I seek thoughts and welcome suggestions on the topics below. Those toward the bottom are sprinkled with recommendations.

I have been a participant observer in two interactive bot projects and examined other bot projects and development tools. Apart from entertainment conversational agents, interactive bots are another interface channel. They have potential benefits and actual challenges. By striving to appear human, they force designers to understand how humans interact with computers or the designers won’t be among the very few that succeed.

I am interested in the transition from high school to higher education: college application and admission processes and student experiences thereafter. I have a work interest and also a personal one, with daughters in high school. How could technology help more or hinder less? New opportunities and challenges are pulling secondary schools and higher ed in different ways. The seam between them is under stress. Examples: How are applications from students in alternative schools and homeschooling handled? How do students experience changes in pedagogy and technology use? Insights? Please share.

The impact of automation on jobs draws media attention. Driverless cars and trucks are a prominent example. I co-authored one contribution to this wave of print. In studying technology history I have found that predictions of imminent joblessness are a tradition that dates back almost a century. Instead, what happens when technology eliminates jobs—farmers reduce the ranks of hunter-gatherers, machinery eliminates farm jobs—is that new jobs appear, often the professionalization of something that was previously a hobby. We see that happening now. Hardships that arise should be addressed, but don’t sell human ingenuity short.

The irresistible force of technology meets an immovable object, human nature. How we do and don’t use technology reveals our capabilities and limitations. Agriculture enabled us to eliminate hunger, but doing so was lower priority than building pyramids and armies. How will we use our new technologies? We recognize our perceptual and cognitive limitations and build tools to extend our capabilities. Our emotional and social natures are trickier. We try. For millions of years, our ancestors lived in bands or tribes. At great effort and with mixed results, we have worked to convert tribal feelings into broader allegiances, such as to nations and corporations. Several books have explored implications of our heritage. Jared Diamond’s The Third Chimpanzee is moderately optimistic, Michael Ghiglieri’s The Dark Side of Man is not. Charles Mann’s 1491 and Napoleon Chagnon’s Noble Savages examine collisions of different forms of human social organization. Sebastian Junger’s Tribe, which I haven’t yet read, is on the list. Do you have another to recommend?

Robert Ellickson’s book Order without law: How neighbors settle disputes is a short, elegant treatise that distils decades of insightful work. He found that written rules are often not followed unless attorneys get involved, and sometimes not even then. Ellickson addresses society from top to bottom. He doesn’t dwell on practices in organizations, but his observations generalize. It is a powerful analysis of a crucial issue as technology use increases: Digital activity reveals that people behave in ways we did not realize and may not like; enforcement of rules is not uniform; and our leaders have flaws. And that just scratches the surface.

Our understanding of digital technology in organizations is still rudimentary. No one person has a deep enough knowledge of a large organization to confidently predict the effects of a technology intervention. The challenge is magnified by the technology-wrought pace of organizational change: We peer through a streaky viewfinder as we aim at a moving target.

You might think that by now we would have a handle on it, but we don’t. Digital technology was first designed to help individuals produce the same output as before, faster or better. Group support came in the late 1980s. The collapse of the internet bubble in the 2000s revealed how little we understood about technology and organizations. Technology was in place before we got serious about understanding the dynamics around using it. We bring a large wood horse inside our walls and hope that the soldiers inside are benign.

The most useful essay for a design and development team (or a researcher) is Henry Mintzberg’s A typology of organizational structure, in my mildly humble opinion. It was published in Miller & Friesen’s Organizations: A quantum view in 1984 and reprinted in Ron Baecker’s Readings in Groupware and Computer Supported Cooperative Work. (Both are out of print, with inexpensive used copies available online.) It is dense: Take notes and read it twice. It does not mention technology. The framework details the very different ways that people work in five parts of any sizable organization. If you are building something to serve an entire organization, at least three of these groups must be considered individually. The framework is invaluable in interpreting what I’ve found in enterprise adoption of software over thirty years. My overview is in this conference paper. A 2010 analysis of enterprise wiki use traced challenges to Mintzbergian dynamics (we might note that wikis didn’t take enterprises by storm).

A second typology I recommend is in Joseph McGrath’s 1991 Time, interaction, and performance (TIP): A theory of groups. It presents four modes and functions of group activity and stresses the constant need for activities that are not directly linked to production. This paper is also reprinted in Baecker’s collection. McGrath’s framework and examples of technologies that thrived and failed due to such considerations are discussed in this essay.

Significant workflow management systems have proven elusive for decades. An unpublished paper, Steven Poltrock and Mark Handel’s Workflow in Knowledge Work, is a great review of work on this topic.

The Peter Principle asserts that employees rise to their levels of incompetence in organizations. It describes the dynamics, humorous but recognizable. I explored how technology might affect these dynamics. (An earlier version includes additional examples.)