How to Find and Become a Conversation Design Mentor
A mentorship guide for both sides of the relationship
This post was made in collaboration with Voice This! Newsletter, to promote our new section, “CxD mentors and where to find them”.
If you’re a budding conversation design hoping to advance in your career, you’ve probably heard the advice, “find a mentor.” Easy, right? For many of us in conversation design, the challenge isn’t just finding a mentor — it’s figuring out how to make the most of that mentorship.
Believing in others
In preparation for this post, I reflected on my own past, both as mentor and mentee. Mentors come in many different shapes and sizes, varying by: seniority, skillset, capital (we’ll revisit this one), location, availability, communication preferences, and more. If you’re lucky, you can find mentors inside and outside of your company, and, if you’re open to it, you can lean on mentors outside of your role or discipline.
Very early in my conversation design journey (shortly before I would start interviewing for CxD roles), I met a mentor who profoundly influenced my career trajectory… and she wasn’t even a conversation designer! At the time, she was a solutions engineer. Our coffee chat went a little like this (completely paraphrasing here):
Me: I’m not sure I’m cut out to be a conversation designer. I don’t have the credentials for it. My work experience is tangential, but not the same. I’m self-taught, but I don’t have any certifications.
Her: Conversation design is still so new. Elaine, I am confident that you know more about conversation design than most of the hiring managers out there. You got this!
I didn’t learn a new skill. I didn’t get feedback on my portfolio. So why was this exchange so valuable to me? Turns out, what I needed the most at that particular stage in my career was someone to take a chance on me. I was plunging into the unknown by pivoting into conversation design. I didn’t have the connections or the professional background to make the switch. My confidence was at an all-time low. All I needed was someone to bet on me and see the potential of what I could become.
What is a mentor?
A mentor is a mini career counselor. They are someone who takes an active interest in your career, becoming a sounding board, cheerleader, devil’s advocate, tutor, professional matchmaker, and sometimes, in moments of crisis, a shoulder to cry on.
On top of all of this, a design mentor can help you develop hard skills. They may guide you by offering to: review resumes and portfolios, coach you on a specific tool or skill, train you on technical and behavioral interviews, and provide additional resources needed for success.
Typically, we imagine mentors as the older, more mature and experienced senior, and mentees as the wide-eyed junior. This may be the case for a lot of mentorships out there, but, at its core, mentors are anyone who have your best interests at heart and are willing to share their lived experience and knowledge with you. I call this out explicitly in the hopes that some of y’all will cast a wider net in the search for a mentor. Don’t rule someone out simply because they may not have the job title you want or have been in the industry for less than 10 years.
What is a sponsor?
A career sponsor is someone who bets on you, literally. Think of a sponsor as a special kind of mentor who, not only roots for you, but also has enough social capital to send tangible opportunities your way. These opportunities can range from anywhere to free or discounted conference tickets or design education resources, to speaking gigs, job interviews, promotions, and other kinds of real-life impact.
Note: not all mentors have the social capital or professional credibility to be a sponsor, especially if they are earlier in their career. Additionally, some mentors may not be comfortable being a sponsor at all.
Why write about mentorship?
As someone who has done over 120 unique “coffee chats” (yes, I counted), I thought it was important to share what I’ve learned about this topic. I’ve been on both sides of the table. As a mentee, I can truly say that I’ve seen the best of conversation design mentorship— the warmth and humility of our leaders and the instant camaraderie among peers. I have always felt valued by my network. As a mentor, I can also share some of the not-so-great things about CxD mentorship. If I’m being brutally honest, the worst part about being chronically online is being treated like a Starbucks barista during peak times: too many high-commitment asks from strangers.
The goal of this blog post is to help you navigate these waters. Mentorship is meant to be a commitment between 2 people to believe in each other and value each other’s opinion. In the words of Julie Zhuo:
“It’s not a binary thing, like you’re either X’s mentee or you aren’t. In fact, trying to formalize it by asking Can you be my mentor? is awkward, because mentorship should be like any normal relationship — two people who like and enjoy each other’s company want to spend more time together.
Mentorship is like any other human relationship. It can’t be transactional. Whether you’re an early-career designer or an emerging mentor, I’ll share practical tips to create a balanced, two-way relationship and help both sides interact meaningfully.
