For years, the design industry suffered from a shortage of mentorship. Services like ADPList came along and helped to create a marketplace for mentorship. Many professionals offer an option where you can purchase an hour or a few of their time for a fee. Intro gives you access to experts you may not have thought was possible to talk to.

Why do some experts want you to pay anyway? It’s because most of them actually don’t want to do it. Compensation for their time sweetens a pot a bit, but it’s still begrudging, even if they truly want to help others. Of the 522 million search results for the phrase “can I pick your brain?” most of them contain at least some advice on how to politely say no.

The second biggest piece of advice is to have a more specific question in mind than, “Can I pick your brain?” Anna Goldfarb’s NYT article, “The Right Way to Ask, ‘Can I Pick Your Brain?’” doesn’t bury the lede: “Know what you want” is the first phrase in the subhead.

[Change] the language from, “Can I pick your brain?” to the more friendly, “I would like your advice.” People respond more positively to that phrasing because it conveys intention; that you’re approaching a certain person for very particular reasons.

Here are 5 steps to getting the kind of mentorship that’s helpful to you for free from someone you admire.

1. Do your homework.

If you’re a student who wants advice about a career as a designer, don’t just pick a random designer. Pick a designer whose career you might like to emulate. Study their work. Watch their YouTube videos. Follow their Instagram account. Listen to the podcasts they’ve been on. Gain some familiarity with them to understand what they have strong opinions and experience on.

2. Write down 3 specific questions you want answered.

The more specific, the better. Instead of vague questions like “what was your career journey?” ask pointed questions like “how did you decide to quit your job to start your own company?”

Pro tip: in his book Building a Second Brain, Tiago Forte suggests organizing information for action:

The best way to organize your notes is to organize for action, according to the active projects you are working on right now. Consider new information in terms of its utility, asking, “How is this going to help me move forward one of my current projects?”… There are relatively few things that are actionable and relevant at any given time, which means you have a clear filter for ignoring everything else.

Only ask questions that pertain to something you’re working on right now (or very soon). Otherwise, the risk is high that you’ll just forget the advice because you don’t have anything to apply it to right now.

3. Try to predict what their answers would be before you ask them.

This is why it’s important to not just contact any random person but someone who you’ve already researched. If you don’t know them at all, your predictions will be generic at best. If you know them a bit, you might have a high degree of accuracy about their unique perspective, which is why you want their mentorship in the first place.

4. Ask ChatGPT to answer like them.

If your role model is public/published enough, there may be enough existing data for a large language model like ChatGPT to approximate their answers. So ask! For example, Kevin Feige is a person I admire for his ability to architect the teams and stories behind so many Marvel Cinematic Universe movies over so many years. I’d ask for his advice with a problem I’m having right now: not being able to work well with one of my colleagues. I asked ChatGPT instead:

How would Kevin Feige recommend I deal with a team member who’s difficult to work with but talented?

To which the reply is:

Kevin Feige might approach this situation with a focus on balancing the team dynamic while recognizing the value of the individual's talent. Here's a potential approach he might recommend:

1. Private Conversation: Have a one-on-one conversation with the team member. Acknowledge their talent and contributions, but also address the challenges faced when working together. Be specific about behaviors or issues affecting the team.
2. Highlight Impact: Illustrate how their behavior affects the team's dynamics or project progress. Feige often emphasizes the importance of teamwork in achieving Marvel's goals, and he might stress the impact of individual behavior on the overall success.
3. Set Clear Expectations: Define clear expectations regarding behavior and collaboration. Emphasize the importance of working well within a team while utilizing their talents effectively.
4. Offer Support: Provide support or resources if the difficult behavior stems from external factors. Feige often values the well-being of his team members and might suggest offering assistance or guidance if needed.
5. Mediation or Facilitation: If necessary, consider involving a mediator or facilitator to help improve communication and resolve conflicts. Feige might prioritize finding solutions that maintain team harmony while leveraging the individual's talents.
6. Monitor and Follow-Up: After the conversation, monitor the situation and follow up regularly to ensure improvements are being made. Encourage open communication to address any ongoing issues.

Feige might approach this situation with a balance between acknowledging the individual's talent and addressing the impact of their behavior on the team's effectiveness. Ultimately, the goal would be to foster a more collaborative and harmonious team environment while leveraging the individual's skills for the project's success.

5. Apply the advice

Try it out.

That’s it!

Wait, where’s the step where you actually contact them?

That’s the beauty: you don’t always have to. This conjures the powerful psychological techniques of self-talk and self-distancing When you imagine giving advice to a friend or someone else in a situation similar to your own, it creates a psychological distance that can offer you a fresh perspective on your own challenges or decisions. This approach allows you to step outside of your own immediate emotions and biases, enabling you to consider the situation more objectively. By mentally distancing yourself from the issue and imagining advising someone else—or imagining someone specific giving you advice—you might find it easier to be more rational, compassionate, and objective in your guidance or decision-making.

(Yes, this is the modern secular equivalent of WWJD.)

Eventually, you’ll be able to turn “What would Kevin Feige do?” into a confident “What do I think I should do?” Once you try out an option, document it somewhere: a private journal, your blog, Twitter, etc. The bigger library you build up of your own options, the more you’re able to consult your own experience of what’s worked for you and what hasn’t. “What do I think I should do?” turns into “What have I successfully done in the past that I can do again?”

With enough time and documenting, maybe Kevin Feige will want to book time with me someday.

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