The three pillars of IT leadership and the path to the future

No matter the industry, good leadership is crucial when it comes to the well-being and smooth functioning of an organisation. Without good leadership, even the best idea can be poorly executed or not executed at all. But what are the pillars of IT leadership and how do they connect to software delivery management?

There are IT leaders who feel that the three pillars of IT leadership are: everything automated, everything connected, everything resilient. Automation, connectivity and resiliency form the foundation of IT leadership. They go hand in hand with other principles that apply to IT leadership in general and are particularly relevant to software delivery management.

IT leadership is about iteration

At DevOps World 2020, during a session called Taking Extreme Ownership of your DevOps Transformation, former US Navy SEAL and motivational speaker Jocko Willink argues that when you are in a leadership position, you sometimes have to make your best guess and take the smallest possible step in a certain direction. If the feedback is positive, continue to go in that direction; if not, change direction and strategy.

What Willink describes here is an iterative decision-making process. Making decisions iteratively is about making decisions quickly, with the caveat that these decisions have to be small, so that once they're made and a new course of action is established, the progress is immediately reviewed. Iterative decision making goes hand-in-hand with the agile IT concept of 'fail fast', a philosophy based on using incremental development to determine the value of an idea or the outcome of a project. In order to make decisions iteratively and to fail fast, it is crucial to have a mindset that encourages fast decision-making. This mindset deems mistakes as opportunities for change and learning, without dwelling too long on the bitter feeling of failure, so that progress can be made and the desired outcome can be achieved quickly.

Iteration is a strong principle that applies to all three pillars of IT leadership:

• Everything automated means choosing automation tools and processes, implementing them and working with different teams to establish the value, benefits or challenges of automation. It also means permanently reviewing those tools and processes and embracing the opportunity to change direction, if necessary.
• Everything connected means that all teams collaborate and that all tools are connected, in order to surface common data and insights available to all stakeholders. It also means equally assessing the process on a regular basis and ensuring the right decisions are made, even if change is needed.
• Everything resilient means having strength, tenacity and a steadiness of hand - which is at the heart of iteration.

IT leadership is about ownership of the three pillars

Iteration is vital in IT leadership, but ownership is crucial to enabling iteration. Without instilling a culture of ownership, individuals, teams and organisations do not take responsibility for their decisions or actions. Leadership cannot happen without ownership. To own something means to be responsible, to not point fingers when something goes wrong and to be open to feedback. You are actually empowering your teams, by instilling ownership.

Ownership in IT is crucial because of the high number of decisions that need to be made, the high number of people affected by decisions, the fast pace of the organisation and the ever-changing demands of the market. As a leader in IT, you need to own your actions and choices and be aware that they impact not just your colleagues, but also your customers. Owning something as an IT leader means being part of a complex value loop that involves your organisation, as well as the impact the organisation has on customers and even the world.

Same as iteration, ownership is a concept that applies to all three pillars of IT leadership. To own everything automated means to acknowledge the importance of automation, to sponsor the investment in automation processes and to make sure that any tools selected add value to the value loop. They should provide freedom and focus, thereby empowering people. To own everything connected is to realize and act upon the importance of connecting all tools, processes and people and to codify the knowledge base by extracting the distributed tribal knowledge that sits across organisations in people's brains in order to convert it into a common language base. To own everything resilient is to be willing to apply that resiliency to everything you do in your job - to stay strong and strive to ensure that nothing stands in the way of delivering best value, fast and safely.

IT leadership is about connecting the dots

When we think of everything connecte d, connecting tools, processes and people is just one part of the puzzle. The other part is completing the whole puzzle. To do so, IT leaders have to connect all the other dots: connect the present to the future, connect all parts of the organisation to the IT department and make software delivery management a core business value.

Because of its nature, leadership is strongly anchored in the future. Being a leader means being responsible for decisions that will impact the future of your team, organisation and customers. However, leadership in IT, especially in the context of 2020, should focus even more on connecting the present to the future.

IT teams have always been known for working with tools that enable sharing of data and information. These tools are even more important today, with so many people working from home - and will be even more important in the future, as the whole world adapts to a new way of working. Equally important is the culture of these teams, as people need to be open to communicate and collaborate asynchronously, relying on the best tools and processes to deliver results and satisfy customers.

As the world advances towards a technology-first approach, IT leadership will be more about connecting IT teams and departments to the rest of the business and about making software delivery management a core business function. By doing so, the whole organisation will know what's happening in the software delivery process, all teams will be connected and integrated tools will allow for better planning and remote collaboration.

Working together across the organisation in order to create a system of record that can be accessed at any point, from any corner of the world, will be the recipe for future-proofing IT leadership. Being able to drive value to the business while connecting all the dots in the organisation, therefore connecting the organisation to customers and to the rest of the world, will be paramount to ensuring good, agile and resilient IT leadership.

Brian Dawson is senior director of product at Cloudbees