Suppose $\dim V = \dim W$. Given $\phi:V\rightarrow V$ and $\psi:W\rightarrow W$ when do we have bijective linear maps $a,b:V\rightarrow W$ such that $$\require{AMScd} \begin{CD} V @>\phi>> V \\ @VaVV @VVbV \\ W @>\psi>>W \end{CD} $$ commutes?
My intuition says that if the rank of $\phi$ and $\psi$ match there should exist $a,b$. Of course with $a=b$, this requires that $\phi,\psi$ are similar (after identifying $V$ and $W$ in any way you like), but with $a\neq b$ allowed, it seems this is much weaker.
This is essentially the change of bases.
Suppose that $\phi$ and $\psi$ have the same rank $k$. Take a basis $\{v_1,\dots,v_n\}$ of $V$ such that $\{\phi(v_1),\dots,\phi(v_k)\}$ is a basis of the range of $\phi$.
Choose similarly a basis $\{w_1,\dots,w_n\}$ for $W$.
Now complete $\{\phi(v_1),\dots,\phi(v_k)\}$ to a basis $\{\phi(v_1),\dots,\phi(v_k),v_{k+1}',\dots,v_n'\}$ of $V$. Similarly, complete $\{\psi(w_1),\dots,\psi(w_k)\}$ to a basis $\{\psi(w_1),\dots,\psi(w_k),w_{k+1}',\dots,w_n'\}$ of $W$.
Define $a$ by $a(v_i)=w_i$; define $b$ by $b(\phi(v_i))=\psi(w_i)$ for $i=1,2,\dots,k$ and $b(v_i')=w_i'$ for $i=k+1,\dots,n$.
Then $a$ and $b$ induce bijective linear maps and, for $i=1,2,\dots,n$, $$ b(\phi(v_i))=\psi(w_i)=\psi(a(v_i)) $$
Can you show the converse?
Without bases, you can use complements. Write $V=V_1\oplus\ker\phi$, so $\phi$ induces an injective linear map $V_1\to V$, with the same image as $\phi$. Write $V=\operatorname{im}\phi\oplus V_2$.
Do similarly for $\psi$, writing $W=W_1\oplus\ker\psi=\operatorname{im}\psi\oplus W_2$.
By assumption $\dim V_1=\dim W_1$ and $\dim V_2=\dim W_2$. Choose suitably the isomorphisms, noting that $\phi$ and $\psi$ induce isomorphisms $V_1\to\operatorname{im}\phi$ and $W_1\to\operatorname{im}\psi$. However this is not really different from choosing bases.