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Why You

Need a Digital

Roadmap

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Many companies in the middle market purchase and implement technology for specific, narrow, and often

functional needs. It becomes more challenging to be strategic as the projects get larger, more complex, or

more frequent. To mitigate the risks associated with this and enable the business benefits of technology to

compound over time, companies need a plan that ties their digital efforts to their business strategies.

Businesses in the middle market are particularly prone to making technology changes to address immediate

needs. Day-to-day activities require constant care and feeding from executives, which makes it difficult to

create momentum that deliberately moves you towards implementing your strategy.

How do you achieve this momentum? We recommend starting with a digital roadmap. A roadmap helps

executives invest in and manage technologies that best align with their strategy for the company. It benefits

owners, executives, and managers, and encourages collaboration that aligns everyone on priorities and

new investments.

Most importantly, a roadmap provides a clear picture of how to implement your technology ecosystem to

achieve your strategy. Digital transformation fails not because of issues with the technology itself, but

because of poor planning and execution. In fact, 61% of executives say their firms fail to convert their

strategies into effective execution plans.

So, what is a digital roadmap?

A roadmap – digital or otherwise – is a governing document that shows which technologies are required to

drive and support the growth of the business. It specifies how technology will be implemented and evolved

to support the business strategy over the next 18–24 months. The best roadmaps contain:

1. A strategy statement with a list of digital priorities for the business

2. A timeline of the initiatives that need to occur to achieve the strategy

3. Justifications for each project

4. The estimated cost and duration for each project

5. An owner (manager) who will be accountable for each project

It’s important to recognize the distinction between a roadmap and a project plan. The roadmap is longer-

term, higher-level, and is not intended to be driven on a task basis. Rather, the roadmap should consist of

discrete initiatives. As an example, implementing a customer portal could be a discrete initiative, whereas

an ERP project may need to be split into several initiatives – selection, core financials implementation, and

operations implementation. The roadmap should not include phases of those projects or the steps the

business will take to execute a specific project – those are best reserved for the project plans.

There are a few different roadmap formats which we recommend:

THE DETAILED, LONG-TERM VIEW: This roadmap contains a list of all the detailed projects on the horizon. These typically extend for 12–18

months and are updated monthly or quarterly. Long-term roadmaps are designed to help bring a full

perspective to all of the activities planned but are not detailed enough to guide day-to-day project execution.

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THE MORE DETAILED 60- OR 90-DAY PLAN: We recommend that most of our clients run their roadmaps in 60- to 90-day increments, depending on the

level of difficulty, cost, and length of their roadmap projects. These plans still get a visual, but they contain

the milestones for each project within each time period.

For the scrum folks reading this, I deliberately avoid “sprint” here, although in some cases that may be the

appropriate framework. We generally use a combination of scrum techniques and waterfall techniques to

execute enterprise technology projects. Pure waterfall or pure scrum may work best to execute an individual

project, but for a roadmap that maps to the business model strategy, something more comparable to the

waterfall approach is best – it’s easier to manage, easier to communicate changes from, and easier for

executives to understand what has been done and what is coming up.

THE PROJECT PLAN: The lowest level of detail that rolls up to the roadmap is the project plan. In our methodology, every project

needs a project plan. If it’s a small, simple project with few milestones and deliverables, this can be as

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simple as a spreadsheet or a slide containing the core elements of the plan. For larger projects – especially

those with multiple teams or sensitive timelines – we use a full project plan, generally managed in either

Smartsheet or Microsoft Project.

How will you use it? The roadmap has three primary functions:

1. Prioritization: Facilitate investment discussions with the rest of leadership. The roadmap will serve

as a reference point when discussing changing priorities. It will help everyone understand how to

balance priorities and visualize tradeoffs. There will always be more digital priorities than there is

budget.

2. Planning: Plan time for resources and costs for capital needs. Only 11% of managers say they

have the resources they need to pursue the company’s strategic objectives. The roadmap will help

anticipate resource needs and capital costs ahead of time and make it possible to integrate key

projects into each department’s day-to-day plans.

3. Accountability: Create individual and departmental accountability for execution. Digital

transformation cannot fall only to IT and neither can executing the roadmap. Cross-functional

partnerships are crucial and leadership from executives in the business functions are more likely

to drive success in design and adoption. IT should have accountability for some deliverables and

they should be involved at every step of strategy and roadmap governance, but they should not be

accountable for all initiatives. Active management of the roadmap will result in better executive

alignment and stakeholder buy-in before projects even begin and give those accountable a

smoother road to success.

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The Roadmap Should Not Make You Rigid Having a roadmap does not commit you to it permanently. You do not need to stick to the plan you set out

at the beginning. In fact, it would be in your best interest to change the plan (in an orderly fashion on an

established schedule) as business conditions change. The roadmap itself provides the structure in which

to manage those changes effectively – it is not intended to prevent them.

