It is intimidating to reach out to people and ask them for favors, especially if you don’t feel you have anything concrete to offer in return.
July 23, 2025
You hear the word everywhere. If you’re like me, you feel awkward pronouncing it, never sure how drawn-out the ‘o’ should be. If you’re lucky enough to have one (or more), you probably appreciate them beyond words. Having a career mentor can offer invaluable (or, in sales, very valuable) advantages. These can range from the more situational—introductions to hirers, recommendations—to the macro—career advice, encouragement, and role modeling.
First, let’s be candid: like any industry, sales is easier to enter, easier to navigate, and easier to succeed in if you have connections. Not everyone has access to this. So how do you find a mentor when there’s no obvious one for you to tap?
Step one, says Dean Rodriguez, is to “determine your mentorship goals. Before you start looking for the perfect mentor, take some time to figure out what you want out of this relationship and what expectations you have. Are you looking for someone to introduce you at networking events, help you find resources to learn a new trade, or provide guidance on how to find better clients?” Different people excel at different things. Mentors are people, too. Take a moment to map out your current priorities.
Sure, having a crystal-clear idea of what specific career goals you are aiming to accomplish in the near future is great. But not everyone does. Sometimes, the most helpful thing a mentor can do for you is to help you clarify those goals and make recommendations as to what next steps might best serve you and your career.
My theory, and this is just one approach, is that it can be helpful to divide your “mentor wish list” into two groups: those “dream mentors” you might seek to approach once you have a little bit more of an idea of what you’re looking for, and then a few “beginner mentors” whom you might tap to guide you through the more underdeveloped beginning of your mentor hunt. The latter group would be people who are a bit easier to access than the “dream mentor” category.
One avenue, says Sistas in Sales, a sales leadership community for women of color, is to seek out organized events that provide a natural context for connection. “Conferences, industry panels, and networking events provide excellent opportunities to connect with potential mentors.” Not into events? Understandable! Many of them cost money, either directly or indirectly (travel, professional clothing, etc.). Asynchronous networking is a thing! SIS recommends looking through your LinkedIn connections and alumni groups to find professionals with whom you’d like to connect.
Okay, this will be more than a word. It is intimidating to reach out to people and ask them for favors, especially if you don’t feel you have anything concrete to offer in return. Try as best you can to wipe this fear from your mind! I recently spoke to an accomplished sales professional who basically complained—yes, complained—to me that not enough people reach out to her for guidance, even though she has explicitly, and publicly, offered to be of help where she can.
It’s true that some people are not going to be available to help out an aspiring…them (for lack of a better word), due to time and bandwidth constraints, inclination, comfort, and a host of other reasons. But many will be. And many are incredibly generous with their time, advice, and even proverbial Rolodex.
The very same skills you hone in your sales career can be useful in finding a mentor. “Use cold outreach,” says Shopify, who offers a simple template for said outreach. “Cold emailing or messaging is a good way to network, create business partnerships, and develop your business. But it’s also a good way to seek out advice from experienced strangers.”
Also, says Shopify, visit the interwebs. “Reddit is home to all manner of subreddits where you can look for mentors, including r/entrepreneur or r/smallbusiness. Do a search for ‘mentor’ in these subreddits for examples of how others have asked about mentorship opportunities in the past.” Other venues Shopify recommends are organizations such as SCORE that connect mentors and mentees for free and local small-business development centers. For more on other ways sales professionals use Reddit, see Maestro’s previous blog on the topic.
Do you remember that gesture? Not entirely sure where it came from. Here are some hypotheses. Anyway, yes, it can be really awkward to ask for something from a stranger. Although I’m not sure I agree with Rodriguez on the in-person meeting request (if I had to guess, many professionals would probably shy away from the in-person invitations, whereas online messaging or email may seem less threatening—and time consuming), I think they are spot on when they say, “don’t make them guess how much of a time suck you’ll be.” Which brings us to…
For some people, being asked directly to be a mentor can be intimidating, not least of all for the above reason: time. Starting with a specific question for a prospective mentor or telling them what specifically about their online content, ideas, projects, careers, or accomplishments you admire, and then asking if they’d be willing to either email/message or jump on a short call (Maestro always recommends being explicit, e.g., “a 15-minute call”) to tell you about their experience can be a more digestible way of engaging.
There are also companies and apps, like growthmentor and Sales Enablement Collective (this one also has some Freemium features, but mentorship is part of their paid packages), but as with all paid services, do your research. (Maestro does not have experience with either of these companies and can therefore not make any endorsements.) My personal opinion? Start with what’s free.
As with any type of people-searching, it’s a bit of a numbers game, and it can take a few (or many) tries to find an ideal mentor who also has the time and inclination to help out. The internet is vast. Sales is vast. And—trust us—there are tons of good people out there who want to help.
If you are one of those people, please drop us a line at mastery@maestrogroup.co. The Maestro team loves matchmaking and assisting where we can!
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