Asking a Mentor for Career Guidance

I get a lot of messages from folks looking for support and guidance, whether it’s about growing a speaking career, advancing in a role, or starting a business. I've reached to folks too and been turned down or ignored plenty of times. In hindsight it's probably because I didn't follow these guidelines: 1️⃣ Be specific. Instead of “Can I pick your brain?” try something like, “I’m working on breaking into this industry and could use some advice on this specific challenge…” or “I’d love tips on structuring my keynote.” The clearer you are, the easier it is to help. 2️⃣ Be flexible. Someone recently told me, "I’ll meet you anywhere, anytime within 10 minutes of your house…”—and that kind of openness caught my attention. Remember, when you’re asking for someone’s time without cost, being flexible (and eager) goes a long way. 3️⃣ Be kind. It sounds simple, but a warm, genuine acknowledgment of someone’s time and expertise can mean a lot. Something like: "Hi [Name], I’ve been following you on LinkedIn, and your recent post about [topic] really resonated with me. I admire how you handle tough conversations. I’m facing a challenge at work and would love your thoughts. I promise to keep it under 10 minutes. I know this is a favor, so I’ll be as flexible as I can." 🌟 See how these three steps work? It’s about being specific, flexible, and appreciative. It makes it easier for the other person to say yes. 💡 Bonus tip: You don’t have to worry about offering something in return. Just be upfront about asking for a favor and express genuine gratitude. If this approach speaks to you, I hope it helps make your future networking asks a little easier!

Tired of sending "tell me about your job" DMs? Here's how to make mentorship requests stand out! I get DMs every week from folks interested in my path to being a software engineer. Most start with, "Hi, I see you work at [company] – what's the culture like? How'd you get in?" While I want to help, these generic questions are tough to answer meaningfully. What works so much better is showing initiative and tailoring your questions. Here's my recommended approach: 1. Introduce yourself with impact. "Hi [Name], I'm [Your Name] with a background in [area of expertise]. I'm currently building [project] using [technologies]." 2. Ask targeted questions. Replace vague inquiries with: "I loved your blog post on [topic]. Could you elaborate on [specific idea]?" "How do you balance [skill] with [skill] – an area I'm working to improve?" "Your work on [project] is impressive. How did you approach [challenge]?" Why this works: Tailored feedback: Specific questions get you answers that directly help you grow. Skill practice: Articulating your background and goals upfront is like a mini-interview prep. Give before you get: Demonstrate your interest and work ethic, making experts more invested in your success. Instead of asking "what's your job like," show who you are and ask for targeted help. You'll stand out and get the insights that truly matter. Let me know what you think in the comments! #mentorship #softwareengineering #careergrowth #networking

The best mentors won't find you, You have to find them. My core values for career development: • Ownership - Taking responsibility for your growth • Courage - Moving through discomfort for what matters • Reciprocity - Creating value, not just taking it What I can't stand is seeing people wait for career opportunities while mistaking passivity for patience. Here's how to ask potential mentors (without feeling awkward): 1/ Be direct about your goals Don't beat around the bush. Tell them exactly what you need. "I was promoted to senior engineer and want to level up my systems architecture skills. Would you be willing to mentor me?" 2/ Tell them why you chose them People appreciate knowing what drew you to them specifically, showing you’ve done your homework. "I'm reaching out because of your experience leading engineering teams at high-growth startups." 3/ Start with a small ask Don't request a long-term commitment right away. "Would you be open to a 30-minute video call to connect?" 4/ Be gracious if rejected Sometimes people don't have bandwidth. That's okay. "I understand you have significant demands on your time." 5/ Ask for alternatives If they decline, their network might be your next opportunity. "Is there anyone you'd recommend I connect with instead?" 6/ Approach with the right mindset Confidence in your goals. Respect for their time. Gratitude for their expertise. I've seen too many careers stall because of fear of rejection. But I promise: The temporary discomfort of reaching out is nothing compared to the permanent pain of career stagnation. Stop waiting for the perfect mentor to appear. Make the first move today. What strategies have worked for you when finding mentors? Image Credit: GraciousQuotes --- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

Here's my "Never ask for a mentor" framework that led to: - Mentorship from an NYC food entrepreneur - Writing for Ryan Holiday - My first 6-figure job - $2k to speak with zero experience - Getting on top business podcasts (before I had a business) - Moving from teaching to tech - Quitting my job and going solo I know this is going to help people: 1. Never use the "M" word - Never ever ever ever (ever) ask someone to be your "mentor" - This creates instant pressure - Start with a specific, thoughtful question about their work - Show you've done your homework on their background - Ask one simple question that will help you (that they can answer is less than 60 seconds) - Be SPECIFIC (Not "whats your best tip for somebody starting out..") - Keep initial outreach brief and respectful of their time 2. Take their advice and ACTUALLY DO IT - This is where 99% of people fail - When someone gives you advice, implement it immediately - Don't wait for perfect conditions - just execute - Document your process and results 3. Circle back with results - Return with "I tried what you suggested and here's what happened..." - Be honest about both successes and failures - Express genuine gratitude for their guidance - Nobody does this - they'll be genuinely surprised 4. Use that momentum to ask the next question - This creates natural permission to continue the conversation - Each exchange builds more trust and access - Focus on quality questions that show you're serious - Create a cycle of value exchange rather than a one-sided relationship 5. Repeat consistently - Continue this loop with multiple people in your industry - Be patient - relationships build over time - Gradually deepen connections through consistent follow-through That's basically it. People love seeing their advice put into action. While everyone else is asking for mentorship and doing nothing with it, you'll stand out by simply following through. Do this enough times and you'll build a network that creates true freedom - freedom where you will always have work if/when you want it and a support network that lasts a lifetime. Any questions? Was this helpful?

Don't ask for a job. Ask for guidance. Over the years, I’ve learned something powerful: If you ask for a job, you might get silence. But if you ask for guidance, feedback, or perspective, you open doors. Every move I've ever made has been because of relationships or reputation, or both, but mostly relationships. If you are looking for a job, your primary mission is to de-risk the hiring manager's decision and become the overwhelmingly obvious choice. While even that does not guarantee a role, you can put the odds in your favor by casting a wide net, creating relationships, and helping them understand why and how you with your experiences and superpowers would transition into the role successfully. That's why people hire people they know or who are referred by someone they know: it's lower risk. When I’m reaching out, I don’t lead with, “Can you help me get hired?” Instead, I say things like: 👉 “I’m interested in parlaying my experience into your industry.” 👉 “I’d be grateful for your feedback on where I might be a fit—or who else I should meet.” A simple 15-minute ask for advice instead of opportunity lowers the barrier. It invites conversation, not pressure. It shows respect. It builds relationships. And often, that connection becomes the very bridge to the opportunity you never thought you’d get. People hire people they believe in. And people believe in those who ask to learn, not just to earn. If you’re navigating a career pivot or job search, remember this: 🙌 Seek relationships, not just results. 🎯 Ask smarter questions. 🚪 And more doors will open. Have you ever landed a role or made a connection simply by asking for advice instead of a job? I’d love to hear your story. #Careers #Networking #JobSearchTips #Leadership #PersonalBranding #ProfessionalGrowth #LinkedInTips #OpportunityKnocks #AskForAdviceNotJobs