Why You Need a CTO: Avoiding Costly Mistakes in Document Management

In this riveting episode of Breakfast Bytes, host Felicia King delves into the often overlooked but crucial aspect of business technology: document management platforms. With a sharp focus on how organizations of all sizes can benefit from these systems, Felicia underscores the importance of operational maturity and strategic decision-making.
Through compelling narratives and real-world examples, she illustrates the perils of inadequate technology leadership. From misguided IT directors to costly missteps, Felicia shares stories from her 30-year career, shedding light on the vital role a Chief Technology Officer (CTO) plays in safeguarding a company's resources and ensuring seamless technology integration.
Listeners are invited to explore the intricacies of technology planning, from policy formulation to platform selection, and the far-reaching consequences of neglecting expert guidance. This episode is a must-listen for business leaders eager to avoid lighting money on fire and to achieve sustainable growth through informed technology investments.
 
Quick recap
Felicia King discussed the importance of document management platforms and the need for a technology executive in organizations of all sizes. She emphasized the significance of strategic architecture choices, operational maturity, and inclusive decision-making in implementing these platforms. Felicia also highlighted the challenges of managing contracts with consulting firms and stressed the importance of having a clear engineering and implementation plan before purchasing any technology.
 
 
Next steps
• Business leaders to consult with a qualified CTO before making strategic technology decisions, especially for document management platforms.
• Organizations to develop written requirements, document business processes, and create an engineering/implementation plan before purchasing new technology systems.
• Companies to review and potentially modify contracts with technology vendors to ensure compliance with organizational policies and support protocols.
 
Summary
Document Management and Operational Maturity
In the meeting, Felicia King discussed the importance of document management platforms for organizations with more than one employee. She emphasized the need for operational maturity and the use of systems to scale a business. Felicia also highlighted the necessity of a technology executive, even for small organizations, to navigate complex issues. She stressed the importance of understanding these matters, as they are too complicated to be handled by IT support alone.
 
 
Importance of Technology Executives in Orgs
Felicia discussed the importance of having a technology executive in organizations, emphasizing that an IT director often lacks the necessary skills and capabilities. She shared a past example where an IT director made a costly mistake due to lack of oversight, leading to significant financial losses and compliance issues. Felicia advised business decision-makers to use their technology executive in an advisory capacity to avoid such problems, particularly when making large purchases or embarking on significant projects.
 
 
Avoiding Costly Technical System Mistakes
Felicia discussed a long-standing relationship with a client that migrated to a new system, resulting in numerous issues. She reviewed the service contracts and master services agreements, discovering that the client was sold a system that was technically impossible to achieve an effective outcome with. The system violated its own requirements, leading to constant issues and financial losses for the client. Felicia emphasized the importance of using a chief technology officer to avoid such costly mistakes.
 
 
Strategic Architecture Choices in Document Management
Felicia discussed the importance of strategic architecture choices in document management platforms, emphasizing the need for operational maturity, understanding of business processes, and inclusive decision-making. She highlighted the cost implications of using platforms like Atlassian, Sharepoint, and iManage, and the need for a written set of requirements for any project. Felicia also pointed out the challenges of outsourcing document management platform implementations and the need for a highly qualified CTO for consultation. She suggested that Microsoft 365, with its advanced premium licensing and purview, could be a viable alternative to other platforms.
 
 
Managing Contracts With Consulting Firms
Felicia discussed the challenges of managing contracts with consulting firms and the importance of having a CTO to navigate these complexities. She highlighted the need for clear communication and contractual agreements to ensure project success, as she has often encountered issues with support protocols and project kickoffs. Felicia emphasized the importance of having a CTO who understands business, legal, and economic aspects to ensure smooth project implementation, completion, and ongoing support.
 
 
Clear Engineering Plan for Tech Purchases
Felicia emphasized the importance of having a clear engineering and implementation plan before purchasing any technology, likening it to buying a server without understanding its capabilities. She stressed the need for a Chief Technology Officer (CTO) to review proposals and ensure they meet the business's requirements, as well as to avoid potential breaches of contract with other vendors. Felicia also highlighted the value of having a CTO with the right skills, rather than relying on IT personnel, to make informed decisions.

