I could blather for hours around this space. A few random highlights:

* The very first thing I read about requirements was Weinberg, and it's still worth reading. (Even if you are a contracting house, with a hopeless client, and you want to go full reactive scrum participatory design, to unblock you for sprints with big blocks of billable hours, not caring how much unnecessary work you do... at least you will know what you're not doing.)

* When interviewing people about business or technical, learn to use a Data Flow Diagram. You can make it accessible to almost everyone, as you talk through it, and answer all sorts of questions, at a variety of levels. There are a bunch of other system modeling tools you can use, at times, but do not underestimate the usefulness and accessibility of a good DFD.

* If you can (or have to) plan at all, find and learn to use a serious Gantt chart centric planning tool (work breakdown, dependencies, resource allocations, milestones), and keep it up to date (which probably includes having it linked with whatever task-tracking tool you use, but you'll usually also be changing it for bigger-picture reasons too). Even if you are a hardware company, with some hard external-dependency milestones, you will be changing things around those unmoveables. And have everyone work from the same source of truth (everyone can see the same Gantt chart and the task

* Also learn some kind of Kanban-ish board for tasking, and have it be an alternative view on the same data that's behind the Gantt view and the tasks/issues that people can/should/are working on at the moment, and anything immediately getting blocked.

* In a rare disruptive startup emergency, know when to put aside Gantt, and fall back to an ad hoc text file or spreadsheet of chaos-handling prioritization that's changing multiple times per day. (But don't say that your startup is always in emergency mode and you can never plan anything, because usually there is time for a Kanban board, and usually you should all share an understanding of how those tasks fit into a larger plan, and trace back to your goals, even if it's exploratory or reactive.)

* Culture of communicating and documenting, in low-friction, high-value, accessible ways. Respect it as team-oriented and professional

* Avoid routine meetings; make it easy to get timely answers and discussion, as soon as possible. This includes reconsidering how accessible upper leadership should be: can you get closer to being responsive to the needs of the work on the project (e.g., if anyone needs a decision from the director/VP/etc., then quickly prep and ask, maybe with an async message, but don't wait for weekly status meeting or to schedule time on their calendar).

* Avoid unnecessary process. Avoid performances.

* People need blocks of time when they can get flow. Sometimes for plowing through a big chunk of stuff that only requires basic competence, and sometimes when harder thinking is required.

* Be very careful with individual performance metrics. Ideally you can incentive everyone to be aligned towards team success, through monetary incentives (e.g., real equity for which they can affect the value) and through culture (everyone around you seems to work as a team, and you like that, and that inspires you). I would even start by asking if we can compensate everyone equally, shun titles, etc., and how close can we practically get to that.

* Be honest about resume-driven-development. It doesn't have to be a secret misalignment. Don't let it be motivated solely as a secret goal of job-hoppers that is then lied about, or it will probably be to the detriment of your company (and also, that person will job-hop, fleeing the mess they made). If you're going to use new resume keyword framework for a project, the whole team should be honest that, say, there's elements of wanting to potentially get some win from it, wanting to trial it for possible greater use and build up organizational expertise in it, and also that it's a very conscious and honest perk for the workers to get to use the new toy.

* Infosec is an unholy dumpster fire, throughout almost the entire field. Decide if you want to do better, and if so, then back it up with real changes, not CYA theatre and what someone is trying to sell you.

* LeetCode frat pledging interviews select for so much misaligned thinking, and also signals that you are probably just more of the same as the low bar of our field, and people shouldn't take you seriously when you try to tell them you want to do things better.

* Nothing will work well if people aren't aligned and honest.

Many thanks for the detailed answer!

How do you know when to call it quits? How do you know when people are not aligned or honest, or that you are not right for the team, or when the team is not right for the client/project?

How much time is normal for a team/project to get its bearings? (It depends, I know...)

For anyone else who had no idea who was https://en.wikipedia.org/wiki/Gerald_Weinberg (also known as Jerry Weinberg) also his blog is still online https://secretsofconsulting.blogspot.com/2012/09/agile-and-d...