Company Updates
Company Updates
Asking better questions with AI
July 17, 2025
Alex Bilmes
When we launched Endgame with the promise that you could Ask Anything, we meant it. Want to know why a prospect went quiet? Ask. Need to understand a complex competitive landscape? Ask. Curious about the best way to approach a new market? Just ask.
But after watching our customers actually use Endgame—and using it ourselves every day to understand our own customers and prospects—it’s become clear that how you ask makes all the difference.
We noticed two initial approaches
In our early days, we noticed two distinct buckets of users in Endgame (we fell into both camps as well!):
The "Quick Hitters" would jump in with questions like "Tell me about Microsoft" or "How do I win this deal?" They'd get solid answers, but often seemed to be using Endgame like a very smart search engine.
The "Conversation Starters" would begin with questions like "I'm trying to expand at this account, but I'm not sure where to start. What should I be thinking about?" Then they'd build on each response, diving deeper, asking follow-ups, and treating Endgame like a thinking partner.
Guess which group was seeing better results?
The conversation starters weren't just getting information—they were developing genuine insights. They were uncovering angles they hadn't considered, building conviction in their strategies, and walking away with clearer action plans.
This got us curious: What exactly were the most successful users doing differently? And more importantly, how could we help guide people toward these better approaches?
Over time, a clearer set of patterns emerged
After analyzing hundreds of conversations including our own, we started seeing clear patterns in how the most effective approaches worked. We noticed they fell into four distinct modes, depending on what the user was trying to accomplish:
When they were exploring new territory. The best users would start broad and gradually narrow down. Instead of "Tell me about Company X," they'd ask "What should I know about Company X that might help me identify expansion opportunities?" Then they'd follow up with questions like "Tell me more about that digital transformation challenge you mentioned."
When they needed comprehensive analysis. For systematic research, they'd use structured approaches: "Analyze Company X across these three dimensions: growth challenges, technology gaps, and competitive pressures." They'd build frameworks into their questions rather than hoping for comprehensive coverage.
When they had a goal, but were open about approach. When they knew what they wanted to achieve but weren't sure how, they'd state their objective clearly: "I need to get a meeting with their CTO. What are three different approaches I could take?" Then they'd explore the most promising path.
When they needed something specific. For precise deliverables, they'd provide context and structure: "I want to help my champion convince their CTO to pilot us. I know we've built a solid ROI case, but we need to tie it to near-term business priorities. Can you write a one-page business case that combines priorities, quotes, and ROI?" Often, they’d work with us to build a template into Endgame for quick, repeatable use across accounts.
The users who treat it like a search engine get search results. The users who treat it like a strategic thinking partner get strategic insights.
This distinction matters because the best salespeople aren't just great at executing—they're great at thinking strategically about their accounts. They see patterns others miss, identify opportunities others overlook, and develop approaches others haven't considered.
Endgame amplifies that strategic thinking, but only if you engage with it strategically.
The framework we’ve built
Based on these patterns and our own daily experience using Endgame, we've developed a simple 2x2 that can help you choose the right approach for any situation. We've been teaching this framework to new users and refining it based on both their feedback and our own evolving practice.
Discovery mode: flexible exploration for discovery and early research
Research mode: structured exploration for systematic analysis
Strategy mode: flexible outcomes for strategic planning with multiple approaches
Execution mode: structured outcomes for specific deliverables
Each quadrant has its own best practices, example questions, and follow-up patterns. (You can find the complete framework in our documentation.)
But the framework is just the starting point. The real magic happens when you start treating Endgame like a conversation partner rather than a just search engine—something we've learned firsthand from using it to research our own prospects and think through our own deal strategies.
One of our users recently discovered a particularly clever technique: they started giving Endgame their intent or goal along with a draft prompt, then asking Endgame to recommend a better version. For example: "My goal is to get a meeting with their CTO. Here's my draft prompt: 'How do I reach the CTO at Company X to talk about our product?' Can you suggest a better way to ask this?" Endgame has proven remarkably good at this meta-prompting, often suggesting more context-rich questions that lead to much better insights.
The bigger picture
When we said you could Ask Anything, we were thinking about the breadth of topics Endgame could handle. What we've discovered through both observation and our own practice is that the real power lies in not just asking more questions but asking better questions.
Better questions lead to better insights. Better insights lead to better strategies. Better strategies lead to better results.
And that's exactly what we're seeing from our most successful users. They're not just using Endgame to work faster—they're using it to think better.
What this means for you
If you're already using Endgame, take a step back and look at your recent conversations. Are you treating it like a search engine or a thinking partner? Are you asking for information or insights?
If you're new to Endgame, start with this mindset: you're not just getting answers to questions—you're engaging in strategic conversations that will shape how you think about your accounts and deals.
The technology is the same either way. But the outcomes are dramatically different.
After all, you can ask anything. But asking better? That's where the real value lies.
Ready to start asking better questions? Check out our complete Prompting Guide for specific frameworks, examples, and best practices.
