Think of Sharpe ratio, Treynor ratio, or anything where (excess) returns $r$ are divided by something that represents risk, $\sigma$:
$$\mathrm{performance} = \frac{r}{\sigma}$$
If the returns are negative (let's say for a short period), a performance indicator based on such a ratio is better (=less negative), the higher the risk (e.g. volatility) is.
First question: Does this make sense? I would not say the true performance is better (less poor), if the risk increases – even when the returns are negative.
Second question: Are there established (or even proposed) risk-adjusted return measures that penalize (or at least don't reward) high risk even for negative returns? I'd be quite happy to derive one, but I would expect that someone has already figured this out.