First, make sure your Calendly account is linked to Hoolr. Here is a guide on how to link Calendly to Hoolr.
Your Calendly will sync sessions with Hoolr once per day or when you press the Sync Calendly.
If you are not seeing sessions appearing that you would expect to be synced it could be because you do not have the coachee added to your Hoolr account. You can add a new coachee by following this guide.