In this episode, you'll learn how to win support for a tough proposal, avoid getting blindsided in meetings, use informal conversations to map your allies and blockers, and turn neutral teammates into advocates.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

Timestamps: 

[00:00] Introduction

[01:04] A failed pitch story and key lesson

[02:18] The importance of having a playbook

[02:55] Why great ideas get shot down

[03:12] Stage 1: Test the waters

[04:40] How early insights shape your pitch

[05:30] Stage 2: Understand the numbers

[06:00] Identify veto players and the majority needed

[06:45] Plan around timing and meetings

[07:30] The power of loud voices in group settings

[08:10] Stage 3: Strengthen your supporters

[08:50] Ask for feedback, not support

[09:30] Involve people by including their suggestions

[09:50] Win over key skeptics

[10:20] Turning opponents into advocates

[10:50] Leverage respected voices in the group

[11:15] Why being heard matters more than being right

[11:35] Coaching for executive communication

[12:10] Why logic often loses to emotion

[12:50] How storytelling wins the room

[13:20] Stage 4: Engage the neutrals

[13:50] Connect your idea to their priorities

[14:15] Use win-win framing for middle-ground people

[14:40] Avoid turning neutrals into opponents

[15:00] Use social proof to tip the balance

[15:30] Stage 5: Presentation and decision

[16:20] Call out contributors by name

[16:45] Make it feel like the next logical step

[17:00] Keep the decision meeting short and smooth

[17:45] How to avoid meeting debates and delays

[18:00] Creating watercooler moments in remote work

[18:30] How to test ideas before remote meetings

[19:25] Follow-up strategy after remote conversations

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.