The Encouraging Mentor

To become a great mentor, you must do two things: Encourage and Challenge

How can you tell if someone needs encouragement? The easy answer is simply check for a pulse. Whether successful or struggling, we all need encouragement.

But we also need to be challenged. These two seemingly disparate approaches can work together to help people flourish, develop their natural gifts and talents, and subsequently make their lives and our world a better place.

In my nearly 40 years of professional experience working in private industry, local government, non-profit management, and higher education, I have discovered good mentoring conversations can simultaneously encourage and challenge people when done at the right time and in the right manner. Whether co-workers, colleagues, students, those you supervise, or even family members, mentoring can be a powerful tool anyone can deploy. But how you approach mentoring is critical. Determining the right questions matters. Your approach determines your effectiveness.

Here are two conversation previews to give you a flavor of how anyone can use this book with no training.

Conversation #3: Five Things to Have, Do, Help, and Be

Instead of asking someone what they want to do in their life, ask them who they want to become.

Purpose: This exercise can help those you mentor envision and create the future they desire. It challenges them to think in distinct but related categories.

Background: Everyone… every company, every non-profit, etc. has two options for the future. These are the one that will be if we do nothing and continue the status quo or the one that could be if we work to achieve it by planning and acting to reach desired ends, goals, dreams, mission.

The Discussion: Remind your mentee that most people are asked at an early age, “What do you want to be when you grow up?” We often prompt young minds with examples: “Do you want to be a firefighter? A teacher? A farmer?”

What if the more important question is: “Who do you want to become?” This is qualitatively different. This is perhaps the best question to ask to prompt future thinking, focus, and goal setting.

In your mentoring meeting, divide a blank paper into fourths, write “5 things I want…” at the top, and then write one prompt in each quadrant. Give your mentee time to jot down one or two items in each box as you discuss them. When completed, challenge them to carry this around, think, reflect, and update it over the next few weeks. Reflection over time is powerful. Afterward, suggest they discuss insights with a trusted friend or family member.

What are 5 things you want…

…to have: (These can be tangible or intangible.)

…to help: (These can be big and small. Think broadly.)

…to do: (This is about what you might do: jobs, career, things for fun, Bucket List items, etc.)

…to be: (Not what you might do, but who you might become.)

Analysis: Look at the things you want to have and to help. Really consider them. Now, will the things you want to do move you in the right direction to accomplish them in the future?

Challenge Activity: The To Be category will reflect how people remember you. (i.e., When someone thinks of you, what pops into their mind?) Consider two action items that will help you accomplish who you want to be and how you want to be remembered. Some may be short-term, some long-range. For example: If you want to be remembered as someone who was kind, what can you start doing to accomplish that? Jot a few ideas down.

Preview Conversation #9: From “Why?” to “What?”

When bad news hits, can you change the question in your head from, “Why is this happening?” to “What can I learn?”

“I am sorry Mr. Raison. You have cancer.”

I heard nothing after that.

It was August 2014. I’d gone in for a routine colonoscopy having hit the magical age of 50. Outpatient screenings had become quite accessible and recommended. But at 50, I knew how these things were supposed to go. If they find anything slightly suspicious, the doctor says, “We found a small spot and have sent it to the lab for a biopsy. We’ll not even call unless there’s a reason for a follow-up test.”

Right? No doctor ever just walks in the room, sits down, looks you in the eye, and says, “I’m sorry. You have cancer.” That’s not how it works. Or so I thought.

It’s remarkable how many things can run through your mind in an instant. There is an explosion of thoughts… pictures of those you love… of your hopes and dreams… of questions like, “How long do I have?” But after a few hours of settling down (often protracted and greatly worsened by Googling things like, “colon cancer survival rates”… which I would NEVER recommend), one question emerges, and often lingers: “Why is this happening to me?”

I think it’s a legitimate question, and I think it’s natural to ask. But it’s dangerous to remain in that space. Asking “why” does nothing helpful because there is no answer. Cancer happens.

And guess what. Job loss happens. As does stress. Emotional breakdown. Pain. Death. Or how about criticism? (That can be extraordinarily painful.) Write your own list. Better yet, don’t. Instead, see if you can reframe the question (and your thinking).

The Switch:
When faced with a major life challenge or pain-point, here is perhaps one of the most powerful things a person can do: Instead of asking: “Why is this happening?” Ask, “What can I learn?”

As a mentor, if you can help someone shift their response from “why” to “what,” you can literally change their life.

The Final Challenge:

Once you’ve changed the question from “Why is this happening?” to “What can I learn?”, it’s now time to ask yourself: What can I do?

Let your mentee know it’s okay to take some time with this question. Continue your discussion as you feel comfortable.