Mentor Everywhere was created by a few folks at Automattic. Read more about Mentor Everywhere here. At Automattic, a fully-distributed company with no offices, we believe strongly in the power of remote working and how, no matter where you are in the world, you can be an equal participant in the work we do.

We’d like to share some tools and resources to help the Mentor Everywhere participants to facilitate their interactions, collaborate remotely, and get the most out of the mentoring program. Have a resource to suggest? Get in touch.

How to Be an Effective Mentor/Mentee for Mentor Everywhere

First, thank you for volunteering to be a mentor/mentee! This program literally wouldn’t be possible without you. We wanted to put together some quick resources to help you make the most out of your mentoring sessions.

Keep in mind that these are all just suggestions! The aspects of your mentor/mentee relationship (the tools you use, when you meet, how often you meet, etc) may differ depending on your unique situation. These are just guidelines, not mandates.

The Basics – Outlining Who, What, Where, and When

At its core, Mentor Everywhere is about connecting mentors with mentees regardless of their physical location. The conversations could include career development, goal setting, overcoming specific challenges, general advice, etc.

You’ll be paired up with a mentee, and the two of you can direct the relationship in whatever direction you both feel would be most beneficial. We’ll provide some tips and even suggested discussion topics, but keep in mind those are just suggestions.

You’ll be paired up with a mentee over email. The two of you can then work together moving forward. We’ll look to pair up mentors/mentees that have similar backgrounds and areas of interest. This does not mean we expect you to be an expert in a specific area! While mentorship does include offering advice on career decisions, mentorship also involves bouncing ideas back and forth, sharing your experiences, and acting as a sounding board for your mentee. You’ll likely have some experience in a given area, but you certainly aren’t expected to know everything and anything.

In general, you’ll probably connect with your mentee once every few weeks at least. Voice or video is preferable when possible, but text can also work in a pinch. During your first session, you’ll lay the groundwork for future sessions including what you want to discuss, how often you want to meet, and how you want to communicate moving forward. Then, the two of you can set some goals to work towards together.

Collaborating and Communicating while Remote

Some Tools and Software:


  • Be on time
  • Provide at least 24 hours notice if you must change your meeting time with your mentor or mentee
  • Overcommunicate – never assume! If something isn’t working the way you want it to, say so.

Resources for Mentees

A gentle reminder, but your mentors are not your life or career coaches. Please be respectful of their time! It’s one of the most valuable resources they’re sharing with you, and you’ll be able to appreciate their experiences and perspectives.Although you might be the one seeking mentorship (aka the mentee), you still play a large role in the success of the relationship! As the mentee, you’re going to be expected to do the bulk of the ‘work’ and come prepared, on time, and ready for your mentoring sessions with topics at hand. Additionally, your role as a mentee includes receiving feedback, trying suggestions, and implementing what you’re learning. Here are some tips for making the most of each session with your mentor:

  • Prepare ahead of time. Spend 5-10 minutes before each mentoring session listing out the topics you would like to cover, specific examples from your past week, and general discussion topics. This small time investment will pay huge dividends down the road.
  • Follow through on advice. Mentors are volunteers who are excited to share their experiences with those who are looking to improve and develop their careers. As you develop goals and strategies with your mentor, follow through on the tasks and advice they give you. You get what you give 🙂
  • Ask good questions. When chatting with your mentor, come prepared with an agenda to make sure you’re getting the most out of your time together. Think back to what you’ve worked on in the time from your last check-in and now. What’s worked and what hasn’t? Did you learn anything new? Do you have any situations or dilemmas that you could use an outside perspective on? Bring those questions to your mentor.
  • Don’t be afraid to disagree. The mentor/mentee relationship is a two-way street. If your mentor gives you advice that you don’t agree with, don’t follow along because you think you should. Open a dialogue. Express your thoughts, communicate, and use any available opportunities to build rapport and learn from one another.
  • Remain open. By its nature, the mentor/mentee relationship is designed to help you step outside of your comfort zone. The more you step outside of what feels familiar, the more opportunity for discomfort arises. Do your best to embrace that feeling of discomfort and challenge yourself, using your mentor as a resource for how to deal with that fear. Be open to their feedback and suggestions even if you disagree. Listen to what they’re saying, take notes, and reflect. This doesn’t mean you can’t disagree; it just means you have to listen to the other side while presenting your opinion. Remember that all success comes after tons of perceived failure.  
  • Keep a journal. If all goes right, you’ll be implementing suggestions throughout the week, reading articles on discussion topics, and bringing new topics to each session. Keep a list in your phone, notepad, etc that you can add to when something comes to mind. Journaling is a powerful and effective tool to help you organize your thoughts, glean important lessons from your interactions with your mentor, and reflect on what you’ve learned (or still need to learn). Although it requires discipline to maintain a journal, the benefits far outweigh the time and effort you’ll invest in it. A journal can be a physical notebook, or an online blog This is a surefire way to make sure you’re prepared for each session too!
  • Read up! Check out related blogs, websites, articles, and books on how to make the most of your mentorship. To start, you can check out Six Habits of Highly Effective Mentees, How to Be the Mentee a Mentor Would Die For, and How to Be A Good Mentee.
  • Practice suggestions. End every call with some variation of this simple statement: “The 1-2 things I took away from this discussion that I can try this week are…” If you fill in that blank every time and actually try to implement the suggestions, the sessions will be much more productive.

