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.

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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.

To accelerate your career, focus on developing 'agency'. This means moving beyond assigned tasks to proactively solve unspoken, systemic problems. Instead of chasing high-visibility projects, look for the unaddressed issues that keep leaders up at night. Solving these demonstrates true ownership and strategic value.

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.

When meeting with senior leaders, shift the focus from your status updates to their priorities. Ask what's top of mind for them, what challenges they face, and how you can help. This reframes you from a direct report into a strategic ally, building trust and social capital.

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.

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.

When confronting a talented but abrasive CTO, don't just critique bad behavior. Frame the conversation around their effectiveness. Horowitz suggests saying, "You're a fantastic Director of Engineering, but not an effective CTO," because a true CTO must marshal resources across the entire company, not just manage their own team well.

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.

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.

Complete transparency can create panic and demotivation. A leader's role is to filter harsh realities, like potential layoffs, and deliver an authentic message that is both realistic and optimistic enough for the team to absorb productively, rather than sharing every fear.