Some lessons learned from the past are signposts pointing to how the Trump administration will function. It's time, for example, to re-read Max Weber's analyses of government and politics. The German sociologist identified, for example, the "charismatic" style of leadership which the new president seems likely to use. [The link is to wikipedia, but even better is the real thing, as in Weber's essay on "Politics as a Vocation."] Weber saw special dangers in politicians driven by vanity.
A much different look back to the future can be found in a 1987 book assessing how well the Reagan administration did in capturing and revolutionizing the federal government. Robert Rector and Michael Sanera edited Steering the Elephant: How Washington Works [Universe Books]. While the various authors tell some stories of conservative victories over liberal-oriented bureaucracies, many also report failures and suggest ways to avoid them in future conservative revolutions.
One of the better chapters is available on line: Fred Smith's "Learning the Washington Game: Political Strategy and Tactics." Smith describes the conservative's "tendency to pre-compromise;" a tendency to "dawdle" or do "excessive pre-planning." He warns especially against agency capture of the political appointees, who "go native." He suggests an approach of educational outreach and coalition development to minimize those flaws. While aimed at conservatives, I think his points are relevant to any political appointee.
If the Trump people do look at the Reagan administration experience, I hope they also include Robert Retor's chapter explaining how different the public sector is from the private. He notes, for example, that while the marketplace is the ultimate manager in the private sector, "the political appointee, Congress, the bureaucracy and interest groups compete over the role of ultimate manager" in the public sector. He says "The information system used in private sector management, based on profit-and-loss statements, does not exist in government." And he admits that governments have many competing goals, not the simple profit-maximization of businesses.
Another lesson from the Reagan book is that "personnel are policy." That means that new people are likely to continue in the same trajectories as they have until now. What we see is what we'll get.