Career treasure hunt: A comprehensive guide to mentoring from both sides

Not so long ago, I talked with a friend about my ongoing experience as a mentee. I was positively gushing; all my experience with being mentored has been absolutely amazing. It lead to them asking an important question:

"Why don't I have a mentor?"

What followed was surprising, though - they equated having a mentor with watching a self-improvement course. They didn't realize what mentoring truly was about, nor that it required them to put in active effort.

There's a lot of other misconceptions about mentoring I've heard through the years - that a mentor has to be the mentee's manager, that the mentee is expected to follow the exact same path as the mentor and doesn't have any say in the relationship, that the mentor is supposed to hold the mentee's hand and micromanage them...

So, what is mentoring really like? What does it mean to be a mentor or a mentee? What to expect when entering such relationship from either side, and how to get the most value out of it?

What is mentoring?

According to Wikipedia, a mentor is someone who teaches or gives advice to a less experienced person (mentee). Mentors are also supposed to give feedback to their mentee and support them in achieving their career goals. While typically the mentor is more senior to the mentee, it's not a requirement - all that matters is that the mentor has experience the mentee can learn from.

That is why mentors shouldn't be assigned completely blindly, but picked based on having experience in the area the mentees want to improve in. Which brings us to the first point...

The mentee drives the relationship

If you're considering getting mentored, think first about what you want to get out of the mentoring. Do you want to get better at public speaking? At writing design proposals? At collaborating? Is your goal to get to the next rung on the ladder of your career, and you need pointers about how to achieve that?

Nobody is going to decide your goals for you. It's your life and your career, you are the one who decides what happens. You need to know where you want to get. And then you need to put in the work to actually get there. The mentor isn't there to hold your hand; they are the friendly genie that provides hints along the way so you can avoid the pitfalls and get to the treasure.

What does it mean in practice? Let's take the example of public speaking mentoring. The mentor can give the mentee advice and resources on how to prepare for public speaking, how to structure their slides, they can review the talk proposal and even listen to a rehearsal and provide feedback about it. They share what worked and what didn't work from their experience, so the mentee doesn't repeat the same mistakes they did. But the mentor is not responsible for picking the talk topic or for actually putting together the presentation points. It's on the mentee to figure out what talk they want to do and to prepare it, as well as to discuss their concerns and incorporate the mentor's feedback on their execution.

The mentee is the one that prepares the topics for the meetings. People are not mind readers, and mentors are just people. If the mentee doesn't tell the mentor what they are struggling with, the mentor has no way to navigate them out of the murky waters. Which brings us to the next point...

Open communication

I just said that mentors are not mind readers, but neither are mentees. Communication truly is the key to a successful mentorship (or any relationship, really) and no matter whether you're a mentor or a mentee, you have to be open.

Be open about your goals, so you both know what you're aiming for. Your concerns, so they can be addressed. Your experience, as past encounters shape your feelings and directions you may wish or not wish to take. Do you think your mentor's advice won't work for you as you've tried that approach multiple times before and it led nowhere? Speak up, maybe there's something that you missed in those previous attempts. And if not, the mentor is at least aware of the situation and can think of alternative ideas instead of you both wasting time. Did you have zero time to prepare for the next meeting, or cannot be fully present? Reach out and reschedule to a time that suits you both better.

As every other type of a relationship, mentoring thrives on trust (confidentiality of discussed topics is implied). You may have to be vulnerable. Neither of you has to share anything you're not comfortable with, but to get out most of the mentoring sessions, do consider sharing information that have direct impact on the discussed topics. As a mentee, you communicate your boundaries and weaknesses so the mentor can help you figure out the best path forward. As a mentor, you can motivate your mentee by sharing how you overcame your struggles.

Speaking of experience and goals...