Advice for CxD mentees
Getting mentors to meet with you
To get the most out of your mentorships, be proactive. This means: creating opportunities to meet with potential mentors and bringing topics to discuss once you do meet them. As a mentor, I’m more drawn to those who make their introduction personal, giving me context as to where they are in their career journey, and who make it personalized, telling me the reason why they reached out to me specifically. Make sure to include these details next time you’re cold messaging someone on LinkedIn. Here’s an example that stood out to me recently. Notice that it doesn’t have to be very long.
Hi Elaine,
My name is {name}, I recently finished {degree/course} and am interested in a career in Conversation Design. I found your articles on Medium and found them extremely informative!
I’d love to buy you coffee and learn more about your work.
Of course, my favorite kind of messages to receive are the longer, drawn out ones. These can be templatized as well, but the more personalized you can make them, the better.
Hi Elaine,
Love your unconventional journey and how you broke into design. I’m {name}, a Product Designer based in {location}, and I’m currently pursuing {degree/course}. Your path into design, especially how you’ve integrated conversational AI, really resonates with me. It’s fascinating how you use your insights to make complex tech concepts accessible and engaging — exactly what we strive to understand in our studies.
A few friends and I, including {mutual connection}, were just chatting about the impact of your work — it’s a frequent topic among us! I’m working on a project about {topic} and I’m aiming to bridge that gap with AI. I believe your expertise in conversational design could greatly illuminate my approach.
Could we possibly have a 15-minute chat next week or the week after? I’d love to hear about your experiences and maybe get some guidance on my project.
Thanks so much!
They agreed to meet with you, now what?
The most effective mentorships are mentee-driven. This means coming prepared to the session with questions, concerns, or challenges to share. On the other hand, this means taking it slow with any requests you might have. Assume you only have 30-minutes of your mentor’s time. Would you ask someone to marry you after chatting for 30 minutes? If the answer is no, then avoid making high-commitment asks in your first meeting.
Example Low-commitment asks:
- Do you have any… book / course / conference recommendations?
- Could you tell me… your day in the life / what your job responsibilities include / what kind of cross-functional partners you collaborate with?
- Who else would you recommend I reach out to in the CxD community?
Example High-commitment asks:
- Could you take a look at my resume / portfolio and give me feedback?
- Could you comment on my LinkedIn post or reshare it?
- Could you refer me for a role at your company?
Your first meeting with a potential mentor should be all about building trust. In order for your mentor to be someone who listens, supports, and empathizes with you without judgement, they need to get to know you. It’s important to share your story and any career ambitions you might have. If it helps you stay organized: try to make an agenda for the meeting or write down your questions beforehand.
How to keep the relationship alive (as a mentee)
Let’s assume you‘ve successfully avoided scaring away your mentor and they’ve agreed to a second meeting, or better yet, a recurring 1:1 series, you, my friend, still have work to do.
As a mentee, you should own various responsibilities:
- Documenting your goals and your progress toward them
- Sharing questions, real problems, or achievements 🏆
- Keeping your conversations confidential, especially if your mentor recounts work anecdotes
- Taking notes of your 1:1 sessions and saving shared resources
- Telling your mentor if you’ve taken any of their suggestions
- Reflecting on the mentorship (is it working out for you?)
Doing all of the above shows your mentor you’re serious about your commitment and implicitly gives them feedback on whether or not the effort and time is beneficial to you. All your mentor wants is to see you grow and succeed! Even if you’re not meeting regularly, you can still share important career milestones to maintain the relationship async.
Mentees, what you bring to the table is so, so important. Many CxD mentors I know don’t charge for their mentoring services, even though they very well could. Instead, what a mentor gets in exchange for lending support is pride about your progress and energy from the enthusiasm and ambition you bring. Your excitement keeps mentors inspired and our small community fresh with newer perspectives. Your mentor wants to see you… in the words of my favorite Peloton instructor: “Bring your own energy!”
Frequently asked questions (things you might be wondering)
How do I know if someone is a good mentor for me?
Ask yourself: do you like spending time with them? Can you trust them with your story? Did you learn something new by talking to them? Usually, if you’re able to find someone who checks off these 3 things, you’re in good hands. The synergy part is probably the most important of the 3: again, do you vibe with them? You should feel excited to come into the meetings, not obligated!
Do I have to formalize the relationship?
No, do not ask someone point blank, “Can you be my mentor?🥹” I know your intentions are pure, but as a mentor, it feels like I’m forced to say ‘yes’ before figuring out if we’re a good match. Instead, let the mentor formalize the relationship. The most you can do is: step 1, ask to meet, step 2, send a thank you note and ask to meet again, step 3, repeat.
