The Leadership Cohort Program

The Leadership Cohort Program

Let’s be honest: shipping software is hard.

A typical modern system involves myriad moving parts with multiple teams contributing to the final result. Each team usually has its own set of responsibilities and priorities, but is dependent on the other teams to get their work done. That interdependency can create organizational gridlock when priorities are not aligned.

Further, most organizations find it difficult to carve out the time and attention needed to make needed investments to address parts of the system that customers don’t see, whether that’s improving infrastructure or paying down technical debt.

Finally, many organizations find that the process that served them well years ago isn’t serving their needs now. Yet changing that process—or even agreeing on what “good” looks like—can be remarkably difficult.

This program provides a framework for a cohort of managers to address these kinds of cross-organization challenges in a supportive environment with industry experts.

Cohort members select a project, define objectives, and team up to accomplish those objectives. Along the way, they improve their technical leadership skills; learn about industry-standard technical practices; and become adept at driving change across their organization. The result is improved teamwork within the cohort, meaningful improvements in the organization’s ability to deliver software, and professional growth for cohort members. Because of the emphasis on accomplishing a real objective, this program is ideal for a cross-organizational group who need to collaborate more effectively or who struggle with breaking through cross-team interdependency gridlock.

How It Works

The program brings together a small cohort of up to 6 colleagues. It runs for 10-12 weeks (depending on scheduling) and involves a combination of group working sessions and 1:1 discussions.

Cohort members are usually in senior leadership, management, or senior contributor positions. They may already be on the same leadership team or work in different parts of the organization.

Group Discussions

A pair of Curious Duck facilitators lead each of the 10 group working sessions, providing relevant information and resources and actively guiding the discussion when necessary.

Although every cohort is different, a typical timeline looks like:

  • Meeting 1: kickoff
  • Meeting 2: defining the problems
  • Meeting 3: choosing a mission
  • Meeting 4-9: executing on the mission with regular retrospectives
  • Meeting 10: final meeting and next steps

We hold these meetings over Zoom, using Miro as a shared collaborative workspace.

Individual 1:1s

In addition to the group work, cohort members can schedule individual sessions with one or both of the facilitators. We encourage them to do so at the beginning of the program so that we can get to know each cohort member personally and understand their goals and motivation for participating in the cohort. Cohort members can also take advantage of these private sessions for individualized advice or coaching.


We tailor the practices and principles we discuss to the cohort’s interests and shared objective. Examples of topics introduced in the group sessions or individual discussions could include:

  • Exploring tradeoffs in branching strategies and continuous integration
  • Mapping the series of decisions and decision makers needed to support a given policy change
  • Structuring work to support continuous delivery
  • Identifying and addressing bottlenecks and sources of technical risk
  • Paying down existing technical debt
  • Garnering grassroots support for process changes
  • Creating visibility around otherwise invisible pain points
  • Tightening feedback loops to reduce risk


As the cohort jells into a team over the series of meetings, the facilitators step back from actively guiding the working sessions to supporting the cohort. That means even after the program ends, the group can self-facilitate to continue the work.


As a result of this program, participants:

  • Improve their ability to work together as a team while boosting the organization’s ability to deliver software faster, safer, and more sustainably.
  • Define the objectives and key measures they are working toward in concrete terms, focusing on outcomes rather than activity.
  • Improve their understanding of industry-standard technical practices around topics such as testing, branching, continuous integration, and continuous delivery.
  • Establish a shared vocabulary around the improvements they’re trying to make that is independent of vendor jargon.
  • Establish an ongoing forum to work through challenges in achieving those objectives.


This is a remote program. We hold all sessions on Zoom, use private Miro boards and Google docs for real time collaboration, and use email for asynchronous communication. Curious Duck is responsible for the Zoom and Miro accounts and handles all needed access and invitations.


Because the program is so customizable, the cost varies a great deal depending on the duration and size of the cohort. Usual ranges are from US$10K - US$40K.

Ready to talk about possibilities? Please reach out!