6 steps to modern mentorship

Finding a design mentor can be incredibly difficult. Organizations are shifting away from traditional design silos to cross-functional teams, eroding design support systems in the process. Certain design leaders in your organization may not be trained in the digital expertise of the current market.  

And due to the ever-changing standards of design, both junior and senior designers are struggling with what to learn next. Senior designers are required to continuously expand their digital tool set; junior designers may be are proficient in more tools, but lack real-world practice and leadership qualities to level up.

Fortunately, it’s easier than ever to connect with talented, experienced professionals. By taking a less formal approach to mentorship, you can speak with mentors across disciplines, industries, and locations. Instead of choosing one person as your long-term guide, gather various opinions all at once, and make decisions based on your collective research. You’ll receive a wealth of information that will greatly level up your skills, regardless of what the future brings.

Step 1: Start with yourself

To prepare for your mentor search, first ask yourself: 

What kind of person are you now?
Do a SWOT analysis to identify your personal:

• Strengths
• Weaknesses
• Opportunities
• Threats 

What comes easy to you? What tasks do you struggle with? What would you like to accomplish, and what will help or hurt your chances?

Remember, this is just a way to assess who you are right now, and these characteristics will change over time. Re-evaluate yourself throughout your career.

If you aren’t sure how to answer these questions, ask a colleague you trust to help.

What are your goals for the future?
Draft a life blueprint to define your ambitions. Or set SMART goals:

• Specific
• Measurable
• Achievable
• Relevant
• Time bound

Spend the necessary time to think about your goals. (This is more important than learning the newest tool.) If you don’t know what you want, it’ll be impossible to find a mentor to help you get it.

Again, remember that these goals reveal what you want in this phase of your life. Plan to revisit and refine these goals over time.

What are you willing to struggle for?
Everything you want requires a sacrifice. Trading money for freedom, creativity for security, or free time for more work are all possibilities—especially if you’re a designer. Decide what you can part with, as well as what you can’t, and be honest with yourself. If you aren’t willing to make certain sacrifices, you may need to reevaluate and redefine your goals.  

Step 2: Find your mentors

Mentorship doesn’t have to be a formal agreement between you and a senior person—you can learn something from everyone. Think about people you respect who are already in your life: current and past colleagues, friends and their spouses, and family members. What traits do you respect in each of them? Who has steadily progressed in their careers?

Expand your search and review friends of friends on LinkedIn. Read the bios of upcoming speakers at events you’d like to attend. Or try Officehours.io, where you can browse potential advisors for free advice. Seek those who have acquired the titles you want, accomplished the goals you’ve defined, built the products you love, or worked with companies you admire.

Don’t limit your mentor search to people in the design industry. Consider leaders in industries you’d like to work with—they can give you insight on what they value most in designers, and why. Or find specialists in areas where you lack expertise—perhaps you’d like to strengthen your business acumen, presentation skills, or digital knowledge. Look for people who have shown tenacity and endurance, and have gracefully transitioned their careers to match the needs of the market.

Widen your search to cities other than your own, both nationally and internationally. We often work with others who don’t live in our own city, and may not consider subtle factors that shape beliefs in other regions. It’s well documented that San Francisco has an engineering history, while New York is rooted in finance and media. But you might not know why the startup scene in Beijing has more engineering talent than Hong Kong. Speaking with people from these different areas worldwide will only enrich and expand your possibilities.

Make a list of 10-30 people you could learn from.

Step 3: Initiate contact 

You must make the first move. If you don’t, no one else will do it on your behalf.

To ease yourself into it, start with reaching out to your own network, and work your way up to speaking with strangers. With practice, it gets easier to approach those you don’t know very well. And people can be surprisingly generous with their time—the smartest leaders know that they don’t know everything, and they’ll want to hear your perspective in order to enhance their own knowledge. 

When introducing yourself to your prospective mentor, be sure to communicate:

• Specifics on what you admire about their career path (or anything else)
• A brief overview of your strengths and unique perspective (from Step 1)
• A personal goal you have (from Step 1)

Then, ask if they could spare a future 15 minutes, either in person or via phone/video chat, to discuss their perspective on your goal, and what they think would help you achieve it. 

Example: “I’ve been thinking about switching career paths to your area of specialty. I’ve done a lot of research, but it’d be great to hear first-hand about your experience. Would you be able to spare 15 minutes for a quick chat next week? I can meet whenever or wherever is convenient for you.”

Ways to make contact:

Ask people you already know
Send casual emails to your colleagues, friends, and family, and start practicing the process.

Get a friend to introduce you
This works well when your good friend is also good friends with your prospective mentor (acquaintances are less successful). Use an email introduction to ask for their 15 minutes.

Go to their speaking events
Be the first in line after the event, tell them what you enjoyed in their talk, and transition into your mentor ask. This is the easiest way to secure a future meeting with a stranger, because they get to vet you in person first.

Send emails to people you don’t know
Practice with your alumni network or Officehours.io, then branch out and send short, friendly messages to people you greatly admire via Twitter, Medium, or their personal site.

If you’ve contacted 10 new people, you should have at least one new appointment.

Step 4: Set the agenda

Remember, this chat is about using their valuable experience to inform your career path. Research each person so you don’t waste time asking questions that Google can answer. 

Demonstrate that you’ve done your homework, and tell them why their background is especially relevant to your goal—because you’re struggling with (work-life balance, changing of technology, etc.).

Ask smart questions targeted towards achieving your specific goal. Use this opportunity to learn answers that aren’t “one size fit all” and that are directly related to your problem at hand.

Example: “I noticed on LinkedIn that you switched career paths from ______ to ______. How did you successfully manage to do that? What was the hardest part? What do you wish you had known then that you do now?” 

Show them your personality to see how you communicate and react to each other. With some people, you’ll get viewpoints that won’t resonate with yours. With others, light bulbs will go off and you’ll want to refine your approach with their advice.

Take the advice of one person and repeat it to others—does it ring true to them? You’ll find that everyone has a slightly different opinion, and the more people you speak with, the better informed you will be for the next meeting.

Step 5: Aggregate the data, and repeat the process

Once you start gathering all this information, you’ll realize you have more questions that need to be answered by people with different skills and expertise.

After every meeting:

• Send a thank you note that reinforces the most valuable parts of your conversation (so they know what resonated with you)
• Ask for recommendations on who you should speak with next
• Reshape your goals based on the new information you have received
• Repeat your search for 10 new people

Think of yourself as the product you’re looking to improve, and these meetings as user research interviews. Define the target segments you should speak with next, and reach out to them.

And don’t forget to keep in touch with updates on your progress. Share how their information has directly helped you so they can keep it in their problem-solving toolkit.

Step 6: Make your own rules

Steps 1-5 are based on what has worked well for me. I’ve constantly sought out leaders to inform my own career path, and I’ve personally met with product managers, business development, strategists, data analysts, and designers at dozens of companies, including Baidu, Google, The New York Times, MasterCard, MyFitnessPal, and Amplify. Speaking with people in all different areas opened my eyes to new ways of approaching problems. I’ve been humbled many times by realizing how much more there is to learn.

You can use these steps as a guide to modern mentorship, but I encourage you to experiment and find what works best for you. And don’t hesitate to contact me and tell me about your approach so I can try it.

If you’re in NYC next Thursday, October 27th, I’ll be speaking about Surviving Design Politics at Alpha headquarters. Location, details, and RSVP here. Come and say hi!

Read more posts on mentoring

• How to be a great design mentor
• What’s the best advice you’ve received from a mentor?