Non-negotiables? There are several items that need to appear on every roadmap:

▪ Ecosystem strategy: While it may sound like hollow jargon, you will be curating a digital

ecosystem that your business will rely on for virtually everything it does. Some key decisions you

make early in the roadmap will either deliberately or incidentally set you on a path to that

ecosystem. It is important that this is a deliberate choice – not all ecosystems will support the

business equally.

▪ Enterprise architecture: This typically covers your process flows, data flows (example below) and

system landscapes. Documenting the types of systems in the ecosystem, how those systems

interact with each other from a data flow perspective, and how they will be layered in over time will

make sure that requirements for integration are factored in with each system implementation

upgrade. The enterprise architecture documents are living documents that should be maintained

as changes are made to the system’s environments.

▪ Reporting and analytics: It would be easy to absorb reporting and analytics into each individual

project, but don’t fall into this pattern. Data is paramount. The quality of data will drive reporting and

analytics success. Virtually every initiative on the roadmap will produce data. Each project needs

to understand how data should interact across workstreams, and the reporting and analytics should

be looked at as a layer over all of this data rather than separated by system.

Leading practices? ▪ System selection: For big enterprise systems, split the effort into system selection and

implementation. The vast majority of businesses have a number of systems they could consider,

and there is no obvious, industry-level “right” answer for any one of them. If the replacement or

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upgrade of ERP, CRM, or other broad enterprise systems is being considered, be sure to include

a selection phase for each.

▪ Security and compliance: There needs to be an overarching security and compliance component

to all technology investments, including cybersecurity. If this is considered from the beginning of

the roadmap, building and maintaining a secure technology framework will be comparatively

simple. If you revisit security and compliance only on a periodic basis and with a narrow focus, it

will be difficult and expensive to achieve cohesive security, and it is likely you will miss some major

risks.

▪ Don’t skimp on process review and design! Having clarity on the workflow within a business is

important, both for knowing what the hand-offs between roles and systems are, as well as

identifying areas for improvement where parts of the business may be underserved from a digital

perspective. Often there is the temptation to replicate current ways of work within new systems –

challenge yourself by asking “What can I do differently with the new system?”.

Finally Did you notice what wasn’t listed above? Specific references to technology solutions or stacks. There are

two reasons for this. First, the technology marketplace changes fast, but good digital discipline does not.

This framework can be used now and it will still be relevant three years, five years, and probably eight years

from now when you are still living with the downstream impacts of the decisions you make today. Second,

it is critical for this approach to be modified by both technology and non-technology people. As the executive

leadership becomes engaged in developing the digital roadmap, we strongly caution against making the

substance of those discussions overly technical or vendor-focused. The goal isn’t the tech, it’s the business.

Keeping the focus on the business itself throughout these roadmap discussions will dramatically increase

the probability of success when you execute it.

Who benefits from it? FUNCTIONAL LEADERSHIP: The roadmap is designed to structure communication between department managers and company

executives in a manner that allows everyone to:

▪ Act strategically when making investment decisions and managing projects.

▪ Secure buy-in from executives with a structured process. This also makes it easier to earn buy-in

from business users.

▪ Negotiate effectively with executives or staff who request new initiatives that require significant non-

operating effort.

EXECUTIVES: The roadmap allows executives to be strategic when they evaluate new initiatives. They can use the overall

strategic plan to determine which types of projects will be required to achieve the company’s goals and

make it clear to managers and staff why a specific project is important. It will explain the value proposition

for each department and suggest how to maximize its value.

The roadmap provides resourcing forecasts when staff needs to be assigned to projects, traceability to

costs, and the detail for why those resources and dollars are required.

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Finally, it provides a strategic, structured manner for governing changes to the projects as business needs

arise. A roadmap ensures all necessary voices are represented at the table when decisions that will require

ongoing leadership support are made, and it helps balance priorities across the business, diffusing conflict

before it arises.

STAFF AND PROJECT TEAMS: The roadmap spells out why particular projects are important; as items on the roadmap move or are re-

prioritized, it forces project managers to explain why and how those priorities are shifting. The roadmap

encourages a clear and regular line of communication between leadership and staff.

The Bottom Line As valuable as the roadmap is as a document, it is even more valuable as a communication and

management tool. All executives and key managers should be involved in developing and managing the

roadmap, and the process itself should be owned by someone with credibility and authority. Because of the

strategic nature of the document and how critical leadership buy-in will be, the roadmap will need

widespread support at the highest levels of the business.

If you are a manager, encourage your executives to support the development of a roadmap so you can

invest strategically and have structured conversations around priorities with other executives.

If you are an executive, take a breath, find the right guidance, and start building a roadmap. Once the

document and proper leadership are in place, you will understand how to develop tangible value and

success.

All of our rapid assessment methodologies end with a full roadmap, as described above. To learn more

about the assessment process behind a great roadmap, take a look at our:

▪ Rapid Business Assessment

▪ Rapid Finance Assessment

▪ Rapid Automation Assessment

To start developing your own roadmap, please contact us.

Steve Ronan Principal

sronan@citrincooperman.com

Smija Simon Manager

ssimon@citrincooperman.com