One of the best things about working at TransferWise, is how seriously we take the autonomy of our teams. Each team can (and needs to) set its own Key Performance Indicators (KPIs), come up with a mission statement, and a vision for the team. Once those are worked out, a team then writes out its own plans — there’s no influence from the Leadership team. This process helps our teams do their best work.

As a new product manager to TransferWise, planning can seem daunting. You’ll have little input from the Leadership team or your manager on what to plan or how to do it. I wanted to share my experience planning in the Transfer Experience team, so you can you can confidently plan for your next quarter.

Why is planning so important?

We worked out that we spend about three weeks every quarter planning in the Transfer Experience team. Which feels like a lot. Why spend all that time planning, when we could be doing something else? Mostly because planning is about the process rather than the outcome. So while it’s great having high-quality plans, it’s how you arrive at those plans that matters.

Here’s what you need to get out of your team’s planning sessions:

  1. Get the team to commit. This one’s important. If your plan’s got a chance of succeeding, then it’s got to come organically from everyone on the team. Planning shouldn't just be engineers breaking tasks down into good old-fashioned man hours. It should also have them challenging the products you’re building, and the priorities of those products. Ultimately, everyone inside the team should own the plans for next quarter.

  2. Use it as a chance to gauge the team’s health. While part of planning is thinking about the future, it’s also a great opportunity to think about how things have been working so far. Have the team run retrospectives, check the team’s progress against your previous plans and try to get a feel for everyone’s happiness levels.

  3. Prioritize, prioritize, prioritize. As a product manager, it’s your job to create great products that solve customer problems. And prioritization is one of the ways that a product manager can help make that happen. Planning, by virtue of bringing together your team, is one of the best venues for prioritization.

How we organize planning

We tend to divide our team planning into four parts. They roughly fall into these categories:
Retrospectives. We usually run two kinds of retros: work-based and feelings-based ones. Both are equally important.

  • Work-based retrospectives try to answer the question “How did we do last quarter compared to our plans?” These start by tracking the team’s progress against the plans made last quarter, so having a higher-quality plan from last quarter will help you do better work-based retrospectives. This session usually leads to questions like:
    • How can we become more efficient as a team?
    • What did we spend most of our time on last quarter?
    • How can we do things faster?
    • Do we have too little/too much tech debt?
  • Feelings-based retrospectives aim to answer the question: “How happy are you in the team?” We like to get a feel for everyone’s happiness levels, because we care about creating a positive work environment. Because when people are happy where they are, they can give their all in their work. These kind of retros are hard to run — it’s not easy getting people to open up and share everything they’re thinking — but also the most rewarding. Usually the conversations revolve around these kinds of questions:
    • How well do we get along with each other?
    • Are we holding each other accountable?
    • Are people happy about their work-life balance?
    • How are we interacting with other teams in the company?
    • Do we get along with each other?

Mission & vision for the team. This one’s both fun and incredibly important. Every quarter, we review how we did against our KPIs, and challenge our mission and vision to see if they still fit us. We talk through how the products and features we worked on helped us get closer to achieving our mission and helping our customers. The team should come out of these sessions feeling 100% committed to their renewed mission and vision.

Internal organization & processes. This is normally a short discussion where we work out if we need to change how we do things as a team. Because we’re a distributed team of 15+ people, we usually only come together once a quarter. So when we do, it’s a great opportunity to talk through changing sensitive processes or the structure of the team.

Planning. Yes! Finally, we get down to actually planning. During these sessions, we mostly do the following (in this order):

  1. Review the products that we want to build, and prioritize each product. This should be a product-led session.
  2. Break down each product into tasks, and come up with estimates for how long it would take to build each product. This should be an engineering-led session.
  3. Review and reprioritise according to how long each product is estimated to take. We also try to bring up constrains such as cross-team dependencies, deadlines, upcoming vacations during this session. This session should be a product oriented session.

What improving planning looks like

The Transfer Experience team has been getting stronger and stronger at planning every quarter. Here are a couple ways we have seen we have been getting stronger at planning. If you see your team has improved in some of these aspects, it might be also because you have been improving the way you plan.

We spend less time wondering what to build and more time building. This is a great side effect of having great plans. you’ll spend less time discussing why/what and more time discussing how, because your team members should already be committed to the why. This time saving can be put into improving the quality of the execution, thus improving the outcome for your customers.

Better cross-team collaboration. Writing detailed and realistic plans has helped us with cross team collaboration. It makes it easier for people outside the team understand why and what we want to spend our time on. It also makes it easier for us to call cross-team dependencies, and inform them on the progress we are doing on several projects.

Better retrospectives. Since ideally everyone is committed to the plans, if plans don’t become reality, the team should feel responsible for that in the retrospective. Which means, team members should be pushing each other to understand how they can improve both execution and the plans.

Ultimately, we have been able to improve a lot as a team thanks to better planning, yet we are always looking for ways to improve how we do things here at TransferWise. What is your experience with planning? Leave your thoughts in the comment section below!