Today's IT leaders are much more than technology experts \u2014 they\u2019re business leaders charged with driving timely results. And that requires knowing not only how to prioritize IT initiatives, but when, and how, to say no to projects that won\u2019t advance business goals.\n\n\u201cWhile saying \u2018yes\u2019 to a project can seem like the easiest way to spark innovation, the ability to say \u2018no\u2019 is vital to ensure companies focus on projects primed to deliver long-term value,\u201d says Prasad Ramakrishnan, CIO at software company Freshworks. \u201cEvaluating these decisions requires a deep understanding of company and stakeholder priorities.\u201d\n\nFor Matt Richard, CIO at the Laborers' International Union of North America, that means doing what's best for the organization's membership.\n\n"When we think about technology initiatives, we always have a set of leadership-driven, non-negotiable projects that are always going to take priority to make sure we're supporting our membership," he says. "But then within our various departments, projects pop up and we still have to ask ourselves if those projects can help them meet the goal of supporting members."\n\nIT leaders facing a surfeit of worthwhile technical projects, however, can find themselves in a difficult \u2014 and nerve-racking \u2014 position, says Barry Shurkey, CIO at NTT Data Services. What if the chosen initiatives don\u2019t work out? What if you make the wrong choice and foregoing other options ends up having a negative or detrimental impact on the business?\n\n"Sometimes, this forces CIOs to delve in and quantify the potential success and the impact of failure for each initiative," Shurkey says. "To enable us to be connected with the pulse of the business and to strike the right balance and prioritize the right projects, it\u2019s also important for IT leaders to build strong relationships with their counterparts in the C-suite and with the next level of leaders in the business functions."\n\nTo help you avoid project choice remorse, here are seven things CIOs should scrutinize to ensure they stick fast to the business case regarding digital transformation.\n\nAssess business value\n\nThomas Phelps, CIO of ECM provider Laserfiche, prioritizes digital transformation initiatives based on which ones will create the most business value and are likely to have the most impact.\n\n"This needs to be balanced with the time to value, resources required, estimated project costs, and risks," he says. "Along with meetings on running our business, our leadership team meets weekly to discuss transformational initiatives. Our agenda includes a discussion of initiatives to innovate and change how we do business, capture new business opportunities, and build new organizational capabilities."\n\nBalance near-term and long-term strategies\n\nFor Jen Felch, CIO and CDO at Dell Technologies, it's critical to balance near-term needs with long-term goals.\n\n"Within the IT organization of a large company like ours, we need to nail the basics \u2014 maintain a resilient, secure, cost-efficient infrastructure and efficient operations \u2014 while fostering a culture of innovation and transformation," she says. "Each investment and project we take on must thoughtfully support the company\u2019s near- and long-term strategies."\n\nAs such, Felch and her team work with Dell's senior leadership to identify key transformational initiatives that align with the company\u2019s strategic priorities, and then partner with business leaders to help propel these initiatives to achieve agreed upon goals.\n\n"We also know new priorities are going to arise, unforeseen challenges will present themselves, and we need to be flexible," she says. "Taking a step back and shifting the order of priorities or projects \u2014 whether large or small \u2014 can be tough calls CIOs need to make so teams can focus on the highest priorities at all times."\n\nWeigh technical and non-technical factors\n\nBalancing between transformation initiatives depends on technical and non-technical factors, says Sunny Azadeh, CIO at GlobalLogic. \n\n"Once you\u2019ve solidified broader business, operational, and technical approaches, and goals, there\u2019re also non-technical considerations," she says. "Factors include staffing and training costs, appetite for change and adoption, design capabilities, board and investor commitments, and others.\u201d\n\nDemocratization of the digital transformation journey makes it possible to be inclusive to a wider range of stakeholders, and land on attractive initiatives to move forward on together, she adds.\n\nObtain stakeholder support\n\nBuilding trust with stakeholders is paramount, emphasizes enterprise software provider Rimini Street CIO Steven Salaets. Transparency and business involvement in the decision-making processes is a must, as is consistently communicating the reasoning behind choices and bringing in key stakeholders in the evaluation phases.\n\n"By involving them in the process, they have ownership of a project\u2019s success as well," he says. "This collaborative approach not only garners support but also brings diverse perspectives, refining the full digital transformation journey and lessening the chance of overlooking key components to its success."\n\nJim Palermo, VP and CIO at software company Red Hat, agrees.\n\n"The CIO has to be able to clearly articulate the outcomes needed to achieve company goals across the entire organization, and enable the teams to plan capabilities to achieve them," he says. "This can be complex and difficult to maneuver. They have to manage stakeholder expectations since the business often lacks knowledge of competing resources from project to project."\n\nCIOs also need to be able to help business partners understand the cost and how to best leverage resources to get the biggest bang for the buck, Palermo says.\n\n"Prioritization against outcomes is key and it requires all the organization leaders to be in agreement and hold their organizations accountable," he says.\n\nPut data into action\n\nSoftware developer Alteryx CIO Trevor Schulze says the best way to balance continuous digital transformation efforts, maintain stakeholder support, and align with business objectives is by using an asset CIOs already have: data.\n\n"Data is the lifeblood of the intelligent systems supporting digital transformation efforts, which is why CIOs need to prioritize and deploy the key components of the modern data stack that will impact broader business outcomes through analytics," he says. "It\u2019s also critical to democratize data and analytics so everyone has access to the insights to make informed decisions. Siloed data that\u2019s available to only a few people or departments within an organization will severely hinder that organization\u2019s transformation aspirations."\n\nOne way using data and analytics intentionally can help CIOs and IT leaders prioritize work is by enabling them to derive strategic and operational insights to make more informed decisions without hindering innovation, Schulze says.\n\nEmpowering stakeholders with key actionable data insights to help make informed and timely decisions is critical, adds Chetna Mahajan, CDIO at digital analytics company Amplitude.\n\n"The most successful CIOs and IT organizations are data-driven, so it\u2019ll be no surprise that my advice for prioritization is to let data guide your path," she says. "By taking a data-driven approach, modern CIOs can turn their organizations into massive growth drivers for their companies."\n\nConsider existing technology roadmaps\n\nWhen it comes to deciding which promising initiatives to approve and which to pass on, Aflac CIO Shelia Anderson assesses whether they align to the company's existing technology roadmaps, or if they\u2019d require new architectural directions.\n\n"We consider not only the investment required but also things like what the operational impact would be and if [the initiative] would require added costs or resources with new skills," she says. "[We also consider] if the initiative would replace an existing capability, and if so, do we have the investment and decommission plans needed to reduce any future technical debt and [duplicate] costs we may encounter."\n\nInnovate with purpose\n\nThere are many ways to look at innovation, says Nate Kurtz, CIO at Veeam Software. It doesn\u2019t always come as a brand new technology or by trying to completely change how businesses work. Rather, innovation simply helps businesses become more efficient, agile, and resilient. \n\n"CIOs need to look at digital transformation through this lens," he says. "Projects that align with business goals and make the business more effective, if even in a small way, should always be considered first."