CEO Dylan Field combats organizational slowness by interrogating project timelines. He seeks to understand the underlying assumptions and separate actual work from "well-intentionally added" padding. This forces teams to reason from first principles and justify the true time required, preventing unnecessary delays.

To fix a failing process like cash collections, the CEO should hold a daily 8 a.m. meeting with the team. By repeatedly asking a direct question like, "Where's my money?", you force the rapid resolution of small, overlooked blockers and create an unscalable but effective communication channel.

To truly disconnect, empower your team with financial autonomy for problem-solving. Define a clear budget (e.g., '$400 per problem') within which they can act without your approval. This forces resourcefulness and prevents you from becoming a micromanagerial bottleneck.

To move beyond static playbooks, treat your team's ways of working (e.g., meetings, frameworks) as a product. Define the problem they solve, for whom, and what success looks like. This approach allows for public reflection and iterative improvement based on whether the process is achieving its goal.

When a project stagnates, it's often because "everyone's accountable, which means no one's accountable." To combat this diffusion of responsibility, assign one "single-threaded owner" who is publicly responsible for reporting progress and triaging issues. This clarity, combined with assigning individual names to action items, fosters true ownership.

Instead of over-analyzing and philosophizing about process improvements, simply force the team to increase its cadence and ship faster. This discomfort forces quicker, more natural problem-solving, causing many underlying inefficiencies to self-correct without needing a formal change initiative.

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.

To prevent resentment in high-pressure teams, implement a scheduled forum for fearless feedback, like a "Sunday SmackDown." This creates a predictable, safe container for airing grievances—personal or professional. By separating critique from daily operations, it allows team members to be open and constructive without the awkwardness or fear of disrupting morale, thereby preventing small issues from escalating.

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.