"Flexibility", "innovation" and "disruption" are the buzzwords for the digital workspace. What these buzzwords mean and how to achieve them are complex questions that businesses have yet to answer. The answers, are not so easily found. How then do you begin to imagine the future of service, and its employees? Digital workplaces seems to make the assumption that if an organization reaches the upper levels of digital workplace maturity, especially in terms of enterprise social network adoption, the business and employee performance will be transformed. In reality, every digital workplace performance depends on building excellent relationships with suppliers and customers and facilitating the flow of information along the entire supply line. Businesses also tend to have their own work agreements, which regulate extra issues such as core hours and conditions of employment, including where work is performed and the process by which such arrangements are altered. The employment model is built around a culture of face-time and flextime as a way of monitoring performance. Collaboration in the workplace is now high on the priority list of many organizations seeking to leverage social technologies to free-up knowledge and provide opportunities for co-creation, co-production and innovation. To drive a new era of growth, companies will be required to collaborate with enterprises outside their corporate boundaries. Many organizations conduct employee engagement surveys and increasingly use these as one of the metrics in assessing the benefits of digital workplace deployment. Certainly a digital workplace strategy needs to identify core suppliers and customers and ensure that there are good channels of communication and even joint application development. This will ensure that cross-enterprise collaboration is as effective as it needs to be. Understanding the barriers and obstacles is the first step to identifying potential solutions. Individuals acting alone may not be empowered to make the desired changes, but if there is a real desire to collaborate and share knowledge, most if not all of these obstacles can be overcome or circumvented.