Creating Great Roadmaps By Drift Director of Product

This week Product School hosted Maggie Crowley Director of Product at Drift for an #AskMeAnything session. Maggie talked about transitioning roles within the product industry and using effective roadmaps. She also addresses different processes such as MVPs and talking to stakeholders. 

Meet Maggie Crowley

Maggie is a Product Manager with years of experience in analytics and marketing. Currently, she’s Director of Product Management at Drift: Conversational Marketing, a platform that combines chat, email, video, and automation to remove the friction from business buying. Prior to her current role, Maggie was a Director of Product Management at BevSpot, easy-to-use online technology solutions for bars and restaurants, and before that she was a PM at TripAdvisor.

Addressing debt, stakeholders and MVPs and teams

“How do you approach technical debt for a product that’s been running for almost a decade?”

My approach to tech debt is to always try to understand the impact on the customer. So will tackling it mean we can solve for something new that they need? Or maybe solving for it will reduce latency (speed is a feature IMO)? Once you figure out the customer impact it gets easier to prioritize that work against other “feature” work.

“What do you say to stakeholders who want to by-pass any discovery or don’t see value in creating 1-pagers and want to go straight to JIRAs?”

This is pretty much NEVER a good idea, I’ve been burned every time I skip this step. For these stakeholders, I will just do it anyway on the side. Even just spending an hour writing up the problem and outlining some open questions can help – especially if you then start to ask that stakeholder those open questions often times I find that the person has a couple of foundational assumptions that either I don’t have/share or they’ve just gotten too excited and need to take a minute to think. No one has ever been upset when I’ve taken some extra time (even if it’s my own nights and weekends time) to do some problem exploration.

“How do you balance between validating customer problems and quickly launching an MVP for a feature or product? At what point do you decide it’s worth testing the hypothesis by creating an MVP? Does the company’s risk tolerance impact this?”

Classic answer: it depends.

Typically I think it depends on how “big” the problem is, how well aligned or not it is from the core of what you do as a product, and how much information you have on the problem space.

The less information I have on the problem, and the further away the problem is from the “core” of what I work on, the more time I’m going to spend validating and understanding that problem.

It also depends on the type of problem you’re working on: is it a workflow? Is it something that relies heavily on the interactions/live experience of the product? I love working with designers who are able to pull together more advanced prototypes to solve for that type of thing.

I will also say that at Drift we don’t subscribe to the idea of an “MVP” because we find that it often means that you ship buggy, unfinished work to customers. Instead, we try to scope our work to a “SLC” or simple, lovable, and complete version. Then, we will launch to an Early Access Program to iterate quickly based on the feedback of a small group of customers.

I have to admit that in the early days of our startup we were more prone to shipping features quickly and learning afterwards – now that we’re bigger and have more customers/more enterprise customers, that’s much harder so we spend more time validating before shipping.

You might also be interested in: What Is a Minimum Lovable Product?

“What are the largest difference makers when working across teams? Have you seen or come across any universal truths when developing budding product managers?”

On your first question: the difference maker is having a really clear strategy that explains where you’re headed and why (and helps you say no to things). The more clear the strategy and the plan is, the more coordinated the teams will be, because they’re all working with the same info/the same direction. If teams are starting to diverge I find it’s almost always a process or communication problem at the leadership level. Marty Cagan has a LOT of great writing on this topic on his blog with SVPG

On your second question: the best PMs I’ve ever worked with all share a deep curiosity about the user, they’ve all been people who can separate themselves from the work (meaning they can speak critically about stuff they’ve worked on and don’t get defensive), and they’ve been great storytellers about the work.

You might also be interested in: The Basics of Storytelling for Product Managers — And Why It Matters

Transitioning between Product Roles

“What are the most important things to do when kicking off a job transition?”

1. You’re bringing a unique perspective to the PM team that no other PM has and that can be your secret weapon. You know how the products will be sold and can help frame what you work on in a way that will help your company.

2. Talk to customers. Listen to them, learn about them, and go way beyond what you had to know to sell to them.

   I’d line up at least 3 interviews in your first week!

