Why I Wrote This

Throughout my 30 year career in technology, I have led and transformed all kinds of challenged organizations. Technical teams, project teams, program teams, national practices, delivery centers, proposal teams, commercial organizations, and public sector organizations at both the agency and enterprise level all experience similar performance challenges. Perhaps it is a performance gap where the organization is not meeting their business commitments. Perhaps it is an opportunity gap where the organization is stale and not exploiting innovation. Perhaps it is a combination of all of the above. For whatever reason, the technology organization is disappointing its stakeholders in leadership, the lines of business that they support, and the staff in the organization. Almost everyone is unhappy and all collectively stuck. Nobody wants to be on a troubled project or work in a low morale organization. Nobody wants to play for a losing team.

Prior to becoming a state employee, I was a business consultant and we were taught to focus on the pain points. Where is the organization hurting the most? That is where we should focus and target our efforts. However, what do you do when everything hurts? Some organizations are in such bad shape that leaders, stakeholders, and staff are collectively frustrated and just don’t know where to start. This website is for the frustrated (technology leaders, business leaders, senior executives, staff in the organizations). For the many tech workers and leaders who are passionate to serve but are somehow misaligned, misunderstood, misskilled, and missing the mark.

As a leader who has been asked and called to help improve struggling technology organizations for several decades, I have looked for resources and solutions. There are thousands of books on leadership and technology. There are millions of articles and blog posts. There is no lack of information and advice. The challenge is to distill all that data and information into a practical course of action to accomplish results and make an impact. A practical “how to” recipe book for technology organizational transformation does not seem to exist. So much of what we do as transformational leaders is to figure it out as we go along. We read whatever we can find, learn through trial and error and strive to do better every day. Either we improve and succeed or we find a different opportunity. It can be very Darwinian and sometimes brutal. If we are fortunate, and I have been very fortunate, then we have senior leaders who can mentor and guide us through the trials such that we successfully take on increasingly challenging opportunities and grow through our experiences. Our capabilities are a function of ourselves and the people we can get help from. This website is my way of sharing and giving back the advice that I have been given to all the future tech leaders who are looking to do better and solve the technology organizational challenges of the future.

The nature of this website’s content is a combination of my insights and practices from 30 years of technology organizational leadership with generative artificial intelligence (GenAI). My theory is that our best work will be accomplished with the assistance of artificial intelligence (AI) so I am testing that theory with this offering. Each chapter starts with a prompt and I will paste in the GenAI output. As the author and human in the loop (HITL), I will then expand on the output to interpret, clarify, and amplify its value. Being GenAI, you as the reader can refine and reuse that prompt to get results that are even more meaningful, tailored, current, and better for your unique situation. I selected a website as the delivery channel because content is changing so fast and I was concerned that a book would become obsolete as soon as it was published. A website allows me to freely share my ideas (really, no charge) and constantly update the material as new lessons are learned. If you find what you are reading helpful, then please post about it on social media. The world needs more great leaders and I hope that my work can help you become better leaders and deliver better results!

Sincerely,

CIO Bob