U.S. President Barack Obama (JASON REED/REUTERS)

Jena McGregor is a columnist for the Washington Post’s On Leadership section.

It’s hard to know where to start when compiling a list of must-reads about Barack Obama’s leadership style. The president has been the subject of countless profiles, a multitude of books—including several of his own—and more news analysis pieces that pick apart his approach to governing than any sane person can really take in. What’s worth reading after more than four years of scrutinizing one person has become harder and harder to discern.

The deluge of articles over the president’s first term means that even those who have only a passing interest in politics can rattle off words used to describe just how the president leads. Aloof. Unflappable. Cool. Consensus-building. Insular. Pragmatic. The characteristics and criticisms are so well known that they’ve become caricatures of the man currently leading the country.

With that in mind, I’ve compiled a list of a few of the best long-form articles that dissect with more nuance how the president leads. There are, of course, plenty of shorter pieces (as well as books by everyone from Ron Suskind to Bob Woodward) that have analyzed the president’s leadership. But for this exercise, I tried to stick with an array of meaty profiles from over the course of the president’s first campaign and first term that best explore the job Obama has done and how he has done it. There are many, of course, but here are a few that shouldn’t be missed:

The Conciliator,” by Larissa MacFarquhar in The New Yorker

MacFarquhar’s 2007 portrait of candidate Obama is memorable both for how well it holds up after all the turmoil of his first term (“Obama is always disappointing people who feel that he gives too much respect or yields too much ground to the other side, rather than fighting aggressively for his principles”) and for how much has changed (“Obama’s voting record is one of the most liberal in the Senate, but he has always appealed to Republicans, perhaps because he speaks about liberal goals in conservative language”).

What was then a fresh, detailed look at a rising star on the political stage helps readers to unpack and re-examine views of the president after years of leadership stereotypes. MacFarquhar’s deeply reported profile pushes to explain the president’s “drive to compromise” in personal, not just political, terms — depicting that drive as “instinctive, almost a tic,” rather than as a failing he has the ability to control.

Obama, the loner president,” by Scott Wilson in The Washington Post

Any chief executive’s job, and especially the president’s, is a lonely one. But White House correspondent Scott Wilson deftly weaves together a look at one of the defining characteristics of Obama’s presidency: that he is, as Wilson puts it, “a political loner.” Whether it’s his small circle of advisers or his unwillingness to work the rope lines and glad-hand supporters, Obama has repeatedly come under question for a cool, detached personality that appears to favor policy over people. Wilson’s 2011 piece poses a smart question (“Is it possible to be America’s most popular politician and not be very good at American politics?”) and carefully examines how much not being a traditional “people person” hurts Obama’s leadership.

“The Obama Memos,” by Ryan Lizza in The New Yorker

If MacFarquhar focused on Obama’s compromise and Wilson on the president’s coolness, Lizza’s version of the “education of the president” narrative looks at the other word most used to describe the president’s leadership — pragmatism. In his profile earlier this year, Lizza describes Obama as being the type of leader political scientist George C. Edwards III calls a “facilitator of change” rather than a “director of change,” which is particularly interesting given how his campaign initially positioned him. “Directors are more like revolutionaries,” Lizza writes. “Facilitators are more like tacticians. Directors change the system. Facilitators work the system. Obama’s first three years as President are the story of his realization of the limits of his office, his frustration with those constraints, and, ultimately, his education in how to successfully operate within them.”

Obama, Explained,” by James Fallows in The Atlantic

Fallows’ 2012 epic tour de force is some 12,000 words long, so you’ll be lucky if you finish it before the election is over. But it provides one of the most in-depth critiques of the president’s leadership so far by examining four main categories of weaknesses—his inexperience, his coldness, his “complacency about talent” and the “symbolic mismatch” that exists between the “sweeping ambitions for political change” that Obama, the candidate, promised and “the incrementalist operator” that Obama really is. Fallows’ lengthy opus is grounded in the historical context that all presidents have failings, “each in a different way.”

The Competitor in Chief,” by Jodi Kantor in The New York Times

While much shorter in length than some of the epic pieces listed here, Kantor’s September profile of Obama’s competitive drive fills out the contours of a leader so frequently described as pragmatic and ready to buckle under pressure from opponents. With great anecdotes (Obama even gets competitive when he reads children’s stories) and telling quotes (“I think that I’m a better speechwriter than my speechwriters,” he apparently said at the beginning of his 2008 campaign), Kantor’s piece shows the upsides and downsides of the president’s self-assuredness. “Four years ago, Barack Obama seemed as if he might be a deliberate professor of a leader, maybe with a touch of Hawaiian mellowness,” Kantor writes. “He has also turned out to be a voraciously competitive perfectionist.”

Obama’s Way,” by Michael Lewis in Vanity Fair

One might think by now there would be little left to learn about how Obama manages or how he thinks about leadership. But Lewis, the popular author of Liar’s Poker and Moneyball, was granted what appears to be unprecedented access to the president and comes away with some true gems (“You’ll see I wear only gray or blue suits,” Obama tells Lewis, because “I’m trying to pare down decisions. … You need to focus your decision-making energy. You need to routinize yourself”). We learn how Obama structures meetings (he does it so they’re not debates, but “mini-speeches”) and more about how he makes decisions (“Any given decision you make you’ll wind up with a 30 to 40 percent chance that it isn’t going to work. You have to own that … You can’t be paralyzed by the fact that it might not work out”).

Lewis attempts to get inside not just how Obama leads but what it’s like to be president, by repeatedly asking Obama what turns out to be a brilliant question: “Assume that in 30 minutes you will stop being president. I will take your place. Prepare me. Teach me how to be president.” It works, leading to more introspection that one might expect from such a restrained politician after four years in office.

More from On Leadership:

Great leadership profiles of Paul Ryan

Great leadership profiles of Joe Biden

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