Operational Maturity is required to have Information Security Risk Management

Felicia is joined by Laura Conrad, a Security Architect with 30 years of experience in enterprise environments. Laura currently reports directly to a CISO, and has been an integral part of the information security program at two large enterprises.
Felicia has consulted with 26 large enterprises and numerous SMB organizations in the last 30 years. She finds that the same problems occur in every organization that lacks operational maturity. 
Are you a person working in information security frustrated by the lack of progress of a security program in an organization because of the org's lack of operational maturity? Do you struggle in dealing with toxic, unproductive people? What approach could address these problems and more? Learn from two experts how they have seen companies engage in self-destructive and resource wasting approaches simply due to the lack of drive by executive leadership to install a structure for governance, accountability, and transparency in the organization. 
Org structure required for CISOs to be effective
This article and its impact are briefly covered as they are related to this topic.
https://www.darkreading.com/cybersecurity-operations/cisos-struggle-csuite-status-expectations-skyrocket
It is quite a good article, but it implies that if the CISO reports directly to the CEO, the problems in an organization will be reduced. While that is partially true, that by itself will absolutely not fix the problems. Felicia and Laura deep dive the decision-making failures that occur throughout an organization and what drives them. Also discussed are methods to truly and structurally correct the problems across an entire company.
95% of information security risk management issues are HR management issues
Executive management want to run the company, not manage people. This leads to toxicity and unproductivity being tolerated when personnel issues are not fully investigated and actioned. The desire to make an emotional problem go away cannot override the need to get to the core of the issue and put a system in place to prevent it from happening again. This is not about firing people. This is about instilling a culture where the facts matter, personnel issues will be investigated, and structural systems will provide the governance to drive productive staff behavior.
Org executives are unaware of the real costs of inputs
It seems to be a pervasive problem across most organizations that there is no financial management structure which facilitates the tracking of expenses as inputs to a service or product delivery to customers. Without this real understanding, leaders persistently price products and services incorrectly. This leads to one business division or a product line losing money and needing to be subsidized by another.
Executives rarely understand that by tolerating operational immaturity in their organization, they are actually failing in their duty to stakeholders to effectively manage the assets of an organization to maximize value.
Drive change and org-wide staff effort alignment with dashboards that drive transparency and healthy internal competition
Felicia and Laura discuss in detail the how and why of dynamically updating dashboards which help CTO, CIO, CISO manage upward to the CEO and board, while driving downward alignment to objectives.
Governance, Accountability, Transparency in IT Security
Felicia and Laura discussed the importance of governance, accountability, and transparency in IT security and business processes. They emphasized that these principles could help prevent problems caused by a lack of collaboration and understanding between IT and business units. Felicia cited instances where poor prior planning led to unnecessary expenses and internal toxicity, which she believes could be avoided with a more mature approach to operations. Laura added that these principles could also lead to cost savings and risk reduction. 
Harden the procurement policies
Felicia and Laura provide many examples of problems that could have or were avoided by having an enforced procurement policy which resulted in all technology purchases being signed off on by the CISO or security architect and often the enterprise architect. It is infinitely easier to rectify issues before an implementation and before signing a contract than to do so after a purchasing decision has already been made.

Managing the impact of changing IT service providers

Felicia shares insights on the pitfalls of changing IT service providers or MSPs for both clients and the IT service providers themselves. This content is based upon a number of questions that other MSPs have posed to Felicia asking for advice as well as numerous first hand experiences on the subject.
This podcast is primarily for IT service providers or MSPs, but business decisions makers who are considering making a change would also benefit from the content.

Information Security, Cybersecurity, and Everyone’s Responsibility

What is information security versus cybersecurity?
What are policies and why do we care?
Isn't that IT's problem?
Examples to learn from