The CEO's Operations Health Check

A Plain-English Self-Assessment Checklist

The Work Smarter Company

How to use this checklist: Read each question and check the box if it applies to your organization. At the end of each section, review your score. If you checked multiple boxes, that area needs attention.

1. Manual Work Assessment

Identify where your team spends time on repetitive, low-value tasks.

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Do you know how many hours per week your team spends on repetitive manual tasks?

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Do you have processes that require manual data entry across multiple systems?

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Are there tasks that "everyone knows how to do" but aren't documented anywhere?

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Can you quantify the time spent on manual work in specific departments or processes?

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Do you have employees who spend more than 20% of their time on data entry or copying information between systems?

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Are there weekly or monthly reports that require manual compilation from multiple sources?

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Do you find yourself saying "we've always done it this way" about certain processes?

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Are there tasks that take hours but could theoretically be done in minutes with the right tools?

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Do you have processes where one person waits for another to finish before they can start their part?

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Have you delayed hiring because you thought "we should automate this first"?

Scoring: If you checked 5 or more boxes, manual work is likely costing you significant time and money. Consider mapping these processes and identifying automation opportunities.

2. Scaling Readiness

Assess whether you can grow without proportional headcount increases.

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Can you handle 20% more volume without adding headcount?

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Do you know which processes will break first as you grow?

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Are your best people stuck doing repetitive work instead of strategic thinking?

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Have you had to delay growth because you couldn't hire fast enough?

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Do you find yourself hiring to handle volume rather than to add new capabilities?

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Are there bottlenecks where one person or department becomes overwhelmed during busy periods?

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Have you avoided taking on new business because you weren't sure you could deliver?

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Do you have processes that require more people as volume increases, rather than becoming more efficient?

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Are you spending more on labor as a percentage of revenue as you grow?

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Do you have a clear plan for how operations will scale if revenue doubles?

Scoring: If you checked 4 or more boxes, scaling without adding headcount will be challenging. Focus on automating high-volume processes first.

3. System Integration & ROI

Evaluate whether your tools work together and deliver measurable value.

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Do your tools talk to each other, or do you copy/paste data between systems?

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Can you prove ROI on your software investments?

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Do you have software you paid for but rarely use?

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Do you have a clear picture of where automation would have the biggest impact?

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Are you entering the same data into multiple systems?

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Do you have disconnected tools that create duplicate work?

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Can you generate reports automatically, or do they require manual compilation?

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Do you know which software tools your team actually uses versus which ones they avoid?

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Have you bought tools that promised efficiency but didn't deliver measurable results?

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Do you have a baseline for measuring improvement before implementing new systems?

Scoring: If you checked 5 or more boxes, your systems aren't integrated and ROI is unclear. Consider a systems audit and integration roadmap.

4. Team Training & Adoption

Determine if your teams are ready to use new systems effectively.

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Do your teams know how to use the tools you've invested in?

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Are people anxious about AI or automation changes?

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Do you have documented processes that people actually follow?

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When you launch new systems, do people actually use them?

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Do you have training materials that are clear and practical?

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Have you seen teams revert to old ways after implementing new systems?

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Do you measure adoption rates for new tools and systems?

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Are there workarounds or "shadow systems" that teams use instead of official tools?

Scoring: If you checked 4 or more boxes, training and adoption need attention. Focus on role-based training and change management.