Snakes & ladders:
IT edition The moves that set you back and the ones that send you flying forward
Snakes & Ladders: IT Edition
Turns out the path to getting AI right is less straight line, more board game. Some squares send you flying forward. Others have a very long snake on them and an uncomfortable meeting waiting at the bottom.
Ladders
Fix your data and map your processes before touching AI → foundation that actually scales
Start with one small, high-impact AI win → earn trust, unlock the next project
Build feedback loops, measure outcomes, turn what works into playbooks → repeatable systems you can actually sell
Get AI working internally before you take it anywhere else → credible conversations, real stories
Address your team's fears before you roll anything out → smoother adoption, sharper thinking
Snakes
Deploy AI on a broken workflow → it won't fix it, it'll collapse it faster
Let an AI agent run without scope or oversight → slide back to a very uncomfortable room
Overpromise on what AI can resolve and how fast → reality will correct you, loudly
Use AI in your services without telling anyone → trust problem, hard to undo
Skip documentation, rely on tribal knowledge → slide back to square one the day someone leaves