In today’s rapidly evolving digital landscape, IT leaders face a myriad of challenges as they strive to drive transformation and innovation within their organisations. From overcoming departmental silos and ensuring strategic alignment to bridging internal skill gaps and justifying technology investments, the path to a successful digital strategy is fraught with obstacles.  

This blog is part one of two and delves into three common barriers that IT leaders encounter and offers practical strategies to navigate these challenges effectively. By addressing these hurdles head-on, IT leaders can position their organisations for sustained growth and measurable business outcomes. 

Ahead of our IT Leader’s Lunch on October 2nd, we’re exploring six common barriers that arise when embarking on a digital workplace project, and how to overcome them. These insights are drawn from conversations with enterprise and mid-market CIO and CTOs over summer. 

 

1. Relationship with the business 

IT functions can find themselves operating in a silo, focused on their own priorities that range from managing information security to technical debt. With so much IT orientated work to do, some IT teams can become disconnected from the broader business agenda and lose sight of the challenges the wider organisation is facing.  

When IT isn’t fully plugged into business challenges the function can struggle to act as an enabler to the business, limiting the measurable impact of the department as a whole. 

How to overcome this challenge 

Make business engagement a KPI: For any orientation towards the business to be meaningful it needs to be a cultural change within IT. Establish formal accountability with a business engagement function by role, or introduce this activity to existing roles. If you do the latter be sure to formally add it as part of role guide(s) so that team members are measured on business engagement.  

Open the lines of communication: Proactively seek out opportunities to join early conversations about new initiatives so technology can be a strategic enabler to business goals. 

Get closer to the business strategy: Establish regular touchpoints with business leaders to listen to their challenges, then loop back and share how technology can address them. These conversations shift IT from being reactive to being a trusted adviser.  

 

 

2. Internal capability 

Even with the right strategy, execution can falter if the IT team lacks the skills or confidence to deliver. IT teams can hesitate to launch a new initiative when they’re unsure whether the solution is right, their teams are ready, or the wider organisation has the digital literacy to adopt new tools and technologies.  

How to overcome this challenge 

Assess internal skills 

Look at your priority projects for the next 12 months. What skills are needed to execute them? Who in your team has these skills, or could have these skills if provided training? The key thing is to have a 12 month view, rather than assessing each project only when it is about to start. 

Assess your internal capabilities against priority projects. Use tools like skills matrices or AI-powered HR platforms to identify skill gaps and strengths. Additionally, when forming project teams, ensure there’s a mix of technical expertise and change management skills.  

Bridge the skills gap or buy them 

Once the skill gaps have been identified, the next step is to actively bridge them. This can be achieved through a mix of targeted training, mentoring, and external support. Consider a blended approach where it’s convenient to do so. 

 

3. AI Adoption Paralysis  

AI is everywhere, and that’s part of the problem. The hype can be paralysing when so many global vendors are making multi-billion dollar investments. IT teams can hesitate to get beyond analysis when there’s the possibility that AI might be able to do it soon; nobody wants to be part way through an AI project only to find the capability has landed somewhere that the competition can take advantage of today.  But in the meanwhile, doing nothing when possibly nothing will emerge from a vendor in the space you need, feels risky.  

How to overcome this challenge 

Clarify the value 

It is important to clarify what you need and the value you are looking for AI to deliver. Often it is easier to assume ‘AI can do it’ without being specific about what we want it to do. This creates the perception that AI is the answer, even if there are other ways to meet the need. 

Table all the options 

Being clear on the specific needs that should be met will allow for a market-vendor AI tool assessment and/or internal cost exercise to build the capability. It is also worth looking at alternatives. If you specifically want AI to guide a process, can automation and workflow deliver the value needed? Does it have to be AI? 

Consider the medium term 

An AI option might look great now, whether bought or built, but what about in 12 months time? Is there a likelihood of a rapid increase in cost, or decrease in value? 

With the AI market in flux, having an AI investment criteria that formally assesses the risks (which will vary from need to need) will be vital to making consistent and rational decisions.  

Next month we will look at three further barriers to a high value digital strategy and how to overcome them. 

Join the Conversation 

If you’re an IT leader looking to transform your digital workplace to enable business growth, we invite you to sign up for our upcoming IT Leaders’ Lunch.

By attending, you’ll get the chance to connect with peers, share strategies, and explore how Microsoft 365 can help you lead the next wave of business transformation – over lunch.