Navigating Planning & Prioritization Challenges

planningMid10–15 min
How to Use This: Run this roleplay with 2–3 people, or try it solo by voicing each role. Add curveballs to test adaptability. Reflect afterward to see what worked well—and what didn’t.

Roleplay Scenario

Scenario Overview

Your team is in a planning session for the upcoming sprint. You're juggling a long list of features and bug fixes, and need to figure out what's actually doable. The goal is to sort out the priorities without anyone feeling blamed or overwhelmed.

Roles & Setup

Role A – Team Lead (You)
You're guiding the team through planning.
Your goal: Help everyone agree on realistic priorities without blaming anyone for the workload.

Role B – Product Owner
You've got a list of features and fixes you want done to deliver value.
Your goal: Work together to make sure the most important items make it to the top.

Role C – Senior Developer (Optional)
You’re concerned about whether everything can be delivered.
Your goal: Provide technical insights to make sure the plan is feasible.

Suggested Openers

Team Lead:

  • “Looks like we’ve got a lot on our list for this sprint. Let’s talk about what’s most crucial and what might wait.”
  • “I’d like us to review our tasks and make sure we’re focusing on the right things. We don’t want to overload ourselves.”

Product Owner:

  • “Let’s focus on what aligns with our goals. I’m open to discussing what can be prioritized.”
  • “I know we’ve got a lot to cover. Let’s figure out which items will give us the most impact.”

Senior Developer:

  • “Some tasks look pretty complex. I can help figure out what might take longer than anticipated.”

Sample Roleplay in Action

Team Lead:
“Thanks for jumping into this planning session. We’ve got a big list, and I want us to be realistic about what we can achieve. Let’s prioritize and make sure we’re not overcommitting.”

Product Owner:
“Sure thing. The user dashboard and the checkout system bug are my top priorities because they’re key to the release.”

Senior Developer:
“The checkout bug is pretty tricky and might take a while. We should consider its impact on our timeline.”

Team Lead:
“Good point. How about we focus on the bug and the dashboard first, and push smaller tasks like UI tweaks to the next sprint?”

Product Owner:
“That works for me. It’s crucial we get the core features stable before moving on.”

Senior Developer:
“Sounds good. I’ll dive into the bug fix, and we can touch base mid-sprint to see where we’re at.”

Team Lead:
“Perfect, let’s update the sprint board and communicate this plan to the team. Thanks for the collaboration.”

Post-Scenario Tools

Curveball Mode (Optional)

Throw one of these into the mix to see how participants adapt:

  • Product Owner insists everything is equally important.
  • Senior Developer uncovers unexpected technical debt.
  • A last-minute high-priority task comes up.

Reflection Checklist

As the Team Lead:

  • Did you keep the discussion positive and constructive?
  • Did you help guide the team toward clear priorities?
  • Did everyone feel heard and part of the decision-making?

As a Participant:

  • Did you clearly state your priorities?
  • Did you stay open to different solutions?
  • Did you contribute to a balanced discussion?

Common Mistakes to Avoid

  • Letting the discussion get tense or confrontational
  • Failing to prioritize effectively and overloading the sprint
  • Ignoring technical feasibility

Pro Tip

Treat planning as a team effort. When everyone understands the goals and constraints, you’re more likely to make informed decisions together.