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How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone

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A New York Times Bestseller!

Bestselling author and transformational speaker Ryan Leak shares research-based strategies for working with even the most challenging people to create more collaborative and productive teams.

Who is the most complicated person you work with?

You probably don’t have to think very hard to answer that question. You already know their name, their job title, their quirks, and their flaws. You have firsthand experience with the mental and emotional fallout they leave in their wake. You’ve seen the problems their complexity creates for everyone on their team. You wish you could fix them, solve them, ignore them, or teleport them to a parallel dimension.

But you can’t.

You have to work with them.

(You could quit, but your next job will have a complicated person waiting for you.)

That means you need effective strategies to collaborate with (nearly) anyone. Especially the picky, prickly, problematic ones.

Drawing from his global consulting experience with teams and leaders from the glitz of sports and entertainment, to the number-crunching world of finance, to the meticulous realms of insurance, pharma, and manufacturing, Ryan Leak provides proven strategies for…
Seeing challenging individuals as human beings to understand rather than problems to solve Detoxing unrealistic expectations and getting comfortable with complicated Learning to communicate effectively in complex environments Embracing healthy disagreement as a tool to discover better solutions Setting boundaries that let people into your world without letting them run your world
“The process of learning to collaborate with difficult individuals is transformative—it’s a gateway to greater creativity, stronger teams, and increased productivity,” Leak explains. “On the other side of complicated is the wonderful, wide-open world of effective collaboration and a workplace you love.”

303 pages, Kindle Edition

Published April 15, 2025

231 people are currently reading
1041 people want to read

About the author

Ryan Leak

7 books101 followers
Here's what you need to know about Ryan Leak: He's a husband to Amanda and dad to Jaxson. After that, he's an author, filmmaker, and speaker. He's known as an ultimate risk taker from his two documentaries: The Surprise Wedding and Chasing Failure. Ryan proposed to his wife and married her on the same day, having planned their wedding in secret for two years. That documentary went viral in 2013 and the Leaks have been featured on Good Morning America, The Today Show, The Queen Latifah Show, and many other various media outlets. Ryan's most recent film is called Chasing Failure where he went on a journey to conquer his fear of failure by trying out for an NBA team. Ryan travels the country and teaches people how to remove the limitations that keep them from dreaming. And now, he teaches people how to be UnOffendable. You can follow Ryan on Instagram + Twitter: @ryanleak

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Displaying 1 - 30 of 46 reviews
Profile Image for Sarah Cupitt.
839 reviews47 followers
June 24, 2025
Work would be a lot easier if it weren’t for all the people, right?

(had to eye roll a lot at this book cause it assumes you can empathy your way out of dealing with people who can't do their job, weaponised incompetence and a bunch of other shit)

notes:
- No matter how great your job is, complicated people can make it feel like a daily battle. And the truth is, you can’t opt-out. Wherever there are humans, there will be complexity, misunderstanding, and a few relationships that test your patience.
- Nearly half of Americans say they deal with complicated people daily, and most face them at least weekly. But here’s the twist: it’s not just them – it’s all of us.
- We’re usually the hero of our own story, while others are cast as bit players or villains. But they’re doing the exact same thing with us.
- That person who constantly drains your energy? Even a one percent improvement in that relationship can make your work life feel lighter and more manageable.
- you actually need complicated people. Their different approaches, skills, and perspectives can complement your own in ways that spark creativity and drive better results
- When you’re speaking upward, it’s crucial to “think C-suite.” You need to frame your message in terms of the broader, company-wide interests and pain points.
- stop being surprised. Expect people to be complex

FINALLY
Sometimes, no matter how many books you read or tactics you try, collaboration just isn’t going to happen. Some people simply aren’t willing or able to meet you halfway – and that’s not a reflection of your effort or attitude. It’s on them, not you.
- Clear, respectful communication gives your boundaries the best chance of sticking.

