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Leading with Questions, Insight, and Partnership

Leading with Questions, Insight, and Partnership

Shifting from Transactional Selling to Transformational Relationships. Post #24

Mort Greenberg
November 16, 2025

In Partnership with Boostr: The Purpose-built platform by media pros to power the future of ad sales.

Good morning,

In today’s world, clients don’t want to be sold to, they want to be understood. The best sellers, leaders, and advisors aren’t the ones with the flashiest presentations; they’re the ones who ask the questions that change how buyers think.

When you lead with curiosity, insight, and partnership, you build trust that outlasts any single campaign, product, or quarter.

As a seller, asking the right questions helps you uncover what really matters to the buyer, the problems behind the RFP. As a manager, it transforms one-way coaching into a two-way development conversation. And as a business owner, it allows you to build partnerships rooted in shared strategy, not transactions.

The truth is simple: great questions unlock great relationships. They lead to deeper insight, smarter strategy, and faster growth. When you lead with questions, you lead the conversation.

Turn to Best View Tables Below

TEST YOUR KNOWLEDGE

Question	Format	Answer Key
1. What is the purpose of leading with questions in a sales or client conversation?	A) To collect data B) To demonstrate curiosity C) To uncover the customer’s truth and align value D) To fill time before pitching	C
2. True or False: The most powerful insights come from having the best answers.	True/False	False, they come from asking the best questions and listening deeply.
3. Write one example of a question that reframes how a client might see their current challenge.	Short Answer	Example: “What’s the cost of doing nothing for another quarter?”

DO’S AND DON’TS

Do’s	Don’ts
Do ask open-ended questions that start with “what,” “how,” or “why.”	Don’t use leading questions that force agreement.
Do connect insights to the buyer’s business outcomes, not your product features.	Don’t jump into pitching after the first answer.
Do use questioning to show partnership and respect for the buyer’s expertise.	Don’t make assumptions about what success looks like for them.

THE WORKSHOP > 3 MODULES

MODULE 1: LEADING WITH QUESTIONS. THE ART OF DISCOVERY THAT BUILDS TRUST

OBJECTIVE: Learn how to use strategic questioning to uncover goals, motivations, and hidden barriers that influence every deal.

EXAMPLE: BUILD YOUR DISCOVERY QUESTIONS MAP

Type of Question	Example	Purpose
Situation	“How are you currently measuring success in this area?”	Understand baseline context
Impact	“What happens if this problem continues for another quarter?”	Quantify the business cost of inaction
Opportunity	“If you could improve one part of this process overnight, what would it be?”	Identify the buyer’s desired future state

TIPS

Start broad, go narrow, don’t interrogate; explore.
Use silence strategically to invite deeper answers.
Always summarize what you’ve heard to confirm understanding.

CASE STUDY: A publisher noticed ad buyers disengaging mid-pitch. The sales lead replaced product demos with 15-minute “question-led discovery sessions.” Within two months, meeting-to-proposal conversion jumped 40% because buyers felt understood before being sold to.

DISCUSSION QUESTIONS

Question	Answer
1. What makes a good discovery question?	It’s open, neutral, and rooted in the buyer’s outcomes.
2. Why does silence matter?	It allows the buyer to reflect and reveal deeper motivations.
3. How can you confirm understanding without summarizing word-for-word?	Paraphrase key insights using business language they use.

MODULE 2: LEADING WITH INSIGHT. TURNING QUESTIONS INTO VALUE

OBJECTIVE: Learn how to use insight and data to guide the buyer’s thinking, reframe their challenges, and demonstrate expertise.

