Some people are just difficult. Here are 6 books on how to handle them

CNA

09-05-2025

Earlier in my career, I worked for a hot-tempered woman who, according to an office rumour, had thrown a shoe at one of my predecessors. Rattled by her blowups, I tiptoed and stammered around her, fearing the day when she'd wing a pump at me.
Then a friend passed along Coping With Difficult Bosses by Robert M Bramson, which was published in 1992. The book's solid, seen-it-all advice helped me stop perseverating and find my spine. I learned from Dr Bramson to stand tall when my boss exploded, to call her by her name (to humanise the relationship) and, if I couldn't quite look her in the eye, to focus on her forehead – close enough that she couldn't tell the difference.
If you're struggling with a difficult colleague, family member or friend, books can validate your experience and teach you helpful communication skills, said William Doherty, a professor emeritus of family social science at the University of Minnesota and a co-founder of Braver Angels, a nonpartisan nonprofit that facilitates conversations between people with differing political views.
But, he added, be wary of books that give you 'one large global theory' about whatever is wrong with the other person. Most relationship problems are caused by both parties, at least to some degree, he said, so books that encourage you to consider your part are generally more helpful.
We asked therapists, psychologists and other workplace experts to recommend books that can help you get along with difficult people – or at least disagree with them more constructively. Here are six titles that rose to the top of the list.
1. HOW TO WIN FRIENDS AND INFLUENCE PEOPLE (DALE CARNEGIE)
In this classic advice book, originally published in 1936, Carnegie, a pork salesman turned public-speaking sensation, draws on his experience and the experiences of others to explore ways to ease tension 'when personal problems become overwhelming.'
He also details effective strategies for getting people to stop noxious, bullheaded behavior, including by admitting your own mistakes first so they are more receptive to your feedback.
Jonathan Haidt, a professor of social psychology at NYU's Stern School of Business and the author of The Anxious Generation, said in an email that he assigns Carnegie's book to his students and has found it helpful personally. 'It taught me to avoid arguments and instead listen, learn, take the other person's perspective and then, if warranted, persuade skillfully,' he said.
2. WHY WON'T YOU APOLOGIZE? (HARRIET LERNER)
This 2017 title from Dr Lerner, a psychotherapist and best-selling author, offers a framework for understanding how skillful, sincere apologies can repair even profound rifts in relationships. It also delves into why some people overapologise, while others can't say 'I'm sorry' without a blame-reversing rider that only makes the injured party feel worse.
Calling it 'the best self-help book' he'd ever read, Dr Doherty recommended it because of the generous, detailed way Dr Lerner describes the intricate back-and-forth dance between the offended and the offender, normalising familiar problems with apologies so we can understand and potentially improve them.
3. THE ASSHOLE SURVIVAL GUIDE (ROBERT I SUTTON)
In this 2017 follow-up to his organizational-psychology bestseller The No Asshole Rule, Dr Sutton writes that he thought the topic 'would be a brief side trip.' But the thousands of requests for advice that he received after the book came out persuaded him to stay on the beat.
The resulting guide is packed with tips and strategies for dealing with demeaning and disrespectful people, including by using humour to save your sanity and carefully documenting evidence of workplace harassment to give yourself leverage if you decide to go to human resources.
Adam Grant, an organisational psychologist at the University of Pennsylvania's Wharton School of Business and a contributing Opinion writer at The New York Times, said in an email that he has recommended the book to more people than he can count, calling it 'an impressively evidence-based, surprisingly actionable read on how to deal with abusive bosses, difficult colleagues and toxic customers.'
4. THE DEFINING DECADE (MEG JAY)
Daphne de Marneffe, a clinical psychotherapist in the San Francisco Bay Area and author of The Rough Patch, said in an email that this book, first published in 2012, about navigating one's 20s had really stuck with her.
Dr Jay, drawing on research on brains and human development, argues that our 20s are a potentially future-defining decade. When young adults, who are more likely than older adults to feel walloped by criticism, decide to bail out on difficult situations with difficult people – including cranky, faultfinding bosses – they miss out on valuable opportunities to learn how to calm themselves and develop confidence.
While Dr Jay's point about the benefits of gaining enough mettle to withstand jerks at work (or wherever they crop up) may be particularly helpful to young adults, 'I think it's applicable to all ages,' Dr de Marneffe said.
5. DIFFICULT CONVERSATIONS (DOUGLAS STONE, BRUCE PATTON, SHEILA HEEN)
This international bestseller, first published in 1999, dives below the surface of personal and professional disagreements to show how quickly they breed distrust and negative assumptions about the people with whom we disagree.
'This was one of the first books I read on how to have difficult conversations, and I find myself going back to it again and again with clients,' Elizabeth Earnshaw, a licensed marriage and family therapist based in Philadelphia and the author of the book 'Til Stress Do Us Part, said in an email.
Among its 'clear and actionable suggestions,' the book outlines a process for both parties to 'own their part' in creating the problem in the relationship, Earnshaw said. The first person to admit any wrongdoing is ' modelling to the other person that it is safe for them to express their own contribution, too,' she explained.
6. THE ART OF POSSIBILITY (ROSAMUND STONE ZANDER, BENJAMIN ZANDER)
First published in 2000, this is an eclectic book of practices for achieving personal and professional fulfillment. Filled with stories that underscore the high costs of leaping to conclusions and labelling other people as dangerous or difficult, it shows readers how, with a shift in perspective or adjustment toward generosity, they can improve challenging relationships and live happier lives.
'Without a doubt, we've got more than a few 'difficult' people in the world,' Seth Godin, a marketing expert and author of This Is Strategy, said in an email.
'But often, the most productive way forward is to realisethat they have a hard-earned self-talk that's driving their behavior. Just as each of us do,' Godin said. 'The Art Of Possibility is the best book I know about empathy,' he added.