><i>I’m in a in a conflict of measuring my people and understand what they do and if they do the right things to being too bossy and nudge them too much, which may hurt their productivity and retention.</i><p>Your approach will probably be tailored to every individual's characteristics. Some are laser-focused. Some know how to prioritize. Some will need your involvement to move forward, others will move forward inspite of you. Some get tired fast, others have a lot of stamina. Some can handle complexity, some understand business, some this and some that.<p>Clear communication is important. Your thoughts are only obvious to you, and they make sense mostly in your head. Writing them down exposes holes. Repeating sucks, but it's worthwhile when you say something and someone says: "You know... you must have said this a hundred times, but it's only now that it clicked.".<p>The major focus in my opinion ought to be the product, the roadmap, on the clarity of the objectives and making sure everyone understands what you're building and why and why you're <i>not</i> building and why, and what you will build but not now. When this is taken care of, people will get to work and give it a shot. If you want to measure something, introduce quantities for the phenomena that matter most, the output of the system: user satisfaction, experience, ease of use, stability, and work your way back.<p>Low tech things work: having a Slack workspace for users where all your team answers questions and supports users pretty much guides you. You prioritize the issues faster according to what's causing the most pain. When almost every message is on problem X, you have your work cut out for you. Suddenly you realise some of your users have low bandwidth and are the application doesn't even load. Who would have known? It also puts pressure on the team when real people are having problems, and it's also satisfying.<p>I've written a few replies to similar topics.<p>[0]: <a href="https://news.ycombinator.com/item?id=21808439" rel="nofollow">https://news.ycombinator.com/item?id=21808439</a><p>[1]: <a href="https://news.ycombinator.com/item?id=21598632" rel="nofollow">https://news.ycombinator.com/item?id=21598632</a><p>[2]: <a href="https://news.ycombinator.com/item?id=21614372" rel="nofollow">https://news.ycombinator.com/item?id=21614372</a>