Define Success, Build Alignment, Get Results with Brianna Sylver
Summary
In this episode of Your Customer, Your Success, Gary sits down with Brianna Sylver, founder and president of Sylver Consulting and author of Leading Through Free Fall: How Innovators Turn Turbulence into Trust.
Organizations rarely struggle because they lack ideas, information, or smart people.
The harder problem is turning what they know into action.
Brianna calls this the Activation Gap, the distance between an organization’s intent and what actually gets executed. Her argument is that many execution problems begin much earlier than leaders realize: the team never clearly defined what success should look like, aligned the right stakeholders, or surfaced the assumptions and concerns that could derail the work later.
Brianna walks through her Five Intention Setting Questions, including why she deliberately starts by asking what people do not want to happen and how they do not want to feel. Getting those concerns into the open can create the clarity and candor needed to have a more productive conversation about what success really looks like.
She also shares two contrasting business cases. In one, individual stakeholder conversations created the appearance of alignment, but the organization ultimately struggled to act on the findings. In another, stakeholders came together at the beginning, clarified expectations and guardrails, and built alignment around the work. That initiative ultimately contributed to four product launches that exceeded market projections.
The larger lesson is straightforward:
Actionability is not something a great presentation creates at the end.
It is something leaders design into the work from the beginning.
Gary and Brianna also explore why more data does not automatically produce better decisions, how hierarchy can suppress candid feedback, why emotion belongs in serious business conversations, and how leaders can create an environment where people are willing to say what they actually think.
And in Does It Hold Water?, things get considerably more colorful when Brianna explains why a difficult business problem might be exactly the right time to break out the LEGO! 🙂
What You’ll Learn
- What Brianna means by the Activation Gap
- Why more information does not necessarily lead to better decisions
- Why defining success should happen before the work begins
- The Five Intention Setting Questions Brianna uses with leadership teams
- Why starting with negative concerns can create better conversations
- How separate stakeholder conversations can create a false sense of alignment
- Why collective alignment matters before an initiative moves forward
- How leaders can uncover hidden assumptions and organizational guardrails
- Why actionable insight is created through the process, not just the final deliverable
- How LEGO Serious Play can expose team dynamics that ordinary conversation misses
Chapters
00:00 Cold Open
01:06 Introduction
02:46 The Activation Gap
05:43 Five Intention Setting Questions
12:47 When Stakeholder Alignment Is Missing
20:54 Alignment That Drives Business Results
25:17 Creating Candor Across Hierarchy
30:58 Defining Success Before the Work Begins
32:45 Does It Hold Water?
37:15 Chip Shots
Book Recommendation
The Go-Giver by Bob Burg and John David Mann
Connect with Brianna Sylver
Website: https://www.sylverconsulting.com/
LinkedIn: https://www.linkedin.com/in/briannasylver/
Read the first chapter of Leading Through Free Fall:
https://leadingthroughfreefall.com/chapter1
Connect with Gary Marra
LinkedIn: https://www.linkedin.com/in/gary-marra/
YouTube: https://www.youtube.com/@yourcustomeryoursuccesspodcast
Gary is also a Schooley Mitchell Strategic Partner, helping businesses identify opportunities to reduce operating expenses while maintaining or improving service levels.
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About Your Customer, Your Success
Your Customer, Your Success is a leadership and business growth podcast built around a simple idea: client focus is not merely a service philosophy. It is a growth strategy.
Hosted by Gary Marra, the show explores the intersection of customer experience, employee experience, leadership behavior, relationships, and operational discipline. Each episode features practical conversations with executives, entrepreneurs, advisors, and business leaders about building trust, strengthening client relationships, improving execution, and creating sustainable growth.
About Gary Marra
Gary Marra is a business advisor, customer experience leader, Schooley Mitchell Strategic Partner, and host of Your Customer, Your Success. Drawing on extensive experience in financial services, client management, operations, and cross-functional leadership, Gary brings a practical business lens to the relationship between client experience, trust, execution, and growth.
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