We already talked about how the mentor should have experience in the area the mentee wants to improve in. However, that doesn't mean that the mentee's path will be identical to the mentor's. In fact, it's very unlikely - we're all different people, with different backgrounds, different strengths and weaknesses and goals. The mentor's experience is there to be a conversation starter. It's meant to be an inspiration the mentee should be able to take tips and ideas from; and it's meant to be a warning of pitfalls along the way the mentee should now be able to avoid, as somebody already walked that path and set up the signs for them. The objective is not for the mentor to create a Mini-Me, but for the mentee to improve and achieve their goals, utilizing the experience of their mentor on their path.

There's a lot of advice anyone experienced can give you without having to live through the circumstances, but as a mentee, you do want to try to find someone who has personal familiarity with what you need the most. So before you start looking for a mentor, go back and think about what the core of your goal is.

If you change your goals, or don't feel like you can learn any more from your current mentor, it's completely okay to let them know that and seek a different, more fitting one! The current mentor may even be able to recommend you someone. Same applies in the other direction - if as a mentor you feel someone else may provide more value to your mentee, ask them if they'd be willing to take on the mentoring and recommend them!

Mentoring is for everyone!

And I mean that both as being a mentor and a mentee.

As a mentee, you'll get advice on how to achieve things. And that is the goal of being mentored - to learn and improve. Nobody is born perfect, and thus even if you're a senior in your area of expertise, you can find something related to get better at and a matching mentor. The ocean of knowledge is so vast, each and every one of us has something to learn from others. Having a mentor is not a weakness; it shows that you're able to reflect on yourself and are open to continuous learning. That is a good thing!

As for being a mentor, do not confuse "everybody can become a mentor" with "everybody can be a mentor right now". If you want to become a mentor, you need to develop some skills first: you need to be able to actively listen to your mentee, encourage and inspire them, help them solve their problems, and most importantly, not get frustrated by the differences between you and have the enthusiasm and dedication to work with them and help them become better.

If you're considering becoming a mentor but don't feel your mentoring skills match the expectations, get a mentor to help you hone the skills you need! Then, you can start slow: are there any juniors or interns on your team that would appreciate your help in navigating the field? It shouldn't be a formal mentoring session (remember, those are always driven by the mentee!), rather a conversation where you answer their questions and offer them advice if they want it. That will both help the not-mentee to move forward, and you to improve the skill set used in mentoring.

Where do I find a mentor?

Things will be different based on your organization, but here are some ideas:

• Some companies, like Red Hat, offer mentoring programs associates can join. You just select whether you want to be a mentor or mentored, fill in some information about your focus areas, and get paired with someone who should be a reasonably good match.

• Ask on a fitting mailing list or chat channel. Similarly to the mentoring programs, companies often have spaces to discuss career improvement or mentorships. Look around to see if yours has some too!

• Ask on a more generic mailing list. If your organization doesn't have a specific area for mentoring discussions or matchups, you may get lucky on a more generic open discussion one. A good place where to ask may be a chat specific to your location, or for free conversation (like the once-so-popular "Friday lists").

• If you have no idea where to look for a mentor, ask someone! Your manager or senior acquaintances may be aware of mentoring spaces, or may even know specific people you can reach out to.

So, how is it actually supposed to work?

We've talked a lot about the theory, but how does a typical mentoring agreement look like, and what are the specific steps a mentor and mentee should take? Let's take a look at the flow of a mentoring relationship first:

1. Introduction: Both the mentor and the mentee introduce themselves and share their experience. They agree on organizational details: meeting cadence and format, alternative means of communication in between meetings, etc.

2. The mentee shares their current goal(s) they want to work on, what they did so far, how well it worked, and any relevant strengths and challenges. Don't worry if something is forgotten, it will come up in further conversations! Obviously, the mentor can ask clarifying questions as needed.

3. The mentor and mentee create an action plan to achieve mentee's goal(s). The mentor offers advice to help them get there. The mentee should ask for advice as they need it. They agree on the specific steps the mentee should take before the next meeting.

4. The mentee incorporates the mentor's advice and works on achieving their goal(s). E.g. if their goal is to become good at giving talks, they pick out a topic to do a presentation about and write an abstract; then they can ask for feedback on the abstract on the next meeting or async.

