When asked about technology purchase regrets, veteran tech exec Sanjay Macwan digs deep for a classic hyped technology that has yet to pan out: smart glasses.\n\nNearly a decade ago, as the technology was hitting the market, Macwan and his executive colleagues were \u201chugely interested in leveraging the technology,\u201d he says. So they took a leap, spending on both hardware and software products in their bid to develop augmented reality experiences. But the venture didn\u2019t pan out.\n\n\u201cThe technology was not mature enough at the same time the business model \u2014 how to make money making augmented reality content \u2014 wasn\u2019t mature enough. And we had to retreat,\u201d says Macwan, currently CIO and CISO of Vonage, adding that the experience helped him refine a four-point framework he now uses when buying technology.\n\nBefore investing, Macwan, his IT team, and other stakeholders ask four questions:\n\nMacwan approves a purchase only when he and his teams can answer yes to those questions with a high degree of confidence. The framework, he adds, helps ensure all the pieces needed for success are in place before inking a deal.\n\nHe acknowledges that had he implemented this approach a decade ago, he would have recognized that the investment in the smart glasses and AR technology wasn\u2019t a good move.\n\nCIOs seeking to avoid similar regrets going forward would benefit from a similar approach to IT purchasing, tech leaders and industry experts say.\n\nTech purchase regret on the rise\n\nResearch shows that many organizations still struggle to make good IT purchases. In a recent survey, Gartner found that 56% of organizations have a high degree of \u201cpurchase regret\u201d when it comes to their largest tech-related purchase in the prior two years. Gartner categorized a purchase as \u201chigh regret\u201d when respondents agreed that the purchased offering is failing or failed to meet expectations and that they considered offerings that were much more ambitious than what they decided on.\n\nThe research, which was based on 1,120 respondents at the manager level and higher in North America, Western Europe and the Asia-Pacific region, determined, however, that the technology itself wasn\u2019t the issue, says Hank Barnes, a distinguished vice president analyst and a research chief focused on enterprise buying behavior at Gartner. Rather, it\u2019s the buying process.\n\n\u201cIt\u2019s much more around the decision practices,\u201d Barnes adds.\n\nThat, though, can be fixed \u2014 as Macwan shows. There are indeed steps that CIOs can take to strengthen the buying process to limit the chances of ending up with a purchase the organization regrets. Here are five such moves.\n\nProvide more guidance to non-IT tech buyers\n\nGartner\u2019s research shows that an organization\u2019s level of regret varies based on the processes it uses to make tech-buying decisions, as well as who and how many stakeholders are involved.\n\nFor example, the research shows that 67% of people involved in technology-buying decisions are not in IT and that non-IT buyers are more likely to regret a tech purchase when CIOs aren\u2019t the ones making the final decision, as organizations report regret only 38% of the time when the CIO is final decision-maker compared to the overall rate of 56%.\n\nGartner also found that non-IT buyers are more likely to scale back their plans, which also leads to higher levels of regret.\n\nAnd with tech spending on average split evenly between IT and non-IT departments, such as marketing and finance, according to CIO.com\u2019s 2022 State of the CIO survey, there is a rising risk of purchase regret at most organizations these days.\n\nBut Barnes sees an opportunity for CIOs to turn this around by offering more specific and formalized guidance on tech spend they don\u2019t control \u2014 for example, by working with non-IT decision makers on how to scope out their planned purchase, vet vendors, review case studies, and plan for implementation.\n\n\u201cAs buying gets distributed, CIOs and their teams have to help others recognize what they need to do to make a purchase decision,\u201d Barnes adds. \u201cCIOs can help [non-IT buyers] look at the integration impact, operational impact, security, and how to get those functional groups involved to help. CIOs can coach, orchestrate, enable these other groups.\u201d\n\nTake a strategic approach to engaging vendors\n\nGartner\u2019s research also shows that sound vendor management practices can greatly impact purchase outcomes. For example, while it\u2019s natural to take in information from vendors during the buying process, no-regret buyers take a more strategic \u2014 and selective \u2014 approach to information-gathering, Barnes says, adding that they aren\u2019t doing deep dives with all the vendors, a move that can cause confusion, information anxiety, and the fear that they could be missing something in the deluge of details.\n\n\u201cBuyers today are dealing with too many choices, and it\u2019s too many good choices,\u201d Barnes says. \u201cSo smart buyers study; they go in-depth with vendors; then they pick a lead and go deeper.\u201d\n\nMacwan takes a similar approach, saying he challenges vendors to ensure they can deliver on the capabilities his company needs. \u201cThen I\u2019ll take the top vendors and ask their viewpoints on how to operationalize [their products] within my shop. And I\u2019ll ask how they\u2019d measure our success using their products. We have internal metrics, but I also want to hear from them on how best to measure. They should have a proof point to share,\u201d he says.