funny you ask that question today because somebody who is also a cyclist was asking me just yesterday and I did some research. I will be not able to assess him myself. So here is a great reference article http://www.active.com/cycling/articles/tight-it-band-3-simple-exercises-… Of course, nothing is as simple as ‘3 Simple Exercises’.
I find hip strength often lacking, particularly hip abductors. And while it may be tempting to roll up and down the IT band with a hard roller, I would combine hip abductor and glute exercises with a soft roller for the inner thigh. The MELT Foot Treatment should also become part of the approach (I saw that you are an instructor).
Has he seen a physical therapist? There should be some recommendations as well that can serve as a starting point.
Here is the link again. Not sure why it did not come up. http://www.active.com/cycling/articles/tight-it-band-3-simple-exercises-…
Too add to what Karin posted:
1. Manual crossfiber massage of IT band in addition to lower leg musculature such as tibialis anterior and lateral calf.
2. Avoid exercises that irritate the area if possible
3. Work on improving or normalizing walking and running gait, reducing valgus collapse, and engaging the glutes
4. bodyweight or ankle weighted knee extensions with isometric phases. Emphasize maximally engaging VMO
5. If able, work on proper squat technique and single leg squat mechanics. Use a 1/4 single leg squat or TRX assisted single leg squat. focus on knee position (abduction and external rotation) as it is controlled from the hip. If these worsen the pain then do not continue until more progress is made with the above recommendations.