OTL Newsletter: Why mentoring others helps you - more than you realize

Observation 🧐

Mentorship isn’t just for leaders. 

Mentoring others, whether you're an individual contributor (IC) or already in a leadership role, is one of the smartest career moves you make. 

When I hired a sales leader who had never led a team before, there was one thing that stood out: he had mentees I could speak to in depth about his approach to leadership. Through those conversations I was assured that he had the leadership qualities needed to succeed.

Mentorship is a powerful tool that shows you can add value at every level of your career.

It’s hard to prove you can do a job before you have it 

No matter where you are in your career, getting to the next level requires you to show you can handle more responsibility and you’re a leader amongst your peers. 

For first line managers looking to get to 2nd line Leadership, seek mentees who are also managers (but earlier in their leadership journey). 

For ICs looking to get into management, seek mentees who are also AEs (perhaps selling to different segments or earlier in their career) 

Hiring managers are looking for proof that you can do the job. Mentorship gives you a platform to demonstrate leadership, coaching abilities, and your potential to lead others.

Solving this challenge opens up new career opportunities

Mentorship helps you achieve the next step in your career. Here’s why it matters:

• It demonstrates your potential and builds credibility, even if you don’t have a team yet. Being a mentor shows you can take on coaching responsibilities and help others succeed.
• It builds your network and reputation as someone who invests in others. Your mentees become advocates for your abilities, both within and outside your organization.
• It teaches valuable leadership skills like coaching, giving feedback, and problem solving skills that translate into senior roles and more responsibility.

Simply put, mentorship is an investment in your future career goals, regardless of your current role.

HOW you mentor is as important as WHO you mentor

The mistake so many of us make with mentorship is we treat it as one off conversations. You only connect with mentees when they reach out to you with a problem. You don’t have a structure to these meetings and it’s often just small talk over coffee.

Here’s why these approaches often fall short:

• Sporadic mentorship doesn’t create lasting value. You need consistent, meaningful engagement to build trust and demonstrate real leadership potential.
• Surface level meetings won’t lead to real progress. Effective mentorship isn’t about casual check ins. It’s about diving into challenges, strategizing together, and offering real, actionable advice. What are each of you getting out of your interactions? If it’s just a free coffee, that’s not enough. 
• Mentoring just for the sake of it won’t help your career. If you’re not truly invested in helping your mentee grow, the relationship won’t offer the benefits you’re looking for.

Mentorship isn’t something you do to check the box. It needs to be real, ongoing, and focused on growth and progression over time.

How to get the most out of your mentorship relationship

If you’re ready to invest in mentorship for your career, here’s how to structure the relationship:

• Meet regularly. Consistency is key. Whether it’s once a week, every other week, or monthly, make sure the cadence is regular and predictable.
• Go beyond small talk. Make each session count:
• Discuss current challenges or opportunities you’re both facing.
• Strategize around a project, deal, or problem you're both working on.
• Practice important skills, like delivering a presentation or handling tough objections.
• Play the role of a coach. Offer constructive feedback, ask open-ended questions, and help your mentee work through their challenges.
• Support long-term growth. Don’t just mentor for a few months and move on—keep in touch, especially if your mentee changes roles or companies.

By structuring your mentorship relationships with this level of commitment and focus, you'll be investing not only in your mentee's success but also in your own career growth. 

Here’s what you’ll get out of mentorship—whether you’re an IC or a manager:

• Powerful references from your mentees. They can speak to how you’ve helped them grow and how you’ve added value.
• A deeper understanding of leadership. Mentoring gives you real experience in coaching and developing others, skills you can apply when you take on a formal leadership role.
• A stronger network. You’ll expand your connections by helping others succeed, and those connections will come back to benefit you throughout your career.
• Proof of your ability to handle more responsibility. Whether you want to move into management or become a more strategic IC, mentorship shows you can thrive in roles that require coaching and leadership.

Mentorship isn’t just for managers. It’s for anyone who wants to advance their career, build their leadership skills, and make a lasting impact in their organization.

Start mentoring today, whether you’re an IC or already in a leadership role. By building meaningful, long term mentorship relationships, you’ll not only help others succeed but also set yourself up for success in the future.

Thought Starter  🤔

Love 🥰

An amazing book on the value of mentorship is "Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell" by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle. It dives into how mentorship played a critical role in shaping leaders at Google, Apple, and beyond.

Campbell started as a football coach at Columbia University before transitioning to business and he became the CEO of Intuit. Despite his corporate success, he was best known for coaching and advising tech leaders behind the scenes. His leadership philosophy was:

• People first: Business success comes from developing and supporting people.
• Tough love: Honest, direct feedback combined with deep care.
• Trust & teamwork: Great teams, not just great individuals, drive success.
• Service mindset: He mentored without expecting anything in return.

Campbell never wrote a book or sought publicity, but his influence was so profound that Google’s top executives wrote "Trillion Dollar Coach" to share his leadership lessons with the world.