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.
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.
Effective delegation of decision-making authority is impossible without first ensuring leaders are deeply aligned on organizational objectives. When individuals are empowered to make choices but pull in different directions, the result is a quagmire, not progress. Alignment must precede autonomy.
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.
Contrary to the popular bottoms-up startup ethos, a top-down approach is crucial for speed in a large organization. It prevents fragmentation that arises from hundreds of teams pursuing separate initiatives, aligning everyone towards unified missions for faster, more coherent progress.
Go beyond visual roadmaps. Create a monthly written document for executives that explains *why* the roadmap changed, details priorities, and includes data from recent launches. This forces intentionality, builds trust, and fosters deeper, more accountable conversations with leadership.
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.
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 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.
Gaining genuine team alignment is more complex than getting a superficial agreement. It involves actively surfacing unspoken assumptions and hidden contexts to ensure that when the team agrees, they are all agreeing to the same, fully understood plan.