A High Schooler or Someone with only an High School Diploma just asked you to be a mentor for them. You’re honored, sure, but maybe a bit nervous about filling such an important role in their life and career.

Totally normal. Fortunately, there are some steps you can take to start things off well and make this a valuable experience for both of you.


You’ll start off by setting the right expectations. First, what does the mentee want and need?

  • Their area of focus
  • More specific goals to achieve
  • Timeframe
  • Form and frequency of meeting
  • Defining what exactly is meant by “mentoring”

This last one is particularly crucial, because the word “mentor” isn’t well defined in our culture. Often mentees might come with: “I’m stuck, so tell me what to do.” But this is more of a boss role, where you’d have the right and duty to direct your employees.

A better mindset would be: “I’m stuck, can you help me to figure out where to go next?”

Or: “I’m not satisfied, and I’ve decided that I want to follow the path you’ve taken.”

Or: “I respect your thinking, and since two heads are better than one, would like to bounce ideas off you.”

Or: “I know I have some blind spots, and I think you can help me become more aware and therefore successful.”

These statements progressively show that the mentee is becoming more self-aware and more open to making deeper decisions.

So when you start off a mentoring relationship, make sure you’re on the same page regarding the area of focus and what you can both expect by working together.


A successful mentoring engagement starts with clear goals. What is the mentee hoping to actually achieve?

  • Clarity on career decisions
  • Building skills
  • Opening doors

And then what would the results be?

  • A new job or internship that I’m happy with
  • More influence in my organization
  • Getting paid better because I’m more valuable

Then, what are YOUR goals as a mentor?

  • Help someone like others have helped you
  • Build long term relationships
  • Learn things yourself

The more clearly you can define the end goals, the more productive and focused your conversations will be. Always be asking: Does this help advance toward our shared goals?


Being a mentor can really feed your ego. But the challenge is that it’s about the mentee’s goals, not making you feel appreciated.

One result is that you can spend a lot of time pontificating, giving advice, and feeling smart. The mentee will give you positive feedback for doing this, because it feels useful.

But often it’s not.

The reality is that people learn by going through their own internal struggles and decisions, then taking action and seeing what results. Mentoring can be a great wonderful space for mentees to do exactly that, with safety and support.

Your best role as a mentor is to:

  • Listen
  • Ponder
  • Reflect
  • Suggest
  • Support

You’ll know you’re on the right track when you listen a lot more than you speak, and you ask questions more than state declarative sentences. Remember that what worked for you may not work for the mentee, especially if your goals were different than the mentee’s goals.


The purpose of your mentor-mentee relationship should be to actually get something accomplished. Ideally it’s measurable, timely, and valuable.

So part of your role is to help your mentee to stay accountable to their goals. Note that I didn’t say they’re accountable to YOU – your role is only to hold up a mirror to their progress so they can see what’s moving and what’s stuck.

Imagine that the mentee comes to you today and says they haven’t done anything you talked about a month ago. Consider this range of interactions:

  • “I’m disappointed in you.”
  • “I had hoped you’d do more.”
  • “What was the problem?”
  • “Are you OK with that progress?”
  • “Where did you get stuck?”
  • “Do want to change your approach next month?”
  • “What support do you need from me?”

The first ones sound quite judgmental, and can lead the mentee to be overly self-critical or assign blame to others. As we proceed down the list, it’s more about helping the mentee to reflect and learn from what happened. The bottom one might be OK sometimes, but may also lead the mentee to give ownership of the progress to you, rather than owning it themselves.

The mechanism you use for tracking progress should be something which helps and motivates the mentee without discouraging them. Some people really like checklists, while others want to create some kind of project plan. Some love things written down, while others are motivated by the verbal conversation. Some are hoping to see external indicators of progress like improved job evaluations.

So work with your mentee to create an accountability mechanism which achieves the right balance. It should prompt them to be a little more courageous and take some risks, while not demotivating them when things don’t proceed perfectly.

Have fun!

I’m a big fan of keeping my coaching sessions light rather than heavy. After all, we’re all human and things never go perfectly.

If the mentee feels that you’re just adding weight to their shoulders, things will fall apart pretty quickly and they won’t achieve their goals. So neither will you.

Keep the conversation optimistic, forward-looking, and engaging. Avoid blaming, shaming, and creating useless work.

In the end, you’ll both have a wonderful time and improve lives!

Carl Dierschow is a small business coach homed in Fort Collins, Colorado, USA. He specializes in leaders and owners who strive to better society and the planet through thoughtful business practices. He is currently available for free coaching sessions for those whose organizations are struggling with the impact of the pandemic. Feel free to connect with him here on the Foundation platform!

Foundation is an Online Job Marketplace were employers can find quality candidates and where job-seekers can find jobs, internships, job-shadowing, mentorship, apprenticeships, and general advice. This site is mainly for High Schoolers, individuals with only a High School Diploma, employers that higher Job-Seekers that only have a High School diploma, or jobs that don’t require one. The goal of the site is to help our community members make quality transactions with each other. If you want to know more please click here


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