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Why do so many teams keep switching tools — and still fail? Jira. ClickUp. Notion. Monday. New platform, same chaos. 🔥 This episode is brought to you by GitProtect - our go-to backup solution, trusted and recommended to every customer who takes their security seriously 🔗 https://bit.ly/4pHDXyg In this episode, Gray MacKenzie (ClickUp expert, ZenPilot) and Josh Golosinkiy (Jira expert, GRYD.IO) break down the uncomfortable truth: 💥 It’s not about tools. 💥 It’s not about features. 💥 It’s about habits, process, and discipline. We go deep on: • Why teams switch from Jira to ClickUp (and back again) • The hidden cost of tool fatigue • Why “flexibility” often creates chaos • How AI is exposing — not fixing — bad workflows • The difference between process maturity and tool addiction Contrarian POV: “You don’t need a new tool. You need new habits.” If you’ve ever felt like your tech stack is growing but your output isn’t — this one will hit hard. Chapters📍 01:36 – Thanks for being here → Why ClickUp? 01:49 – 71 tools reviewed → 3 reasons for ClickUp (flexibility, dev velocity, hierarchy) 04:03 – Was Jira viable back then? (engineering-first era) 04:25 – Jira pain then: flexibility, speed, onboarding complexity 05:33 – Today’s Jira familiarity + migrations off Jira 06:20 – Who moves Jira → ClickUp & why (single source of truth) 07:27 – Biggest pain: two systems, no unified way of working 09:06 – The habits problem: points vs hours, standards vs preferences 10:53 – Feature envy vs focus: serving pro-services; competition equalizes features 13:43 – Copycat effect helps users (Notion ↔ Confluence, industry lift) 14:27 – ClickUp Chat vs Slack: why they switched (and when not to) 17:10 – Will it rival Slack? Connect gap & cross-platform messaging wish 19:30 – Future: AI front-ends; many back-ends that feel like one tool 21:50 – Will consulting go away? Moving up the value chain, not out 23:25 – AI adoption reality: Rovo/Notion AI vs “just use ChatGPT” 24:54 – AI pricing: $30/user vs labor; rollout quality matters 26:04 – Org-wide licensing pain → push toward consumption pricing 28:46 – Built-in AI vs best models: catching up fast, budget tradeoffs 30:56 – Wishlist: Notion synced blocks; utilization/profit reporting; agents 32:19 – Building an AI “coach”: transcripts + email + metrics → actions 34:50 – The missing universal assistant; Rewind’s lesson: capture ≠ coaching 36:19 – Interfaces & form factors: phones vs glasses (what wins?) 37:23 – Find Gray / ZenPilot; right-tool philosophy over short-term wins