\n\nIf those questions sound familiar, Macwan\u2019s approach to vendor engagement shows the advantage of being intentional about gathering the targeted information you want as part of your IT purchase assessment framework.\n\nBuyer beware: Know what you\u2019re getting \u2014 including hidden costs\n\nExecutives must keep in mind the dictum \u201ccaveat emptor,\u201d or \u201clet the buyer beware.\u201d\n\nMore specifically, CIOs \u2014 whether purchasing technology on their own or working with colleagues \u2014 need to thoroughly understand what they\u2019re buying: its capabilities, its integration and support requirements, its shortcomings, and so on, says Michael Spires, principal and Technology Transformation Practice lead at The Hackett Group, a consulting firm.\n\nIt sounds basic, Spires admits, but many don\u2019t do thorough enough reviews.\n\n\u201cYes, there are people who can help you and systems integrators you can hire, but if you haven\u2019t worked with a technology before, you have blind spots. You might not realize how hard it would be to drive adoption, or change from one set of services to another, or how easy or not it is to configure, or whether there\u2019s a standard way to do it, or if it will be too rigid to meet your needs,\u201d he says.\n\nSpires says organizations also often fail to perform a thorough accounting of costs related to tech purchases, so they don\u2019t have accurate total-cost-of-ownership figures. That\u2019s not surprising, Spires adds, given how easy it often is to be distracted by the promises a new technology investment offers.\n\n\u201cThe benefits are sold upfront,\u201d he says, \u201cand the challenges are minimized or hidden. But those challenges can lead to cost surprises or those challenges for some organizations can be insurmountable, both of which leads to regrets.\u201d\n\nAssemble the right purchasing team\n\nThe players on your purchasing team also have a profound effect on investment outcomes, according to Gartner\u2019s research, as buyers with no regrets were shown to have more diverse buying teams with more functional groups involved.\n\nThis finding, however, doesn\u2019t suggest that more people in the process is the answer, Barnes says. In fact, too many can be detrimental. Rather, the key is to create a collaborative process that ensures just the right staffers with the necessary expertise are performing a more thorough assessment of possible purchases so that questions, issues, and needs are addressed in advance, he says.\n\nOrganizations that don\u2019t assemble that expertise during the selection process often see delays as they hit requirements (such as security reviews) that they didn\u2019t know in advance they needed to address, Barnes says. More problematic, those organizations are also more likely to realize after the buy that they missed issues that either can\u2019t be addressed or can\u2019t be circumvented easily, leading to a higher likelihood of buyer\u2019s remorse, he says.\n\nSunil Kanchi, CIO at UST, notes that CIOs should think broadly about who may have valuable insights that could impact buying decisions when assembling their purchasing teams.\n\nFor example, Kanchi is working with his firm\u2019s CHRO, in addition to other executives, to understand the company\u2019s projected staffing needs to ensure new enterprise systems will work not just in the short term but can adequately scale as the workforce grows.\n\nBe ready to pivot and move fast\n\nWhen it comes to technology purchases, another regret can be not moving fast enough. Merim Becirovic, managing director of global IT and enterprise architecture at Accenture, says his clients often wonder whether they\u2019re falling behind.\n\n\u201cWith the level of technology maturity today, it\u2019s a lot easier to make good decisions and not regret them. But what I do hear are questions around how to get things done faster,\u201d he says. \u201cWe\u2019re getting more capabilities all the time, but it\u2019s all moving so quickly that it\u2019s getting harder to keep up.\u201d\n\nA lag can mean missed opportunities, Becirovic says, which can produce a should-have-done-better reproach. \u201cIt\u2019s \u2018I wish I had known, I wish I had done,\u2019\u201d he adds.\n\nBecirovic advises CIOs on how to avoid such scenarios, saying they should make technology decisions based on what will add value; shift to the public cloud to create the agility needed to keep pace with and benefit from the quickening pace of IT innovation; and update IT governance practices tailored to overseeing a cloud environment with its consumption-based fees.\n\n\u201cSo you can fail fast through proof of concepts, so you\u2019re not committing and finding out a year later that it\u2019s not going to work. It\u2019s much easier today in a cloud world to try things fast, to try things quicker; there\u2019s no better time to do that,\u201d he says.\n\nHis own company is doing just that. Becirovic points to ongoing tests around artificial intelligence capabilities that aren\u2019t quite ready for prime time. \u201cWe\u2019re trying a lot of different things and throwing them out fast or putting them on the shelf and saying we\u2019ll come back in six or nine months when we see a little bit more capability being delivered,\u201d he explains.\n\nCreating the environment to take that approach, Becirovic says, helps head off both bad purchases and missed opportunities.