Get a Quote
Articles Tagged with


Home / mentoring
Career Development, Enablers, Leadership, OD, Staff Development

Difficult Conversations – Keeping Mentoring Relationships on Track

The Quality of a Relationship relies on the Quality of the Conversation.

At some point in a mentoring relationship, the need for a difficult conversation will arise. Whereas every conflict is different, and there is no one-size-fits-all advice, there tend to be patterns to what goes wrong, and what helps. Every difficult conversation has three different dialogues that occur simultaneously. The What-Happened dialogue, the Feelings dialogue and the Identity dialogue. As you prepare for a meeting with your mentor/mentee, consider asking yourself some simple questions in order to navigate through these three dialogues.

1. Difficult Conversation – The “What Happened?” Dialogue

The first part of the conversation is about the context and content. Who said what, who did what? Who intended what? What did you each contribute to the problem? This question focuses on three main areas:

Understanding Each Other’s Story

A Difficult Conversation Keeps a Mentoring Relationship on Track

Difficult Conversations Keep Mentoring Relationships on Track

Cultivate the attitude of discovery and curiosity. We often get stuck thinking that our story is “right” and their story is “wrong,” when in fact there is almost always some reasonable basis for both sides’ stories. Explore each other’s stories, instead of attacking his/hers and defending yours. Your goal is to tell the story in such a way that the third party might say, “Wow, that view makes a lot of sense.” Note: As you try to do this, you’ll notice yourself thinking things like, “Yeah, but they’re wrong,” or “That’s their view, but it’s not justified.” This kind of thoughts are natural. But remember, they don’t think they’re wrong. Your goal is to understand their view as they understand it. Understanding their view does not mean you agree with it, or that you have to give up your view.

Sorting out Contributions

Just as it takes two to tango, most problems stem from things both sides said or did. With a few important exceptions, it is rarely helpful to assign blame for what went wrong. What is more helpful is to explore what each side contributed to the problem at hand. The purpose of exploring what each person has contributed is to better understand the past, and plan ways to change interactions in the future.

Disentangling Intent and Impact

We are in the habit of demonising others’ intentions and sanitizing our own: “If he did something that hurt me, it is because he meant to. If I did something that hurt him, it was an unintended consequence – I had good intentions!”

As a rule for life we should always assume that there is no one waking up in the morning with the intention of hurting someone else.

2. Difficult Conversation – The Feelings Dialogue

This part involves the feelings each person in the conversation is grappling with. What should you do with these feelings? Should you tell them how you feel? And what about their feelings? What if they become angry, or start to cry? What will you do then?

My Feelings

Make a list of some of your feelings regarding what has happened. Common feelings include anger, frustration, hurt, shame, confusion, fear, anxiety, and loneliness. Many conversations also involve feelings that are considered positive, but which are nonetheless difficult to manage or express. These include joy, pride, and love. Which feelings are hardest for you to express, and why?

Their Feelings

Make a list of what you imagine the other person might be feeling. Which of these feelings are hardest for you to hear, and why?

Note: Being aware of your feelings does not mean you have to express your feelings. Simply being aware of them is helpful to recognise how you think about the situation and the conversation. If you do choose to share your feelings, be careful to express feelings and not your judgments about the other person. For example, if you feel that you are rejected by the team, say “I feel that I am not accepted by the team,” instead of “Why are you rejecting me?” The difference between the two is crucial: the first invites conversation, the second invites an argument.

3. Difficult Conversation – The Identity Dialogue

This is the conversation you have with yourself, about yourself. It is the conversation that asks, “What does this all say about me? Am I a good person? Loveable? Competent?”

My Self-Image

Conversations are difficult because they often threaten some part of our identity. We see ourselves as competent, generous, or fair, so anything that challenges that notion of ourselves knocks us off balance. Recognise what is at stake for you, but also “complexify” your image of yourself so that all does not hang in the balance of this one conversation (i.e. even if in this situation you have in fact behaved irresponsibly, it does not necessarily make you an irresponsible person. Think of other times when you have acted responsibly).

