When you identify a deal blocker, don't confront them alone. First, approach your champion and ask for their perspective on the dissenter's hesitation and advice on the best way to engage them. This provides crucial internal political context and helps you formulate a more effective strategy before you ever speak to the blocker.
A silent dissenter won't respond to "What are your concerns?". Instead, "soft-float" several potential objections, like giving them a multiple-choice question (e.g., "Is it our integrations, our pricing, or something else?"). This lowers the barrier for them to engage and allows them to latch onto a specific point, revealing their true apprehension.
Multi-threading isn't just a seller's tactic; it empowers the buyer. An internal champion feels more confident and strengthened when they can approach their CFO with the backing of two or three peers who also see the value. This shared internal momentum makes it easier for them to secure budget and push the deal forward.
Securing executive buy-in is its own sales stage, distinct from champion agreement. Don't just repeat the demo for the boss. Use executive-level tactics like reference calls with their peers, exec-to-exec meetings to build relationships, or roadmap presentations to sell the long-term vision and partnership.
Don't be afraid to surface problems to executives, as their job is almost entirely focused on what's not working. Withholding a problem is unhelpful; clarifying and framing it is incredibly valuable. Your champion isn't offending their boss by raising an issue, they're demonstrating strategic awareness.
When a senior stakeholder proposes a potentially disruptive idea, direct resistance ('pushing') is counterproductive and strengthens their resolve. Instead, 'pull' them into a collaborative exploration. Acknowledge the idea, discuss the underlying problem it solves, and then gently steer the conversation back to how it aligns with the agreed-upon North Star, defusing tension.
Building influence requires a strategic approach. Actively survey your professional relationships, identify where you lack connections with stakeholders, and methodically invest time in building alliances with leaders who can advocate for your ideas when you're not in the room.
When progress on a complex initiative stalls with middle management, don't hesitate to escalate to senior leadership. A brief, well-prepared C-level discussion can cut through uncertainty, validate importance, and accelerate alignment across teams or with external partners.
Don't just hand your champion a perfectly polished soundbite or business case. The act of creating it together—getting their feedback, edits, and "red lines"—is what builds their ownership and conviction. This process ensures they internalize the message and can confidently sell it on your behalf.
Use a four-step framework for high-stakes talks: define your Purpose (your mission), Listen actively, Ask clarifying questions instead of assuming, and determine the Next steps for resolution. This structure keeps you anchored and prevents emotional derailment.
When meeting an influential person with opposing views, effectiveness trumps the need to be 'right.' The best strategy is to suppress personal indignation and identify a shared interest. Propose a policy or idea within that common ground that they might be receptive to and champion as their own.