Over the last three decades, E&P software development has focused on building tools to help perform human tasks more efficiently and effectively. This has enabled the human employee to be promoted to the position of System Integrator of Tools. The wave of digital transformation over the last several years has promised to deliver value, yet the realization of that value has not been straightforward. As the industry enters a turbulent cycle with increased market volatility, the impending energy transition, and a need to scale with potentially marginal gains, how should we re-evaluate digital transformation? Based on our collective experience, how do we set about successfully implementing artificial intelligence and machine learning solutions and leveraging cloud automation? This dialogue covers these topics and will engage in a discussion around common questions related to digital efforts in the industry.