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All senior leaders are familiar with the need for a 100-day for 30/60/90-day plan when entering a new leadership role. These leaders can now expect Digital Transformation to be a key part of their next role. A challenge where you need to tune your plan to meet the new realities driven by the growing digital component of your role. Here is a perspective on how to tweak your standard planning concept.

This blogpost summarizes a path based on the seven steps articulated in previous blogs, with links provided in each section.

What make 100-day plans for digital transformations different

The nature of digital transformations makes installations of new leaders more demanding. Not only do you face new, you need to lead in a different way. The changed leadership is a critical enabler for success with digital transformations.

Your leadership need to bring down silos and foster collaborations from day 1. You need to support a higher degree of experimentation, with a higher failure rate. You need to design operations for a higher degree of incremental learnings. Information transparency can be challenging to deal with. Breaking down silos and releasing information earlier and broader.

Last but not least your role requires more of your own input to shape the role up to your potential. Less of a pre-cooked frame and more for you to expand and experiment around.

The last 2 weeks before you start – role & relationships

Leverage the last two weeks to shape the role and to build relationships with key stakeholders. Expect a broad set of stakeholders to interview you, and leverage the initial contact to solidify your network.

Refine the articulation of the role to include both what you must do and what you can add based on your unique capabilities. And be humble with where you have gaps. Your journey is about filling the gaps through exciting on-the-job experiences.

First 15 days – Business focus, human capital & leadership agenda

As in all 100-day plans you want to emphasize business focus from start and to get to know the team. Activate your team through focus on the current business. A vital source for quick wins.

Spend time with your team to get their views on the business and their roles. Interview members 2-3 times to digest the input. A great test for your listening skills

The digital element is to set a clear leadership agenda early on. What you stand for as a leader. What you see it takes to lead digital transformations. What your role looks like.

Day 16-30 – Customers, Governance & Tools

The focus here on customers and governance is not surprising. What might be different is how you collaborate with customers. If you have customer discovery journeys defined and drive progress towards customer buying processes.

When reviewing governance processes you are looking for agility and speed of decisions. Securing the governance is not a bottleneck but a backbone enabling an action centric approach.

With regards to digital tools you can expect a big spread. From simple collaboration tools to customer insight tracking and lean task follow-up. A critical part of your set-up and where large improvements are likely as a part of digital transformations.

Day 31-45 – Hypothesis, revisit focus and human agenda

As you approach the mid-point of your program you are starting to set up Hypothesis based on your initial findings. A strategy tuning hypothesis for direction. A hypothesis for how to use your team, and where to change. A hypothesis of which flows to focus on.

Your own onboarding need to be complete to a point where all you want to stay are ready to bet on you. Most professionals make up their mind the first 45 days under a new leader.

Halftime is great for tuning the scope of your 100-day plan. To secure you focus your energy on the right areas.

Day 46-60 – Validate your observations and assumptions

An opportunity to validate your observations and assumptions. Your raw direction benefits from facts and details. It represents a strong signal you want to create a more fact driven organization. With a high degree on information transparency.

Put extra attention on the digital initiatives and identified learning needs. These are likely to be your largest transformation initiative.  A need divided in smaller blocks,

Day 61-75 – Stakeholder anchoring of proposed direction

By this time your plan should be solid. Solid enough to serve as a basis for stakeholder anchoring and the execution direction for the first 2 quarters.

Your organizational plan should represent a clear base to build from. Your platform should be clear, but all changes don’t need immediate implementation. The organizational boxes are the easy task. The more critical one which value adding flows to focus on and to secure interfaces to peer contributors.

Expect the goals setting and execution in shorter stints to be a significant job for your team. And at this stage being more of a start for the journey ahead.

Day 76-100 – Transition to quarterly execution

As your 100-day plan come to an end you want to get a flying start to your first operational quarter.

You want to operate with crisp and clear near term goals an exciting long term direction. You have set-up a frame for the first quarterly plan. Tied to monthly governance.

How fast you can progress depend on how change ready your team is. A big leadership contribution here is to set the tone for continuous change and adaptation to a moving environment. A step that can be smooth if played right

Good questions to ask

1. What are the key steps to address in my 100-day plan – see this plan as a directional idea.
2. How ready is the organization to take on the change – expect change readiness to vary.
3. Which stakeholders are key to success – you can’t break down silos alone.
4. How do I best articulate and validate critical hypothesis – be open to elaborate and test during your 100-day plan
5. Are we opportunity, capability or leadership constrained – critical insights as execution input.

Additional reading suggestions

• The first 100 days of a new CIO: Nine steps for wiring in success [ARTICLE] – by McKinsey
• The first 100 days of a Chief Data Officer [BLOGPOST] – by Gartner
• Creating a digital transformation plan [BLOGPOST] – by Smart Insights
• IT Careers: 5 Tips and ideas for crafting your 100-day plan [BLOGPOST]
• 5 things CIO should do in first 100 days of leading digital transformation [BLOGPOST] – by Star CIO