You’re surrounded by leaders making tough calls, teammates carrying invisible loads, and a world that rarely hands out easy answers. And yes – you’re complicated, too. But here’s the good news: complexity doesn’t have to be a barrier. It can be a bridge. When you bring humility, curiosity, and resilience into your interactions, you create the kind of change that can ripple out far beyond you.
Profile Image for Jung.
1,941 reviews45 followers
Read
June 25, 2025
In "How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone", Ryan Leak explores the messy reality of workplace relationships and offers practical strategies for navigating them with clarity, empathy, and strength. He doesn’t promise that all difficult people will suddenly become easy to deal with, but he does propose that by changing how we perceive and interact with others, we can dramatically shift our experience of work. Rather than focusing on controlling or fixing others, Leak encourages us to take ownership of our own mindset and behavior. The result is a book that’s as much about personal growth as it is about professional collaboration.

One of Leak’s foundational ideas is that every person, including ourselves, is complicated. It’s easy to see other people’s flaws while ignoring our own. That frustrating coworker who won’t compromise, the manager who communicates poorly, or the team member who complains constantly – these are common figures in most workplaces. But Leak flips the script by pointing out that to someone else, 'we' may be the complicated person. Acknowledging this doesn’t mean tolerating toxic behavior, but it does create room for understanding and humility. The more we accept our own quirks and limitations, the better positioned we are to extend grace to others, and to find workable solutions in tough relationships.

This mindset shift also involves examining the stories we tell ourselves. Often, we see ourselves as the hero of our own story and others as the obstacles. But everyone is doing this, creating conflicting narratives that amplify tension. By recognizing that we might be wrong—or at least incomplete—in our judgments, we open up the possibility for empathy. Leak suggests reframing our perceptions: what we see as stubbornness might be passion, and what we interpret as negativity might be caution. This reframing doesn’t erase differences, but it makes them easier to navigate. Instead of trying to win every interaction, we can aim to understand. And that shift can lower defenses on all sides.

The book also emphasizes the return on investing in difficult relationships. While it’s tempting to avoid or work around challenging people, Leak makes the case that confronting those dynamics directly is a worthwhile pursuit. Even small improvements in a strained relationship can significantly improve your daily work experience. Fewer emotional landmines, less stress, and a stronger sense of control are all benefits that come from leaning in instead of retreating. Moreover, improving these relationships can influence workplace culture. One positive interaction can inspire another, creating a ripple effect that fosters a more collaborative and human environment. And importantly, working with people who see the world differently can lead to better outcomes. The creative friction that comes from diverse perspectives is often the source of innovation.

To support this kind of growth, Leak outlines four powerful habits: self-awareness, ownership, curiosity, and connection. Self-awareness requires asking what it’s like to be on the receiving end of your own behavior. Ownership pushes you to acknowledge your part in every interpersonal dynamic. Curiosity leads you to consider what pressures or perspectives might be shaping the other person’s actions. And connection encourages you to seek common ground, even when it’s small. These habits, when practiced intentionally, help shift the energy from conflict to collaboration. They allow for a more thoughtful and intentional response rather than a reactive one.

Communication, naturally, plays a huge role in all of this. It’s not just about what you say, but how, when, and through which medium you say it. Leak underscores the importance of tailoring your message depending on your audience—speaking to leaders requires big-picture thinking, while communication with peers and subordinates demands clarity and respect. He also highlights the nuances of tone, particularly in emails, where intentions can easily be misread. Video calls and in-person conversations each have their own dynamics, and knowing how to adapt to these contexts can make the difference between clarity and confusion. Small talk, positive tone, and active listening aren’t fluff—they’re bridges to smoother collaboration.

Of course, even the best communication strategy can’t eliminate conflict entirely. Leak doesn’t pretend otherwise. But he does suggest that conflict, when addressed early and fairly, can actually strengthen relationships. The key is to deal with issues factually and respectfully. Avoid personal attacks or defensiveness, and aim for resolution, not retaliation. What he calls 'fighting forward' is the process of moving through disagreement in a way that leaves both parties better off. It requires maturity and self-control, but the payoff is a deeper sense of trust and respect—even with complicated people.

Another core theme is managing expectations. Much of our frustration comes from wishing others were different. Leak challenges us to stop being surprised when people act like people: inconsistent, emotional, distracted, or just plain difficult. When we go into interactions expecting some level of complexity or resistance, we’re better prepared to handle it without being thrown off course. This mental shift protects our energy and gives us more agency. Rather than wasting effort on changing others, we can focus on our own responses.

