Instead of approaching leaders first, engage end-users to gather 'ammunition' about their daily pains. They may not have buying power, but their firsthand accounts create a powerful internal case (groundswell) that you can then present to management, making the approach much warmer and more relevant.
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Stop trying to convince executives to adopt your priorities. Instead, identify their existing strategic initiatives—often with internal code names—and frame your solution as an accelerator for what they're already sold on doing. This dramatically reduces friction and speeds up deals.
Instead of pitching the abstract value of 'delight,' connect it to concrete business objectives. By asking a founder, 'Are users proud enough to recommend our product?' the focus shifted from a vague concept to a clear driver of word-of-mouth growth, making it easier to get buy-in.
Avoid pursuing prosumer and enterprise motions simultaneously. The optimal sequence is to first build massive bottoms-up love and brand trust with individual users. This creates internal champions within target companies, providing crucial momentum and turning a cold B2B sale into a pull-based motion.
After a group discovery call, don't just set one follow-up. Schedule brief, individual breakout sessions with every stakeholder. This creates multiple parallel threads, uncovers honest feedback people won't share in a group, and builds momentum across the entire buying committee, dramatically increasing deal velocity.
Don't pitch big ideas by going straight to the CEO for a mandate; this alienates the teams who must execute. Instead, introduce ideas casually to find a small group of collaborative "yes, and" thinkers. Build momentum with this core coalition before presenting the developed concept more broadly.
The most effective way to build strategic alignment is not top-down or bottom-up, but 'inside-out.' Engage middle managers (Directors, VPs) first, as they have crucial visibility into both executive strategy and the daily realities of their teams and customers, making them the strongest initial advocates for change.
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.
Structure your final presentation by calling out specific problems you learned from individual contributors by name. Then, immediately pivot to show how solving their problem directly contributes to the high-level business objective owned by the executive decision-maker. This makes every stakeholder feel heard and demonstrates their strategic value.
To find the true influencer, ask how a low-level problem affects high-level business goals (e.g., company growth). The person who can connect these dots, regardless of their title, holds the real power in the decision-making process. They are the one paid to connect daily actions to strategic objectives.
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.