You might also be interested in: Customer Feedback Loops: The Tools You Need

“How do you recommend breaking into a Group PM (manager) role without direct management experience?”

This is such a hard jump – my advice would be to find ways that you can start to demonstrate that you’re ready for the role. This can be mentoring other PMs at your company, maybe you have interns that you can work with, maybe there are opportunities to train earlier career PMs on a subject that you have a superpower in. I would try to find those opportunities and show you work on them.

I would also talk to your manager! My approach to making jumps like this is to be really clear, that is what I want to do, and I start the conversation saying, “my goal is to get (wherever), what are the steps I can take to get there?” rather than just hoping it will happen.

“What skills does a PM or Group PM needs to develop in order to become Director of Product?”

Making the jump is all about your ability to transition from doing the work yourself to being able to work through a team. Showing you can coach PMs to great results (and also hire/let go of teammates when necessary) is important here.

The other big difference is that your job also becomes more about how to make the right decisions between products and priorities instead of within one product area.

What helped me make the jump was spending more time on the “why” behind my work, and putting my work into context every time I talked about it, so telling the story of how/why what I’m doing fits in with the business strategy, the product strategy, our go to market strategy, etc.

The Importance of Roadmapping

“What tools do you use to keep track of product roadmaps, prioritization across features and reporting progress to leadership?”

This is probably an unpopular answer: Google slides mostly (although the individual teams we have use JIRA)

We of course have key metrics we track across our product and a couple of dashboards, but the main way I keep track is a doc that has all of the team’s goals in it, a sheet with the evolving milestones (or plan) that each team is working against, and a cadence of bi-weekly meetings where we hear from each team where they’re at in terms of progress.

You might also be interested in: How to Use OKRs for Roadmap Prioritization and Planning

“How would you articulate the importance of including a product roadmap (now, next, later) to someone who favors time management/gantt chart project tracking?”

This is SO hard, especially if that person is the Boss.

I think Ryan Singer articulated this really well in his book Shape Up, where he talks about how you can’t have both fixed scope and a fixed deadline – that will make it nearly impossible for teams to hit their deadlines, so that’s the logic I use for more practical people.

Another argument is that a Gantt chart roadmap will prevent your team from being customer centric. The more you’ve planned ahead, the less your team will be paying attention to what’s happening in the market, with your customers, etc. and all of a sudden they’re delivering things that don’t really “matter” because they don’t reflect the current lived reality of the customer. Gantt charts can be dangerous because they don’t communicate the level of uncertainty involved.

Landing a Product Management Job

“What is the best way to get the hiring manager’s attention when applying to an APM role?”

Tell a really great story about why your past experience will help you with the core activities that an APM does (understanding users, influencing others, understanding data, etc.), and if you can, show some side projects or work that you’ve done in your current role that gets at some of these skills.

You might also be interested in: Answered: Why Is It So Hard to Get a Job as a Product Manager?

“What problems do you see for an MBA in digital product management? What skills to learn to prepare oneself to excel at the role after MBA?”

I get this question a lot. The pitfalls are when you assume that because you have an MBA it means you DESERVE a management role or even a product role. I used business school as a way to switch careers, but I knew that I had some hard work ahead of me to learn how to be a PM, so I started off hungry and ready to learn.

As far as the skills, I think the most important ones are empathy, communication (simple, clear, to the point ability to outline problems and tell the “story” of your work), systems thinking, and the ability to understand/use data. I’ve found that the things I learned in business school have really only started to become super helpful now that I’m working a lot more on strategy and questions like, “what’s the best choice for the business?”

“Any final advice for aspiring Product Managers?”

My advice to aspiring PMs: this is a hard job! Don’t get discouraged – instead, try and stay curious about your customer, your market, and your business. You will absolutely fail along the way (I failed so hard last year we had to scrap a project and restart it with another team) but as long as you learn from it you’ll be just fine.

Also, two things that have helped me in my career:

1. Find a group of peers at other companies in your same role/on your same path.

   Meet with them quarterly. I have a group like this and it is a HUGE bonus when I”m working through tough problems

2. Spend time writing/reflecting on the work that you’re doing.

   The more you can learn from what you do, the faster you’ll get better.

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