Going into your first hundred days with a plan

Starting a Chief of Staff role is exciting, but daunting. You're stepping into a position that sits at the heart of organisational decision-making.

To help navigate this critical period, I've developed a companion tool to structure your first 100 days. This framework follows MECE principles (Mutually Exclusive, Collectively Exhaustive) to ensure you cover all bases without overlap or gaps. Of course, you might find that your principal has a plan for you already. If so, you can use this framework to structure your own thinking.

Start with your north star

First, always start with your principal's goals and targets for the short and long term. That's your north star. Assume that everything you do should ladder up to these objectives - unless you know from the start that you’ll also be owning certain special projects (although these too will of course link back to company strategy).

Schedule dedicated time in your first week to understand not just what these goals are, but why they matter and how success will be measured. Don't assume you know what your principal wants. Ask directly, take notes, clarify ambiguities.

Important : These templates are for structuring your thinking and approach. Always make your own local, password-protected copy, and don’t input confidential or sensitive information about your organisation, colleagues, or strategic plans. Keep your actual analysis and findings in secure, company-approved systems.

The three-phase framework

Phase 1: Discover – observe and understand

Your first priority is to listen, learn, and observe. Resist the urge to jump in with solutions immediately. The most successful Chiefs of Staff spend significant time in discovery mode, building a deep understanding of the organisation, its people, and its challenges.

This phase can last 30-45 days, but adapt according to your context - and remember that it never really stops, as you’ll always be facing new situations.

Phase 2: Analyse and plan – but remember context matters

Once you've gathered sufficient information, move into analysis mode. What patterns do you see? Where are the biggest opportunities?

Remember that the extent to which your plan is your own will vary greatly by principal. Some CEOs will give you significant autonomy and special projects. Others prefer Chiefs of Staff who execute their vision with minimal independent planning. Neither approach is wrong.

Phase 3: Do! – execution starts sooner than you think

You'll probably find that you start the doing phase much sooner than you expect. Most Chiefs of Staff begin executing tasks from day one. Don't let this derail your discovery and analysis work. Instead, parallel run alongside phases 1 and 2.

Apply the framework internally and externally

To ensure comprehensive coverage, apply your three-phase framework both internally and externally, whether to your “listening tour” or in your broader thinking about the business.

Internal analysis

Company strategy, business model, and operating model Understand how your organisation creates, delivers, and captures value. Don't just read the strategy documents – understand how strategy translates into day-to-day operations.

Products or services Get hands-on experience with what your organisation offers. Use your own products. Speak to customers. This knowledge will prove invaluable in strategic discussions.

Operations Map out key processes, systems, and workflows. Where are the bottlenecks? Understanding operational realities will help you spot opportunities for improvement.

Culture Observe how decisions are made. How do people communicate? What behaviours are rewarded?

People – including your principal's and your key stakeholders Map out the key players in your organisation. Who has influence? Who has information? Who makes decisions? These relationships will determine your success.

External analysis

Market – size, fragmentation, regulation Understand the competitive landscape in which your organisation operates. This context will help you assess strategic options and identify growth opportunities.

Customers or service users – what do they need, what do they want, how do they behave? Spend time understanding your customers deeply. What are their pain points? Customer insights should inform every strategic decision you support.

Competitors – who are they, what do they offer Know your competitive set inside and out. This knowledge will help you identify differentiation opportunities and competitive threats.

Though designed to be immediately actionable without additional support, the complexity of taking on a Chief of Staff role may mean you’d like further support. 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, find out more about Chiefly coaching and advisory here, or book a short discovery call here.

Chiefly tool: A Chief of Staff’s first 100 days