CEO’s report: Your IT questions answered

Your IT questions answered brings together real-world questions from mid-market leaders and expert responses from experienced IT professionals. Everything you wanted to know about IT and technology but were afraid to ask.

We wanted to know what mid-market business leaders were thinking about when it came to their IT and technology. So we solicited their questions. Then we had our own IT leaders respond.

The result is this free CEO’s report. It’s a fascinating collection of real-world questions and answers about cyber security, integration, ERPs, private equity, compliance and more. Download it now and feel free to share it with our compliments. The answers may surprise you!

Your IT questions answered in practice 

As companies grow, their IT inevitably needs to change and develop. But most companies don’t follow a well-planned path. This report outlines how an IT roadmap will help you streamline your systems and processes – and how IT can help you achieve your business goals in 2025 and beyond.

It’s impossible to run a business, let alone grow it, without IT and technology. And yet it can be the least-planned aspect of a company’s operation.

It’s entirely normal to have relied on quick solutions to keep things moving – for instance, ad-hoc subscriptions to online services and systems that have become integral parts of the business operation. Frequently there will be informal workarounds, like spreadsheets, and key individuals manually performing critical tasks.

Over time, however, the result is an overly complicated infrastructure which makes it exceedingly difficult to grow the business or introduce new initiatives like automation or AI. Economies of scale don’t materialise, service begins to suffer, and morale and culture are eroded by constant issues and snags.

The solution is an IT roadmap – a plan for how IT can support and drive growth, allowing a company to scale up confidently, without sacrificing profit margins and customer service.

For many leadership teams, Your IT questions answered provides a practical framework for turning complexity into clear action.

An IT roadmap allows a company to scale up confidently, without sacrificing profit margins and customer service.

A roadmap ensures that your technology, processes, and organisation develop at the right rate as the business grows. It ensures that your team have systems that allow them to do their jobs well and efficiently, that the Board can leverage opportunities for partnerships or acquisitions, and that leadership can delegate authority to managers who can make solid judgments using the latest data. Finally, a roadmap helps to optimise the value of the business in the event of an exit.

In short, an IT roadmap transforms systems and processes from a source of frustration into a means of helping a business achieve its goals.

What happens when you don’t have a roadmap

It isn’t always easy to create an IT roadmap, especially if there is no senior leader on the Board able to own it. Nevertheless, without one, companies may end up in a cul-de-sac, with their business impacted in harmful ways:

1. A lack of clear and efficient processes erodes margins, impedes automation and AI, and makes good service difficult or expensive. The issues increase as the business grows, damaging profitability and cash flow. Short-term problems dominate management, and there is little time or money to plan for expansion.
2. Poor reporting tools make it tough to determine which products and customers are profitable. It’s too difficult to analyse costs, revenues, efficiency, and profitability. The lack of data also means that marketing and sales ideas run aground.
3. Lack of standardisation means the business is reliant on key individuals who keep their own vital lists and system workarounds. This makes these individuals choke points that limit growth and expansion. When these key people are on vacation or out sick, the whole business is affected, and if they leave it’s a major problem!
4. A coherent online strategy is impossible because back-end systems can’t provide a simple platform. Seamless back-office processes are necessary to allow for must-haves, such as consistent product and stock data, or effective product searches.
5. Issues and concerns about reliability and compliance are a constant distraction. Basic IT doesn’t always work; people can’t do their jobs and easily impress customers. There are lingering worries about compliance. Disaster recovery plans may not be adequate, and there is a sense that the IT is simply not fit for growth.
6. Departments create their own systems, often using cheap software downloaded from the web. This leads to systems and data becoming fragmented, which in turn makes it much harder to reconcile data and create reports. Inevitably these unofficial systems are integrated into the company infrastructure, creating even more complexity.
7. IT projects are ad-hoc. And they’re isolated from other parts of the company, so they frequently don’t get approved – there seem to be no credible options that executives can understand and make informed decisions on.

