This Week #4: Motivating engineers to hit deadlines, PM career ladders, and aligning with execs

Hello and welcome to my humble newsletter, where I answer your questions and offer candid advice about building product, driving growth, working with other humans, and anything else that’s stressing you out at the office. I’ll tackle three reader questions each week (keeping your name and company anonymous) until you quit sending me questions. I definitely won’t have all of the answers, and it’s just my one perspective, but hey, it’s free! 🤝

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New this week: Let’s experiment with comments 🤷‍♂️ If you have any of your own suggestions to share, on any of the topics we cover below, open up the newsletter in a browser, scroll to the bottom, and post a comment. 🤙

On to this week’s questions…


Q: The biggest question I'm dealing with is how to motivate my eng team to hit deadlines that aren't necessarily connected to anything specific. It feels like they've been dragging their feet and nothing I’ve done has helped.

Since a PM’s primary job is to marshal the resources of their team to drive business impact, it’s understandable why one would be concerned, frustrated, maybe even question their ability to product manage when things aren’t moving fast enough.

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. 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:

  1. Ask questions — Talk to your engineers and/or eng manager to understand why things take as long as they do. Come at it with genuine interest, not an agenda. You may discover they also feel like it takes too long to ship, and can point you to something you can actually help unblock or streamline for the team.

  2. Look at other teams — Are your engineers working slower than those on other teams within the org? Talk to other PMs to get a rough benchmark. At most modern eng orgs, there are a lot of steps engineers must go through before they can ship code. This including manual Q&A, code reviews, unit tests, going through architectural reviews, and launching brand new services. These are generally good things, and in the long-term make things move faster.

  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. I’ve found these meetings to be one of the most effective ways to root out problems large and small. Nothing helps you get better, at product or at life, than a feedback loop.

  4. Re-evaluate how you use deadlines — It sounds like your deadlines are arbitrary. Which is fine. Having deadlines is a super useful tool to get sh*t done. However, it’s important to be up-front about this. I like to say “Let’s come up with an arbitrary deadline!” when setting the date, just to be super up-front about this. Some may ask why have a deadline at all? In my experience, it actually does help get more stuff done, helps a cross-functional team coordinate deliverables around a unified date, and it helps you coordinate all of the other moving pieces in the business (e.g. sales training, CX roll-outs, etc.). It also creates some accountability.

  5. Alternate between hard and soft deadlines — Building on the last point, sometimes deadlines are actually important, and sometimes they aren’t. With soft-deadlines, be upfront but also encourage your team to build muscle to accurately estimate work in order to get it right when it counts.

Following this, assuming you are still feeling like the team can work harder 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):

  1. Connect the work they are doing to their personal motivations: Find out each person’s individual 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 this goal. For example, how does this project help the person build the skills to start a company in the future, or manage others, or get a better shot at a promotion? Make sure they see that.

  2. Connect the work they’re doing to the higher 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. It’s often hard to see it, or we take for granted that everyone sees that connection. Make it explicit in team meetings, project kickoffs, 1-Pagers, decks, and 1:1’s.

  3. Partner with their manager: As a PM, there’s only so much you can do through influence. It’s difficult to be super direct sometimes, especially if you want to maintain a healthy relationship with the team. Your best friend in changing team-member behavior will always be their manager. It’s critical that you have a good relationship with them, and that you see eye-to-eye. If you do, then you should work together to make change. If you don’t, try to get there. Help them see what you see by leveraging some of the things I mention above and below.

  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. If that’s the issue, when you are setting timelines, ask your team members how long they expect something to take. It’s OK to push back occasionally, but generally, just trust them. Then, work out the sequencing based on everyone’s direct estimates, confirm everyone feels good about the plan, lock it in, and then share it widely. Check-in on how things are going in your regular team syncs.

  5. Align incentives: People respond to incentives, so figure out how to incentivize hitting dates. In addition to the other points noted above and below, a few additional incentives to explore:

    1. Connect impact to employee performance: Does delivering impact on the business reflect on people’s performance review? If so, shipping quickly will directly follow. If not, make sure it does. This is critical.

    2. Status: When someone hits a public deadline, celebrate them publicly. But be careful punishing people who don’t — otherwise people will pad deadlines or ship crappy code.

