HeyJaredWinning Strategy
Battle-tested and ready-to-use recipes, strategies, and how-tos for Scrum Masters and Product Owners to systematically navigate an Agile environment | 2x a week
- Indexed issues, last 90 days
- 15
- Latest publication
- Sep 27, 2026
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- Earliest in this view
- Aug 9, 2026
Latest issues
Team committed to 15 stories after delivering 9 (opens the original)
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In the last two sprints, this team delivered 11 stories, then 9.On my first day with them, in sprint planning, they committed to 15.The Product Owner asked twice whether that number was realistic. She received “should be fine” from two different people. <di
I was asked to justify hiring a new Scrum Master (opens the original)
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I recently took on a project at a Toronto bank.One of their teams had lost its Scrum Master five weeks earlier to a different company. The position was still funded. It was still open. And the VP had not actually said no to filling it, which would have been easier to deal with. He said, “Prove it.”Then the Director, who was also my sponsor, told me what the VP said in their meeting:“Why would we spend a 130K on somebody who runs a 15-minute meeting?”<a class="image-link image2 is-viewabl
How and When to Change Your Team’s Working Agreement (opens the original)
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Q: We created a working agreement when the team formed, but nobody really looks at it anymore. Should we update it?<img alt="" class="sizing-normal" height="813" src="https://substackcdn.com/image/fetch/$s_!mEAt!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:s
9 Signs your team has outgrown Scrum (opens the original)
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<img alt="" class="sizing-normal" height="1355" src="https://substackcdn.com/image/fetch/$s_!XxFt!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8012795d-8970-4bea-9918-a0703588a6f2_2523x1355.
When Should a Scrum Master Stop Protecting the Team From Stakeholders? (opens the original)
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One of the first things we teach new Scrum Masters is to “protect the team.” Shield them from distractions. Keep stakeholders from hijacking the Sprint. Guard the focus.It’s good advice… until IT IS NOT.Somewhere along the way, the “feeling” changes from protecting the team to insulating the team. And “insulation” is a problem. An insulated team never develops the muscles it needs to navigate the messy, political, high-stakes reality of product development.<div class="captioned-image-contai
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