If you\u2019re not planning or executing a digital transformation strategy, you better be at least thinking about it so you\u2019re ready when the bosses ask what your game plan is.\nBut how do you peer over the long-term horizon when the IT world seems to be constantly shifting? Start by ensuring you have a realistic assessment of your IT assets and how you\u2019ll leverage or dispose of them in the coming years.\nFirst off, you must be willing to think outside of traditional boxes. \u201cBy 2018, 70% of siloed digital transformation (DX) initiatives will ultimately fail because of insufficient collaboration, integration, sourcing, or project management,\u201d predicts IDC.\nInsight is key\nDavid Dubois of the INSEAD Business School writes that C-suite executives and entrepreneurs must be able \u201cto identify possibilities and drive change concurrently in three areas where digital technologies can make significant differences and change the face of organizations:\n\nIntelligence\u2013 Seeing digital data as a source of insight and using this data in knowledge-creation processes to create competitive advantages.\nIntegration\u2013 Leveraging digital channels to transform organizational processes and create agility.\nImpact\u00a0\u2013 Rethinking how digital dynamics can improve a company\u2019s value proposition.\u201d\n\nIt\u2019s also a good idea to study up on past IT failures that may still echo and cause skepticism.\n\u201cIn the past, IT failures often meant high-priced flops, with large-scale software implementations going on way too long and way over budget,\u201d Mary K. Pratt writes at CIO.com in a feature highlighting failures and lessons learned.\nMake sure it really is transformational\nAnd don\u2019t be too glib in applying the term \u201cdigital transformation.\u201d For many organizations, writes CIO.com\u2019s Clint Boulton, \u201cdigital transformation is really digital optimization in disguise, as new digital initiatives merely augment existing services. In the end, many who struggle to define digital transformation resort to the old adage: \u2018They know it when they see it.\u2019\u201d\nAfter ticking through some of the characteristics of true transformation, Boulton concludes: \u201cAsk yourself whether what you\u2019re doing is disruptive to your business and to your industry. If you can say yes with a straight face, you may well be conducting a bona fide digital transformation.\u201d\nIn a Harvard Business Review article, Barry Libert, Megan Beck, and Yoram (Jerry) Wind provide insight into the five-step PIVOT process they use to help clients navigate digital transformation (heavily condensed here):\n\nPinpoint your starting place\nMake a complete inventory of all your organization\u2019s assets\nVisualize\u00a0a new future as a digital network where your firm partners and co-creates with one of your external networks\nOperate\u00a0a pilot of your network business by shifting small amounts of capital (including time, talent, and money) to the new initiative\nBegin to\u00a0track\u00a0the progress of your network initiative\n\nSkirting digital hype\nOf course, whenever a term takes hold as an industry buzzword, every vendor is going to lay claim to it, just to ensure it doesn\u2019t lose mindshare to competitors. So the vendor\u2019s digital transformation strategy may not always map to your transformation needs. For example, when your ERP vendor advocates swapping out all the systems you invested in over the last decade for new \u201cdigital-ready\u201d systems, you have to ask at what price and for what benefit?\nGartner advocates a \u201cpost-modern ERP\u201d model that optimizes core investments and focuses new investments where they can have the most impact and drive competitive advantage. That\u2019s going to take some effort, though.\n\u201cIntegration has emerged as a critical component of postmodern ERP strategies, but solid integration strategies remain elusive for many organizations,\u201d cautions Gartner\u2019s Denise Ganly. \u201cYou can\u2019t have both flexibility\/agility and less complexity. There will be more integration challenges with postmodern ERP in hybrid environments than with on-premises, monolithic approaches.\u201d\nPay up\nAnd then there\u2019s the matter of funding your transformation initiatives. Unless you\u2019re lucky enough to be handed newfound money, you\u2019ll need to squeeze every last available dollar out of existing IT assets. One place to start: ditch traditional vendor support models and create a new model based on third-party support services.