Mentorship and Relationships

Mentorship has been a cornerstone of my career, but my approach to building a network of mentors has evolved over time. Early on, I thought the best mentors were those who mirrored my role—essentially a more successful, more experienced version of myself. But I’ve since realized that this myopic approach often misses the mark. Some of the most valuable mentors I’ve had weren’t in venture capital at all. They came from adjacent industries like asset management, tackling challenges that are analogous to mine but offering perspectives I couldn’t see from within my own field. Here’s why this works: 1. Outside perspectives reveal blind spots: Mentors outside your industry can identify dynamics in your business that might be invisible to you because you're too close to them. These insights are invaluable for seeing the bigger picture. 2. Diverse thinking adds depth: A broader, more diverse network of mentors exposes you to new ways of solving problems, offering frameworks and strategies you might not encounter within your immediate circle. Building a mentor base is critical, but diversity is key. Don’t just look for people who are “you in 20 years” with more success. Instead, seek mentors with fresh perspectives and different lenses. That’s where the real value lies.

A candidate told me she hadn't had a proper one-on-one with her manager in eight months. No feedback. No development conversations. No visibility into where she stood. She wasn't in a toxic situation. Her manager wasn't malicious. He was just checked out — busy, distracted, and not particularly interested in developing anyone on his team. This is more common than people admit. And it quietly derails careers that should be going somewhere. Here's how to manage upward when the person above you isn't doing their job. Stop waiting for feedback that isn't coming If your manager doesn't give feedback, ask for it directly. "I'd like fifteen minutes this week to get your thoughts on how I'm tracking." Most managers will engage when asked specifically — they just won't initiate. Do this quarterly at minimum. Don't let a year pass without knowing where you stand. Create your own visibility Your manager isn't showcasing your work. So you have to. Send brief written updates after completing significant projects. Copy relevant stakeholders where appropriate. Not to go around your manager — to ensure your contributions are on record. "Completed the client migration ahead of schedule. Happy to share the summary if useful." Two sentences. Professional. Visible. Build relationships one level up Your manager's manager matters more than most people realise — especially during appraisals, restructures, and promotion decisions. Find legitimate reasons to interact. Volunteer for cross-functional projects. Contribute in meetings where senior leaders are present. You're not undermining anyone. You're making sure the right people know who you are. Find mentors outside your reporting line A checked-out manager can't develop you. Someone else can. Look internally first — a senior colleague in a different team, a leader who's shown interest in your work. Then externally — industry contacts, former managers, professional communities. One good mentor who challenges your thinking is worth more than ten performance reviews that never happen. Know when the situation is costing you too much A passive manager is manageable. A manager who actively blocks your visibility, takes credit for your work, or gives you no path to progression? That's a different problem. Track what you're learning. Track whether you're growing. If the answer is no for six months straight, the issue isn't your manager's style — it's your trajectory. Some situations are worth working around. Others are worth leaving. The reality: Your manager's job is to develop you. When they don't do it, most people just wait and hope things change. They rarely do. The candidates who advance in spite of a weak manager are the ones who take ownership of their own visibility, relationships, and growth — without needing anyone's permission to do it. Don't let someone else's checked-out attitude become the ceiling on your career. #CareerAdvice #JobSearch #Recruitment

A lot of people look for mentors who’ve walked the exact same path they’re on. If you’re in sales, you want a senior sales leader. If you’re in marketing, you look for a CMO. Logical, right? Sure. But it’s also limiting. Some of the best professional advice I’ve ever seen didn’t come from a direct industry peer - it came from someone in a completely different line of work. Think about it: - A sales professional with a finance mentor learns how deals impact the balance sheet...so they start selling with profitability in mind, not just volume. - A marketer with an operations mentor gets insights into supply chain constraints...so they stop over-promising what the business can’t deliver. - A product leader with a legal mentor understands risk better...so they build with compliance in mind instead of retrofitting it later. We all operate in silos more than we realize. And the fastest way to level up is to step outside of them. Find a mentor who doesn’t do what you do. Someone who sees the same business through a different lens. The insights you get will separate you from everyone else who’s just recycling advice from people who think exactly like them.

