within the workplace.

Should you report to higher management?

Situation 5:

You have been approached to be a mentor/advisory board member for a non- profit organisation. You meet up with the Founder and feel energised – you immediate answer is a resounding “yes”. You are also swayed by the membership of a prominent mentor who is a well recognised figure. You convince yourself that you are in very good company.

However, as time progresses, you discover that you are not regularly updated with the organisation’s progress and your membership does not create much bearing with the organisation’s activities and direction.

Do you stay? Or were you never meant to be part of that organisation? Discuss your decision-making matrix.

Situation 6:

As a mentor, how do you ensure that you make a difference in the business decisions of a Startup or Non-profit organisation? Can you be sure that your views are valued, not just your immediate contacts?

Situation 7:

Your ex-student asks you for a favour. He has a group of friends who are talented in music. You watch their singing on YouTube and am very impressed. You suggest that they compose jingles for ads to get exposure.

Do you have other suggestions?

Situation 8:

You have been approached to be part of a Startup that is involved in creating a business strategy board game. However, your progress in the company is impeded by the lack of trust that the board game’s creator has in revealing to you the complete business idea.

How will you proceed?

Situation 9:

You are the class monitor and have been assigned to be a buddy to a new student who has come from a country where English is the second language. The new student is very motivated in improving his English competency and insists in joining the class debate team to improve. You are the class captain and you need the team to do well to boost your chances of getting into a good secondary school.

What should you do?

Situation 10:

You discover that a subject teacher’s blog provides enough clues for his own students to do well in a Science exam. You are also teaching the same subject.

Should you follow suit?

Situation 11:

You have been asked to be a mentor for a a group of students who want to raise funds for a non-profit organisation. During the course of meeting up with them, you feel that the leader of the group has aspirations of using the fund- raising as an opportunity to get attention and maybe a job in the non-profit organisation.

What should you do?

Situation 12:

You are part of a parents group that is setting up a food stall to support the school’s fun fair. The stall that raises the most will win a prize and get recognition. In the morning of the fun fair, you happen to see a parent buy from a very popular hawker stall, which contradicts the rules of complete food preparation by volunteers.

As a mentor, should you help to improve the quality of your own stall or blow the whistle?

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