If you get stuck at step 2, you can also nudge your potential mentor with more specific asks. For example, if you talked about the conversation design interview process in your first meeting, you can follow up with: “I have my first interview next week! Do you mind reviewing my resume to make sure it matches the job description?”
How often should I talk to my mentor?
There’s no “right” cadence for mentorship. Find the rhythm and structure that works for both of you! Each mentor will have different availability, communication style, and mentorship structure. In my experience, I’ve had mentors I’ve only met with once, but we keep meeting in group settings, so that’s the time I use to catch them up on my life. I’ve also had mentors who I’ve met with 5+ times and regularly talk to online.
Do I have to compensate my mentor?
Unless your mentor has specifically mentioned their rates, the answer is no, you don’t. Keep in mind that a lot of the work mentors do, asking hard questions, critiquing your work, or steering you, is a premium service they’re offering for free. And if you’re wondering, wait, what’s the catch? The catch is that sometimes mentors are nosy and just want to know what’s happening in the field or design job market.
Please do not “tip” or send money for a mentor’s services without asking first, as some mentors might have strict contracts with their employer that prevent them from having multiple income sources related to each other, i.e. a conflict of interest policy.
Advice for CxD mentors
Taking a chance on strangers & prioritizing impact
So, you decided to put yourself out there as a CxD mentor and now your inbox is flooded with requests for a “quick chat to learn about the work you’re doing at {your_company}”. How do you prioritize who to meet with? Well, that all depends on your availability. Let me explain.
You won’t truly ever know for sure, based on an introduction message alone, if you’re investing time on someone who will benefit the most from it. There’s no hard and fast rule or evaluation criteria for that kind of thing. That’s where taking a chance comes in. You won’t know until you meet them face-to-face.
For mentors with more availability (hours per month), you may need to be available and willing to spend some time in one-time encounters. I can attest to this as someone who has put themself out there (online) for more than 4 years now: I spend a lot of time educating people on conversation design sometimes, even if the conversation doesn’t go anywhere. I’ve seen people choose a different career or a different mentor, and that’s okay! It’s been my goal for a while to introduce more designers to CxD and have more conversations with non-CxDs, so I actually sort of expect it. Because of my personal goal, I’ve taken big risks before, like betting on people who have only sent me 2 sentences of an intro :)
If you don’t have that much free time, it’s okay to be more risk-averse. You’ll need to investigate each request with more scrutiny and look for mentees with a similar background (same degree), similar interests (what stands out to them about conversation design? is it the same thing you love?), or a really, really smooth, detailed, and low-stakes introduction.
Meeting mentees halfway (having “the talk”)
Mentors, it’s on you to formalize the relationship. I usually do this at the end of meeting someone for the first-time. If they passed the vibe check, I will explicitly offer myself as a mentor and let them know they are free to ask me questions or schedule more time with me. If I *really* clicked with someone (and I have the capacity) I’ll take it one step further and offer them the chance for long-term mentorship.
Short-term vs. Long-term mentorship (a case study)
Shortly after becoming a design mentor, I realized different asks require different amounts of hands-on review and feedback. Some asks were small, limited only to polishing a resume or recommending a design course. Other asks, like getting someone job ready, required a lot more depth and focus. That’s when I started keeping time aside to meet with one particular mentee in a more structured way. We went over everything: the day-to-day responsibilities of a CxD, voice design fundamentals, companies that were hiring CxD, case study development and steering, portfolio review, resume review, interview prep, assessment prep, pretty much everything needed to get someone hired into their first role.
Since my mentorship style is pretty flexible (I’m a certified yapper after all), I struggled a lot to maintain structure and make sure my mentee was not only making progress, but also staying motivated to keep applying for jobs, despite the many rejections. As a novice mentor, it was tremendously helpful that my mentee was very patient with our scheduling process. I tried setting up recurring biweekly check-ins, but I couldn’t keep them due to increasing work demands. My mentee kept us accountable, sometimes scheduling the calendar invites herself when I simply didn’t have the brain capability to do it. As for mentoring the “hard skills”, it wasn’t too difficult after all. Most times, mentees just need to know how real-world CxD works: why something they designed feels “off”, where you’ve made trade-offs in the past, historical context or current-day legislation that may be relevant to them, etc. It’s no different than design crit at a large company.
I’m happy to say my first ever long-term mentee was hired into CxD! Since then, I have taken on 1–2 long-term mentees every year. I’ve also adopted the following “structure” for recurring series: SMART goal setting.
- Specific — What is your mentee hoping to accomplish? Is it finding a job? Honing a particular skill?