Everyone says, “Find a mentor.” Nobody tells you how. So here’s how: 1. Think like a recruiter. Define who you’re looking for. A past founder? A subject matter expert? An operator at a scaled startup? 2. Figure out where they spend time - online and offline. Slack groups, LinkedIn, Substack comments, conferences, virtual AMAs, pitch nights. 3. Add value before you make an ask. Follow them. Comment thoughtfully. Share something they’ve written. Then DM with a very clear ask. 4. Don’t say “Will you be my mentor?” Say: “I admire the way you [specific thing]. I’m facing [specific issue]. Would you be open to a 20-minute call to walk through how you’d think about it?” 5. If it goes well: → Send a thank you note. → Implement the advice. → Follow up with results. → Ask if they’d be open to a check-in in a month or two. 6. Formalize and document the relationship. Set guardrails. Time commitment. Topics. Expectations. Everyone’s busy. Structure builds trust. 7. Make it mutual. Ask what they’re working on and where they need help. Share a relevant intro, article, tool, or resource. Even if you’re early in your journey, you have something to offer. Mentorship is at its best when it’s a two-way street. The best mentors aren’t assigned. They’re recruited with respect, clarity, and a plan.

4 Topics To Include In Your One-on-Ones To drive personal & business outcomes 🚀 I believe mentees should own the agenda for their one-on-ones. It's theirs to drive.   However, mentors should not be passive. Great leaders cover these 4 key-areas 👇 ____________________ 1 _____________________ ✅ Connection: Start with genuine connection. - "How was your weekend?" - "What are you looking forward to this week?" - "Is there anything you'd like to share or discuss?" Actively listen and show you care. #Empathy ____________________ 2 _____________________ ✅ Performance & Goals: Dive into their work. - "How are you progressing on your goals?" - "What challenges are you facing?" - "What are your priorities this week?" Review key metrics & offer support. #PerformanceManagement ____________________ 3 _____________________ ✅ Growth & Development: Help them stretch and grow. - "What are you learning right now?" - "What skills are you hoping to develop?" - "What opportunities for growth are you interested in?" Ask thought-provoking question. Challenge them to think bigger. #Mentorship ____________________ 4 _____________________ ✅ Support & Collaboration: Offer your assistance. - "How can I help you achieve your goals?" - "What resources do you need to get there?" - "Who can provide additional support ?" As a leader, often our job is just to put amazing people in the same room, then the magic happens naturally. #Teamwork ________________________________________ Elevate your leadership and empower your team with impactful one-on-one meetings! 💪 ♻️ Found this helpful? Repost it to add value to your network.  ➕ Follow Luca Senatore for leadership, mindset and business content.

My younger daughter just wrapped up an internship at a large US investment bank. She was lucky. Her manager mentored her, taught real-world skills, and trusted her with real responsibility while giving her the support to succeed. It reminded me of the mentors who shaped my own career, and of the people I’ve had the privilege to mentor. Great mentorship isn’t coffee chats. It’s a working relationship with outcomes. What great mentors do • Set the bar, then lift it. Share clear expectations and the “why,” then add a stretch assignment with guardrails. • Teach judgment, not just tasks. Narrate trade-offs, risks, and how you decided. Let them see you think. • Give visibility. Put them in the room, give them a speaking role, share credit in public, and coach in private. • Offer specific feedback. Point to the behavior, the effect, and the fix. Make it timely and kind. • Sponsor, not only advise. Open a door, make a call, attach your name to an opportunity. That signal compounds. • Build safety and ownership. Create space to ask “naive” questions, and insist on owning the deliverable end to end. What successful mentees do • Show up prepared. Bring a one-page update with goals, progress, blockers, and a draft to review. • Ask for feedback on real work. “Which two changes would most improve this note?” beats “Any advice?” • Take the stretch. Say yes to hard things, then clarify scope, resources, and deadlines. • Close the loop. Send a crisp follow-up with what you heard, what you’ll do, and by when. Then do it. • Build a learning log. Capture decisions made, what worked, what you’d change next time. Share it. • Pay it forward. Teach someone else the thing you just learned. Teaching locks in mastery. A simple frame I like, for both sides REAL mentorship: Responsibility, Exposure, Accountability, Learning. Give and take real responsibility. Create exposure to rooms and decisions. Hold each other accountable for commitments. Turn every project into a learning cycle. Rituals that work • A standing 45-minute 1:1 each month, plus ad hoc check-ins when decisions are live. • Shadow, then lead. Observe once, co-pilot once, then fly solo with a safety net. • Post-mortems without blame. Three questions, what surprised us, where were we lucky, what will we change next time. To Shreya ‘s manager, thank you for modeling the craft. To my mentors, I’m still drawing on your lessons. And to everyone who mentors or seeks one, what practice on your side makes the biggest difference?

