When asked by the interviewer

[Bassim]

I am wondering if my sentence sounds natural.

When asked by the interviewer if he had any brush with the law, Bob was not straightforward. He told him he had none, although he did time for a couple of robberies.

[teechar]

I am wondering if my sentence sounds natural.

When asked by the interviewer if he'd had any brush with the law, Bob was not straightforward. He told him he'd had none, although he did had done time for a couple of robberies.

I'd use "(entirely) honest" instead of "straightforward."