Their Self-Image

What identity issues might you be triggering for them in the conversation? Are they reacting because they hear you calling them an incompetent professional, insensitive manager?

Choosing My Purpose

Too often, we enter a difficult conversation without a clear purpose, or we adopt purposes we cannot control – like changing them or persuading them. Only they can decide to change or be persuaded, so this sets us up for frustration.

My purposes for having a conversation. Make a list of those things you would like to get out of the conversation. In doing so, consider three purposes that are helpful for almost any difficult conversation:

  • Learning: Listen first to understand, then to be understood. You almost never know everything you need to know about the situation. Seek out the pieces of the puzzle you do not have.
  • Expression: You are an unparalleled expert on you. So, speak for yourself and how you are experiencing the problem and what impact it has on you. Consider sharing your perspective, interests, feelings, and requests.
  • Problem-Solving: You take the lead. Once you have listened to their views and expressed your own, then you should proceed to problem solving. Ask: “Can we find a way to move forward that works for both of us?”

Prepare an Opening Line

Think in advance about how you might begin the conversation. One useful way to go is to set forth your purposes, so you might say: “I would like to hear your thoughts on this problem and express my own. Then I think we should take some time to problem solve. Does that make sense to you as a way to spend the conversation?”


A difficult conversation will always be part of the relationship with your mentee/mentor – as they are part of life. Even if your difficult conversation does not go well, you can review the tips above and ask yourself what you might try differently next time. Many difficult conversations are held over a period of time. While there will be ups and downs, eventually – with some thought and preparation – mutual understanding often increases and some learning takes place. This gives you the best chance for relationships to deepen and for problems to be solved.


Douglas Stone: Difficult Conversations – How to Discuss What Matters Most. Penguin Books, 2000.

Career Development, Enablers, OD, Staff Development

Being a Mentee – How to Benefit from a Mentoring Relationship

Congratulations, mentee. Someone has decided to be your Mentor.

When Odysseus gave the task of protecting, guiding and educating his son Telemachus to his old friend Mentor, he did this knowing that Mentor would be the best person possible to care for his only son during his absence from Greece. Since then, Mentor is synonymous for someone who is willing and able to provide guidance and support to bring out the very best in his mentee – without any other personal agenda.

The success of your mentoring relationship does not only depend on your mentor, it is significantly more dependent on you to help your mentor in helping you. Your ability to develop a relationship of mutual respect and trust with your mentor defines what you receive in return.

1. Be Serious

If you have been invited to go through the mentoring programme by your organisation, share with your mentor your fears or concerns. This is to avoid you (mentee) feeling “victimised” or “forced” to undergo the programme. If this were truly the case, your mentor would be feeling equally as lousy.

Siew, one of my mentees, was nominated for the High Potential Mentorship Programme. He was very quiet for 2 meetings, he did not show much interest but showed up for both meetings. On the 3rd session, I decided to share with him how I feel and I told him that we can cancel this relationship since it may be wasting both parties’ time. Finally, he spoke up and told me that he is very sceptical about such programme as he did not have a good experience with his previous company. He shared with me what he would really wish to get out from this programme. I heard him and much later, he turned out to be one of the best mentees I ever had.

2. Be Prepared

Spend some time to prepare yourself before entering into the mentoring relationship; do some planning and self-assessment. This includes setting your own goals and what you expect from your mentor.

  • What’s important to you now? (e.g. leadership capability, personal effectiveness, career, professional development)
  • What do you expect to gain from your mentor?

Jot it down and share with your mentor on the first meeting. Ask your mentor what his/her expectations are of you. A discussion to align expectations at the beginning of the relationship can prevent misunderstandings that can damage the partnership. Clarify this topic and let it serve as a guide for your relationship. You will be surprised by the new things you would have learned when you reflect back on this a few months down the line.

Here is a template for you to do a self-assessment, i.e. self-reflection activity for you, the mentee, on your own with the purpose of identifying what you wish to gain from a mentoring relationship.

