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Strategic Product Planning as a Team / part 2

If you’re looking for Part 1, it’s here!

At Alan we love to share the way we work. In our last blog post, we defined the first steps to review your Product Strategy and Plan it as a team. You will find here the last (but not least) 2 days.

During the first part of the week we have focused on:

  • Re-exploring and sharing the mission of the company

  • Gathering all our ideas, big and small

  • Exploring, defining and storyboarding the most promising ones

  • Starting to assess the value of our ideas for our users and for us

It is now time to finalise the evaluation and define your priorities and the way you are going to work in the next months with an actionable and ambitious roadmap.

Day 5

Objectives of the day:

This day is about creating the tools for a clear vision of all your ideas and how they are going to impact you, so you can select the most important ones, meaning with the best ratio value to cost.

  • Define the cost of each item

  • Put every item on a cost / value matrix

  • Select the best items for your roadmap based on this matrix


We want now to build and define our cost grid so we have a simple decision framework for estimating the cost of our ideas:

  • Each one writes separate post-it on how to cost a project (the work on values during Day 1 will make you more efficient)15 minutes

  • Put the on a wall⏰ 3 minutes

  • Vote for them with small dots, 3 dots per person.⏰ 5 minutes

  • Discuss them: each one can ask question on post-it if he does not understand it⏰ 1 minute max per post-it

  • Decider chooses the final framework and we put it in Excel⏰ 10 minutes

Caption: Our cost Grid

🍐 🍋 🍌 BREAK 🍉 🍇 🍓

It is time to actually cost all your ideas:

  • Rotate the groups so you don’t cost the items you valued

  • Fill the cost grid ⏰ 12 minutes per idea

  • Use a shared Google Sheet with a “total column” per category

  • Notes from ‘-’ to 2. Be really clear within the different subgroups so everybody gives note the same way. “-” is not applicable, 0 is very low cost, 1 little cost, 2 big development cost.

🍐 🍋 🍌 BREAK 🍉 🍇 🍓

It is now time to list all these ideas in a visual perspective:

  • Adjust again the scale for costs even if it was discussed in the beginning to be sure everybody has the same appreciation⏰ 10 minutes

  • Split evenly all the items to each person, and let them review what is the cost and value to be put on Value / Cost Matrix⏰ 2 minutes per review

  • Use post-it that you divide in four (so you have small post-its)

  • Draw on a whiteboard the Value / Cost Matrix

🍽 🍱 🍦 ☕️ 🍽 🍱 🍦 ☕️ 🍽 🍱 🍦 ☕️Afternoon:

  • Put on the Matrix the different post-its

  • Explain how you understood cost / value⏰ 1 minute per post-it

  • Small discussion⏰ 1 minute

🍐 🍋 🍌 BREAK 🍉 🍇 🍓

We will now select the ideas we want to remove and the ones we want to keep. We called it the “Screaming contest” 😱 😱 😱 😱 😱⏰ 1h30

  • The facilitator goes the the board

  • First we remove the high cost / low value

  • Then the very low value / medium cost

  • Then we keep the low cost / high value

  • People have the right to scream 😱 when they don’t agree and we have a short discussion (no more than ⏰ 4 minutes)

With iteration we managed to put everything out or in the roadmap. We used Trello to save everything.

Day 6

Objectives of the day:

It is your last day! Your goal is to wrap up all the ideas and have clear and simple roadmap for your next 3 months, and have the right order of priority for the rest of the year (it is really hard to plan more than three months away).

  • Finalise sizing of each selected ideas

  • Prioritize them (should be easy after all the work done previously)

  • Have a detailed roadmap for the next 3 months

  • A priority ranking for the rest of the year


  • Write all the selected ideas on post-its⏰ 10 minutes

  • Categorize them in XL, L, M, S (one column for each)**⏰ 20 minutes**The size has been well defined during the costing questions. Put them visually on a wall

Now, you can prioritize post-its: the rank it method⏰ 1 min max per vote

  • Within each size category: vote one by one for what you see as the top priority using one blue dot per person

  • The one with the most votes is the the top priority

  • Put it on top of the list

  • If you voted on another ones, your vote remains on that specific post-it

  • The one who voted on the one selected, vote for the second one

  • … and so on until no post-it remains for the category

🍐 🍋 🍌 BREAK 🍉 🍇 🍓

Put the big ideas (L, XL) on a timeline:

  • Split them in separate tracks (in our case, insurance, product, design, eng) if necessary

  • Be precise in timing for the first 3 months, while just set priorities for the remaining big ideas

  • Fill in the M ideas for the next three months.

Outcome: a roadmap *per track* (insurance, product, design, eng) for the next three months that details ‘blocks’ that need execution + a prioritized list of remaining tasks that need to be executed in order afterwards.

Then, update the Trello (or your roadmap tool) with all this new data (XL, L, M, S, High Priority Month 1, High Priority Month 2, High Priority Month 3):


It is really important for a fast growing company to remain very ambitious in its goal while improving the way it is solving them while it grows.

To sum-up, the five big steps to build an ambitious Product Strategy are:

  • Get Ideas

  • Share them within the team

  • Explore them in details

  • Select ideas

  • Prioritize

We are very happy of that week, from which we came back with a shared knowledge of what we want to do, why we want to do it and how we will do it. And we already delivered very quickly after it with our product for freelancers / self-workers.

Structuring your week and the way you process information, helps you be more ambitious, solve problems quicker and deliver very innovative ideas.

A few learnings:

  • Be slow at the beginning and invest on the problem, your target, the best way to get answers

  • It is really good to let people express themselves independently and to have a good way to rank ideas

  • Take decisions quickly

We hope our methodology for Product Strategy Sprint will be useful to your company.

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Updated on 10/05/2023

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