- Measurable — What does success look like to them? If the goal is acquiring a skill, is “success” flexing this technique in a new case study?
- Achievable — Is the goal realistic and attainable by your mentee? Will it motivate them? Is there a risk they might get discouraged?
- Relevant — Is the goal relevant to your mentee’s career path? Are they asking questions about something they might already be able to learn on-the-job with more support?
- Timebound — When is the official “finish line” of the mentorship? Is it 6 months from now, sooner, or later?
Making sure your mentees feel seen
The biggest impact you could have as a mentor is recognizing your mentee’s interests and strengths. The short of it is: they’ve come to you for advice and you’ve agreed to mentor them— they’re not a random stranger on the internet anymore :)
Making sure your mentees feel seen is more than just paying them a compliment. It’s also confirming you understood what is important to them and building future sessions or discussions around that. It’s also getting familiar with their perspective and work and pointing out their strengths as a designer, even if they may not see it yet.
You have a chance to make a mentee’s insecurity their biggest asset. Let them know what they have to offer and what they can improve upon, free of judgement or comparison.
Frequently asked questions (things you might be wondering)
How do I organize mentorship sessions? Which platform do you use?
I strongly recommend using a personal scheduling link for mentoring. I’ve tried offloading design mentorship logistics to ADPList, but unfortunately, ADPList casts a much wider net than I’m comfortable with because they don’t have a way to label yourself as a Conversation Designer. Back in the day too, they didn’t even offer meeting controls for mentors to accept or decline invitations before putting the meetings on your calendar. (They do gate requests now but I get absolutely buried!!! with requests there)
So far, I’ve tried ADPList, Calendly, Cal.com, and direct Zoom or Google Calendar invites. My personal favorite right now is Cal.com due to the visual appeal, advanced controls, and multiple event types that help me sort requests into different categories.
Pro Tip #1: Always require mentees to write a reason for booking along with their invite.
Pro Tip #2: (Cal.com specific) If you toggle on “Requires booker email verification” in Advanced settings, make sure to confirm your mentee has seen the invite on their calendar. Sometimes turning on this feature puts it in spam :(
When should you delegate to other CxDs?
One of your responsibilities as a mentor is to open doors for your mentee. This means, at times, connecting them with someone who is far better equipped to answer their questions on a specific topic. There’s no shame in that! You won’t know everything, but you might know someone who has lived through it, or has more experience in it. That’s the moment you can connect mentees with other CxD mentors.
Pro Tip #3: Always tell someone when you’re referring someone to them, or create a group chat introduction!
What does using “social capital” look like?
As a mentor who has built their social capital brick by brick, I can say: part of the job is saying “no” when required. You have to be selective with who you sponsor— doing so keeps your credibility intact and free to use on others who might need it more.
Since I’ve never been a manager and can’t speak to that experience, my social capital has mostly been in the form of:
- Referrals into the company
- Introductions with hiring managers
- Intel on a hiring manager’s desired candidate (to inform someone’s elevator pitch during interviews)
- Free admittance to CxD conferences
- Free CxD e-books (now that I can afford to lend or buy them for others)
- Employee discounts on my product 😎
What are some mentor resources I can use?
It should come as no surprise that the topics I write about are also the topics I get asked about most often. Many of the resources I’ve created have been in service to a mentee who needed it at the time. Here’s a list of a few informal CxD resources to help you get started!
- CxD portfolios (Convofolios)
- CxD portfolio template
- CxD portfolio example (Elaine’s)
- CxD course materials (VTG)
- CxD compensation ($$$)
- CxD resume workshop notes
- CxD mock interview primer
- Voiceflow canvas example
Where to find CxD mentors
Starting this month, Voice This! is publishing a centralized list of all available CxD mentors in every newsletter issue. You’ll be able to easily find the names of available mentors and the link to schedule time or message them directly. Check out our latest issue for more details!
Final thoughts
Not all stories are success stories, but every time we can make someone’s journey into CxD a little bit easier— that’s a success. Thank you to all the mentors and mentees who have reached out and spent time with me. Thank you for letting me and others into your life. There’s no such thing as the perfect mentor or mentee, but y’all have sure come close to it and, for that, I feel extremely grateful. Thank you!
To all the mentees who brave enough to ask for help, I leave you with this quote from Lemony Snicket:
“There is much more good in [the world] than bad. All you have to do is look hard enough. And what might seem to be a series of unfortunate events may, in fact, be the first steps of a journey.”