Mentee Readiness Self-Assessment Form

Mentee Readiness Self-Assessment Form

3. Be Mature to Manage Up

Managing up is one way of cultivating the mentoring relationship. Managing up means you (mentee) takes ownership of the relationship, letting the mentor know what you need and organise information in the form the mentor prefers.

Finding a successful mentoring relationship is like dating: one cannot expect a perfect fit every time, and a good relationship requires work from both parties. Dissatisfaction may occur from a mismatch of goals, commitments, expectations, or from a reluctance to own and pursue your own development; a reluctance to ask for personal help. There can be power issues, generation tensions (over differences in work schedule expectations) or personality clashes (over differences in communication or work style).

As a mentee, you must express your needs in a direct manner and take responsibility for setting and sticking to a goal schedule. Managing up makes it easier for mentors to help you, and it makes the relationship more satisfying and more successful for both parties because the mentor can target help and you get exactly what you need most.

4. Be Receptive to Feedback

Feedback, although difficult to hear at times, is critical to your personal and professional growth. Demonstrate that you are open to suggestions to bring out your best and overcome any of your blind spots. Take initiative to ask your mentor for feedback. Get feedback on specific issues, for example, how you come across to others. Ask for specific details to ensure you understand the specific behaviours. Use SBI (Situation-Behaviour-Impact) method to ask for feedback.

5. Be Reflective and Make Every Moment Count

Unless we reflect on our experiences, we often miss out the gems in moments we spend with each other, including our mentor. Keeping a mentoring journal is one suggestion for capturing and remembering the lessons learned through this important relationship. After each meeting, ask yourself what you learned from the meeting and how you can apply the learning. Summarise your responses to these questions and share them with your mentor. Let your mentor give you feedback and ask him or her – as well as yourself – if there’s anything else you have learned through the meeting.


As a mentee, you are the ‘gauge’ to measure the success of a mentoring relationship. This success depends mostly on you. Make use of this opportunity and you will gain more than you ever expected. Enjoy your learning journey!

About the Author

Amy BC Tan is a Partner with Centre for Organisational Effectiveness (COE). She has more than 20 years of experience in Human Resource. Her expertise has been in Organisational Development, HR Strategy & Planning, Competency Modelling, Change Leadership Development, Talent Management, Succession Planning, Performance Management, Mentoring and Coaching. Amy’s career experiences were with companies such as AT&T, Nokia, Aon, Ministry of Manpower and Singapore Youth Olympic Games Organising Committee. Amy is also a Six Sigma Black Belt. She can be reached at

Leadership, OD, Staff Development

Being a Mentor – How Not to Disserve Your Mentee

When you agree to mentor another person, you offer to help someone in his/her development in the organisation. By mentoring, you have no agenda of your own and thus you are able to create a safe arena within which to develop a trusting relationship.

Mentoring Relationship

Mentoring Relationship

Mentoring is not always easy and as natural as we expect. Here are some tips on how not to disserve your mentee.

1. Make Time

Cancelling appointments at the last minute, turning up late or leaving early or showing up for meetings in a rush without knowing your mentees’ priorities are common worst practices by mentors.

I agreed to mentor 3 young managers in my previous organisation. After a couple of months, I realised that I am not able to keep to all the meetings with my mentees while performing my daily role as the Head of Department; attending to several internal and external meetings. I found myself dancing on my schedules with my mentees – postponing appointments one hour prior to the meeting.

I knew Eva, Jack and John were not very happy with me changing schedules frequently at the last minute, but they did not dare to tell me how they felt. I only learnt about it during the mentoring mid-way review feedback survey. Luckily I had another 9 months to repair my relationship with my mentees. Things turned out well after I committed myself to allocate the same priority to both my meetings with mentees and other business dealings. I have also learnt to delegate work to my team members – something which I taught my mentees to do!

Mentoring is a commitment – you need to set aside time to prepare for the meeting and afterwards to reflect and prepare notes. Therefore, do not over-commit to too many mentoring relationships at the same time.

