Coaching has four classic 'right time' triggers — most people who hire a coach successfully do so because one of these became unavoidable. Knowing which one applies to you tells you both whether to hire and what to look for in a coach.
Trigger one: the structural plateau. You've trained consistently for over a year, your FTP hasn't moved in three or more months, and you've tried what the internet suggested. This is the most common coaching trigger, and it's the rider profile where coaching most reliably pays back. The diagnosis a good coach makes in 2-3 weeks is what would otherwise take you a year of trial and error.
Trigger two: the target event. You've signed up for an Étape, an Ironman, a stretch sportive, or a serious race, and you can't afford to under-prepare. The cost of arriving at the start line under-fitted, over-trained, or wrongly fuelled is much higher than the cost of 6 months of coaching. Most coached event riders do single-block coaching deals — 12-16 weeks, peak for the event, take stock after.
Triggers three and four: the masters transition and the comeback. After 40, the training that worked at 30 stops working — and most masters riders self-coach for too long before realising the recovery, strength, and fuelling adjustments are non-trivial. After a long break (injury, illness, life), the rebuild is the highest-risk period for re-injury and overtraining. Both are exactly the moments where coaching adds disproportionate value. The Roadman coaching beginners article walks through the readiness signals in detail.