Episode 73

All Things Contracts with Laura Frederick, CEO of How to Contract

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Episode 73

All Things Contracts with Laura Frederick, CEO of How to Contract

Cover of SpotDraft guide titled Building Smarter In-House Teams with photos and names of four professionals: Adam Becker, Akshay Verma, Tommie Tavares-Ferreira, and Kevin Cohn.
Here’s how Adam Becker at Cockroach Labs turned AI from experiment into daily legal ops power.

Summary

Key Insights

1. Contracts Fail When Lawyers Draft for Other Lawyers — Not Operators

Laura explains that companies slow down because contracts are written in legalese instead of business language.
Operators don’t understand terms → negotiations stretch → risk increases.
Her rule: if a business decision-maker can’t explain the clause, rewrite it.
Clear contracts drive alignment, speed, and fewer escalations.

2. Lawyers Overestimate Risk and Underestimate Practicality

Most legal teams redline aggressively out of habit, not strategy.
Laura highlights patterns she sees across thousands of learners:

  • Lawyers fight over minor phrasing
  • Negotiations become adversarial too quickly
  • Teams escalate issues that don’t matter

Her advice: prioritize material risk, not academic precision.

3. Fallbacks and Playbooks Are More Powerful Than Templates

Companies obsess over templates, but templates fail when negotiators don’t know:

  • what each clause means,
  • how to explain it,
  • what alternatives are acceptable,
  • where the edge cases are.
    Playbooks, clause libraries, and decision trees give teams flexibility without losing control.

4. Train the Business Early — Or You’ll Pay for It Later

Laura explains that business users make contracting mistakes when they are forced to self-serve without guidance.
Training reduces escalations, improves quality of intake, and increases legal’s credibility.
Teaching people why clauses exist is more effective than telling them what to do.

5. Good Contracting Is About Communication, Not Perfection

Lawyers often treat contracts as technical documents, but Laura frames them as communication tools.
The job is to express intentions clearly so the parties avoid disputes — not to show off drafting skill.
The best contracting teams are the ones who simplify relentlessly.

6. AI Will Accelerate Contracting, But Judgment Is Still the Differentiator

Contracting AI can draft, summarize, compare versions, and surface issues.
But AI cannot:

  • understand business context,
  • weigh risk trade-offs,
  • manage stakeholder expectations,
  • or communicate decisions.
    AI handles the volume; lawyers handle the nuance.

7. There’s No Shortcut to Becoming a Strong Commercial Lawyer

Laura built How to Contract because traditional legal education doesn’t teach:

  • commercial awareness
  • negotiation basics
  • business alignment
  • practical drafting
  • cross-functional collaboration
    These skills come from repetition and mentorship — not casebooks.

In this podcast, we cover

0:00 Introduction
6:15 Why Laura chose contracts as her core practice area
10:48 Drafting contracts for energy and renewables
14:39 Laura’s favorite types of deals
16:28 Contract drafting tips and tricks
18:45 Considering a more generalist role
24:35 Common mistakes during contract drafting
26:33 How to negotiate more effectively
29:29 Tips for breaking a negotiating log jam
34:43 Lessons from mentors
38:27 Founding How to Contract
41:59 Leaving Tesla to make the leap to business owner
46:26 Focusing on mental health
53:29 Finding Laura’s businesses online
56:39 Rapid-fire questions
57:47 What Laura wishes she’d known as a young lawyer

View AI generated transcript

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