5. The mentor reviews the progress and provides feedback on mentee's work. The mentor and mentee discuss any challenges and successes the mentee had, and decide how to move forward.

6. Repeat steps 2-5 until the mentee achieved their goal(s). Then work on next goal(s), or end the mentorship agreement.

Despite the formalized steps, do let your personalities and preferences guide you! Don't be afraid to deviate from the template if that's what works for you best. Communicate.

Communication is also how you build trust between you. Talk about what motivated the mentee to look for a mentor, or what mentors did the mentor have in the past. Celebrate your successes. Share your interests and strengths even if they seem unrelated to your jobs - who knows, maybe you'll be surprised how they can be utilized! And if not? Nothing. We're human. Get to know each other. Only that way can you build trust, and you need that for a successful mentorship.

Besides communication, you also need respect to build trust. Respect each other's ideas, opinions and experiences. If you don't, then the other won't be willing to share as much, or even work with you! Mutual respect is critical.

Finally, what specific steps does a mentor take to guide their mentee? Here is a short, non-comprehensive list to give you an idea:

• Act as a sounding board. The mentor should not fix the problems for the mentee, they have to do it themselves in order to learn. Let's look at the public speaking example again: The mentor shouldn't tell the mentee a specific talk topic, but offer feedback or adjustments and discuss them. They may also give the mentee ideas on how to find a potential topic.

• Help the mentee discover potential career opportunities. It may mean sharing calls for papers they might join, or discussing different career paths they may find interesting and aren't aware of, getting them in touch with people working on large efforts in their area, etc. Speaking of which...

• Introduce the mentee to people who may help them achieve their goals. For example, if the mentee has a proposal for adjusting the department strategy and the mentor knows the head of the department personally, they should get them in touch. Networking is critical for career growth and as a mentor, you likely know more senior people than the mentee. Give them the boost!

• Provide learning resources. Is there any book or talk that deals with the problem the mentee has? Then the mentor should send the resources their way!

• Describe things they tried that didn't work and why. The mentor likely went through at least some of the struggles the mentee is going through, and there's no reason for the mentee to suffer if there's a way to avoid (or at least minimize) the damage.

• Help the mentee to recognize their strengths and successes. We, as people, are in general more tough on ourselves than on others. Impostor syndrome is also very common. The mentor should always tell their mentee when they did a great job, as they may not recognize it as such.

Again, don't get too attached to this (very much incomplete) list! Each mentoring relationship is unique. Let the relationship and opportunity guide you in what's the right thing to do in that specific situation.

Do you have a tip that I didn't mention? Share it in the comments so we can all learn!

Anything else?

It was mentioned a couple of times but it bears repeating once more: the mentee is in charge of the mentoring relationship. They are the ones to define their goals, and they have to actively work on achieving them. As a mentee, you only get as much out of the mentorship, as the effort you put in. If you don't work on your goals and prepare discussion points, there's nothing the mentor can help you with. So be prepared to put in the work in order to fully benefit from the mentorship!

Another point that should be repeated is that there's no single solution on how to do mentoring. Every one of us is different, and thus a combination of two people will also be unique. Keep your hearts open and be prepared to adjust your methods. Communicate and work together!

And finally, you can keep in touch with your mentor/mentee even after your agreement is over. You've built a relationship and a connection, right? Don't let it disappear! Reach out to see how your counterpart is doing, chat about their achievements or those hobbies you discussed. Don't forget each other. We already talked about networking benefits for the mentee, but it goes both ways - having personal connection across the company is beneficial for both of you, from both the personal and the professional side.

It's great to learn from other people, and it's an even more amazing feeling to help others grow. I've been getting mentored over the years and have been mentoring others both unofficially and officially, and I've thoroughly enjoyed both roles. Even as a mentor you learn new things, whether a technology you were not familiar with before but the mentee is, or different experiences, or you expand your soft skills. There's always room for improvement. And what better way to go around doing that, than by also building a new relationship with someone?