Breaking into asset management?

I'll bite - currently work as an Asset Manager at a vertically integrated retail-focused REIT.

1. I got hired through a headhunter. My prior experience was not relevant to CRE, but helped build a good foundation of familiarity with contracts/financials. I graduated from a T20 undergrad program with a business degree. During my time in AM I have yet to come across someone with what this board would call a "blue chip" background. Lots of people with "humble" paths that are just really good at what they do.

2a. Best: Our AM team is set up such that we handle anything important at our shop. We handle the transactional work and are the team that the C-suite comes to if they need something done quickly/quietly/correctly. This means getting to work on interesting projects that are relevant to the direction of the company. AM is, on the whole, very stable. You have your busy periods, but for the most part your workdays are predictable. This makes planning things outside of work a lot easier than a pure front office role. You get to touch a lot of different aspects of CRE as an AM. You're expected to be proficient in every discipline and know how/where to push back on the subject matter experts. You are the "mini-CEO" of your portfolio in a lot of ways. At the higher levels your compensation begins to be tied to your portfolio's performance, so you have to make business decisions that ensure your portfolio's success.

2b. Worst: The core job function of AM is reporting. An AM's responsibility expands/contracts based upon the fund/shop, but a lot of what you will be doing is budgeting/forecasting based. You are a jack of all trades but a master of none. This means that while you are expected to know enough to be dangerous regardless the subject, there will always be someone else in the room who's opinion is more well learned. If you're the type of guy that likes to be the smartest guy in the room on "your" vertical (ie. Leasing), AM is likely not for you. It depends on the shop you're working at, but if you work at a vertically integrated shop you'll have PM/Leasing/Etc. in house. This makes it much more challenging to make personnel changes in your portfolio. Employing 3rd party management/leasing/etc, allows you to cut bait much easier if/when someone stops caring or is otherwise under-performing. Asset Managers are often viewed as "in the way". You'll be the one who has to kill the development project, to tell leasing that no, AM isn't on board with giving a tenant $10M in TA at a 1.5% return, or to tell the PM that they can't do a particular CapEx project this year. These disciplines tend to hold the message against the messenger.

3a. The most prevalent quality I see in successful AM's is people skills. Again, as an aggregator, you rely on everyone else to do the work. You need to have people skills to get people to pick up the phone and make them feel like you're on the same team. People need to view you as a person rather than an annoyance/gatekeeper.

3b. Somewhat topical as I just went through the process of hiring a couple analysts. I'm (relatively) experience-agnostic in that I don't hold someone's past against them. If you can prove to me that you're strategic, analytical, and actually want to be in asset management (ie. not using the role to learn the business then jump to acq/dev), you'll be in good shape. If you want to 'wow' an AM in an interview, do your homework on their portfolio, ask strategic questions, and try to show that you're capable of thinking critically in the context of what they do.