The Most Dangerous Answer a GC Can Give: Yes to Everything.

Hello friends and colleagues,

A GC from a global company recently told me about a week that nearly broke her team.

Her inbox delivered three urgent requests: finance wanted a 20 percent cut in outside counsel spend, operations demanded faster contracting cycles, and IT pushed hard for another AI platform.

Each request, on its own, was reasonable. Together, they were impossible.

“If I say yes to one, I fail the others,” she said. “If I try to do them all, my team burns out. And if I wait, the business loses patience.”

This is the reality of modern in-house leadership. The pressure is not one big ask, but competing asks stacked on top of each other.

From Overwhelm to Tradeoffs

The problem is not that Legal cannot deliver. The problem is when Legal tries to deliver everything.

Old mindset: stretch to cover every demand.

New mindset: frame the tradeoffs clearly and guide the business in choosing.

This GC shifted her approach. She piloted AI automation only in low-risk areas, then built dashboards that showed how Legal accelerated revenue instead of slowing it. She also sat down with finance, sales, and operations to prioritize openly, using the language of business that leaders understood. (For a practical guide, see this resource on communicating effectively with CEOs, CFOs, and other executives.)

She did not eliminate risk. She reframed it. That shift earned trust.

Tools That Clarify Choices

The best way to manage impossible asks is to make them visible. Data helps.

Milada Kostalkova explains how legal data intelligence turns contracts into structured, benchmarked insights. Instead of arguing over gut instinct, Legal can show the business which clauses align with the market and which introduce risk.

The same goes for AI. Adrienne Go ’s piece on AI literacy for product counsel shows how counsel who can translate between code and case law uncover risks earlier and partner more effectively with engineers.

And when it comes to litigation, Kassi Burns ’s guide on negotiating ESI protocols proves that the right clauses upfront prevent costly disputes later. Each of these tools sharpens visibility and frees Legal from being cornered by impossible demands.

Zoom Out: Legal Architects Alignment

This is bigger than one inbox. Legal is shifting from a reactive service function to an architect of alignment.

The role is not to chase certainty or cover every ask. It is to surface the tradeoffs, make risk and value visible, and guide the business toward intentional choices. That is how Legal becomes a trusted partner rather than a bottleneck.

Small Practices for Hard Choices

When your inbox feels stacked against you, try three practices:

1. Name the tradeoff in the meeting. Silence creates pressure. Visibility creates alignment.
2. Visualize choices with simple dashboards that show cost, speed, and risk impacts. Numbers move the conversation faster than memos.
3. Start with one visible win. A small, low-risk success proves Legal can act quickly and wisely.

Small steps reduce paralysis and restore momentum.

Wrap-Up: A Question to Change the Room

The next time three urgent asks land in your inbox, skip the scramble to cover them all.

Instead, ask: “Which tradeoffs create the most value for the business, and how can Legal guide us there?”

In a world of competing demands, the leader is not the one who says yes to everything. It is the one who helps the business choose wisely.

Until next time,

Olga

P.S. This Thursday, I will be speaking at the Contract Nerds 📝 🤓 5-Year Anniversary Celebration, a virtual free event full of insights and stories from the contracting community.

And if you want to shape how legal content gets written and delivered, JD Supra is running a short survey on what makes insights most useful in the age of AI.

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Olga V. Mack is a leading innovator in the legal field, driving digital transformation and championing the use of technology to modernize law. With a focus on efficiency, accessibility, and client-centric solutions, she has redefined traditional legal practices through groundbreaking tools, strategies, and advocacy. As an award-winning CEO, General Counsel, accomplished author, and sought-after thought leader, Olga is dedicated to empowering the legal profession to embrace transformative technologies and stay adaptable in an ever-evolving world.