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OODAcast – A Conversation with Technology Executive Lewis Shepherd (Part Two)

In this second of a two part OODAcast, OODA CTO Bob Gourley was joined by Lewis Shepherd, seasoned federal technology executive and a senior director of technology strategy at VMware for an interactive discussion on the actionable lessons we should all be learning from the current crisis but also how the events of today are shaping the future of technology.

The world’s leading tech companies and select government agencies rely on Lewis for his expertise in strategic planning, tech forecasting and concept development. He has led multiple waves of R&D innovation both in government and in industry. He is active in leading efforts on a wide range of projects in artificial intelligence, machine learning, augmented reality/virtual reality, data visualization, social media, encryption and cybersecurity. Lewis is a member of the OODA Network and was one of the scheduled speakers of our now postponed OODAcon “Future Proof“.

In this second part Lewis provides context on topics of high interest to technology executives seeking to better serve the federal market, including understanding of government mission needs and perspective on why sometimes the government decides to build their own capabilities, even when it is not logical that they do so.  He also provides additional advice relevant to thought leaders seeking ways to better serve government missions, as well as insights into what the future of tech may have in store for us all.

Podcast Version:

Related Resources:

  • A Decision-Makers’s Guide to Artificial Intelligence: A plain english overview with the insights you need to drive corporate decisions
  • The Executive’s Guide to Quantum Computing: What business decision-makers need to know now about quantum superiority
  • The Executive’s Guide to the Revolution in Biology: An overview of key thrusts of the transformation underway in biology and offers seven topics business leaders should consider when updating business strategy to optimize opportunity because of these changes.
  • OODA COVID-19 Sense-making: A dynamic resource for OODA Network members looking for Coronavirus/COVID-19 information to drive their decision-making process. We’ll update it with new links as we encounter them. This is not meant to be a comprehensive list, but rather a compilation of the most useful resources.
  • Context on Make vs Buy in the Federal Ecosystem: If you know of anyone anywhere in government who is thinking of building/coding a new data system to track issues around the pandemic they should just stop and should buy a commercial platform.
  • Elon Musk on Make Vs Buy: Every large enterprise faces decisions on whether to code something using internal talent, code something using contractors, or buy a commercial product. For complex and sometimes hard to understand or explain reasons, the government has always had a hard time optimizing on these decisions.
  • OODAcast on YouTube: OODA’s YouTube Channel
  • OODAcast Podcast: For audio to go
  • Additional Resources:

    A Practitioner’s View of Corporate Intelligence

    Organizations in competitive environments should continually look for ways to gain advantage over their competitors. The ability of a business to learn and translate that learning into action, at speeds faster than others, is one of the most important competitive advantages you can have. This fact of business life is why the model of success in Air to Air combat articulated by former Air Force fighter pilot John Boyd, the Observe – Orient – Decide – Act (OODA) decision loop, is so relevant in business decision-making today.

    In this business model, decisions are based on observations of dynamic situations tempered with business context to drive decisions and actions. These actions should change the situation meaning new observations and new decisions and actions will follow. This all underscores the need for a good corporate intelligence program. See: A Practitioner’s View of Corporate Intelligence

    Optimizing Corporate Intelligence

    This post dives into actionable recommendation on ways to optimize a corporate intelligence effort. It is based on a career serving large scale analytical efforts in the US Intelligence Community and in applying principles of intelligence in corporate America. See: Optimizing Corporate Intelligence

    Mental Models For Leadership In The Modern Age

    The study of mental models can improve your ability to make decisions and improve business outcomes. This post reviews the mental models we recommend all business and government decision makers master, especially those who must succeed in competitive environments. See: Mental Models for Leadership In The Modern Age

    An Executive’s Guide To Cognitive Bias in Decision Making

    Cognitive Bias and the errors in judgement they produce are seen in every aspect of human decision-making, including in the business world. Companies that have a better understanding of these cognitive biases can optimize decision making at all levels of the organization, leading to better performance in the market. Companies that ignore the impact these biases have on corporate decision-making put themselves at unnecessary risk. This post by OODA Co-Founder Bob Gourley provides personal insights into key biases as well as mitigation strategies you can put in place right now. See: An Executive’s Guide To Cognitive Bias in Decision Making

    OODA On Corporate Intelligence In The New Age

    We strongly encourage every company, large or small, to set aside dedicated time to focus on ways to improve your ability to understand the nature of the significantly changed risk environment we are all operating in today, and then assess how your organizational thinking should change. As an aid to assessing your corporate sensemaking abilities, this post summarizes OODA’s research and analysis into optimizing corporate intelligence for the modern age. See: OODA On Corporate Intelligence In The New Age

    Useful Standards For Corporate Intelligence

    This post discusses standards in intelligence, a topic that can improve the quality of all corporate intelligence efforts and do so while reducing ambiguity in the information used to drive decisions and enhancing the ability of corporations to defend their most critical information. See: Useful Standards For Corporate Intelligence

    In Business, Like In War, Data Is A Weapon

    Broadly speaking, a weapon is anything that provides an advantage over an adversary. In this context, data is, and always has been, a weapon. This post, part of our Intelligent Enterprise series, focuses on how to take more proactive action in use of data as a weapon. See: Data is a Weapon

    Fine Tuning Your Falsehood Detector: Time to update the models you use to screen for deception, dishonesty, corruption, fraud and falsity

    The best business leaders are good at spotting falsehoods. Some joke and say the have a “bullshit detector”, but that humorous description does not do service to the way great leaders detect falsehoods. Bullshit is easy to detect. You see it and smell it and if you step in it it is your own fault. In the modern world falsehoods are far more nuanced. Now more than ever, business and government leaders need to ensure their mental models for detecting falsehood are operating in peak condition. For more see: Fine Tuning Your Falsehood Detector: Time to update the models you use to screen for deception, dishonesty, corruption, fraud and falsity

Bob Gourley

Bob Gourley

Bob Gourley is the co-founder and Chief Technology Officer (CTO) of OODA LLC, the technology research and advisory firm with a focus on artificial intelligence and cybersecurity which publishes OODALoop.com. Bob is the co-host of the popular podcast The OODAcast. Bob has been an advisor to dozens of successful high tech startups and has conducted enterprise cybersecurity assessments for businesses in multiple sectors of the economy. He was a career Naval Intelligence Officer and is the former CTO of the Defense Intelligence Agency.