Your 1:1 meeting with your Manager is YOUR meeting, so take control and set the agenda. As a leader I love when my direct reports come prepared for our 1:1 meetings - Great CSMs understand that this time is their time, with their leadership team, to discuss what's important to them. Step 1, make sure you have a recurring 1:1 with your leader on the calendar. I am still shocked to hear from CSMs (or any employee) that they don't have regular recurring meetings scheduled. It doesn't have to be 60 minutes every week but find a cadence and duration that work well for the both of you. Leaders will likely have a few things that they want to discuss, so perhaps split the time; give each person an opportunity to discuss what's most important to them. But as a CSM, don't expect your manager to drive this meeting, it's for you, not them. Here's an easy way to manage these 1:1's - Grab a Google Doc (or Word Doc) and create a meeting template for each week - Include the date and then have this agenda framework: 1) Personal Updates - How are you doing this week? 2) Feedback - Solicit feedback from your manager 3) Highs / Lows - What went really well this week and what didn't 4) Business Performance - How are you tracking towards your KPIs or OKRs 5) Customers - Which customers need to be discussed this week; who's doing well or who's struggling; Great time to escalate 6) Career Pathing - Perhaps not a topic for each week but add this every so often to make sure you are both on the same page Fill in each agenda topic with a few bullets to discuss - this does not need to be lengthy, you are going to have a discussion so there is no need to write everything out. Under that put both your names - each of you can add things that don't fit into the areas above but need time to discuss. Easy peasy. This is valuable time for the both of you so use it wisely.

It's surprising how many people have never had meaningful career conversations with their managers (or their direct reports). I don't mean conversations that are solely backward-looking about recent performance or forward-looking about the next promotion. I mean holistically taking stock of the journey: where you've come from, where you are now, where you're headed, where you'd like to go, the tools you need in your toolbox to get there, and the people you need in your support crew. Several years ago, I created a framework to guide career conversations with my direct reports. It's a somewhat cheesy framework, but it leads to rich conversations and strategic, as well as tactical, action plans. It's not meant to be prescriptive, but rather a guide for meaningful reflection and action. I offer it in case it's helpful to anyone here. (I'd also love to know how others approach leading or engaging in career conversations. Do you have your own framework that you'd be comfortable sharing?) Here’s mine: GROWTH G is for Goals. Personal and professional aspirations: How do you think about these today, and how have they evolved over the past 2, 5 years? What matters to you when you reflect on your career adventure thus far? What do you want to build on and carry forward, or leave behind? R is for Reflection. Self-awareness and feedback: What significant milestones or achievements have you accomplished in your career so far? When have you felt strongest and most fulfilled? Least? Where are you currently stretching and reaching the most? Where do you feel most uncomfortable – both positively and negatively? O is for Opportunities. Skill development and growth path: Together, we’ll identify the skills needed to develop further on the current path, or to strike out on a new path. W is for Wellbeing. Personal and professional balance: How are you balancing your work and personal life? What strategies do you use to maintain your wellbeing? Are there any areas where you feel you need more support or resources to ensure a healthy balance? T is for Team: Collaboration and mentorship: Who are the key people in your professional network? How are you leveraging relationships for growth? How are you contributing to others' growth? Who can and should we expand your network to include? H is for Holistic Action Plan. Actionable steps and accountability: What specific actions will you take to move toward your goals? How will we track your progress? What milestones will we set to ensure accountability and continuous growth?

