Based on speculation as to how this Barry might be poached away or kicked upstairs, it seems quite possible that Barry may be a model for how the PHB got to where he is. Altho he's usually somewhat more sophisticated, the PHB is typically just about this incompetent. It might also explain the PHB's otherwise inexplicable tolerance of and perhaps even secret admiration for Wally's "Zen" approach to "work."
Barry may have been taking a few lessons from Wally. The vendors are treated as imaginary, so phone calls to or from them are irrelevant, and thus the impression of work is maintained. The Zen of Wally....