Chapter 12: Understanding What's at Stake
"What's at stake?" determines your pricing confidence and proposal effectiveness.
What You'll Learn
- Why stakes matter for pricing
- How to ask the question effectively
- Real-world examples of stakes
- Using stakes in follow-up and proposals
Why Stakes Matter
"When you don't know what's at stake, all your thoughts around pricing come from an internal feeling of how much you think you're worth. But once you understand how big the problem is, you get much more confidence to charge appropriately."
The Transformation
| Without Stakes Knowledge | With Stakes Knowledge |
|---|---|
| "I think I'm worth $200/hour" | "This problem costs them $500K/month" |
| Pricing feels arbitrary | Pricing feels justified |
| Proposals are generic | Proposals are specific |
| Follow-ups are weak | Follow-ups reference their urgency |
Understanding stakes transforms you from hoping you're worth the price to knowing you're worth it.
The Four Essential Questions
On service request forms and in discovery calls, ask directly:
| Question | What It Reveals |
|---|---|
| What is at stake? | The real business impact |
| What is your timeline? | Urgency and commitment |
| Can you measure ROI? | Sophistication and value potential |
| What is your role? | Decision-making authority |
These questions help you: - Tailor your pitch precisely to their needs - Create more effective follow-up communications - Determine appropriate pricing ranges - Gain confidence in asking for higher fees
How to Ask About Stakes
Direct Approach
"What's at stake if this doesn't get solved?"
Indirect Approaches
"What happens if you don't address this in the next 6 months?"
"How is this problem affecting the business right now?"
"What opportunities are you missing because of this issue?"
The Follow-Up
After they answer, dig deeper:
"You mentioned [specific stake]. Can you help me understand the scale of that?"
"When you say it's affecting revenue, do you have a sense of how much?"
"What would solving this unlock for the team?"
Real-World Examples of Stakes
Clients reveal stakes when properly questioned:
| Situation | Stakes Revealed |
|---|---|
| Expensive API calls | Company running out of money without solution |
| Lost Head of AI | Happening right before fundraising round |
| B2C product growth (30K to 200K MRR) | Serious churn problem threatening growth |
| Public company considering acquisition | Deal worth $20-100 million |
| Half the team quit | Need AI to replace human judgment temporarily |
| Content quality issues | Customer trust and retention being damaged |
Example: The Churn Problem
Surface request: "We need help with our AI system"
Stakes uncovered. - Revenue went from $30K to $200K MRR - But churn is eating gains - Each point of churn costs $X - Solving it would free resources for growth
Pricing implication. Now you can price against churn reduction value, not "AI consulting hours."
When Stakes Are Unclear
Red Flag
When clients don't have good answers about what's at stake, you're likely seen as a "nice to have" rather than a necessity.
What This Means
- Engagements are more likely to end prematurely
- They may never actually start
- Price sensitivity will be high
- Priority will shift away from your project
What to Do
Propose a smaller engagement that clarifies stakes:
"Based on what we've discussed, it sounds like we need to first understand the scope of this problem. I'd suggest a 2-week diagnostic where we [specific activities]. This will clarify the stakes and inform a larger engagement if warranted."
Or offer a lightweight retainer:
"Given the uncertainty, a monthly advisory retainer might make more sense. That gives you access to my expertise while we continue exploring the problem space."
Using Stakes in Follow-Up
Instead of generic check-ins, reference their stated stakes:
Generic (Weak)
"Hey, just following up on our proposal. Do you still need help?"
Stakes-Based (Strong)
"Hey, this is Jason. I reached out earlier. Are you still committed to reducing churn by Q3? Happy to discuss how we can accelerate that."
Why It Works
- References their priority, not your proposal
- Creates urgency tied to their goals
- Shows you were listening
- Reframes as partnership, not sales
Using Stakes in Proposals
Your situational assessment should directly reference stakes:
Example Structure
Current Situation
"[Company] is experiencing [problem]. Based on our conversation, this is costing approximately [amount] per month and putting [specific outcome] at risk.
What's at Stake
Without addressing this, [Company] faces: - [Quantified risk 1] - [Quantified risk 2]
- [Opportunity cost]
The Opportunity
Solving this would enable: - [Quantified benefit 1] - [Quantified benefit 2] - [Strategic advantage]
Reframing POCs with Stakes
Stop thinking of Proof of Concepts as technical demonstrations:
Traditional POC
"Let's see if this technology works in your environment"
Business Case POC
"Let's co-create an ROI model that justifies the full engagement"
The Process
Frame every POC as a 30-day sprint to build a business case together:
- Agree on inputs. "How many hours does this process take today?"
- Validate assumptions. "What's the fully loaded cost of those engineers?"
- Calculate together. "So that means this is costing you $X per month"
- Project outcomes. "A 50% improvement would save $Y annually"
When clients agree on inputs, they rarely challenge the outputs.
Creating Urgency from Stakes
Urgency should come from their stated needs, not your sales pressure:
Reference Their Timeline
"You mentioned needing this solved before [their deadline]. Working backwards, we'd need to start by [date] to meet that timeline."
Highlight Opportunity Cost
"Every month without this solution costs approximately [their number]. A three-month delay means [calculated impact]."
Use Market Dynamics
"Your competitors are already implementing similar solutions. The window for first-mover advantage is closing."
Create Scarcity Authentically
"I have capacity for one new engagement next month. After that, my next opening is [later date]."
Stakes Discovery Exercise
For your next discovery call, try this exercise:
Before the Call
- Research the company (funding, news, competitors)
- Hypothesize what might be at stake
- Prepare questions to validate or discover stakes
During the Call
- Ask "What's at stake?" directly
- Follow up with quantifying questions
- Connect stakes to specific outcomes
After the Call
- Write down the stakes in their words
- Calculate the financial impact
- Reference stakes in your proposal and follow-up
Action Items
-
Add stakes questions. Put "What's at stake?" on your intake form and discovery question list.
-
Practice the follow-up. Rewrite your last 3 follow-up emails using stakes-based language.
-
Calculate stake impact. For your current prospects, estimate the financial impact of their stakes.
-
Build stakes into proposals. Update your proposal template to include a "What's at Stake" section.
-
Reframe your POCs. If you offer pilots, restructure them as business case development exercises.
Key Takeaways
- "What's at stake?" determines your pricing confidence
- The four essential questions: stakes, timeline, ROI measurability, and role
- When stakes are unclear, you're a "nice to have"—propose a diagnostic or lightweight retainer instead
- Use stakes in follow-up for dramatically more effective communication
- Proposals should directly reference stated stakes and quantify the impact
- POCs should build business cases, not test technology
- Create urgency from their stakes, not your sales pressure