Pillar 2: Context Over Content

Mentorship in the Age of AI

AI can give you an answer in seconds, but it cannot tell you whether that answer is right for your organization, your stakeholders, or your moment.

This is where mentors become essential.

The future belongs to leaders who can navigate complexity and nuance; the subtle, relational, deeply human elements of work that come from leadership sensibilities. Mentors help people interpret the landscape, not just gather information. They offer “what works here,” not just “what works in general.”

Core Principles

Social norms and inside knowledge cannot be automated.

AI doesn’t know your embodied culture or the hidden fault lines of your team. It would need to be constantly updated on the political micro movements within reporting lines and outside of them. Basically, for AI to effectively help a junior employee navigate the organizational landscape, it would need to be feeling into the environment. It just isn’t there yet. Political dynamics, communication preferences, and interpersonal expectations are absorbed through real interactions

Wisdom comes from lived experience.

People grow when they can learn from someone who has walked the path before them. For example, I designed a leadership development program for a coaching firm early in my career. I was fresh out of graduate school and applied all of my learning to create a customized program based on the proprietary knowledge of that particular coaching firm. The senior coaches of the organization said, “This looks great! Who is going to deliver it?” They knew something I did not. My academic background prepared me to write out a sound experiential educational program. But I was not yet trained as a coach and I had not yet spent time with the clients of their niche demographic. Everything I offered was theoretical, and somewhat practical, but none of it lived in me yet. I would need the support and guidance of those who had been there before me to know the next steps. I was good at the content, they understood the context.

What This Pillar of “Context Over Content” Helps Solve

• Over reliance on AI for decisions that require judgment
• Misalignment with an organization’s unwritten rules
• Slow adaptation for new hires who lack context
• Poor cross-functional collaboration due to misunderstandings or unspoken expectations

Signature Tools and Practices for Mentorship for Creating Context

1. Teach the “Why” Behind Decisions

People need more than direction. They need meaning. They need the thinking behind the thoughts.

How to do this in practice:

Use a simple three-part explanation anytime you’re making or reviewing a decision with someone:

• Here’s what I chose
• Here’s why it mattered in this context
• Here’s what I considered but didn’t choose AND why

This builds judgment, not dependency. In coaching, I often invite senior leaders to coach their junior folks on critical thinking. “Coach them in thinking how you think so in your absence, they already know what to do next.”

Example script:

“Here’s what made this approach work in our culture. Another option would have been X, but it wouldn’t have landed well because Y.”

2. Joint Problem Solving That Surfaces Tacit Knowledge

Some of the most valuable organizational knowledge is invisible until you talk through a problem together.

Try this tool:

Use a “Think Aloud” session:

• You narrate how you’re approaching a decision given the obvious context and constraints.
• Your mentee asks questions as they notice patterns.
• You both pause to name the assumptions you’re making.
• You both reflect to consider what is missing in the approach so far.
• You both come up with 3 possible paths forward.
• Together, you land on the option that best fits the current context and constraints.

This reveals the nuance AI will never see.

3. Transparency About Tradeoffs and Stakeholders

Most decisions in leadership involve competing priorities. Being transparent helps others learn the realities behind the work. Think of it as mapping the org chart behind the org chart.

Tool: The “Who Will This Impact?” map

When making a decision, ask your mentee to name:

• Direct stakeholders
• Indirectly affected groups
• Hidden influencers
• Potential resistance points

Then walk through how those dynamics shape the right path forward.

4. Sponsorship Moments That Teach Navigation

Mentors don’t just give advice. They open doors. They teach how the organization really works. They offer insights about the places where being politically savvy is not manipulation but maturity.

Try this:

1. When you introduce someone to a new stakeholder, explicitly explain why that person matters. Not just their title but where this person brings value.
2. When you bring someone into a meeting, narrate the dynamics afterward. Explain the nuance that would be easy to miss without additional context.
3. When you endorse someone publicly, name the strengths you’re reinforcing. Make the messaging clear and simple.

Example script:

“I wanted you in that room so you could see how decisions are made at this level. Here’s what I hope you noticed…”

Closing Thought

AI may help us move faster, but mentorship helps us move wisely. The leaders who thrive in the age of AI are those who can interpret nuance, and who actively develop others to do the same.