Without delving into too much prattle here this is an old school business school question and a common way to get hired into a C-level role.
Its' an emotionally charged question that tends to cut through some informality to get to what matters.
So let's ask ourselves that with regards to this team.
And I'll try to run though my takes on key concerns or comments I have seen over the off-season.
Trevon Diggs gives up too many yard. –This one is pretty easy for me. Doesn't even raise my blood pressure one bit much less keep me up at night. Diggs will likely be targeted far less and give up fewer yards because teams who test him get punished.
WR depth is awful and no one has proven much. –Not quite as solidly no as Diggs but nearly so. No WR has proven much until they do. This team has Ced Wilson with 22 catches on his career before last year and he got targets and blew up. Randall Cobb blew up 2 years prior when Dak was healthy. Dallas needs CeeDee to be healthy for sure but they have CeeDee and Schultz as the top 2 targets. Other guys are goign to run free and get receptions.
Zeke is washed. –Not much here either. Zeke is rock solid. He may not be rookie Zeke but he had the 7th most yards in the league last year on a very "down" year. I don't think he carries this offense by any means but given the state of the OL I think he has tremendous value in all phases. Not losing any sleep over Zeke's play.
OL has no depth. –Ding, ding, ding. This is the one for me. We have an OL with a major reliance on a LT who has played 11 billiionty snaps. –obvious exagg intended– So yes that scares me quite a bit to have no one of note in the depth department. I think letting La'el walk at that salary and with his lack of production the prior 24 months was smart but I also think you need to use some of that money to backfill. ***Tyhere are3-4 veteran old man tackles out there to be brought in. I can understand why Dallas might want to wait and bring them in AFTER the cuts and even as far as week 3 to reduce any guaranteed money and risk exposing someone else to the waiver wire.
Stephen Jones as Cap Boy. –Yes, this is worrying. We cannot expect the Swing OL to some week 3 or OBJ to be brought in week 4. Stephen views players over the age of 19 as best investments. No RKelly jokes here please. In all seriousness Dallas needs to show an ability to bolster their young roster with smart low cost signings. You cant win with just big-name signings and you can't win with just drafting. You are going to need to marry the two and become efficient.
Mike McCarthy sucks. –Zero concern here. MM is at worst a replacement level coach. Which just is a fancy way of saying at worst he is average as an NFL head coach. Guys are generally well prepared and have a scheme they can execute and win with most games. He's went rah rah in a few scenarios which feels like cheese and yet they have won often those games. But he hasn't dug this team out of its playoff doldrums. No one is drawing up his statue yet.
Dak is overpaid and sucks. –This is just goofy stuff. Dak is the 8th highest paid QB and he is also the 8th rated QB in many unbiased takes. He overcame a very serious injury so well last year people basically ignored he was ever injured. If you say this keeps you up at night you are probably very familiar with the nightly gunshots going off all over Philly.
Kickers suck. –Kickers do in fact suck. Not just the ones in Dallas right now but in general. Playign a football game for 3 hours and have it won or lost on a 185-pound dude who is somehow still out of shape is strange stuff indeed. but no this doesn't keep me up at night. Dallas isn't wed to any of these kickers and unlike Greg z we aren't going to lose 3-4 games watching them get right. Miss kicks and get fired.
Jerry Jones only cares about money!! — First, lets be honest. Most of the dudes ranting about this would climb a wet pole in below freezing weather in nothing but a speedo for 1200 bucks. But secondly welcome to logic 101. The Cowboys are worth more money and make more money when they win.
A Cowboys Super Bowl would make the NFL, it's media partners and most specifically Jerry Jones a small fortune. Jerry isn't saving 10M a year on roster costs to pad his bottom line. He just can't get winning figured out. He's tried high priced free agency and credit card style cap spending. It failed miserably. He's tried building through draft and team just never has enough talent in the playoffs. It's almost like he should build through the raft then augment that on a player-by-player basis with no sharp dictum mandating or forbidding it. So toss up here. The Cowboys front office as a whole keeps me up at night… but not because they are squirrelling away a few M's yearly.