After working a lot of examples, I came up with the following conjecture:
"Let $p, q$ be unequal primes, and $\alpha \geq 0, a$ integers. Suppose $l > 1$ is the multiplicative order of $p$ modulo $q^{\alpha}$, and $d$ the largest power of $q$ which divides $a$. If $d < \alpha$, then the smallest number $t$ for which $p^ta \equiv a$ (mod $q^{\alpha}$) is exactly $l/q^d$."
Using these online calculators http://ptrow.com/perl/calculator.pl and http://users.otenet.gr/~bpapa/multiplicativeorder.htm may quickly convince you that my claim is true (or may allow you to find a counterexample).
Since $p^l \equiv 1$ we have $t \leq l$, and it is pretty clear that $t$ must divide $l$ as well. When $d = 0$, the assertion is obvious since $a$ can be canceled from both sides of a congruence.
Proving the general statement has so far eluded me. I've briefly tried showing that $p^{l/q^d}-1$ is divisible by $q^{\alpha - d}$ but not by $q^{\alpha-d+1}$ (which would complete the proof), but it doesn't seem trivial. Another approach may be to look at the quotient $\frac{p^l-1}{p^{l/q^d-1}}$ and write this as a sum of powers of $p$.
Does anyone see an obvious reason why the above conjecture is true? Any suggestions for an approach to take in proving it would be very helpful as well.