[guided]Assume that $a$ is a pole of order $m$ of $f$. The definition of a pole of order $m$ says precisely that the singular part of $f$ is one factor of $(z-a)^{-m}$ and that the remaining factor is holomorphic and nonzero at $a$. Thus there are $\rho>0$ and a holomorphic function $g: B(a,\rho)\to\mathbb{C}$ such that $B(a,\rho)\subset U$, $g(a)\ne 0$, and
\begin{align*}
f(z)=\frac{g(z)}{(z-a)^m}
\end{align*}
for every $z\in B(a,\rho)\setminus\{a\}$.
The reciprocal of $f$ will involve $1/g(z)$, so we need $g$ to be nonzero on a whole neighbourhood of $a$, not only at $a$. Since $g$ is holomorphic, it is continuous. Because $g(a)\ne 0$, continuity gives a radius $r$ with $0<r\le \rho$ such that $g(z)\ne 0$ for every $z\in B(a,r)$. On the punctured ball $B(a,r)\setminus\{a\}$, we then also have $f(z)\ne 0$, because $(z-a)^m\ne 0$ and $g(z)\ne 0$ there.
Now define the proposed holomorphic extension of the reciprocal as the map $F: B(a,r)\to\mathbb{C}$ given by
\begin{align*}
F(z)=\frac{(z-a)^m}{g(z)}.
\end{align*}
This function is holomorphic on all of $B(a,r)$: the numerator $z\mapsto (z-a)^m$ is a polynomial, and the denominator $g$ is holomorphic and nowhere zero on $B(a,r)$, so $1/g$ is holomorphic there. For every $z\in B(a,r)\setminus\{a\}$, the pole factorisation gives
\begin{align*}
\frac{1}{f(z)}=\frac{(z-a)^m}{g(z)}=F(z).
\end{align*}
Thus $F$ is exactly the holomorphic extension of the reciprocal.
Finally, $F$ has the required order of vanishing at $a$. Indeed, define $h: B(a,r)\to\mathbb{C}$ by $h(z)=1/g(z)$. Then $h$ is holomorphic, $h(a)=1/g(a)\ne 0$, and
\begin{align*}
F(z)=(z-a)^m h(z).
\end{align*}
By the definition of a zero of order $m$, this says that $F$ has a zero of order $m$ at $a$.[/guided]