iDevie
August 2019
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I know from my early endeavors in finding mentorship that it can be intimidating to reach out to people who may be older, more experienced, and more established in their careers — especially if you’re trying to get started in a new field.

It’s also rare to find someone who will spare time to mentor a stranger. I’ve had one formal mentor (someone I’d asked to be my “mentor”), but it’s important to note mentorship comes in numerous forms. Today, there are many people I consider my mentors — some I’ve never met in person.

Simply put, a mentor is a person who knows something you don’t, and you trust enough to consider their advice. With that in mind, I’m going to refer to mentors as people. You’ll probably also find it’s easier to seek peoples’ help when you stop putting the weight of “mentorship” on your conversations.

If you do struggle to ask for guidance, it’s worth exploring why.

What‘s preventing you from reaching out

These are a few uncertainties that may prevent you from reaching out:

  • Not knowing what you want to accomplish or where to start
  • Not knowing how someone can help
  • Not knowing who to reach out to
  • Not knowing how to reach out

If you hold any of these uncertainties, you’re right to hesitate. Professionals are likely to have full schedules and little time to help you sort through the absolute basics. You need to start with a foundation.

So, how to lay the groundwork?

1. Solidify your goals

Before setting off and enlisting the help of someone else, you need to know where you’re going. You don’t need to know the precise destination, but you should be able to point in a direction.

Some examples (by no means an exhaustive list):

Career preparation

  • Are you looking to break into UX?
  • Are you looking to hit the ground running in your first UX job?

Building specific skills

  • Are you looking to develop your research skills?
  • Are you looking to hone your visual design sensibilities?

Influencing organizational culture

  • Are you looking to build a UX culture in your organization?
  • Are you looking for advice on connecting fragmented teams?

Career development

  • Are you looking for advice on grad programs?
  • Are you looking to move from an in-house team to an agency?

Exploration

  • Are you looking to explore UX as it applies to specific tech (e.g., VR, voice interfaces, etc.)?
  • Are you simply looking to learn about someone’s experience in UX?

These aren’t necessarily specific enough to bring to people but are the sorts of broad goals that will guide your research.

2. Do your homework

You don’t need to know it all before reaching out for guidance but building some foundational knowledge will help you in several ways:

  • You’ll ask better (more specific and more relevant) questions
  • You’ll find some people you could talk to
  • You’ll feel more confident holding a conversation
  • You’ll look like you have your life together*

*critical when you’re about to ask someone to invest their time in you

If your goal is to build your first portfolio, look at all of the portfolios you can get your hands on (especially in your area and at your level). That’s the work you’re competing against. Of course, look at more seasoned professionals’ work, as well.

If you’re interested in building research skills, read up on some basic research methods.

No matter the goal, establishing some understanding of what you’re trying to accomplish will help you and whoever you reach out to. Don’t show up empty-handed.

3. Consider how someone can help you achieve your goal

A person could give you feedback, suggest resources, answer questions you didn’t know to ask, share stories, identify the areas to focus on, etc. What help you need is mostly dependent on where you are and where you want to go.

In the case of creating your first portfolio, you can talk with someone about what you’ve seen in other portfolios and the merits of different approaches. This way, they can help steer you away from bad habits before you’ve formed them. Learning what works well will help you put together a better portfolio, faster.

If you think you’d like to move to an in-house product team but you’ve never worked outside of an agency, you could talk to someone who has transitioned from an agency to an in-house team.

This person could tell you:

  • Why they moved from an agency to an in-house team
  • What they expected from the switch
  • Why it did or didn’t match their expectations
  • What they miss
  • Whether they’d do it again

4. Find your people

Getting to this point, you likely found people who are writing, speaking, leading workshops, or just tweeting about the goal you’re trying to accomplish. Considering these people are interested enough they would dedicate time to teach or think through these ideas publicly, they may be more likely to respond to questions you have.

Who do you need to talk to?

Depending on where your current knowledge and abilities are and what you want to accomplish, you may benefit from broadening your search to find someone who can help.

If you need an introduction to visual design (or user research, or interaction design, etc.), you might be able to broaden your search from exclusively specialists (e.g., Visual Designer, UX Researcher, Interaction Designer) to include generalists (e.g., UX Designer, Product Designer, etc.). Take peoples’ total experience into account. Not to discount the nuance that specialists bring, but when all you know is that you don’t know the basics, take every opportunity to talk to anyone who will help you move forward. If you’re able to broaden your search, you’ve just increased the number of people you can reach out to.

How much time do you need from this person?

Consider the level of effort you’d need from someone to help you accomplish your goal. It’s probably less than you think. If you’re looking for advice on how to break into UX, you could learn a lot about how to accomplish that during a conversation over coffee.

It may take someone time to review your work if you’re looking for feedback on your portfolio, but they would likely be able to give you actionable advice in fewer than 30 minutes. Of course, you could spend more time walking through suggestions, but it’s important to keep the amount of time you’re asking from someone reasonable.

If you respect peoples’ time, they’ll be more likely to give you more as needed.

Places where you might find people

  • Medium (👋 hi)
  • Twitter
  • UX Slack groups (so many)
  • In real life (conferences or other events)
  • LinkedIn*

*LinkedIn is a powerful tool for finding people with specific experiences. Consider how to use these resources in combination.

Look for people whose work, accomplishments, or character you sincerely respect — the people you want to emulate. Your enthusiasm will show.

5. Ask engaging questions

Now that you know who you’re going to reach out to, you need to think about how to ask engaging questions. You’ll have more luck connecting with people when you consider how your questions will be received.

To ask questions they’ll be interested in answering, ask questions that are:

Reflective of their expertise

Your questions shouldn’t be too far out of their area of focus — you should probably avoid asking someone with the title of UX Director about Sketch. Talking about Sketch won’t likely be an intellectually-stimulating conversation for that person. Given they aren’t spending every day working in the app (if ever), they wouldn’t be the best person to talk about it either.

Likewise, you might avoid asking a very new UX designer about product strategy. If they don’t feel equipped to answer your question, they’re less likely to respond. Like the UX Director with Sketch, the very new UX designer probably wouldn’t be the best person to talk to about product strategy. Knowing something about a topic and having the confidence to speak to it are two different things.

Relevant to their interests

Engaging questions are relevant to the recipient’s interests — look for common threads in their writing, tweets, etc. If they haven’t written anything, look at their experience. Be considerate and ask questions they’ll be interested in answering.

Something that hasn’t already been answered

Don’t ask someone a question they’ve already directly answered in some public space. Be familiar with the thoughts they’ve shared to avoid asking them to repeat themselves.

In the same vein, some topics are so thoroughly covered; you should consider seeking alternative sources of information unless you have a strong reason to ask someone about it, specifically. Again, take learning Sketch as an example. Unless someone has written about some particular Sketch workflows and shows an interest in it — look to the many videos, Medium posts, and other sources to learn about it.

6. Show you value their help

Showing you value peoples’ input starts with saying thanks, but if someone gives you useful feedback, incorporate it into your work. Show them you’re acting on their advice before reaching out for more. It isn’t critical to act on every suggestion before checking in, but if you haven’t made any progress, people will be less likely to offer more help.

If someone gives you advice that doesn’t directly translate to some tangible output (like a portfolio), that doesn’t mean you can’t show how you’ve integrated it. Engage with your advisors’ ideas. Something they said may have sparked another line of investigation — point those things out and thank them for sharing their perspectives.

Credit people who help you when you can.


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