Timeline

[runningsloth]

I know it's early, but my wife and I want to be prepared when recruiting season opens for the 2016-2017 school year. We know we will be staying at our school next year, but after that, we are looking to pursue a new opportunity. Search requires updated references to reactivate our accounts, which involves me asking my HOS and principal for recommendations. I have no issue doing this, but just wondering when we should actually tell them that next year is our last? What should we have in place by the time recruiting starts around October? Thanks

[PsyGuy]

End of the academic year is fine but you have until your school requires your notice. I would inform your HOS when youre at the point of requesting the reference if its earlier than the end of the academic term.

You should have your standard application materials ready with an updated profile including references, cover letters, resumes, and your portfolio. Request your fair invitations as early as possible and consider your options for ichiros. At the beginning of the year start putting out early applications if your going to pursue elite recruiting or senior leadership positions.

[sid]

The answer to your question really depends on your relationship with your supervisors, and when you want to tell them.
For my last resignation, I advised my boss in May that I was considering leaving after the following school year. Nothing official, nothing confirmed. I let him and a few others know, and said I wanted to get my ducks in a row, so would they complete the reference requests they'd soon be getting from various search agencies. I tidied up my CV, made sure my search profiles said I was not available until 15 months out, and voila, I was up and running at full steam before the summer holiday. In the fall, I continued those conversations with my boss and key people, and kept them in the loop as I firmed up my decision to leave. By the time it was official, they weren't the least surprised... I put out applications and had interviews all fall, before I had to turn in my notice.
So you could start even now, unofficially, and that's the course I recommend if your relationship/position with your admin is positive.
But if there are sharks in those waters, obviously wait. But you can't wait forever. If your search profiles aren't active by October, you'll be missing really good opportunities that go to the early birds. And since it can take a month or more to get the reference letters you need, that means telling them in September at the latest.... At the least, get your CV and personal statements and such cleaned up and ready to go over the summer.
Good luck.

[PsyGuy]

If the admin are going to be a problem, you way to consider how much and to what degree you can conduct a job search without SA or another premium agency. Some admins/management react poorly to ITs that would even consider leaving their ISs. Most of these admins are well know on the circuit and their reference wont weight heavily on your application. A number of minor factors could significantly influence the most appropriate pathway.

[runningsloth]

Thanks for the comments. Just to clarify, I have great relationships with both my principal and HOS. I am not worried about informing them that we are leaving or the type of reference they will provide. Just want to get our ducks in a row. Yes, because of the nature of our positions and our experience, in the past, we have tended to get interest, interviews, and offers early in the recruiting cycle.

[mamava]

We told our principals and HOS in the fall (October) when we needed to ask for references. We told them we were going to be exploring options but would not be attending job fairs (which was true) so they would be prepared for calls. I think that that's fair time, since schools will start to think about possible openings in the fall and some ask for yes, no, or tentative (non-binding) feedback in the fall.