5 Key Tips for Connecting With Great Mentors Who Are Happy to Support You – Kathy Caprino

Part of Kathy Caprino’s series “Building Your Happiest, Most Rewarding Career”

Achieving supportive mentorship is one of the most powerful tools for career advancement, yet many professionals hesitate to pursue it. Whether it’s fear of rejection, a sense of “unworthiness,” imposter feelings, or uncertainty about how to approach potential mentors, these barriers often prevent professionals from accessing the guidance they need to thrive.

But here’s a truth I’ve witnessed over and over again: Great mentors want to help—when approached in the right way.

Recently, one of my newsletter subscribers shared her dilemma:

“Kathy, I’m in job search mode and looking for a purposeful role where I can thrive. I’ve taken many of the right steps, but I haven’t pursued mentorship yet. I see people who have succeeded in a big way in my field, but I hesitate to reach out. I don’t want to be a burden by asking for help, and I’m unsure of the best way to approach them, or the right language to use. How can I ask for help in a way that inspires someone to say yes?”

This is a very common challenge. To better understand how to navigate it, my book The Most Powerful You and accompanying video training course The Most Powerful You explore what I call Power Gap #4—”Isolating from Influential Support.” This is one of the seven damaging confidence gaps I’ve researched and frequently coach and train on, that significantly limit career and leadership growth. Regarding this particular gap, a staggering 71% of professionals I’ve studied report experiencing these challenges.

For deeper insights, listen to my Finding Brave podcast here:

To support your efforts in achieving empowering mentorship that moves you forward, here are 5 key strategies to help you connect with mentors who will genuinely want to support you—and who have the influence, insights, and experience to help open doors you can’t on your own.

#1: Skip the Cold Ask—Build Trust First

One of the biggest mistakes people make is reaching out to strangers with a generic request like, “Will you be my mentor?” or “Can I please pick your brain?” This approach rarely works because effective mentorship is built on trust and mutual respect first.

Sheryl Sandberg, in her book, Lean In, humorously compares this approach to the behavior of the baby bird in Are You My Mother?, who, waking up in an empty nest, begins asking everything and eveyone he sees the question, “Are you my mother?” The answer is always a resounding “No!”

Instead, start by reaching out to people you already have some form of a connection with—colleagues, former bosses, industry peers, past educators, or individuals you’ve met through networking groups or conferences. When mentors have seen your work ethic and character firsthand, they’ll be far more inclined to help you.

2. Add Value Before You Ask

If you admire someone who isn’t yet in your network, or if they’re not a connection you know but you’d like to explore employment opportunities they might be able to connect you with, don’t immediately reach out to ask for help or mentorship. Instead, find ways to engage with their work and add value to their professional endeavors.

For example:

• Share and comment on their great content on LinkedIn.
• Mention them in a thoughtful post.
• Refer potential clients, leads, or opportunities to them.
• Participate in discussions they lead.

By consistently showing up in a positive and supportive way, you create natural opportunities to build a relationship. Over time, they may take an interest in your work and be more open to offering guidance.

3. Be a Mentee Worth Mentoring

Before seeking mentorship, ask yourself: “Would I want to mentor me?” Great mentors want to invest their time in people who are proactive, already taking action, open to feedback, and eager to learn and stretch.

To become an ideal mentee:

• Commit to your career growth: Take a new helpful course or certification, build new skills, talk to others in your circle for their ideas and suggestions, and demonstrate initiative.
• Be engaged and contributive: Volunteer for new projects, participate meaningfully in discussions, and step out of your comfort zone in ways that will help you build your confidence and leadership skills.
• Support others all along the way: Celebrate the success of colleagues and mentors alike.

When mentors see that you’re serious about your development, they’ll be more willing to invest in you.

4. Make Your Ask Specific

One of the biggest turn-offs for potential mentors whom you don’t know is a vague or overwhelming request. Instead of saying, “I need help with my career,” or “I’m interested in working for your organization,” narrow your focus. What specific insights or guidance do you need at this time?

For example, if you admire a writer and blogger and want to start your own blog, you might say:

“Hi X – I hope this finds you well. I’ve been following your blog for two years and truly love your insights on career and leadership growth. I’m working toward launching my own blog in the next several months and would very much appreciate just a few minutes of your time if you’re available, to learn about how you approached your first year of thought leadership and content strategy. I’d be very grateful to hear what worked best for you.”

This approach is effective because it:

• Shows you’ve done your homework.
• Respects their time with a clear, focused request.
• Provides an easy opportunity for them to say yes.

5. Think Like a Mentor

Whenever you’re unsure about how to reach out to a potential mentor, ask yourself: If I were in their position, how would I want to be approached? Successful professionals are often inundated with requests for help. What would help you stand out?

• Show that you value their expertise and have taken steps to learn from them already.
• Make your request easy to fulfill by being specific and concise.
• Demonstrate that you’re already taking proactive steps on your own to grow in your career or achieve your top goals.
• Be appreciative and respect their time, whether they say “yes” or “no.”

The Bottom Line

Mentorship isn’t a transactional request—it’s a rewarding relationship built on trust, respect, and mutual benefit. Approach mentorship with confidence and self-worth, and conduct yourself as someone worthy of high-level guidance. The right mentors will take notice—and gladly offer their support.

Start today by identifying one person you admire and taking the first step to connect. It might be uncomfortable at first, but the more you do it, the easier it gets. And remember…if the response you receive the first time isn’t what you hoped, don’t despair. There are a myriad of reasons why the individual didn’t move forward to engage with you. Try not to take it personally, but learn from every act of engagement with others so you can hone your approach for more success.

Your next career breakthrough could be just one conversation away.

For hands-on help to build a more rewarding and successful career and professional life, visit Kathy Caprino’s Career Help page, and work with Kathy in a 1:1 coaching program, her courses, and other programs. To accelerate your career growth, work with Kathy in her 6-session private Career & Leadership Growth coaching program today.

To strengthen your confidence, impact and self-esteem right now, read Kathy’s book The Most Powerful You, and take her 8-module video course The Most Powerful You. And sign up for Kathy’s weekly newsletter here.