Linked to expectations is the importance of forgiveness. Not for others’ sake, but for our own. Leak argues that holding onto resentment and grudges takes up emotional bandwidth that could be used more productively. Forgiveness doesn’t mean condoning bad behavior—it means releasing it so it no longer defines us or our day. This choice, like so many in the book, is about reclaiming control. You get to decide how much space someone else takes up in your mind. And that decision can radically affect how you experience work.

Still, there are times when no amount of reframing, communication, or forgiveness will fix a relationship. Leak acknowledges this reality, too. Some people, for various reasons, are not going to collaborate. In these situations, boundaries become essential. Boundaries are not about controlling others; they’re about protecting yourself. Leak encourages readers to set limits on their time, energy, and emotional investment. Saying no, not responding outside of work hours, and communicating expectations clearly are all valid and healthy ways to preserve mental health. And when things escalate, having documentation can be a critical tool for bringing in HR or other support systems.

Boundaries, like communication and collaboration, are a skill. They take time to develop, but they allow you to maintain your dignity and well-being even in the presence of toxic or uncooperative individuals. And sometimes, boundaries also help the other person understand the impact of their actions. While not everyone will respond positively, many people do adjust once they realize the rules have changed.

In the end, Leak’s message is both realistic and hopeful. Complicated people aren’t going anywhere—and neither is complexity. But we don’t have to be passive victims of our circumstances. By taking responsibility for our own mindset, behavior, and boundaries, we can change the way we experience even the most difficult relationships. Collaboration is possible, not because people suddenly become easy, but because we choose to bring patience, grace, and intentionality to our interactions. And when that happens, the workplace becomes less about survival and more about shared success.

Ultimately, "How to Work with Complicated People" is a guide for anyone who wants to grow, not just cope. It’s about shifting from reaction to intention, from frustration to understanding. Leak doesn’t sugarcoat the difficulties of human relationships, but he equips readers with the tools to handle them with strength and compassion. By showing up with a generous mindset and a commitment to self-leadership, we create space not only for better teamwork but for a more fulfilling work life. In a world where complexity is a given, choosing to lead with clarity and kindness becomes a powerful act of change.
Profile Image for Elisabeth.
17 reviews3 followers
June 9, 2025
I liked it, I just didn’t get anything work/life changing out of it, unfortunately. The chapter that included suggestions of different ways to word your emails was useful.
Profile Image for Kelly Ann Meegan.
278 reviews10 followers
September 20, 2025
Excellent and useful tips for life if I could get this audio to listen to every day I would
Profile Image for Bryan Tanner.
788 reviews225 followers
June 25, 2025
TL;DR — It’s not them, it’s your perception of them.

Summary — The real magic doesn’t come from trying to change other people, it comes from changing how you relate to them. It’s about protecting your peace, adjusting your expectations, and building better ways to connect without losing your mind. Because while you can’t control who shows up in your workplace, you can absolutely control how you show up in theirs.

Review — A validating, perspective-shifting read for those who feel burdened by emotional baggage from working around so-called “complicated people.”
Profile Image for Amy.
27 reviews1 follower
December 26, 2025
Straightforward approach to seeing past you and your frustration and providing multiple strategies to keep moving forward. Definitely recommend if it seems like you’ve tried everything with a complicated person in your life, especially at work.
Profile Image for nini.
149 reviews
August 28, 2025
it’s fine just a lot of talk not a lot of steps and feels like everything is on you which sure it’s true but also BLAHH ! what’s unity for again it’s fine just repeats itself — 🚇
8 reviews
July 13, 2025
Don’t be put off by the title, thinking it’s only about dealing with coworkers. The lessons in this book are applicable to all relationships, not just work ones.
Profile Image for Rachael Melot.
56 reviews8 followers
May 19, 2025
The first chapter was really great, then it felt really high level and somewhat elementary in the application of the theories.

