tl;dr: My supervisor chose to try to deliver a new feature within an unfeasible org-wide deadline, put me on development for it (despite my early warnings), made me feel like I'm at fault for it not being ready, and gave me no course of action regarding what to do about it moving forward.
I work at a large software engineering company on a team of 5 others plus my supervisor, Chris. We develop a consumer productivity application, which is part of a larger suite of applications developed by the entire organization. These applications are always released in lockstep with each other, so deadlines affect the entire organization and are set by high-level project managers.
Our work nowadays is primarily adding more features for end-users. It is the responsibility of each team's supervisors to decide which features go into which releases, based on how much work they are estimated to be and how much time we have before the deadline to complete that work.
Chris recently put me onto one of the smaller feature proposals with a very tight deadline. I came up with a gameplan, but determined that we did not have enough time to be ready for the deadline. I relayed this to him in our next weekly one-on-one meeting, and he all but disregarded it. He sort of stammered, trailed off, said something like "we'll see where you're at later in the week." I offered to work late if necessary. He sort of shrugged and said he didn't think that would be necessary. So I just went back to work.
Come Friday, I had made even more progress than I anticipated, but it was still at least a week away from being even close to shippable. I gave him a status update in our team meeting. Afterwards, he pulled down my feature branch and spent the rest of the day testing it out and messaging me every time he found anything at all wrong with it. I started trying to fix things, but quickly grew stressed and reminded him that it's a complex feature and needs more time. He said, "We are out of time." I asked, in the most earnest, non-confrontational way possible, what exactly he wanted me to do at this point. No response. I offered to work a day over the weekend. He said "sounds good."
This is the second time I've been solo up against a really tight deadline like this, but I'll admit to being at least partially at fault the first time. I was not transparent with management about whether or not I was going to get that feature done. I didn't want to have to tell them that I didn't think I could complete the task. After we had a really close call, Chris in our postmortem told me that in the future, if I ever feel like a feature is not going to be ready in time, I should be forward about it and let them know so they have time to coordinate a new schedule for the feature. That's exactly what I tried to do here, and I feel like I've been totally ignored.
I love my job; the work that I get to do; the engineers I get to work with; the satisfaction when I see end users thrilled at the stuff I've worked on. But Chris has been truly difficult to deal with. He was an engineer who became a supervisor, and severely lacking in management skills, which is usually not a problem since there's so much feature overlap and collaboration between teams in the org. But situations like this really highlight his shortcomings.
I am the farthest thing from someone who likes to stir up drama, especially at the workplace. I try to solve interpersonal situations on my own when possible, and deal with them or ignore them when not. But for the first time ever, I've been dreading going into work, and I feel like that's a sign that I should do something about this. Chris' boss, Dave, is an excellent supervisor and very personable. I feel like I should try to have a conversation with him about this "collision course" I've felt like I've been on all week, doing everything I possibly can to deal with a situation and still knowing that it won't be sufficient. But I harbor no ill-will towards Chris. He is a nice guy and a skilled engineer. I don't want him to get demoted or take a pay cut.
Is talking to Dave the best course of action? If so, how can I choose my words to make that conversation meaningful and direct without completely throwing Chris under the bus? If not, what should I do instead?