1. How does Agentic AI move beyond copilots?
This year's theme is the "Agentic Enterprise," focusing on AI agents that can act autonomously. The question is no longer about AI assisting humans, but about AI executing complex tasks independently. Look for proof points of agents that can manage entire
workflows, like researching prospects, drafting outreach, and updating the CRM without a person driving every click. Is this vision a reality, or is it just a more sophisticated chatbot?
2. What is the real path to unifying my data?
Salesforce Data Cloud is positioned as the single source of truth that powers everything, especially AI. But for most enterprises, customer data is a fragmented mess. The critical question is about execution. Look for practical sessions and customer stories that address the hard parts: data ingestion from legacy systems, identity resolution that actually works, and governance that your security team can approve. How long does it really take to get a unified profile?
3. Is the all-in-one platform argument finally a winner?
With AI agents, a unified data layer, and analytics all on one platform, Salesforce is making its strongest-ever case against best-of-breed solutions. For leaders, this is a pivotal question. Does consolidating on the Salesforce platform genuinely reduce complexity and cost, or does it create a new form of vendor lock-in with its own hidden expenses? Analyze the total cost of ownership, including the credits-based pricing for Data Cloud and AI, not just the license fees.
4. How deep do the Industry Clouds actually go?
Salesforce has been building out its industry-specific clouds for sectors like Financial Services, Health, and Manufacturing. The key question is whether these solutions provide true, last-mile functionality or are simply a veneer over the core platform. Ask for demonstrations that solve a problem unique to your industry. Are the data models, compliance features, and agent skills specific enough to replace specialized systems you already use?
5. How do I measure the ROI of Agentic AI?
Boards and CFOs are done with AI pilots and want to see measurable business outcomes. As a leader, you need to leave Dreamforce with a clear framework for measuring the return on investment for agentic AI. It's not just about efficiency gains. Ask how other companies are tying AI agent deployment to revenue growth, margin improvement, and customer retention. Seek out sessions that connect AI features to financial results.
6. What is the end-game for Slack and Tableau?
Salesforce acquired Slack and Tableau to create a seamless productivity and analytics experience. The question is: are we there yet? Look for integrations that go beyond simple notifications and dashboards. How is AI in Slack and Tableau powered by real-time data from Data Cloud? Can AI agents in Slack trigger complex workflows across the entire Customer 360 platform? The answer will tell you how mature the integration strategy truly is.
7. What new skills does my team actually need?
Implementing agentic AI and a unified data platform isn't just a technology project; it's a talent transformation. Your team will need new skills in data governance, AI implementation, and what some are calling "context engineering." Ask what training, certification, and enablement resources Salesforce is providing. How are they helping customers upskill their existing workforce to manage an enterprise where humans and AI agents work together?
8. How is Salesforce solving for AI trust and security?
As AI agents become more autonomous, the risks around data privacy, security, and hallucinations multiply. The question of trust is paramount. Look for sessions on the new security and governance architecture. How does Salesforce ensure that an AI agent doesn't access unauthorized data or take an action that violates compliance rules? Expect to hear about "deterministic guardrails" and find out what that means for your business.
9. Can I see a real customer doing what you just showed me?
Keynote demos are polished and perfect. Your reality is not. The most important question you can ask at any booth or session is for a real-world customer example. Don't just ask who is using the technology; ask how they navigated the implementation, what roadblocks they hit, and what business metric improved as a result. Customer stories are your best source of ground truth.
10. Where does this fit in my multi-cloud environment?
Few large enterprises run on Salesforce alone. Your data lives in Snowflake, Google Cloud, AWS, and other systems. A key strategic question is how well Salesforce's new tools, particularly Data Cloud, play with your existing data warehouses using Zero-Copy connectors. Is the integration seamless and bidirectional, or does it require costly data migration? The answer determines whether Salesforce is a true platform or another silo.
11. What one thing can I implement in the next 90 days?
It's easy to leave Dreamforce overwhelmed with possibilities. The final and most practical question is to identify one high-impact, low-complexity innovation you can realistically deploy within the next quarter. This forces you to filter out long-term roadmaps and focus on immediate value. Whether it's a specific AI-powered workflow in Service Cloud or a new dashboard in Tableau, finding a quick win builds momentum for the larger transformation ahead.
