Preparation Work Before You Start Mentoring / How to Better Your Mentoring Skills

I have been blessed with so many wonderful mentors in my life. Some I owe my craft and attention to detail. Some I owe my confidence and leadership. Some I owe my addiction to inspiration. And some I owe my ability to knock out an amazingly thorough and widely utilitarian spreadsheet. And one, I owe my start.

I cried when I took this. But it’s proof of how important the mentoring responsibility is, since it can have a major impact on how someone works, sets goals, grows and sees their path forward. The effects of mentoring can resonate even two decades later. This picture specifically is also an opportunity to keep sharing how Marcus Dickerson was the best teacher, creative director, and best mentor I ever had. Marcus hired me one year and 3 months after the first email was written. After the second email, I was asked to take on his role when he left.

What was common across the best of my mentor spectrum, was how each mentor pulled from their own experiences. Instead of just giving me advice, they’d tell me where and how they learned what they were teaching or sharing with me.

There are a handful of global mentor matchmaking platforms now, with ADPList being at the forefront. And that’s so awesome and so needed, if you can’t find one through 1st and 2nd connections, colleagues, teachers, managers and peers.

I scoured the hundreds of scholarly “Finding A Mentor Is Crucial” and “Mentoring Is As Good For You As It Is For Them” articles and books for nuggets of wisdom I could put together a few years back, when I was asked to create the onboarding materials and onboarding workshop for my former company’s mentoring program. Younger team members from my office put the program together, so they could grow in their mentoring skills, as well as mentor students and career changers who wanted to get into UX.

The founders and the first cohort collectively didn’t have a lot of mentoring experience, so I put together what I could to make them more successful. Like my best mentors, I pulled from what I knew. I pulled from the course I taught about professional development and knowing yourself.

Suggested Activities to Prepare for Being a Mentor

Before taking on the important responsibility of being a mentor, there is some very intentional work you can do for yourself to be as good of a mentor as you can be. The pre-work will help alleviate any “should I be doing this?” and “am I being a good mentor?” questions that often happen mid-mentoring-relationship (if being a mentor is your only relationship to your mentee). Below is the syllabus for the aforementioned workshop, restructured as a guide for personal introspection and growth.

A Meta Guide to Mentorship

Original introduction to the workshop

It’s hard for someone to mentor if they haven’t been able to identify their own experiences. So the workshop format will take the mentors through the exercises/discussions they should have to lead a formal mentoring relationship with their mentee.

The long game is: you can take your mentee through the same exploration (so you might see “mentee” references).

What You Need to Get Started

• An existing review (360 review, manager review, etc.) and/or a personal Myers-Briggs, Enneagram, or similar read-out.
• Ideally a paper journal / notebook

Before You Start

Pick two of the 9 life lessons that might have inspired you from watching the commencement address below.

Active Journaling

• As you mentor and/or prepare to mentor, actively journal your own goals and experience (and advise your mentees to do the same).
• Create a log / journal of some kind to be able to track your own development and progress over the mentorship / your growth / career.
• Set regular check-ins with yourself or your own advisor / mentor.

Starting Reflections

This is an icebreaker to the process. In your journal, start by answering the following questions.

• Have you mentored before?
• Have you had a mentor before, and if so, what is/was their greatest trait?
• What are the 2 life lessons that inspired you most from the commencement address you watched?

Set your own goals.

• What are your personal goals for mentorship?
• Make your goals “SMART” by being specific, measurable, attainable, relevant and timely.
• Aim for 5 goals total.
• Set check-in times.

Be who you see. Think about and discuss traits of your own mentors and/or people you admire.

• When figuring out what kind of mentor you want to be, it’s helpful to think back to leaders you have worked with directly and indirectly.
• What traits you admire and why.

Bring in existing assessments / reviews.

• If you / your mentee has existing reviews / assessments to reference, review (and discuss) them.
• If you don’t have existing reviews, try Myers-Briggs, Enneagram, etc.

Revise your goals.

• Revise your goals based on your assessments and the traits you admire.
• Are the timelines set appropriate or do I need to reprioritize?
• Get feedback from someone you trust.

Pay it Forward.

Once you’ve done all of the above, you can do these same activities with your mentees. You’ll be able to pull from your own story to advise. Remember: mentoring isn’t about giving your mentee the answers, it’s about leading them to find them on their own.

When you’re ready, here are some low to high effort activities you can work on with your mentees.

