Escaping the Everything in Progress Trap - Part 3 - Assessing What to Do


The last couple of weeks we have talked about pull systems and how to set them up in Microsoft Planner.
This week, let’s discuss how to decide what work needs to be done next.

When deciding what to work on next as a team, it’s important to assess strategic alignment, business value and return on investment, technical feasibility, resource availability, risk profile, stakeholder support, timeline/urgency, and regulatory and compliance areas.

One can do this by considering the following questions and scoring the area on a 1-5 scale (5 being aligned with the criteria, 1 being not well aligned).

Strategic Alignment: Does this project directly support the organization’s strategy, OKRs, or declared annual priorities?

Business Value/ROI: What is the expected financial return, cost reduction, revenue generation, or operational improvement? Is it high, low, or negative?

Technical Feasibility: Is the required technology proven and accessible? Does the team have the skills to execute?

Resource Availability: Are budget, people, and tooling accessible without major reallocation or new hiring?

Risk Profile: What is the overall project risk across technical, financial, schedule, and delivery dimensions? (Score inversely — low risk = high score).

Stakeholder Support: What is the level of executive sponsorship, team buy-in, and support from impacted stakeholders. Strong, good, limited, opposed?

Timeline/Urgency: What is the time sensitivity and urgency? Is it a regulatory deadline, market window, competitive pressure, or internal need?

Answering these questions can give you a good idea on if a project should be started. For a more detailed assessment scorecard, grab our free Basic Project Decisioning Scorecard by clicking here. In addition to letting you score each of these criterion, you can also put a weight on them and make notes and automatically get an assessment on if you should start on the project or work item.

PS: Want a more advanced scorecard? Right now, the first 50 purchasers can get the same scorecard The Outlier Team uses to assess projects and work items to start for 50% off here. After that, the price returns to normal at $24.99.

Perry Myers
The Outlier Team

The Outlier Team

We help small businesses with technology, strategy, and leadership and have a passion for sharing what we have learned. Subscribe to our newsletter to get helpful weekly content.

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