Going from leader to mentor builds a 2-way street to success: Here's why the best leaders are also the best teachers. The mutual learning process is key to rapid growth. Both mentor and mentee gain valuable insights. Mentorship isn't just career advice. It's a career accelerator. Here's how to find and create game-changing mentor relationships: 1. Know your growth areas • Identify specific skills you need to improve • Example: "I need to get better at financial modeling for pitches" 2. Find the right mentors • Look beyond LinkedIn - attend conferences and join forums • Find successful people who aren't in the spotlight • Consider mentors from different industries for new ideas 3. Make a strong first impression • Mention their work that impressed you • Show how their skills match your career needs • Share an insight about their work to start the conversation 4. Be ready for each meeting • Write a brief summary of your goals and progress • Update them on how you've used their previous advice • Prepare 2-3 situations where you need their help 5. Give back to your mentor • Test their new products or projects • Introduce them to new talent in their areas of interest • Help build their personal brand through speaking or writing 6. Build a diverse mentor network • Mix long-term mentors with short-term advisors • Example: An industry expert, a tech guru, and a rotating specialist • Review your mentor relationships every 6 months 7. Set clear goals • Use objectives and key results to guide your relationship • Check progress every three months • Be open about your career moves and ask for their advice 8. Learn from mentors indirectly • Study their career choices through research • Try out one strategy from each mentor every month • Keep a log of what you learn and how it helps you grow The best mentorship relationships evolve into collaborative partnerships. Aim to reach a point where you're brainstorming solutions together, not just receiving advice. P.S. If you found this valuable, repost for your network ♻️ Join the 12,000+ leaders who get our weekly email newsletter: https://lnkd.in/en9vxeNk Lead with impact.

Great 1-1s with your boss drive career growth: 1. Come Prepared ↳ Outline key points, updates, and questions. Preparation shows initiative and respect for your boss’s time. 2. Set an Agenda ↳ Agree on the meeting structure ahead of time. This ensures both parties know what to expect. 3. Prioritize Key Issues ↳ Focus on the most critical topics. Make sure the important issues get the attention they deserve. 4. Track Progress ↳ Be ready to share your accomplishments and key wins since the last meeting. 5. Research Your Questions ↳ Ask meaningful, thought-out questions to show you’re invested in your role and growth. 6. Align with Team Goals ↳ Frame your updates in the context of team and company goals. This demonstrates your focus on the bigger picture. 7. Lead with Progress ↳ Start with the good news. Demonstrating progress builds positive momentum for the conversation. 8. Understand Your Boss’s Priorities ↳ Ask directly about what’s top-of-mind for your boss. Align your work with their focus. 9. Be Honest About Challenges ↳ Don’t hide problems. Transparency is key to getting the support you need. 10. Ask for Feedback ↳ Be proactive in seeking constructive feedback to help you grow. 11. Clarify Expectations ↳ Make sure you and your boss are on the same page about deliverables, deadlines, and priorities. 12. Bring Solutions, Not Just Problems ↳ If you’re facing a roadblock, present possible solutions alongside the issue. 13. Align on Career Development ↳ Discuss long-term career plans and opportunities for skill development. 14. Share New Ideas ↳ Be bold about sharing innovative ideas, even if they’re unconventional. 15. Listen More Than You Speak Give your boss the space to share insights and guidance. 16. Summarize Key Takeaways ↳ Send a quick follow-up email summarizing the main points and next steps. This creates accountability for both parties. 17. Take Immediate Action ↳ Act on the commitments you made in the meeting. This shows follow-through. 18. Track Agreed Goals ↳ Keep a running document of what’s been discussed and decided to ensure progress. 19. Schedule the Next Check-In ↳ Be proactive in scheduling the next meeting. — Found this helpful? Repost it. ♻️ — I’ve guided 100s of Wall St executives to fast-track or reinvent their careers. Take charge of your career in 2025. Start here: https://lnkd.in/eQExi_Qs — Follow me, Misha Rubin, for actionable career insights.