A: Just to set context, my view is that a badly set up design team is one where the designers have not earned: direct access to the company's leadership, responsibility in establishing and refining the company's goals, and credibility across the entire organization. Each of these will need continual dedication to maintain, but ideally over time -- and with good hires -- all of this is achievable. I emphasize earned because some design teams have one or two of these attributes but because they haven't earned them it's likely that the access, responsibility, and credibility will be temporary.
Having said all that, here are some characteristics of ineffective designers and design teams, but some of this is applicable to any role/function:
Spend too much time masturbating. I am not even joking. Working on self-indulgent projects with really narrow views of the world that serve to impress themselves and/or other designers (inside or outside the company) can waste a lot of time. What's even worse is the long term effects of this mindset where the only "lessons" learned are how to better indulge other designers instead of what does the product really need to help advance the overall vision for the company.
Complain about everything without even trying to prioritize the problems, think about the problem's larger context, or work through productive solutions. I am sitting here annoyed just thinking about this nonsense. This is worst when it's someone or a group of people who you know to be talented. These people can become toxic and infect the entire team so it's important to nip this bad behavior in the bud by redirecting the angst to something productive. There are ways to help individual designers turn the corner if you want to invest in the person but oftentimes the best option is to fire them or let them quit.
Believe design is a religion with its own morals. Rules instead of best practices, absolutes instead of context and nuance, etc. Basically, a willful lack of pragmatism. Most likely the result of reading too many blog posts and engaging in too little critical thinking. Sir Jonathan Ive did this so it's gospel. Steve Jobs did that. Helvetica is crap because some famous typographer says so. Amen. This will prevent the team from exploring a lot of areas that might be really impactful. For example, if the team thinks all A/B testing is bad, then they are left with fuzzy means to "measure" the effectiveness of everything they work on which is harmful for the entire company.
A: It depends on what you want from your career.
If you want to make a lot of impact, then work on getting good at identifying and executing on high leverage projects. This is risky because before you are good at identifying high leverage projects, you will work on some stinkers. And sometimes something that looks like a stinker is actually going to be extremely high leverage. Sometimes the project is high leverage but your poor execution makes it a stinker. Maybe there's some shortcut for this, but I don't know it.
If you want to learn how to execute better, then design everything at least 5 different ways, always. Design it to completeness one way and then start over from scratch and do something totally different. You disagree with the direction given? Design the best version of that direction that's possible. Then design it the way you think it should be. Talk to someone else and do a version based off of what they said. There's a measure of discipline with this approach where you have to not let yourself sabotage versions you don't personally like but if the idea is to learn and not to advance your personal agenda, you will see obvious benefits from this approach.
If you want to be in management, then work on the first two things I've listed (impact and execution) and look to improving your interpersonal skills. Realize that the only way to have n times the impact is to empower n people. You can't do that if no one trusts you enough to want to work for you. If you already have the interpersonal skills and you're not yet in management, keep working on the first two things.
If you want a fancy title, then work on sounding professorial, don't be too controversial internally, and for godssake don't put your hands directly on anything, especially if you are a white male. This way you can convince the leadership to let you hire a large team of people that you can play off each other and trade around when projects succeed or fail. This will work in most companies. Eventually you'll be found out but you can hop around companies and make yourself a brand name before that chicken comes home to roost.
A: Know the company's vision, know its strengths, know its goals. Know how the goals were derived from the vision. Know how the strategy is set. Know the importance of each major function, know their strengths, know their function specific goals. Know how design can best be leveraged for your specific company's goals and strategy. Know how design can best help and interact with other functions. Know exactly what the company needs and why and do your best to hire people to excel at only that which is actually needed.
To summarize, do your homework on the company and then show your work to the team.
- Twitter: If you took over the Twitter product team tomorrow, what direction would you take the product/what would you build (or kill) over the first year?
- Web Application Frameworks: When analyzing consumer apps, is there a framework that you typically use?
- Artificial Intelligence: What do you think will happen to software Product Design as AI advances to make interfaces conversational?