Mentor / Mentee Activities

Activity 1: Interview Questions + Prep Work

In a handful of sessions, go through these Interview Questions and Prep Work with your mentee. This is a deep-dive activity that borders on coaching. It entails going through a long list of interview questions together. Even if your mentee isn’t looking for a new job, talking through these questions is valuable in getting to know them. And at the end of the day, if they’re able to answer these questions, they’ll give a solid interview when they do look for opportunities. Effort Level: Medium to High

Activity 2: Network Roll Call

Ask your mentee to read this article about knowing Your Network. Once they’ve read it, ask them, “who are your people?” and use that as a jumping off point for conversation. Effort Level: Low

Activity 3: Personal Vision Inventory

This activity takes time and dedication. In this activity, you’ll walk through and coach your mentee as they create their Personal Vision Inventory. Effort Level: High

Activity 4: Personal Brand Brief

This activity also takes time and dedication, and along with the Inventory in activity 3, were the starting point for a larger vision deck. In this activity, you’ll walk and coach your mentee through creating a Personal Brand Brief for themselves starting with ten questions modeled after the creative brief questionnaires I drowned in early in my career. Effort Level: High

Activity 5: Dream Job Search

This activity can be done in a meeting with some prep-work by your mentee. Discuss what and where their dream job might be. Ask them to come up with a list of 10 places they’d love to work and why. When you meet, discuss their answers with them. Effort Level: Low

Activity 6: Hero List

This activity can also be done in a meeting with some prep-work by your mentee. When you first start your mentor/mentee relationship, plant the question in their mind, “who are your heroes?”. Who do they look up to? If they can’t think of someone(s), ask them what product or service they think is really well-designed, marketed, etc. Let them marinate on this for a month or so, and then give them the assignment of creating their “Hero List” — a list of 10 people, groups, companies or things that inspire them. When you meet in person, discuss their answers with them and dive deep into the “why’s”. How can you help them get there? Effort Level: Medium

Activity 7: Professional Organization Dates

This one is easy-peasy, though it might entail some monetary sponsorship (if you see the need and can accomodate). Encourage your mentee to join a related professional organization, and attend events with them. Find events that align with your conversations and their aspirations.

Larger Scale Mentor / Mentee Coaching Project

If you want to step up from casual mentee to career coach, the following activity is a longer term effort, with major impact. The activity below was one of the major projects of the portfolio and professional development foundations course I taught at the University of North Texas Visual Communications and Design program. This was the class they took the semester before their final portfolio / exit review semester — and sometimes it prepared them for their final semester internships. The semester-long assignment resulted in a final Personal Brand Presentation Deck that served as the foundations for their creative confidence and projection of their skills and aspirations. After they created their brands and thought through all the questions that led them to finish their presentation, a handful of creative directors told me they were the most solid, confident and well-prepared interviews they’ve given. “Even better than some of my senior employees.”

Activity 8: Creating a Personal Brand.

This is a longer term effort. And no, it isn’t a “how to be an influencer” project. Brands are about projecting an essence of character and values. This activity entails working with your mentee to create their own brand deck (however you can nix the logo if they’re not graphic designers or fear branding). This activity starts off with creating a Personal Brand Brief and Personal Vision Inventory (activities 3 + 4).

This Personal Brand Presentation / Package includes:

• Personal logo and design system.
• Refined personal mood board.
• Personal brand vision.
• Values statements.
• A completed SWOT analysis.
• A list and definitions of personal attributes and strengths.
• A: What do you want to create in the future?
• A: Where do you want to be in the future? 1 year, 3 years, 5 years.
• A: What impossible thing do you want to make possible?
• A: What are your goals? 1 year, 5 years, 10 years.
• A: Describe the perfect day in the future as you imagined it.

Activity 9: Journal / Blog

Effort: Low / Satisfaction: High … This is an easy activity you don’t have to actively monitor. But as you mentor your mentee, and take them through the activities above, encourage them to write (and share) about their mentorship experience in a blog of some sort (are they still called blogs?). They can use Tumblr, Medium, LinkedIn to do so. Encouraging them to write about their experience helps them exercise their writing skills and encourages them to think about their needs and what resonates with them. This helps them find their voice, and if you follow their posts, it will also help you see where you’re making an impact and areas you might focus on to keep growing as a mentor.

Hopefully, the above can help you onboard or re-onboard yourself to mentoring. It’s such an important and impactful part of a mentor and mentee’s growth. But don’t let the weight of that take the fun out of it. Enjoy working through the activities above, and make sure to be aware of and allow yourself to experience the joy and fulfillment you feel when you mentor. Great mentors make the world better, so make sure to better your mentoring skills, and pay it forward.