You’ve stepped into a new leadership role and inherited a legacy of platforms, a patchwork of strategies - and the Board wants immediate proof that you can make an impact.
Everyone knows transformation takes time, but perception matters. Early wins build credibility, create momentum, and send a clear message: progress is underway. That's why your first 100 days are crucial.
The first 100 days aren’t just about fixing problems. They’re about showing meaningful progress and earning trust, both at board level and across your stakeholders.
This guide focuses on the right quick wins - the ones that create real momentum, not just easy fixes.
Wait, where did the first few months go?
The first few months vanish quickly, but those big objectives still feel far off. Common challenges include:
- Pressure to perform: Organisational leadership always hunger for evidence of positive change.
- Lack of clarity: Existing roadmaps or shared vision may be lacking the current context and may carry a degree of debt (technical or emotional).
- Team fatigue: The people you’re relying on may be tired, sometimes of “constant change”, or sometimes from the lack a refreshing one.
- Mixed signals: Some stakeholders relish change. Others the status quo, some will not commit.
Your job is to cut through the noise, create consensus, and line up resources. You don’t need every answer today. What you do need is a focused plan for your first 100 days.
Your 3-phase plan for digital progress
Days 1–30: Listen, learn, light the way
Goal: Understand where you are and set a clear point of view.
- Audit the digital estate: Map tools, platforms, and processes. Find the friction.
- Identify the blockers: Tech, people, politics - or all three working against you.
- Invite honest input: Speak to stakeholders, frontline teams, and customers. Their perspective will shape the path forward.
- Set your digital North Star: Create a vision that’s clear, concise, and achievable.
What to share: A simple snapshot of “where we are vs. where we want to be.”
Days 31–60: Prioritise, pilot, prove
Goal: Start small, move fast, show value.
- Pick your quick wins: Choose projects with measurable ROI or clear internal benefit - reporting automation, customer pain point fixes, or process simplification.
- Prototype, don’t over-plan: Treat initiatives as experiments. Validate ideas quickly or learn fast from failure.
- Set governance rituals: Check-ins, Kanban boards, sprint reviews - whatever keeps progress visible.
- Track and share outcomes: Even small gains - time saved, faster response, higher satisfaction - all matter at this stage.
What to share: A clear story of “what we changed, why it matters, and what we learned.”
Days 61–100: Build the case for the future
Goal: Turn momentum into a roadmap.
- Create a Now / Next / Future plan: Show how incremental change adds up.
- Begin platform discovery: Identify where your current tech stack is holding you back. Don’t assume past solutions fit today’s problems.
- Engage the wider leadership: Use early wins to have grounded conversations about investment, dependencies, and risk.
- Define the next 90–365 days: End your first 100 days with clarity on priorities, resourcing, and the technology that will drive future performance.
What to share: “We’ve built momentum. Here’s where we go next.”
Quick wins that deliver
Not sure what to prioritise? These projects show visible progress and build trust fast:
- Fix outdated customer contact points - remove friction, capture better data.
- Introduce dashboards that replace clunky reporting with actionable insight.
- Digitise manual processes to free up capacity and speed delivery.
- Replatform a fragile microservice that’s creating operational risk.
- Pilot a customer feedback loop using lightweight UX tools to guide next-stage improvements.
These small changes are proof that problems are understood and being solved.
The power of framing
How you communicate progress matters as much as the progress itself.
- Focus on benefits, not features: “We saved six hours a week,” not “We used a new tool.”
- Use simple visuals to show improvement over time.
- Frame change as collaboration, not disruption: “This made the team’s work easier,” not “We transformed the workflow.”
The first 100 days are a launchpad
Your first 100 days aren’t the finish line - they’re the start of momentum.
You don’t need a revolution. You need rhythm.
Want a head start?
Contact us to explore our Roadmap & Platform Discovery Services - designed to help digital leaders clarify, prioritise, and get unblocked quickly.