Supporting Coaching
‍At Scale

Adding a new end-to-end feature to the Ambition coaching stack to capture team conversations, streamline coaching, and provide a complete view of performance.

2021 - 2022

project overview

Ambition helps teams track goals, improve performance, and drive engagement through coaching and real-time insights. Our tools focused on 1-on-1 meetings, leaving gaps in tracking team-based conversations like alignments and call coaching—limiting visibility into team dynamics and decisions - so we built Group Check-Ins to give managers a powerful way to track team performance and drive better outcomes.

goals

  • Win Deals – Close competitive gaps to secure enterprise customers.

  • Support Team Coaching – Track and document team conversations and outcomes more effectively.

  • Unify Workflows – Replace fragmented tools with a single solution.
Enhance Data Visibility – Provide a more complete view of team performance 

  • Boost Engagement – Help managers and teams better prepare for and follow up on meetings.

  • Make Scheduling Frictionless - from scheduling in app to invites on calendars.

Process

co-creating with a large customer

The discovery phase involved deep collaboration with a large customer who had expressed a need for team-based coaching functionality. This customer-led feedback was instrumental in shaping the initial solution. However, we quickly realized the risk of designing a solution tailored to just one customer, so we broadened our focus by gathering insights from additional customers to ensure scalability across different use cases.

Solution

initial release

For our initial release, we introduced the concept of group meetings and focused on making coaching smoother and more efficient. Key features included:

  • Flexible Scheduling
  • Unified Documentation with new agenda items
  • Seamless Integration with Google Calendar and Outlook
  • Action Items
  • Improved UI

tracking accountability with action items

The addition of action items makes capturing decisions and next steps in real-time in-app easier, providing a detailed, accessible record of team conversations, enhancing future coaching and performance reviews.

seamless integration with Google Calendar and Outlook

Manual and disconnected calendar scheduling was a frequently communicated pain point across all meeting types. Meetings now automatically sync with calendars, ensuring that scheduling changes are reflected across all tools, eliminating confusion.

    new agenda content

    Previously, there was no support for including non-question content in agendas, which hindered the ability to create accurate, usable agenda content for team meetings. We added Content Blocks and Embedded Iframes, allowing for better-structured agendas that include key resources, links, and content, ensuring teams are fully prepared for discussions.

    consistent UX/UI for meeting pages

    We took this opportunity to revamp the UI for all existing coaching meeting types, ensuring a consistent experience across the platform with a focus on better hierarchy and scannability

    Conclusion & Reflections

    results

    Initial release was successfully adopted by 3+ enterprise customers. Large enterprise customers across industries like telecom, environmental services, and logistics moved their team coaching to Ambition, helping secure many 10's of thousands of dollars in renewal revenue.

    user feedback

    We had a generally positive reception to the initial release. As we gathered feedback, we saw some themes of things to explore for later iterations:

    • Due dates, attachments, and better tracking to action items.
    • More consistent and clearer notifications (in-app, email, Slack).
    • A streamlined presentation view for presenting meeting notes and follow-ups.
    • Visibility into which team members have reviewed or acknowledged meeting notes.

    what I would do differently

    • Broader Customer Validation Sooner – We initially designed the feature based on one large customer’s needs; gathering input from more types of users and company types earlier could have helped us design a more scalable solution upfront.
    • Simplified Scheduling Logic – The recurring meeting logic became overly complex; leading to a confusing UX
    • Take more risks with the UI redesign - If time allowed I would have spent time really exploring visually where meetings could go

    Conclusion

    By co-creating the solution with customers, we successfully designed a feature that positions the platform competitively and supports more effective team coaching at scale.

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    alaina ylitalo
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