Changing variables to $n=T-k$, and letting $x=1+a$, we can write the sum as
$$
S=\sum_{n=0}^{T-1}\frac{x^{-n}}{T-n}=\frac{1}{T}+\frac{x^{-1}}{T-1}+\frac{x^{-2}}{T-2}+\cdots+\frac{x^{1-T}}{1}.
$$
Recognizing that the right side of
$$
Sx^T=x+\frac{x^2}{2}+\cdots +\frac{x^T}{T}
$$
would be the $T^{th}$ Taylor polynomial of $-\log(1-x)$, except for the annoying fact that $x>1$ so the Taylor series does not converge here.
Instead, the series behavior geometrically and is dominated by its last few terms. One way to obtain a somewhat reasonable and explicit upperbound is by keeping the last term and decreasing the denominators of all other terms to $1$, then summing the geometric series to obtain
$$
Sx^T\leq x+x^2+\cdots+x^{T-1}+\frac{x^T}{T}=\frac{x^T-1}{x-1}-1+\frac{x^T}{T},
$$
showing that
$$
S\leq \frac{1}{a}(1-(1+a)^{-T})-1+\frac{1}{T}.
$$
To gauge how tight of an upper bound this is would require knowing how $a$ compares to $1$, and different procedures could be used in the regimes when $a$ is very close to $0$ vs when $a$ is much larger than $1$.