Winning Season

This episode of Winning Season features a real lesson from Jacqueline V. Twillie, originally delivered live to a group of mid-career professionals. In it, Jacqueline unpacks the moment she cracked a high-stakes global project stalemate by identifying the single metric and timeline that mattered most to a senior leader.

She walks listeners through her signature L.A.T.T.E. Framework—Look, Anticipate, Think, Talk, Evaluate—and shows how to use it to translate your solution into the language of decision makers. You’ll learn how to pinpoint priorities, anticipate objections, and present your ideas in a way that earns approvals faster.

Whether you're preparing for a big pitch or navigating shifting priorities, this lesson gives you a repeatable playbook to get a clear yes.

This podcast episode is an actual lesson taught by Jacqueline V. Twillie, founder of ZeroGap and creator of the L.A.T.T.E. Framework. You’ll hear her teaching in real time, not a scripted studio segment, so grab a notebook and get ready to apply these strategies immediately.

📌 Note

Summary

In this episode of the Winning Season podcast, host Jacqueline Twillie interviews Alair Castro, a Director of Diversity and Inclusion Strategy and Marketing at Northwestern Mutual and founder of the AC Consultancy. Alair shares her journey and passion for addressing the racial wealth gap, advocating for Black women, and creating inclusive marketing strategies. The conversation explores the importance of building trust within communities, measuring success beyond traditional metrics, and the significance of maintaining authenticity in consultancy work. Alair emphasizes the need for multiple streams of income and the value of unplugged family time for personal and professional growth.

Takeaways

• Alair Castro is a Director of Diversity and Inclusion Strategy and Marketing.
• Her career is dedicated to advocating for Black women.
• The racial wealth gap is a significant issue affecting the Black community.
• Building trust within the Black community is crucial for financial services.
• Inclusive marketing can drive business goals and community impact.
• Success indicators should go beyond clicks and impressions.
• Maintaining authenticity is key in consultancy work.
• Monetizing your skills can create additional income streams.
• Unplugged family time is essential for mental well-being.
• Effective communication of boundaries is vital in leadership.

Chapters

00:00 Introduction to Alair Castro

01:40 Passion for Racial Wealth Gap

03:48 Understanding the Racial Wealth Gap

05:14 Building Buy-In for Inclusion

06:44 The Business Case for Inclusive Marketing

07:42 Cultural Insights in Marketing

09:23 Measuring Success Beyond Clicks

10:40 Overcoming Analysis Paralysis

12:15 Monetizing Your Genius

14:05 The Importance of Unplugged Time

16:00 Turning Conflict into Collaboration

17:56 Marketing and Money Rules for Change Makers

18:24 Fun and Personal Insights with Alair Castro

Connect with Alair

LinkedIn https://www.linkedin.com/in/alaircastro/

Instagram https://www.instagram.com/acoutoftheoffice/

Online https://www.theacconsultancy.com/

Winning Season Podcast - Mini Episode Show Notes

Host: Jacqueline Twillie
Episode Type: Mini Episode - Career and Negotiation Inspiration
Duration: ~3 minutes

Episode Overview

A quick-hit episode sharing actionable career and negotiation tips from two of Jacqueline's current projects, designed to give listeners a boost in their professional journey.

Main Tip: Highlight Your Unique Value

• Identify what makes you stand out from other candidates
• Lead confidently with your unique strengths in your job search
• Implementation strategies:

When: August 21st
Where: Maven.com
Cost: Free

Core Concept: Going from "Almost" to "Absolutely"

A 5-step method for building a negotiation strategy:

• L - Look
• A - Anticipate
• T - Think
• T - Talk
• E - Evaluate

Framework Benefits:

• Preparation for challenges and questions from the other party
• Addresses potential objections that typically arise early in negotiations
• Builds confidence and prevents being thrown off your game
• Leads to faster, mutually beneficial agreements

• Small tweaks can create significant impact in career development
• Preparation is crucial for successful negotiations
• Confidence comes from being ready to address challenges
• The power to shape your career is in your hands

• The Table: 30-day pop-up career strategy group
• Instant Negotiation Strategy Class: Free class on Maven.com (August 21st)

"The power to shape your career and own your negotiation - it only takes a few tweaks."

Keep winning!

Chapters

00:00 - 00:15 - Welcome & Introduction
Host introduction and episode overview

00:15 - 01:30 - The Table: Career Strategy for Black Women
30-day pop-up group supporting those impacted by 2025 job market

01:30 - 02:45 - The LATTE Framework for Negotiation
5-step method from the Instant Negotiation Strategy class

02:45 - 03:00 - Wrap-up & Closing Thoughts

Summary

In this episode of the Winning Season podcast, Lexie Mendelson shares her extensive experience in building partnerships and launching innovative products like Google Pay. She emphasizes the importance of values such as truth and loyalty in partnerships, the need for adaptability in international rollouts, and the significance of aligning diverse stakeholders. Lexie also discusses the challenges of navigating regulatory environments, the importance of modeling realistic workloads, and the value of genuine relationships in professional networks. She offers valuable advice for emerging leaders on building authentic connections and understanding the needs of others.

Takeaways

Lexie's journey spans art history to tech and finance.

Building infrastructure for new market categories is key.

Truth and loyalty are essential in partnerships.

Understanding success for all parties is crucial.

Adapt products for different markets to succeed.

Meetings enhance communication and stakeholder alignment.

Leaders should model realistic workloads for teams.

Genuine care for colleagues fosters strong relationships.

Empathy is vital in professional conversations.

Emerging leaders should focus on authentic connections.

Chapters

00:00 Introduction to Lexi's Journey

02:16 Connecting Career Chapters

04:27 Values-Driven Leadership

07:45 Launching Google Pay Internationally

09:58 Aligning Stakeholders for Success

12:50 Navigating Regulations in Banking

15:10 Normalizing Workloads for Team Performance

19:54 Building Authentic Relationships

22:13 Foundational Skills for Emerging Leaders

24:03 Rapid Fire Fun Questions

Summary

In this episode, Jacqueline Twillie discusses the intricacies of navigating difficult conversations and negotiations. She introduces the Latte Framework, which consists of Look, Anticipate, Think, Talk, and Evaluate, providing practical strategies for each stage. The conversation covers how to observe tension, anticipate derailments, address bad behavior, maintain composure in power imbalances, know when to walk away, and reflect on negotiation outcomes. Jacqueline emphasizes the importance of preparation, emotional intelligence, and continuous evaluation in becoming a successful negotiator.

Takeaways

• The real negotiation begins before the first word is even uttered.
• Successful negotiators expect derailments to happen.
• Observing the environment and your internal state is crucial.
• Address behavior, not character, to maintain psychological safety.
• Using power phrases can help redirect conversations effectively.
• Maintaining composure in high-stakes situations is essential.
• Knowing your walk-away points is critical for negotiation success.
• Reflection after negotiations helps in learning and improvement.
• Every difficult conversation is an opportunity for growth.
• Practice one technique at a time to build negotiation skills.

Chapters

00:00 Introduction to Difficult Conversations

01:59 Understanding the Latte Framework

06:39 Navigating Tension in Conversations

09:56 Keeping Conversations on Track

10:47 Addressing Bad Behavior

13:46 Maintaining Composure Under Pressure

17:30 Knowing When to Walk Away

21:28 Reflecting on Negotiations