The notion of normality is not relevant here. Let $A\in M_n(\mathbb{C})$ be diagonalizable.
$\textbf{Poposition}$. If $\dim(\ker(A))\leq 1$, then each of its square roots is diagonalizable. Otherwise, there is at least one square root that is not diagonalizable.
$\textbf{Proof}$.
Case 1: If $\dim(\ker(A))\le1$.
- Suppose that $\dim(\ker(A))=1$; we may assume that $$A=\operatorname{diag}(0,\lambda _1 I_{p_1},\cdots,\lambda_{n-1} I_{p_{n-1}}),$$ where the $(\lambda_i)$ are non-zero, distinct and $1+p_1+\cdots+p_{n-1}=n$. If $B$ is a square root of $A$, then $AB=BA$ and $B$ is in the form $\operatorname{diag}(0,B_1,\cdots,B_{n-1})$, where $B_i^2=\lambda_i I_{p_i}$. Then each $B_i$ is diagonalizable and $B$ too.
- We solve the case $A$ invertible in the same way.
Case 2: If $\dim(\ker(A))=k\geq 2$, then $A_{|\ker(A)}=0$ admits a square root in the form $$\operatorname{diag}\left(\begin{pmatrix}0&1\\0&0\end{pmatrix},0_{k-2}\right),$$ that is not diagonalizable. Therefore we obtain some $B$ that is not diagonalizable.
Remark. Of course, we can generalize the previous result even further. Let $f$ be a holomorphic function and consider the equation $f(B)=A$. Then the solutions $B$ are diagonalizable iff, for every $\lambda\in \operatorname{spectrum}(A)$, the equation $f(x)=\lambda$ has only simple roots OR has multiple roots but, in this case, the eigenvalue $\lambda$ is simple.