Whether you're a seasoned mentor or just starting, these strategies will help you confidently navigate those difficult mentoring moments and make a lasting impact.

Mentors can support mentees dealing with difficulties directly. By modeling resilience and problem-solving behavior themselves, they can lead by example. Encourage your mentee to view challenges as growth opportunities rather than obstacles. Share your own experiences and guide them in developing effective strategies to overcome difficulties.

Another important aspect of mentoring in challenging situations is providing constructive feedback. Be specific and focus on behavior rather than personality. Offer guidance on how they can improve while also highlighting their strengths.

It's essential to empower your mentee to take ownership of their decisions. Help them identify alternatives and weigh the pros and cons. Encourage critical thinking and guide them toward making informed choices.

Sometimes, challenging situations can lead to conflicts. Share your best experiences and outcomes in handling effective conflict resolution. Discuss skills to counter conflict, such as active listening and compromise. 

Be realistic: not all situations can be resolved through mentoring. In fact, some of your own experiences may include failure to resolve certain situations. Sharing these can be learning moments as well.  

Remember, as a mentor, your role is not to solve every problem but to guide and equip your mentees with the skills they need to overcome challenges independently. Encourage them to take risks and learn from both successes and failures.

3 Ways to Navigate Difficult Mentoring Conversations 

But what can Mentors do when discussing a challenging topic their mentee is facing? It depends, based on the type of challenge and, of course, the specific situation. Learning to stay positive and supportive while being realistic through such discussions can be helpful to the mentee and your mentorship. 

1. Advice on Handling Difficult People

The workplace is a melting pot of diverse personalities. As a mentor, you should guide your mentees on how to deal with difficult people. The first step is to understand that everyone has different perspectives. This understanding allows for empathy, a fundamental component in managing difficult people. 

 "Seek first to understand, then to be understood." 

• Stephen R. Covey, Author 

What do I mean by difficult people? I am referring to people in difficult situations. It's best not to see people as difficult. Doing so can lead to long-term resentment or a break in the relationship that never heals. Difficult situations can be when:

• the situation is complex

• the understanding is not shared

• Emotions run high

• Others disrespect you or your work

The above quote highlights the importance of understanding another person's viewpoint before getting them to understand your own. Teaching your mentee to cultivate this skill as a mentor can significantly improve their interactions with challenging people.

Statistically, about 29% of workers have reported feeling belittled by a colleague. Could you help equip your mentee with the skills to deal with such scenarios, like maintaining calmness and professionalism and not taking things personally?

People may be seen as difficult because they are:

• are bad communicators

• see thing differently

• have conflict goals 

• may be demeaning or disrespectful

When these situations occur, it may be helpful to suggest the mentee validate the situation with someone close to it but not directly involved. Support for the mentee may be needed inside their own organization (a mentor at the company, their manager's manager, or a manager from another department). Setting boundaries is also important. Help your mentee learn to appreciate their own boundaries and ask others to respect them.

Clarifying situations that go beyond 'managing difficult people' is also important. Harassment, prejudice, and similar issues that impact physical and mental health need stronger solutions. Your job may be to help your mentee identify the need to seek support from HR or legal assistance in these cases. Know your mentoring boundaries in these moments, and don't offer solutions or professional advice. But support the mentee's decision to act on their own behalf.

2. Helping to Navigate Through Challenging Tasks

The business world is dynamic, and challenging tasks are part and parcel of a professional's journey. One way to guide your mentees through these tasks is by encouraging them to break down big tasks into manageable parts. 

"The secret of getting ahead is getting started. The secret of getting started is breaking your complex overwhelming tasks into small manageable tasks and then starting on the first one."

• Mark Twain, writer

Research shows that 92% of successful projects are ones where tasks were adequately defined and broken down. Teaching your mentees this approach enables them to tackle complex projects more easily.

When dealing with difficult tasks, it helps to get organized. One of the best ways to do this is to create a project plan. This can be done in Excel, using an online tool, or with pen and paper. A simple work breakdown structure (or WBS) helps you understand the needed steps and how to organize and timebox the effort to complete the work. See this video on how to use a WBS.

If the task does not make sense or seems illogical, it may be good to discuss alternative solutions. This can help prepare the mentee with valuable analysis capabilities. Learning to bring concerns or problems and alternative solutions is key to upward mobility.

Another option is to suggest they seek help when needed. There's no harm in asking for assistance. US a team workshop to problem-solve. It's a good way to gain insight and consensus on the issue. If issue escalation is needed, it is better to ask for help sooner and get the task right than to struggle alone and end up with a poorly done job or a late deadline.

3. Addressing Seemingly Unsolvable Problems

At times, your mentee may need help with problems that seem unsolvable. In such cases, it's crucial to encourage an optimistic mindset. 

"We cannot solve our problems with the same thinking we used when we created them." 

• Albert Einstein, Physicist

This quote signifies the importance of adopting a new perspective when dealing with complex problems. 

One method mentors can use to help their mentees is by applying the '5 Whys' technique. This technique involves asking 'why' five times to get to the root cause of a problem, allowing for a more comprehensive understanding of the issue. 

For instance, if a mentee struggles with a project deadline, the mentor can ask, "Why can't you meet the deadline?" The mentee might respond, "Because I have too many tasks." The mentor can ask, "Why do you have too many tasks?" This line of questioning continues until the root cause is identified and addressed. 

Of course, it is not always that simple. Some issues are really difficult to solve. An open and honest discussion, including the mentor’s experiences, and providing a sounding board to the mentee may be the best outcome during the mentorship meeting.

Another method to address unsolvable problems is to look for workarounds. This can help to figure out what is possible or how to mitigate issues such as:

 "I cannot get the technology in place in time, but I can run simulations on the demo system to test the user interfaces to use the time well. Simulations will help us to prove the concept while waiting for the technical installation." or

"We will need to run this task in parallel. However, we will need to compress the next step and use 2 days of contingency". 

When tasks seem unsolvable, it helps to learn to:

• Break down the problem.

• Look for workarounds.

• Is it possible to address the parts that can be solved and reduce the impact of the rest?

How to Mentor without getting caught up in the problem

Helping Mentors deal with the challenge is real. In my video on Mentoring and Mental Health, I discuss the impact of mentors dealing with the stress their mentees are under. Mentoring moments for difficult situations is never easy. But can be productive. Here are some tips for Mentors when managing these conversations. 

1. Avoid complaining. It is not productive

2. Document the issue and the potential solutions; don’t let the conversation go in circles

3. Review issues/solutions if the point comes up regularly

4. Don't let the mentoring sessions go off-track; stay positive and on-topic

5. If the issue is beyond the scope of mentoring, confirm the next right action is taken

6. Protect yourself - professionally and emotionally

And remember, you have your own work issues, so try to keep some distance and balance when mentoring others.

"When the storm comes for us all, let's hope we're both on high ground."

• The Morning Show

Mentoring is a critical part of personal and professional growth. It involves guiding another individual through various life events. However, the mentor's role becomes even more crucial when the mentee faces challenging situations. This guide to addressing your mentee's painful situations can help you stay balanced and helpful. It can also help your mentee build their personal process of navigating difficult people, complex project tasks, and seemingly unsolvable problems.

Special thanks to Gijs Abrahams for providing feedback and advice on mentorship in challenging situations!