Introduction
🧭 The Milestone Planner in Howwe helps you break down your Strategic Initiatives into clear, actionable steps. By leveraging AI and the context of your initiative, it assists you in identifying the key milestones that will drive success. This guide walks you through how to use it effectively.
▶️ Want to see it in action? Scroll down to watch a full walkthrough video at the end of this guide.
Step-by-Step: How to Use the Milestone Planner
1. Navigate to Your Initiative
Go to the Strategic Initiative you want to plan.
Make sure your initiative has a clear Purpose and, ideally, a defined Objective. These elements help the AI understand what you’re trying to achieve and provide better suggestions.
2. Open the Milestone Planner
Click the Plan Milestones button.
You will now enter the Milestone Planner for the specific initiative.
ℹ️ The planner will already know:
The Purpose and Objective of the initiative
Any existing milestones already created for the initiative
3. Use AI to Suggest Milestones
🧠 Before clicking "Suggest Milestones", it's recommended to give the AI more context. This helps the Milestone Planner generate smarter, more tailored suggestions.
You can:
Briefly describe what you want help with in the chat box
Or ask the AI to ask you questions that guide your planning
Once you're happy with the context, click Suggest Milestones to generate a first proposal.
💡 You can also choose to click Suggest Milestones directly to get started quickly. However, adding context first usually results in more relevant and actionable suggestions.
4. Review and Edit Suggestions
The AI will generate a list of milestone suggestions.
Use the trash can icon to delete any milestone that isn’t relevant.
You can continue the conversation in the chat to refine or iterate on the milestones until you're happy with them.
5. View and Compare with Existing Milestones
Click on Existing Milestones (top right corner) to view previously created milestones for this initiative.
This allows you to see your full milestone plan as you iterate on new suggestions.
6. Finalize and Save
Once you're satisfied with the suggested milestones:
Set deadlines for each one
Click Save All Milestones to confirm
Best Practices
✔️ Be specific when giving the AI context — the more clarity, the better the suggestions
🔁 Iterate freely — you can continue updating your milestones even after suggesting milestones
🎯 Use Purpose and Objective strategically — ensure they are well written before entering the planner
🧩 Combine AI suggestions with your expertise — the planner is a co-pilot, not a replacement for your insight
🎥 Video: Watch the Milestone Planner in Action
Here’s a full walkthrough where we show how to use the Milestone Planner, step by step.