These issues can get tangled up in a dense knot. Even just one or two of them makes it very hard to plan a way forward and to create credible, cost-effective plans. Ultimately, it creates a lack of confidence – there’s no appetite to seize opportunities and plan for expansion. Whilst it can be difficult to untangle all these problems, everything gets much easier and clearer with an IT roadmap. Here is how to get started.

First, get clear on your business objectives

In our experience, your business objectives are the only starting point. In some cases, they may already be detailed and developed; in other cases, there is a set of growth objectives. Either way, the objectives need to be (a) clarified and then (b) defined in terms that are relevant to your systems and processes.

If the objectives aren’t yet clear, a workshop is a great way to get everyone talking, and (eventually!) in agreement about the challenges and goals.

Once everyone is on the same page, it’s time to get specific about each goal. For example, if the aim is to grow revenue by twenty percent every year for the next four years, what might that mean in more detail?

• How many invoices per month? How many clients? How many currencies?
• How many new products per month should be added to the website? Or how many website orders per second in the peak minute?
• How many SKUs? How many square feet of warehouse space?
• How many inbound and outbound communications per month, and by what channel (email, phone, social media, etc.)?
• How many senior managers will be needed to work on the projects?

We often work with our clients to get specific about the details behind their objectives and then review them against their systems. When there are objectives that will make systems creak and groan, we have a starting point for a plan.

These details also provide a sound basis for contracts with external suppliers. When a business is investing in new systems, the suppliers need to be able to commit. If the proposed Service Level Agreements and Key Performance Indicators are not aligned to growth objectives, then we suggest a supplier review session to bring them back in line – or they’re the wrong supplier.

Ambitious businesses need to plan how their IT can support and even drive growth.

Include all aspects of IT in your roadmap

The roadmap needs to cover all the key areas of IT. So now is the time to audit all your hardware, software, systems, and processes. Some ideas to get you started:

• Back-office systems mean very different things in different sectors: for example, practice management systems, sales order processing, warehousing, finance, and so on – and don’t forget the people, process, and data issues.
• Digital initiatives, from online retail to partner portals and social media strategies.
• Infrastructure, for example, networks, data storage, and transition to cloud, plus all the normal details of laptops, tablets, phones and printers. This may mean a host of other IoT or other devices as well.
• Key data in spreadsheets or other off-system lists. (By the way, where there are persistent problems, who is responsible for sorting them out? And larger SMEs should think about data governance.)
• Future plans for tech investments in automation or AI.

You want to be comprehensive about what you have and where you plan to invest, because the systems have to be integrated to work optimally, front-end and back. It’s a big mistake to allow impressive-looking front-end systems to distract from back-office projects, because the behind-the-scenes projects are what bring out the real value.

We emphasise getting your data organised, because without clean, structured data, you can’t have accurate reporting, and AI is a waste of time.

The important point here is that once you have a clear picture of what you have and what it costs, you can figure out what projects you need to reach your goals.

Identify the roadmap projects.

Again: the best way to identify the options for projects is to work backwards from the business objectives. Identify all the business and IT enablers necessary to deliver these objectives and map it all out as a joint exercise: include executives and experts from around the business (they’re not necessarily the same people!).

Then, for each project, it’s possible to estimate the costs, timeline, and trigger points. The entire roadmap can then feed into the business planning process, and the Board can forecast the impact on budgets, in terms of both direct costs and benefits.

Here are some considerations to keep in mind when working up your projects:

• What projects are absolutely necessary to the continued existence of the business? You need to first consider projects related to security, compliance, and regulations like GDPR, any sector-specific regulations, and NIST standards. If you’re doing business in the EU or US, you of course need to comply with their regulations as well. (If you’re unclear about which regulations may apply to your business, feel free to get in touch.)
• Do you need bespoke software? Some companies will need to develop software products as part of their revenue plans – for example to license data or other intellectual property to clients. This may be for direct income generation, or to improve client retention, or to create a point of difference in the market.
• Do you want major innovations? We increasingly see situations where automation, AI and machine learning offer genuine opportunities in the mediumterm. These plans should be in the roadmap.
• Are you keeping cyber security in mind? Cyber security must be a consideration at every stage of the process. It’s not an afterthought; it’s a necessary part of the day-to-day.
• Are you planning for mock-ups and prototypes? You should plan for them, because they are necessary to help everyone see (literally) how the proposed projects will achieve the business objectives. And they help crystallize the requirements, as well as providing more clarity on the viability of a project.