Resources for Mentors

  • Learn how to sponsor and not just mentor
  • Set expectations. As a mentor, it’s important to provide stability and accountability to your mentee. In the beginning of your mentor/mentee relationship, discuss goals, timeline, and scheduling so that you can set consistent dates, times, and expectations for your mentee to follow-up on any tasks or advice you’ve given.
  • Be open about your own career trajectory. Sharing our failures is much harder than sharing our successes, but that’s where the best lessons reside. As you build rapport with your mentee, be open and honest about your own career development. What do you wish you had known when you first started? What was your biggest mistake or the biggest lesson you learned?
  • Ask for feedback. Mentorship is a two-way street. Just as you provide perspective and advice to your mentee, it’s important to make sure the format and structure of your mentorship has been helpful for them as well. Don’t be afraid to ask your mentee for feedback on how things are going so that you can adjust along the way if anything needs to be tweaked.
  • Keep a journal. Journals are essential tools for both mentors and mentees alike! Make it a regular habit to write your thoughts and experiences as a mentor, what lessons you’re learning as you guide your mentee, what challenges you’re facing together, etc. Mentorship is a learning experience for both mentors and mentees, and a journal is a great way to explore and expand on the many lessons you learn as you progress in the relationship.
  • Develop your mentorship skills. Just like developing your own career skills takes time and effort, so does the ability to share and impart those skills with others. Take time to learn how to be a good mentor through the plethora of resources available online. TED Talks even has a whole playlist of videos on how to be a good mentor.

Resources for Setting Goals With Your Mentee

In a perfect scenario, the mentorship sessions will directly overlap with the goals of your mentee. To make that happen, you and your mentee should work together to set specific goals to work towards. The ideal goal is both specific and shared. For specificity, both you and your mentee understand what this goal/challenge looks and feels like. For example, “I’d like to learn more about feedback” isn’t quite specific enough. On the other hand, “I want to get better at delivering critical feedback to teammates” is very specific and conjures up specific situations to reflect on. For relatability, it’s obviously if you and your mentee have experience in your goal area. Otherwise, the conversation may feel a bit lopsided!

You don’t have to nail down a concrete list of goals after the first session. That can develop over time and stay fluid. However, you should have some general themes you want to explore. Here are some potential areas to kickstart conversation:

  • Feedback – How do you give feedback to teammates? How well do you receive feedback especially when it’s difficult to hear?
  • Leadership – What kinds of challenges have you faced when leading a team or an initiative? What could you have done better?
  • Career growth – How does your current role relate to your desired future role? What is your plan for getting from one to the other? What challenges do you see in your path?
  • Communication – Have you had challenges in the past when communicating with a group? Maybe the message wasn’t well received or didn’t come across as you intended? What could you have improved there?

Preparing For and Rocking Your First Session

The first session is critical as it lays the groundwork for the rest of your time together. Here are some basics we recommend.

First, communicate with your mentee over email to decide the basics:

  • What method of communication do you want to use?
  • How frequently would they like to meet? We recommend at least bi-weekly.
  • What topics are they interested in talking about?

Once you have your first session set, we recommend scheduling a shared calendar event to prevent any miscommunication around timezone.

In your first session, you’ll complete this Mentor Everywhere agreement. It serves as a jumping off point for your mentoring relationship. Together, you’ll identify areas and concerns your mentee wants to address, goals and values they feel are important, and challenges they’re currently facing. Once you complete the worksheet together, you’ll submit it through this form.

Get to know them outside of work as well. What hobbies do they have? What are they like outside of the office? Share these same details about your own story. The goal here is to get to know your mentee but also build on common threads. Undoubtedly, you’ll run into challenges you have both faced, interests you both share, etc.

Keep the first session flexible, but by the end of it, you should have set a recurring meeting schedule and established some specific topics you want to work on that are highlighted in your submitted agreement form. Here are some specific questions you’ll want to have answers to:

  • What are the top challenges your mentee faces that you could help them talk through?
  • What kind of mentorship are they looking for? Do they want a very “hands-on” relationship with regular communication or would they prefer a more laid back style?
  • What kind of goals do they want to set for the Mentor Everywhere program? This could be accomplishing a specific task in their day-to-day work, solving a challenging problem they’re facing, or just learning more about a general topic.

Making the Most of Every Additional Session

After your first session, you’ll know your mentee a bit more. You’ll have a decent idea of their current challenges, goals, and areas of interest. Every additional session should build upon that foundation.

For practical suggestions, we recommend the following:

  • Continue to use a shared calendar invite when scheduling meetings. It nearly eliminates all timing miscommunications!
  • Keep the communication flowing. We recommend sending an email in preparation for the call (“I thought we could cover…”) and a follow-up call afterwards (“It was great chatting with you about…”). When in doubt, over-communicate.
  • Stay consistent. If possible, keep a similar time each week.

There are some other ways to go above and beyond together:


  • Learn together. Share resources back and forth around the topics you’re discussing. Articles and blog posts can be awesome conversation starters. If you find something interesting that’s on-topic, send it over to your mentee and let them know you want to discuss it.
  • Set homework for one another. This should be a two-way street. Assign yourself homework and ask your mentee if they’re up for doing a bit of prep before the next session. Maybe your homework is to find an interesting article on the topic you’re discussing, and their homework is to implement one of your suggestions and report back. Keep it simple, applicable, and fun.
  • Take notes. This shows that you’re actively paying attention in the session, and that you value the time you’re spending together. It also helps you to tie discussions together. If you’re able to relate conversations in week three back to something you discussed in week one, that’s really powerful!

image by Death to the Stock Photo.