2. Be Patient and Don’t Make your Mentee Become You

You may sometimes feel that you know exactly what to do, from similar experiences, when your mentee explains his/her challenges. So, it can be frustrating to see your mentee taking a longer time to find the right solution. Good mentors are patient, letting their mentees find solutions with guidance instead of blunt instructions, no matter how long it takes.

Eve just got her promotion to a Team Leader role in her department. When she related her challenges in people management and her problems in engaging her team members to be aligned with her objectives, I could see the then-me in her. Instead of sharing with her my problem-solving skills and letting her find the solution, I was telling her how to tackle the issues using the same way I did before. I told her what she should say and do. I even called her a week later to check if she had done exactly what I told her.

Later, Eve shared with me that she was not very comfortable in doing exactly what I instructed, and that she would prefer to take more time to build relationship with her team members. It then donned on me that I have made one of the biggest mistakes in mentoring – I was focusing on ME rather than developing my mentee!

Mentoring is about developing mentees’ talents, not turning them into carbon copies of their mentors. A mentee’s success often follows a very different path from their mentor’s. Respecting and cultivating people’s individuality is more rewarding than just solving their problems. By doing so, mentors may even widen their own horizon.

3. Don’t Start Telling Too Many Stories

Sometimes a good personal anecdote is the perfect way to make a point. Your mentee wants to learn from your experience, after all. But don’t start telling too many stories that are more indulgent of yourself than helpful to the mentee.

Jack is a very quiet person. Our conversation tended to be very formal and sometimes I found myself referring to theories I picked up from books or articles, and at times I used my personal ‘war stories’ to relate to the subject. He listened attentively, usually. Our meeting could last about 1 to 2 hours – with me talking most of the time!

I decided to ask him for feedback on our mentoring relationship and how else I could better support him as mentor. Jack said to me that my personal experience is a useful reference but he felt it was rather difficult for him to relate to his own challenges. He told me that it would be good to keep the sharing succinct and focus more on ways to address the issues. He liked the challenging questions I posted to him as they did help him think through the essence of the support and guidance he needed from me.

I have been reminded by this episode that mentoring relationship is a two-way street, not a lecture hall. I have also learnt to make sure I leave room for my mentee to make decisions, and encourage them to develop and trust their own judgement.

4. Mentoring Also Means: Giving Feedback

Every now and then, it might be appropriate to give your mentee some feedback which describes your response to the “story” you have heard. I prefer to package my feedback using the SBI technique:

  • Situation and circumstances at which the behaviour occurred.
  • Behaviour you have observed.
  • Impact of this behaviour on you and others.

You might, for example, want to give him/her positive feedback on how he/she has handled things so far. Or challenge his/her behaviour or attitude in response to the issue.

Whatever form your feedback takes, you should observe the following ground rules:

  • Ask your mentee if he/she would like to hear your feedback and respect his/her right to say ‘no’
  • Focus on specifics and avoid generalisations, especially if you are giving feedback on the person. Use the Situation-Behaviour-Impact (SBI) technique.
  • Give less rather than more; focus on the key resources that will be most useful for the other person to hear
  • Avoid wrongfully highlighting to your mentee that you are an ‘official’ mentor to his/her role.
  • Emphasise that your feedback is an opinion, not a fact. Emphasise that this is only your response, and that it says as much about you as it does about him/her
  • Allow your mentee to respond to your feedback

Mentoring is about believing in someone and then taking action to help that person be his or her very best. Do try to use the above tips while embarking on a fulfilling and rewarding experience.

Categorized Tag Cloud
Privacy Settings
We use cookies to enhance your experience while using our website. If you are using our Services via a browser you can restrict, block or remove cookies through your web browser settings. We also use content and scripts from third parties that may use tracking technologies. You can selectively provide your consent below to allow such third party embeds. For complete information about the cookies we use, data we collect and how we process them, please check our Privacy Policy
Consent to display content from Youtube
Consent to display content from Vimeo
Google Maps
Consent to display content from Google
Consent to display content from Spotify
Sound Cloud
Consent to display content from Sound