Managing change is hard. Here’s how to make big business decisions

Digital leaders will have to embrace risk if they want to deliver great results across an ever-increasing range of digital transformation projects. 

More than half (57%) of board directors have either increased their risk appetite heading into 2022 or are expecting to, according to analyst Gartner, with most citing economic uncertainty, disruptive models from competitors, or cost inflation due to supply shortages as reasons why. 

SEE: What is digital transformation? Everything you need to know about how technology is reshaping business

Delivering to these fresh boardroom demands across a wide span of initiatives is a complex task. Technology chiefs will need to ensure that they and their teams can balance risk with opportunity to produce great results for the organisation and its customers.

Four business leaders give their best-practice tips for becoming a leader who delivers successful digital transformation projects for the business.

1. Give people cover when they need it

Adam Miller, group head of IT at insurance company Markerstudy Group, says the key to being a courageous leader is having confidence in your own decisions – and that requires in-depth personal knowledge and a strong relationship with a team you can rely on.

“The better you know your subject, the more confident you’re going to be in the decisions that you make and how you communicate that,” he says. “Equally, having that strong team around you as well is going to give you confidence in the decisions that you’re making. It’s a mutual thing.” 

Miller says all business leaders must focus on building strong relationships with the people who are going to support the projects they’re executing. Executives should also remember that these relationships are a constant work in progress. Business leaders will be judged by the people they lead on the actions they take.

“So, if you’re looking after the staff who are working for you and backing their decisions – which means giving people air cover when they need it – I think these are the things that help build those strong relationships. And when you’ve got those strong relationships, you can have confidence in the decisions that you’re making,” says Miller.

2. Focus on continually learning new things

Lisa Valentino, executive vice president for client and brand solutions at Disney Advertising Sales, says her “secret sauce” for leaderships success is making sure she continues to be a student of the business. By continually learning from her colleagues, Valentino finds it easier to make courageous calls.

“I think it’s hard to take risks – and the expectation is we’re taking risks every day and, as a business, we’re super ambitious,” she says. “We must have a long-term view on the marketplace and give recommendations and strategies to the company. And to do that effectively, you need to know this business inside and out.” 

Valentino runs a range of data-led initiatives for Disney, including using Snowflake’s Media Data Cloud to bring information assets together. She builds her knowledge of the company’s activities by ensuring she’s an active participant in the various elements of the business, whether that’s across media and streaming or data and technology. 

By focusing on her people and ensuring they understand the business’ grander objectives, Valentino believes she continues to stay on top of the issues the organisation faces – and can make courageous decisions that benefit everyone.

“You need to be the smartest you can be,” she says. “If I know the marketplace, then I’m taking calculated risks every day. They’re still risks, but they’re calculated.”

3. Establish new ways of working

Milena Nikolic, CTO at transport specialist Trainline, believes that the empowerment of staff and the establishment of accountability are the two key factors that allow her to make courage decisions on behalf of the business. 

“I think it’s about providing clear swim lanes and providing clear goals for people, and then just really letting them get on with it. But equally keeping them accountable to that process. I think those two things give you the chance to remove roadblocks and let your people get on with their work,” she says.

Since joining Trainline in July 2021, Nikolic has been focused on creating a new target operating model, which involves establishing new ways of working centred on running cross-functional teams that are oriented around set business outcomes. 

SEE: Building a better commute: How one ticketing company is rolling out new tech for riders

She says the aim of this model is to ensure the engagement and accountability of people and to ensure their workplace activities are aligned to Trainline’s biggest strategic priorities. This agile approach aims to develop a startup culture within the company, allowing people to suggest and then hone innovative services for customers.

“You need a very clear, meaningful goal and then you need to keep your people accountable. And that’s how people can succeed. That was the underlining philosophy that really came through when we were designing a new target operating model with my product counterparts and members of my technical team,” she says. 

4. Delegate decision making to trusted specialists

Craig York, CTO at Milton Keynes University Hospital NHS Foundation Trust, says the key to being a courageous leader is simple: delegation. 

“The size of the organisation and the department that I lead, I can’t be involved in every decision and every meeting,” he says. “You must have trust and delegate real, effective power to your team and others so that they can deliver things. If you want to push forward in many different tracks of digital maturity, you’ve got to feel safe enough to be able to do that.” 

York says he’s fortunate to have established that level of delegation to his team, which affords him the time to explore new strategic opportunities with suppliers and CIO peers across the country and beyond. 

He says it’s also important to recognise that leadership is related to having expert knowledge in the field. York’s organisation employs a chief clinical information officer (CCIO) and a chief nursing information officer who help his team ensure they’re making decisions that have a positive impact.

“You must bring in the clinical voice from this organisation,” he says. “Our CCIO is a consultant surgeon, and she has dedicated time for IT. She has a desk here in the IT department and there’s no barriers and no hierarchy. She’s here in our IT management meeting every week, making sure that our change control board is putting through things in a safe manner. But she’s also checking that what’s on our priority list is also top for a clinician.”