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5 Pillars: The Well Placed Mentor

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Image by Riccardo Annandale via Unsplash.


Cultivate at least one Well-Placed Mentor to co-validate your bridge plan. Continue to engage your general mentors on what they do best.


  1. Study your target. Quarterly financials, news reports. Write 2-3 key benefits for customers. Why select this solution vs competitor alternatives?

  2. Attend the #1 Event. Where do the people doing this role step onstage and present?

  3. Create new contacts at the event. Who can help you identify a Well-Placed Mentor? Who could you benefit from an informational with?

  4. Develop a clear objective and agenda. Present it to the Well-Placed Mentor.

  5. Align on a time-bound plan to bridge Your Next Big Thing.

What is a Well-Placed Mentor?

In one of my first 5 Pillars workshops, a bright graduate student asked for clarification. As a student athlete, he described how long-term mentorship by his high school baseball coach continued to provide inspiration and resilience.

Am I encouraging you to deprioritize beneficial people in your life? Certainly not. I responded that inspiration and resilience are rare commodities we all need more of.

I encourage you to leverage multiple, general-purpose mentors for soft skills (communication, effective writing) or hard skills in a particular area (Python).

A well-placed mentor must be close to the decision point for your Next Big Thing. They deeply understand the people, dynamics and culture involved in the decision on what happens to YOU. This adds several precious percentage points of success to your next evaluation (job, promo, investor).

A Well-Placed Mentor will:

Validate motivation and planning

  1. Eliminate guessing about what matters to these exact decision makers. Careers are complex. Evaluation criteria and expectations reach beyond what is copy-pasted into a job description.

  2. Focus your preparation and time investment correctly. Consider any time-bound career objective (relocate to New York City before the school year starts, get promoted while on maternity leave). You can't afford to miss key requirements.

Without accurate feedback from a Well-Placed Mentor, it's easy to over invest on certain requirements and fail to sufficiently develop others. Only a Well-Placed Mentor can clarify and provide context on the gossip we might hear from peers about what is required.

General vs Well-Placed Mentor Conversations

Here are a few examples contrasting the two. Can you spot which is which?

Managing Strengths & Weaknesses

  1. From what you told me, it sounds like you are doing great at a lot of things!

  2. From what you told me, this hiring manager will love X and be concerned about lack of Y. What actions could you take to enhance your strengths and mitigate the weaknesses? #ReasonsToBelieve #5Pillars

Validate plan

  1. Great that you're working on this cert. What if you passed it before the interview?

  2. An all-purpose mentor isn't close to the decision process.

  3. Your personal pitch focuses on A, but your points on B and C will resonate with these decision makers better

  4. An all-purpose mentor isn't aware of values and priorities for your target team.

Open doors

  1. I know roles about to come open on your target team, at the right seniority. Before I introduce you to the hiring manager, send me 2-3 lines on Reasons to Believe. What makes you Credible and Capable?

  2. I know lots of people hiring, internally and externally. Shall I introduce you to two or three of them?

  3. I know a lot of folks with similar years of experience to you. Would you like to have a general chat with them about their careers?

  4. I know veteran team members in your target team that would be great role models. How about I introduce you and you take them for coffee or set up a shadowing session?

So I only need one mentor..?

Having mentors is not a binary state of 'complete' or 'incomplete', though management teams often measure this way.

As you grow more senior in your career, take the opportunity to develop mentors with different strengths. Ask yourself what skills, knowledge or relationships makes a potential mentor special and differentiated, and focus your work with them on that exceptional area. Take an active approach by defining and sharing your objective in the format:

-Why them?

-Why you?

-Why now?

Why them?

Which skills and traits are they exemplary and recognized for? Which specific capabilities do they have depth of experience with?

Which specific gaps on your learning path can they quickly and easily provide insight on?

What unique moves have they made that parallel with your goals?

Which superpowers are they recognized for that you want to emulate?

Why you?

Which Pillars have you already developed? Which signals have already validated your motivation, and how would this engagement help?

Why now?

What compelling event creates urgency for your objective? What will happen if you 'do nothing' about it?

This helps the mentor prioritize your request over generic asks. Whenever you develop new stakeholders, take steps to demonstrate your thoughtfulness and preparation.

Preparing an informed approach

Becoming well-read in your field is beneficial at any career stage. You discover practical frameworks to try out in your job. It also provides you something memorable to reference in senior leader conversations.

Demonstrate your business acumen and motivation. Broadcast that you are self-reflective and investing in your own development.

You can bet that senior leaders are on top of financial results. Having figures top of mind (like YoY growth %) and observations from financial reporting is key. This plants a seed that you are competent beyond your current station, and someone who could be developed long-term.

Own your feedback

Approaching a mentor without knowing your current developmental feedback hinders you both. None of us are perfect, and we're never finished growing and developing. The point is to understand ourselves as we are (not as we wish to be).

We need to understand 'how we win' with our strengths, and create proven strategies to mitigate and anticipate known challenges. Together with your mentor, you can safely discuss objective feedback from peers and management. You can mix in personality frameworks like Meyers-Briggs through the fun, free online platform:

This should crystallize into actions and clear opportunity targeting on Projects and Events. It facilitates a productive conversation about your ability to be Credible, Capable and Visible at the next level. Conversations like this are a powerful tool in addition to regular career conversations with your direct manager.

Without this, we can't communicate effectively to the mentor about your Credibility and Capability. We're just sharing personal beliefs about our performance.

Capture value

Establishing the relationship and expectation with a Well-Placed Mentor is a big step. Congratulations!

By proposing and developing a plan, you are positioned to begin capturing value.

Define 3-4 major milestones on your timeline, like delivering a relevant Project and passing the #1 certification. #5Pillars

Think about requirements and dependencies for each of those. Present your understanding to the mentor for validation. Where gaps in your resources or access exist, seek warm intros and problem solve together with your mentor.


Certification - selecting the #1 certification

Project - thinking creatively about overlap to your current role and how to create business value


Project - can they introduce a hard skills mentor to support your project?

Skills Training - which trainings have their top performers used to get ahead?

Reading - which industry-specific or next level books stand out to them?


Events - identify the #1 event and gain access

warm intros to informationals and shadowing


A Well-Placed Mentor offers unique benefits and tilts the field in your favor. You'll need to be thoughtful and persistent to identify, cultivate and engage this senior stakeholder. The benefits to you are: validating your bridge plan, unblocking any Pillar you are stuck on, and tuning your final approach based on inside information about the key decision maker. Well-Placed Mentors harmonize the entire 5 Pillars approach. Take steps now to identify and cultivate yours.

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