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Preparing the next quarter — part 2: planning

In the previous post, we saw how you could run a retro under one hour. Today, we're going to look at planning and how you can set the priorities for the next quarter.

Step 1: Outline the risks

You need to slow down and look at the less exciting things before you can start listing cool ideas for growth.

You probably identified some action items during the previous retrospective, but a formal risk evaluation session will help surface core issues that you need to keep in mind.

I have an audit background, and I know first hand how tedious risk assessment can be. But in this case, I'm advocating for something quick and easy. No need for complicated mitigation plans. What you need is clarity of thought — addressing the risks is secondary and can be done later.

Create a simple table with the following columns:

  • Risk: describe what can happen.
  • Why?: go deeper into the possible root causes.
  • Probability: how likely is it? (use high/medium/low)
  • Impact: how bad can it be? (use high/medium/low)

I'll say it again — this is not the time to discuss mitigation plans. Identifying risks can be done rather quickly, but figuring out how to prevent them is costly. You should later give your team enough space and time to think about the most important risks and come up with solutions. Don't try to solve big problems in 5 minutes.

We're evaluating risks first to make sure that you won't forget about tech debt and groundwork when it's time to pick roadmap items.

Step 2: Pick 2-4 focus areas

Your team should have a clear understanding of what happened last quarter (retro) and good insights on what they have to be careful about (risks). You can now lay down the foundations to decide what the next 3 months will be about.

Start by defining focus areas for your teams. I like to simplify things by looking at the AARRR funnel and picking 2 or 3 stages to grow. Do we want to improve Acquisition? Activation? Retention? Referral? Revenue?

Once we have decided which stages to focus on, we flesh out the statements to make it more specific and meaningful. Here's one of our focus area for Q4:

Retention: Increase stickiness by growing goal-tracking engagement and delighting customers

This statement may look bland at first sight, but it packs a lot of little things for us:

  • We focus on goal-tracking rather than expanding into other usages.
  • We want to make Tability more rewarding for users.
  • We want to put the emphasis back on NPS (delight) and make sure that we keep our customers happy.

But not everything fits the AARRR funnel, and you can have focus areas on any aspect of your company. In our case we have 3 high-level objectives covering Acquisition, Retention and Revenue. And then we have a fourth objective around Design/Identity.

One thing before moving on — your focus areas or objectives should not have metrics. They should express intent in such a way that most people can rally around it. Take the previous statement: "Retention: Increase stickiness by growing goal-tracking engagement and delighting customers". It can mean "improving performance" for Engineering, "get better customer satisfaction" for Support, and "work on onboarding material" for Customer Success. But if I say "Increase weekly active users by 30%", then it sounds like a thing that belongs mostly to Product and it'll be hard for others to engage.

Step 3: Add success metrics

Now we're getting to the tricky part. You picked a set of focus areas, but you haven't yet defined what success looks like. So you need to create a set of goals or Key Results that will represent your North Star.

Let's look again at our retention objective.


Retention: Increase stickiness by delighting customers and grow goal-tracking engagement

Success measured by:

  • Ship 10+ features per month
    We dropped the ball in September and we have to make sure we regularly release improvements).
  • Increase our 30-day average NPS above 40
    Make sure that the features we ship improve the experience.
  • Double the number of weekly active users
    Get more customers.
  • Triple the number of status update created per week
    Make sure these new users are also engaging with the goal-tracking feature.
  • Ship a responsive layout
    Critical piece of work to improve the UX.

There are a few rules that we follow to improve our goals. There are not perfect, but I'll share our best practices.

  • Pair metrics for safety — we want to ship more, but we also track NPS to make sure we do it well.
  • Follow the SMART framework — specifically, know how much growth you're going for.
  • Not more than 5 goals/KRs per focus area — the more you add, the more you'll dilute efforts.
  • Avoid binary outcomes as much as possible — try to split big delivery projects into milestones (25%, 50%, etc.)

It will take time to get this right, and you'll probably get some KPIs wrong. We'll see later how you can iterate on the success metrics.

Step 4: Build your roadmap


Now that your high-level priorities are defined, it should be easier to draft your roadmap.

You can brainstorm a list of ideas that will help achieve your goals, and highlights the ones that are most likely to succeed. There are many frameworks you can use (RICE, Impact vs. Effort...) and my general advice is to make sure that you mix some low-hanging fruits along the riskier projects — that way you'll reduce the risk of going long periods of time without delivering value to your customers.

I also recommend to avoid timelines and with absolute dates. Our roadmap has 3 columns that show the priorities while keeping things flexible:

  • In progress: what we're working on right now.
  • Planned: what we intend to do next.
  • Ideas & feature requests: our general backlog.

Once things are shipped, we move them to the corresponding release column. You can see an example in our public roadmap (and you'll see what I meant by dropping the ball in September).

This is a living documents and we iterate weekly to review our bets based on how much we've managed to impact our success metrics. It allows us to drop initiatives that are not moving the needle, and double down on the things that are working well.

Step 5: Track progress

It's good to have a plan, but you'll quickly forget it unless you have easy ways to keep track of progress. Work creates distractions that will take your attention away from the top priorities. There will be dozens of meetings, hundreds of emails, unknown issues to take care of. It's unreasonable to expect a team to stay on top of things without help.

You need a simple way to filter out the noise. That's where Tability comes in handy as it will automate reminders and help you visualize progress on outcomes.

Here's our setup:

  • Quarterly plan write-up (retro, risk, executive summary) lives in Confluence.
  • Goals and OKRs are in Tability
  • Roadmap items are in Trello
  • User stories, dev tasks are in Jira

We always start the week by looking at Tability to see how we're tracking on our North Star. Then we use our assessment to decide if we need to change priorities or scope for items on the roadmap.

The general direction is outcomes -> outputs, but there are times when we will change the success metrics if it looks like we picked the wrong set of KPIs. Be data-driven, but not data-obsessed or you might be going full speed ahead into a wall. This is also why I focus on areas and Objectives matter more than metrics and Key Results.

That's it!

This is a simple approach to planning that works for us and it keeps the roadmap light and agile. Then we use Tability to stay focused and make sure that our projects are having the right impact.


This article is part of our newsletter Scaling Small. Subscribe below to get more posts like that in your inbox. You can also find me on Twitter @stenpittet.