Pushing Back on Unrealistic Timelines

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 strategies worked well and where there's room for improvement.

Roleplay Scenario

Scenario Overview

You’re in a meeting to discuss the timeline for a new mobile app feature. The proposed schedule is tight, and you believe it’s not doable given the team’s current workload and other priorities. Your task is to constructively challenge the timeline and suggest a more realistic plan without causing friction.

Roles & Setup

Role A – Team Lead (You)
You see the timeline as unrealistic and want to negotiate a more achievable schedule.
Your goal: Raise concerns using evidence and propose a viable alternative.

Role B – Project Manager
You’ve set the timeline based on initial stakeholder discussions and want to meet expectations.
Your goal: Understand the constraints and work together on a better plan.

Role C – Stakeholder (Optional)
You’re focused on the timeline due to business pressures but open to hearing the team’s perspective.
Your goal: Balance business needs with what’s practically achievable.

Suggested Openers

Team Lead:

  • “I’ve been looking at our current workload, and I’m concerned about the proposed deadline. Can we chat about the timeline?”
  • “Based on past projects, I think we should revisit the timeline to make sure it’s realistic.”

Project Manager:

  • “Let’s take a look at the timeline and any concerns you have. I’m open to making adjustments if needed.”
  • “I know the timeline is tight. Let’s see how we can tweak it to make it more workable.”

Stakeholder:

  • “I know the timeline is ambitious, but it’s crucial for our business goals. Let’s talk through the challenges.”
  • “I’m open to adjustments if needed. Let’s ensure we’re setting a realistic path forward.”

Sample Roleplay in Action

Team Lead:
“Thanks for setting this up. I’ve gone over our current projects and historical data, and I’m worried that the timeline we have might be too optimistic. Can we discuss this?”

Project Manager:
“Sure, I’m glad you’re bringing this up. What specific data or past project experiences are you referring to?”

Team Lead:
“We’ve seen similar projects take about 30% longer than we initially thought because of unexpected issues. Given our current commitments, I think extending the timeline by about four weeks would help us maintain quality and meet our other deadlines.”

Stakeholder:
“I see where you’re coming from, but we really need to deliver by the end of the quarter. Is there a way we can prioritize the most important features and maybe release in phases?”

Team Lead:
“That’s a solid idea. We could focus on the most critical features for the initial release and then add the rest later. This way, we meet some business goals without sacrificing quality.”

Project Manager:
“That sounds reasonable. Let’s draft a revised schedule that includes a phased release and review it with everyone.”

Stakeholder:
“Agreed. Let’s make sure the phased approach still aligns with our key business objectives. I’m glad we’re having this conversation.”

Team Lead:
“Great. I’ll work with the team on a proposal, and we’ll reconvene to finalize the details. Thanks for being flexible.”

Post-Scenario Tools

Curveball Mode (Optional)

Throw in one of these mid-roleplay to increase the complexity:

  • Stakeholder insists on the original timeline despite concerns.
  • Additional resource constraints come up during the discussion.
  • A new priority project is unexpectedly introduced.

Reflection Checklist

As the Team Lead:

  • Did you express concerns without blame?
  • Did you propose feasible alternatives using data?
  • Did you engage the team in prioritizing features?

As the Project Manager:

  • Did you actively listen and consider constraints?
  • Did you facilitate a constructive dialogue?
  • Did you help move towards a consensus?

As the Stakeholder:

  • Did you remain open to feedback?
  • Did you clearly articulate business priorities?
  • Did you help identify a balanced solution?

Common Mistakes to Avoid

  • Being confrontational instead of collaborative
  • Accepting unrealistic timelines without discussion
  • Overcommitting and risking quality or team morale
  • Focusing solely on technical constraints without considering business needs

Pro Tip

Approach these discussions with a collaborative mindset. Focusing on shared goals and using data can help bridge gaps between technical constraints and business objectives, leading to more sustainable project plans.