A mentor and mentee having a critical conversation

Skills for Effective Mentoring: Difficult and critical conversations

February 2, 2024

Posted by BOLDLY

Sometimes, as part of the mentorship process, you find yourself in situations where you would need to have a difficult/ critical conversation with your mentee eg. you do not think they are putting in enough effort to drive their own success.

The consequence of not having that uncomfortable conversation is costly, and prolonged tension without open conversations lead to disengagement, and even conflict between the mentor and mentee. 

Handling the difficult conversation requires skill and empathy, but here are some tips to guide you in the process. 

  • Be clear about the issue

To prepare for the conversation, you need to ask yourself two important questions: "What exactly is the behavior that is causing the problem?" and "What is the impact that the behavior is having on you and the relationship?" You need to reach clarity for yourself so you can articulate the issue in two or three succinct statements. If not, you risk going off on a tangent during the conversation. The lack of focus on the central issue will derail the conversation and sabotage your intentions.

  • Know your objective

What do you want to accomplish with the conversation? What is the desired outcome? What are the non-negotiables? As English philosopher Theodore Zeldin put it: A successful conversation "doesn't just reshuffle the cards: it creates new cards." What are the new cards that you want to have in your hands by the end of the conversation? Once you have determined this, plan how you will close the conversation. Don't end without clearly expressed action items. What is the person agreeing to do? What support are you committed to provide? What obstacles might prevent these remedial actions from taking place? What do you both agree to do to overcome potential obstacles? Schedule a follow up to evaluate progress and definitively reach closure on the issue at hand.

  • Adopt a mindset of inquiry

Spend a little time to reflect on your attitude toward the situation and the person involved. What are your preconceived notions about it? Your mindset will predetermine your reaction and interpretations of the other person's responses, so it pays to approach such a conversation with the right mindset—which in this context is one of inquiry. Be open to hear first what the other person has to say before reaching closure in your mind. Even if the evidence is so clear that there is no reason to beat around the bush, we still owe it to the person to let them tell their story. A good leader remains open and seeks a greater truth in any situation. 

  • Manage the emotions

Most of us were likely raised to believe that emotions need to be left at the door. We now know that this is an old-school approach that is no longer valid in today's work environments. It is your responsibility as a leader to understand and manage the emotions in the discussion. The late Robert Plutchik, professor at the Albert Einstein College of Medicine, created a Wheel of Emotions to show that emotions follow a path. What starts as an annoyance, for example, can move to anger and, in extreme cases, escalate to rage. We can avoid this by being mindful of preserving the person's dignity—and treating them with respect—even if we totally disagree with them.

In some cases, you may have to respond to a person's tears. As a strategy, it is important that one acknowledges the tears rather than ignoring them, offering the person a tissue to provide an opportunity to gather his or her thoughts, and recognizing that the tears communicate a problem to be addressed.

  • Be comfortable with silence

There will be moments in the conversation where a silence occurs. Don't rush to fill it with words. Periodic silence in the conversation allows us to hear what was said and let the message sink in. A pause also has a calming effect and can help us connect better. For example, if you are an extrovert, you're likely uncomfortable with silence, as you're used to thinking while you're speaking. This can be perceived as steamrolling or overbearing, especially if the other party is an introvert. Introverts want to think before they speak. Stop talking and allow them their moment—it can lead to a better outcome.   

  • Preserve the relationship

A leader who has high emotional intelligence is always mindful to limit any collateral damage to a relationship. It takes years to build bridges with people and only minutes to blow them up. Think about how the conversation can fix the situation, without erecting an irreparable wall between you and the person. 

  • Be consistent

Ensure that your objective is fair and that you are using a consistent approach. Nothing erodes a relationship faster than perceived inequality eg. setting certain standards for your mentee when you show signs of not following through with the same standards. Aim for consistency in your leadership approach, and believes. We trust a leader who is consistent because we don't have to second-guess where they stand on important issues such as culture, corporate values and acceptable behaviors.

  • Develop your conflict resolution skills

Conflict is a natural part of human interaction. Managing conflict effectively is one of the vital skills of leadership. Have a few, proven phrases that can come in handy in crucial spots.

  • Choose the right place to have the conversation

Find a place to have a nice, open and frank conversation. Avoid places where your mentee feels vulnerable eg. in front of colleagues your mentee works together most of the time. If most of the mentorship session is done over video chat, conduct the conversation in a face to face setting if possible. Even simple body language, such as leaning forward toward the person rather than leaning back on your chair, can carry a subtle message of your positive intentions; i.e., "We're in this together. Let's problem solve so that we can get through this together." A private meeting room, or even a cafe/ coffee shop might be ideal for such conversations. 

  • Be direct with the approach

The best way to start is with a direct approach. Being upfront is the authentic and respectful approach. You don't want to ambush people by surprising them about the nature of the "chat." Make sure your tone of voice signals discussion and not inquisition, exploration and not punishment.

Looking for more resources?

Mentoring programs for organisations

How does mentoring differ from coaching?