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Q: How do I motivate my eng team to hit deadlines? It feels like they've been dragging their feet and nothing I’ve done has helped.

👇 5 ways to build understanding + 10 ways to motivate (1/20) 👇
The first thing to know is that this is extremely common — I haven’t yet met a PM that wasn’t at one time frustrated by how long it takes to get things out the door. It’s almost part of the job. (2/20)
That being said, there are often good reasons for why things take longer than you’d suspect, so I’d encourage you to start with listening and understanding: (3/20)
1. Ask questions — Talk to your engineers and eng manager to understand why things take as long so long. Come at it with genuine interest, not an agenda. You may discover they also feel that it takes too long, and can point you to something you can actually help with. (4/20)
2. Look at other teams — Are your engineers working slower than those on other teams within the org? Talk to other PMs, get a rough benchmark. At most modern eng orgs there are a lot of hidden steps, for long-term health, engineers must go through to ship code. (5/20)
3. Do post-mortems — After a project ends, particularly when you missed another deadline, do a post-mortem with the team. Here’s a pretty good guide. The key is that you all come at it with a motivation to learn, not blame and point fingers. (6/20)
4. Re-evaluate how you use deadlines — Having deadlines is a useful tool to get sh*t done, but aren't always the best tool. Test not having deadlines for, or if they aren't hard deadlines, be up-front about that. I like to say “Let’s come up with an arbitrary deadline!” (7/20)
5. Alternate between hard and soft deadlines — Building on the last point, sometimes deadlines are important, and sometimes they aren’t. With soft-deadlines, be upfront and encourage your team to build muscle to accurately estimate work for when it counts. (8/20)
Following this, assuming you are still feeling like the team can work faster and take deadlines more seriously, here are some of the most effective ways I’ve found to motivate anyone on your team (engineers, and everyone else): (9/20)
1. Connect the work they are doing to their personal motivations: Find out each person’s goals (e.g. they want to become a manager, they want to start a company, they want to be promoted), and help them see the connection between the work they are doing and achieving it. (10/20)
2. Connect the work they’re doing to the mission: Assuming they joined your company because they believed in the mission, make sure it’s clear how what they are working on day-to-day helps achieve this mission. Make it explicit in team meetings, kickoffs, 1-Pagers (11/20)
3. Partner with their manager: As a PM, there’s only so much you can do with influence. It’s difficult to be super direct sometimes, especially if you want to maintain a good relationship with the team. Your best friend in changing behavior will always be their manager. (12/20)
4. Make sure you have buy-in: Are your team members actually bought into these timelines? Do they feel like they actually committed to these dates? If not, then it’s obvious why they aren’ hitting them — they never said they would. (13/20)
5. Align incentives: People respond to incentives, so figure out how to incentivize hitting dates. In addition to the other incentives noted above and below, a few additional incentives to explore: Connect impact to employee performance, Status, Autonomy, Financial (14/20)
6. Align passions: As much as possible, make sure people are working on things they are actually excited about. This often includes building mastery in something (e.g. ML, react, growth), or filling a gap they have to address in order to be promoted. (15/20)
7. Align skill-sets: Make sure the people doing the work are actually well suited for. Sometimes things take way longer then they should because the people doing the work are still learning how to actually do it (e.g. learning a new language, learning new tools). (16/20)
8. Sprints: How far ahead are you estimating dates? People are bad at estimating. Consider switching to a more agile product development process where you only need to estimate two weeks out. This alone may address your issues. (17/20)
9. Change the deadline when you have new information: Often after a project begins you uncover unexpected hurdles that didn’t inform the estimate. Instead of trying to squeeze things in, consider simple resetting the deadline. Make it an official change to the date. (18/20)
10. Sometimes, you just need to fire people 😲: Occasionally, people just aren’t good at their job, and can’t deliver what you hired them to do. After doing whatever you could to get them there, it sometimes makes sense to just let people go. (19/20)
High level, all you really need for your team to excel is (1) smart and (2) motivated people. If people continue to take way too long to ship, and you’re confident this isn’t just an incorrect perception, then one or the other is amiss. Figure out which one, and fix it (20/20)
Would love to hear any other suggestions or insights, especially from engineers.
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