Remember, though, that technology is never the entire solution. Sometimes a business may have to change personnel, offices, or processes. Sometimes cultural or behavioural changes are necessary as well (as they often are when it comes to cyber security).

It’s complicated and detailed work, of course. But once all these projects are identified, you can understand the pros and cons, and the Board can make informed decisions about each project.

Remember to build flexibility into your roadmap

In business, the reality never exactly matches the plans. This isn’t a failing, but a normal situation given the exigencies of running a business – a client may surpass their plans or fall short in some aspects. Either way, it’s unusual to hit the nail right on the head. The IT roadmap needs to be flexible enough to cope with this fact.

At the same time, everything in the roadmap is based around meeting (or exceeding!) growth targets. This way, everyone understands the goals of the plan, and the IT team is now pursuing projects entirely aligned with the evolution and growth of the businesses.

Building in flexibility will also help to reduce possible sources of conflict. In entrepreneurial mid-market businesses, there will inevitably be tension between an aggressive approach to growth versus an approach that focuses on minimising risk and ensuring scalability. So the compromise may be to enable the aggressive approach within an agreed scale or time period. In this way, the tension can be resolved by simply reframing the conversation as a matter of phasing.

Who owns the IT roadmap? Who will deliver the projects?

You are about to embark on a complex undertaking that will potentially fuel growth for years to come. So a high-level executive needs to own the roadmap, speak for it, and ensure that it is kept in the forefront of everyone’s mind. Ideally there should also be ownership at executive level for each project; having a senior stakeholder means a project is more likely to succeed and achieve the expected ROI.

Delivery of large IT projects is complicated and requires good governance, strong leadership, and good management. Managers and experts around the business must be involved in delivery of all the components of the project. And their efforts should be coordinated: nothing sinks a project more effectively than when key people can’t make time because they are too busy with their daily tasks!

We advise our clients additionally to break down each project into steps, since large projects need considerable planning before they even start. For example, someone will have to contact potential suppliers and arrange for a pitch; there should be a Request for Proposal stage and price negotiations.

The timeline should reflect these steps – and the understanding that it will all take some time. You don’t want to force yourself into a position where you’re rushing a step to meet some hasty deadline. Finally, there needs to be clear accountability for both delivery of the new technology and for achieving the outcomes.

Keeping the IT roadmap alive

In order to ensure that the roadmap stays up to date, we recommend all key managers and decision-makers review it on a regular basis, say every quarter, with a major re-examination at least every year. These reviews should always be considered in light of the business strategy, particularly when there is significant change – perhaps a major new customer, a new service, or an acquisition.

And don’t forget the people affected by the changes! Sometimes the hardest part is not the implementation of new systems, but the management of the people who have to deal with them. When you underestimate the training requirements – or simply helping your people to understand the need for change and how their jobs will be affected – you’re endangering the long-term success of a project, however well you implement the technology.

On the other hand, when everyone from the Board on down is clear about the roadmap, it can be a huge boost to morale. It provides a basis for sound optimism across the company. It removes uncertainty, wasted effort, and doubt. And as the business grows, its leaders and managers find it easier to make decisions on projects, because they have already been agreed in principle. They can arrange funding in advance, and the business is better able to take advantage of opportunities when they arise.

An IT roadmap removes uncertainty, wasted effort, and doubt.

Revisiting Your IT questions answered helps Boards stay aligned on priorities as systems, data, and business needs evolve.

When put together, the company’s people, processes, technology systems and digital initiatives are critical components of a growing business. An IT roadmap is the basis for managing all of it.