Chiefly tool: Map, diagnose and augment your org!

Sharpen your (virtual) pencils.

Business mapping and diagnostic tools designed for new Chiefs of Staff

This 150+ page tool helps Chiefs of Staff (COS) quickly understand all business functions through targeted questions for CXO leaders. Available as an editable PDF or Google Sheet, it provides structure and confidence when navigating a new organisation (or a rapidly growing one!).

There are two versions: one most suitable for medium to large corporates, another for public sector organisations, with a UK flavour.

It’s deliberately analogue, so as to help COS make their own mental models, but the collected insights can also serve as training data for fine-tuning your company's AI assistant or be used in a retrieval-augmented generation system.

While not offering definitive solutions, it creates a structured framework for critical conversations, covering executive leadership, finance, sales, marketing, product, technology, HR, customer success, operations, and legal compliance - and the public sector equivalents - a whistle-stop tour through the whole organisation for a Chief of Staff looking to build their mental model of how their company runs.

How to use it

Getting started

1. Enter your email address above and click Send me the tool. You’ll get an email with a download link; choose the format you want and download

2. Identify relevant sections for your organisation and establish maturity of existing measurement metrics (e.g., objectives and key results (OKRs))

Working with your principal

1. Obtain formal endorsement to ensure CXO participation; ask your principal to announce the initiative to leadership team

2. Consider your principal joining select sessions to signal importance

Conducting the diagnostic

1. Position as a learning exercise for you as the COS, not an audit of the business or another set of OKRs

2. Schedule dedicated time with each leader - I recommend that you don’t send this out, but rather use it as your own thought prompter

Working with the results

1. Document responses systematically and securely - work with your tech teams (if applicable) to extract findings into a vector database

2. Identify patterns, inconsistencies and gaps

3. Create prioritised list of areas needing deeper investigation

Integration with existing metrics

1. Use diagnostic to add context to quantitative metrics, and to aid your own understanding of the organisation in a structured way

2. Identify misalignment between perceptions and data

3. If metrics tracking doesn't exist, use findings to establish key performance indicators

Leveraging over time

1. Consider running the exercise semi-annually/annually to track organisational evolution

2. Compare responses over time to identify persistent issues

3. Create historical record of organisational thinking. This could then also be used as training data for fine-tuning your company's AI assistant or be used in a retrieval-augmented generation system, creating an enterprise knowledge resource with deep organisational context.

More pointers

• The structure of the diagnostic allows COS to quickly identify areas requiring deeper investigation or specialist attention. By systematically working through the relevant sections, Chiefs of Staff can rapidly develop their understanding of organisational strengths, weaknesses, and potential blind spots.

• The tool is pragmatic in its approach – recognising that not every question will apply to every organisation and that the depth of exploration needed will vary based on organisational size, maturity and specific challenges. The diagnostic provides sufficient flexibility to be valuable across different industries and business models.

• The questions also serve as conversation starters that build rapport between the chief of staff and key organisational leaders. These structured interactions lay the groundwork for productive working relationships whilst efficiently transferring critical knowledge about how the business functions.

• Though designed to be immediately actionable without additional support, the complexity of interpreting and acting upon the collected information may benefit from further guidance. I’d be happy to chat further and coach you through it (in strict confidence) if you’d like - just shoot me an email at poppy@chieflycos.com.