EXAMPLE: BUILD YOUR INSIGHT TO VALUE TABLE

Buyer Challenge	Insight Shared	Reframed Opportunity
“We’re struggling with campaign performance.”	“Inconsistent creative and data feedback loops often drive underperformance.”	“If we standardize metrics across partners, you’ll get faster optimization and higher ROI.”
“Budgets are tight.”	“Leaders in your category are reallocating spend toward audience segments that convert 2x higher.”	“It’s not about spending more, it’s about spending smarter on verified reach.”
“We don’t see differentiation between publishers.”	“Buyers now value contextual expertise and access to niche audiences.”	“By aligning with platforms that deliver decision-maker engagement, you separate from the noise.”

TIPS

Use data to inform, not overwhelm.
Bridge every insight to the buyer’s metrics and language.
Insights should provoke thought, not defensiveness.

CASE STUDY: A sales manager trained her team to start each meeting with one market insight tied to the buyer’s business. In 90 days, the team saw a 25% increase in proposal acceptance, buyers viewed them as strategic advisors, not just media reps.

DISCUSSION QUESTIONS

Question	Answer
1. Why do insights make you more credible?	They demonstrate you understand the buyer’s world.
2. How do you ensure insights stay relevant?	Align them with the buyer’s KPIs and current priorities.
3. What’s the difference between a fact and an insight?	A fact informs; an insight transforms perspective.

MODULE 3: LEADING WITH PARTNERSHIP. BUILDING RELATIONSHIPS THAT LAST

OBJECTIVE: Learn how to shift from transactional selling to partnership-driven relationships that deliver shared success.

EXAMPLE: BUILD YOUR PARTNERSHIP BLUEPRINT

Action	Buyer Benefit	Your Benefit
Co-create campaign success plans	Buyer feels ownership of results	Shared accountability and higher renewal rates
Share learning reports quarterly	Buyer sees transparency and growth	Builds loyalty and long-term credibility
Invite client collaboration on innovation	Buyer feels valued and heard	Early access to pilot opportunities and revenue expansion

TIPS

Partnership starts when selling stops, focus on “we” over “I.”
Ask how success will be measured jointly.
Build post-sale follow-ups into your process, not as an afterthought.

CASE STUDY: A B2B media company launched quarterly “partner planning sessions” with top clients. These meetings reviewed outcomes, shared lessons, and co-created next steps. Over a year, renewals rose 30% and clients began recommending them internally across divisions.

DISCUSSION QUESTIONS

Question	Answer
1. Why do shared success plans deepen relationships?	They align incentives and accountability.
2. What turns a good partner into a great one?	Predictability, communication, and mutual wins.
3. How can you measure the strength of a partnership?	Track renewal rates, referrals, and collaboration frequency.

PATH TO FLUENCY

Timeframe	Focus Area	Fluency Indicators	Manager KPI / ROI Signals
30 Days	Awareness	Uses open-ended questions in every client interaction	Improved discovery notes and meeting engagement
60 Days	Application	Applies insight-driven frameworks in proposals and recaps	Increase in qualified pipeline and follow-up meetings
90 Days	Mastery	Operates as a trusted partner, co-creating plans and sharing insights regularly	Higher renewal rates, referral growth, and client satisfaction

Title	Author	Year	Publisher
The Art of Asking Questions	Stanley L. Payne	1980	Princeton University Press
Insight Selling: Surprising Research on What Sales Winners Do Differently	Mike Schultz & John Doerr	2014	Wiley
The Sales Tactician: Spycraft Techniques For Revenue Success	Mort Greenberg	2024	digitalCORE Publishing

Leading with Questions, Insight, and Partnership

Shifting from Transactional Selling to Transformational Relationships. Post #24

Good morning,

TEST YOUR KNOWLEDGE

DO’S AND DON’TS

THE WORKSHOP > 3 MODULES

MODULE 1: LEADING WITH QUESTIONS. THE ART OF DISCOVERY THAT BUILDS TRUST

MODULE 2: LEADING WITH INSIGHT. TURNING QUESTIONS INTO VALUE

MODULE 3: LEADING WITH PARTNERSHIP. BUILDING RELATIONSHIPS THAT LAST

PATH TO FLUENCY

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