    3. Autonomy: Make it clear the more frequently they hit dates, the more freedom and autonomy they’ll have going forward. Which is true — if you do well, you move up the ranks, and you have more autonomy.

    4. Financial: If they are hitting dates reliably, they’ll be more likely to be promoted. Which leads to a raise. An occasional spot-bonus helps too.

    5. Peer pressure: If they miss a date, they’re letting down the team and customers. It doesn’t feel good to let people down.

  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. If the person doesn’t actually care about the project, it’ll show in everything they do, including missing dates.

  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 a new process, learning new tools). If this is an issue, lean on the more senior team members to help ramp people up more quickly.

  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.

  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, get buy-in again, and share it widely.

  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, and being clear about their underperformance for a period of time, it sometimes makes sense to just let people go. It’s often the best move for both of you.

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 focus on addressing that.

Any other advice from your own experience? Leave a comment below and share your tips 🤜🤛

Q: I've always thought about how to improve my career as a PM. One thing that I wish I could find was a legit career ladder that's actually used in a tech company. Do you know of any?

I’ve shared a bit about what to focus on as your progress in your PM career in this tweet-thread…

… but in terms of official career ladders, borrowing from this juicy collection of links from BestPracticer, here are my current five favorite public PM career ladders:

  1. Intercom

  2. Oscar

  3. Gusto

  4. XO Group

  5. Gitlab

Know of any better examples? Leave a comment and share it with others 👇

Q: We send out a monthly report card to our customers, highlighting some key metrics about their usage. The metrics are mostly vanity so I took over the task of improving it to make it more “actionable.” But every time I present an iteration of it to execs, I get a response saying it is still not “actionable.” Also, all of their ideas are too blue-sky, vague, or difficult to implement (lack of data, accuracy, scalability issues, etc.). Can you give any tips or advice on how to navigate this?

It seems like you’re having a tough time getting your execs onboard with your ideas. A few tips:

  1. Get data: What evidence do you have that backs up your ideas? What convinced you that your ideas are right? Do you compelling quotes from user research you can share? Do you have any metrics that point too your ideas being right? Do you just have a hunch you want to test? If yes, make the case logically, building on the data or experience you’ve built up. If not, get some data. Be prepared to be proven wrong.

  2. Assume good intentions and listen: When your execs tell you that your ideas aren’t “actionable”, dig further. Why not? What would make them more actionable? Why do they think this? When they share ideas that are too blue-sky, what can you do to make them more concrete? It’s your job to take inputs and ship the most impactful work — feedback is a gift 🎁

  3. Figure out the ideal product, and work backward: Check out what I wrote previously about Airbnb’s approach to this (search for “Start with the ideal and work backward”). Don’t limit yourself by what’s easy. Remove that constrained cap for now and think about what the “ideal user experince” would be. Truly assume no constraints. Once you have that, put the cap back on and think about what it would actually take to achieve it. How much work would it really take? Is it that crazy? Pitch it to the execs, and see if they’d actually be on board with making it possible. As someone famous probably said, often times we are limited not by what’s possible, but what we think is possible.

  4. Get out of the building: Stop debating opinions and talk to real users. Show your concepts to at least five users and use that to guide your thinking. Every time I’ve done this I’ve re-remembered how incredibly valuable talking to real users is. Never assume you know what your users want without talking to them.

  5. Work backward from your goal: What metric are you trying to drive with this project — increasing a specific action? more purchases? more invites? Make sure you’re aligned on this KPI with your execs, since that will (and should) inform how you prioritize the ideas. Then, when presenting the ideas, sort them based on which will make the biggest dent in the metrics. If there is disagreement — what’s the quickest test you can run to validate the assumption?

That’s it for this week!

Inspirations for the week ahead

  1. Book: Am I Overthinking This? Over-answering life's questions in 101 charts - True, this is a book by my wife. Also true, it’s extremely delightful and you will not regret checking it out. Also, she doesn’t know I’m doing this.

  2. Article: Three Big Things: The Most Important Forces Shaping the World - Wow, this kind of blew my mind. Don’t miss it.

  3. Show: Inside Bill’s Brain on Netflix - Inspiring, optimistic, and moving. We could do with a bit more of this these days.


If you’d like some advice, or just want to say hi, just reply to this email and ask! And please share this newsletter with your friends if you’re finding this valuable.

Sincerely,

Lenny 👋