When we launched Endgame with the promise that you could Ask Anything, we meant it. Want to know why a prospect went quiet? Ask. Need to understand a complex competitive landscape? Ask. Curious about the best way to approach a new market? Just ask.
But after watching our customers actually use Endgame—and using it ourselves every day to understand our own customers and prospects—it’s become clear that how you ask makes all the difference.
We noticed two initial approaches
In our early days, we noticed two distinct buckets of users in Endgame (we fell into both camps as well!):
The "Quick Hitters" would jump in with questions like "Tell me about Microsoft" or "How do I win this deal?" They'd get solid answers, but often seemed to be using Endgame like a very smart search engine.
The "Conversation Starters" would begin with questions like "I'm trying to expand at this account, but I'm not sure where to start. What should I be thinking about?" Then they'd build on each response, diving deeper, asking follow-ups, and treating Endgame like a thinking partner.
Guess which group was seeing better results?
The conversation starters weren't just getting information—they were developing genuine insights. They were uncovering angles they hadn't considered, building conviction in their strategies, and walking away with clearer action plans.
This got us curious: What exactly were the most successful users doing differently? And more importantly, how could we help guide people toward these better approaches?
Over time, a clearer set of patterns emerged
After analyzing hundreds of conversations including our own, we started seeing clear patterns in how the most effective approaches worked. We noticed they fell into four distinct modes, depending on what the user was trying to accomplish:
When they were exploring new territory. The best users would start broad and gradually narrow down. Instead of "Tell me about Company X," they'd ask "What should I know about Company X that might help me identify expansion opportunities?" Then they'd follow up with questions like "Tell me more about that digital transformation challenge you mentioned."
When they needed comprehensive analysis. For systematic research, they'd use structured approaches: "Analyze Company X across these three dimensions: growth challenges, technology gaps, and competitive pressures." They'd build frameworks into their questions rather than hoping for comprehensive coverage.
When they had a goal, but were open about approach. When they knew what they wanted to achieve but weren't sure how, they'd state their objective clearly: "I need to get a meeting with their CTO. What are three different approaches I could take?" Then they'd explore the most promising path.
When they needed something specific. For precise deliverables, they'd provide context and structure: "I want to help my champion convince their CTO to pilot us. I know we've built a solid ROI case, but we need to tie it to near-term business priorities. Can you write a one-page business case that combines priorities, quotes, and ROI?" Often, they’d work with us to build a template into Endgame for quick, repeatable use across accounts.
The users who treat it like a search engine get search results. The users who treat it like a strategic thinking partner get strategic insights.
This distinction matters because the best salespeople aren't just great at executing—they're great at thinking strategically about their accounts. They see patterns others miss, identify opportunities others overlook, and develop approaches others haven't considered.
Endgame amplifies that strategic thinking, but only if you engage with it strategically.
The framework we’ve built
Based on these patterns and our own daily experience using Endgame, we've developed a simple 2x2 that can help you choose the right approach for any situation. We've been teaching this framework to new users and refining it based on both their feedback and our own evolving practice.
Discovery mode: flexible exploration for discovery and early research
Research mode: structured exploration for systematic analysis
Strategy mode: flexible outcomes for strategic planning with multiple approaches
Execution mode: structured outcomes for specific deliverables
Each quadrant has its own best practices, example questions, and follow-up patterns. (You can find the complete framework in our documentation.)
But the framework is just the starting point. The real magic happens when you start treating Endgame like a conversation partner rather than a just search engine—something we've learned firsthand from using it to research our own prospects and think through our own deal strategies.
One of our users recently discovered a particularly clever technique: they started giving Endgame their intent or goal along with a draft prompt, then asking Endgame to recommend a better version. For example: "My goal is to get a meeting with their CTO. Here's my draft prompt: 'How do I reach the CTO at Company X to talk about our product?' Can you suggest a better way to ask this?" Endgame has proven remarkably good at this meta-prompting, often suggesting more context-rich questions that lead to much better insights.
The bigger picture
When we said you could Ask Anything, we were thinking about the breadth of topics Endgame could handle. What we've discovered through both observation and our own practice is that the real power lies in not just asking more questions but asking better questions.
Better questions lead to better insights. Better insights lead to better strategies. Better strategies lead to better results.
And that's exactly what we're seeing from our most successful users. They're not just using Endgame to work faster—they're using it to think better.
What this means for you
If you're already using Endgame, take a step back and look at your recent conversations. Are you treating it like a search engine or a thinking partner? Are you asking for information or insights?
If you're new to Endgame, start with this mindset: you're not just getting answers to questions—you're engaging in strategic conversations that will shape how you think about your accounts and deals.
The technology is the same either way. But the outcomes are dramatically different.
After all, you can ask anything. But asking better? That's where the real value lies.
Ready to start asking better questions? Check out our complete Prompting Guide for specific frameworks, examples, and best practices.
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