Good book for entry level professionals IMO.
5 reviews
June 4, 2025
Read this in two days. As someone who manages a team of people, this was an excellent read. It helped me refocus my action- oriented brain into making connections with people rather than checklists. Please read if you work with anyone! It’s such a good read!
Profile Image for Lori.
7 reviews
May 5, 2025
This book was insightful and offered doable tasks to improve relationships you have with just about everyone.

It really forced me to look inward and reflect on recent situations where I had a part to play in the outcome but didn’t recognize.

I especially enjoyed the conversational tone and relatability throughout the book
Profile Image for Tasha.
12 reviews
2025read
May 26, 2025
Such an insightful read. This book brought much needed self awareness for me, as a parent, wife, team lead the information in this book is so valuable to all who are open to learning and growing. I talked about this book so much at home that my 24yo got the audio book to listen and she couldn't stop listening. I
Profile Image for James.
777 reviews37 followers
July 19, 2025
DNF. Complete bullshit. I tried to stick with it, but I had to stop reading when he started gushing over late rapist Kobe Bryant.

Look, the "complicated" people I deal with are racists, transphobes, and anti-immigrant assholes. This book was doing fuck-all to help me figure out how to handle them. I had hoped it would have some advice for diverse workers. Nope, nada. One throwaway line about harassment a long way in.

This book rings very "diversity of thought" which is a conservative concept that undermines -real- diversity, equity, and inclusion in the workplace by allowing it to be colonized by cis straight abled white men, usually pretty mediocre ones at that. Don't fall for it!!

Overall, skip this shit!
Profile Image for Jaimie Engle.
Author 39 books264 followers
June 20, 2025
This is a book for everyone. I do not say that lightly. While we live in an age where everyone has a platform and an opinion, it is crucial that we all learn to realize that not only will we encounter difficult people, but that we are also difficult people to someone else. People spout about harmony and diversity and integration, but on a personal level, I rarely see it in action. People tend to be judgmental and critical and quick to cancel one another, and that’s just not a sustainable way to live. Though this book is for the workplace, it is applicable to family and friends as well. I will probably read it a second time and maybe a third. Highly recommend.
Profile Image for Keji A.
5 reviews
June 25, 2025
This book ended strong which I'm grateful for because the beginning chapters felt repetitive for me of things I've read in other resources. If someone is newer to navigating complex people and relationships this book could be a great comprehensive all in one., from that perspective I would give it a 5. As someone who has read a good bit of the books or concepts he was referencing it didn't add to what I knew until the very end so that's the reason for the star. Chapters 11 and 12 gave very practical steps (which I love) in how to bring the content to life. This is a perfect book to listen to the audio version, the author's way of delivering the book spoke to me.
Profile Image for Emi.
16 reviews1 follower
December 18, 2025
I have a hard time with non fiction and usually skim through. Which I also did here, but what made a difference was that the key points were highlighted in a way that really got my attention and I was able to get something out of the concepts. A little too much description of his experiences at conferences/other's life experiences so I didn't read everything but again, the important information was enhanced sufficiently to understand them without reading every single word of the book. Overall a good book to read if you want to improve your own professional skills.
Profile Image for Amanda.
221 reviews4 followers
July 1, 2025
I loved this! I read a lot of books about communication, working with people, etc. but rarely come across ones that are so approachable and useful. I have already recommended this to those I coach, as I think it is both useful for their personal development (as it is mine!) and for their people leadership.

I would highly recommend the audiobook as the author is a delight! However, I liked this so much I also bought it in print.
Profile Image for Dalton Haslam.
25 reviews1 follower
July 5, 2025
A couple things here
1. The formatting of this book really bothered me, ha. Mostly felt like the margins need to be bigger and it was trying to be too creative with formatting.
2. The second half of the book is the best part! I feel like most business/self-improvement books really only have quality content in the first 3rd of the book, and the rest is fluff. This book was a pleasant departure from that and really held its own to the end.
3. It’s a good read!
Profile Image for Meagan S.
49 reviews1 follower
July 13, 2025
While I’m not a corporate person, I still got meaningful information from this book. It’s so true that it’s not just other people that are complicated, but we ourselves are complicated to others as well. Some of the corporate strategies may not apply to my life, but the chapters on people q’s and choices that change you were really great. I listened and read in hard copy - the audiobook had additional thoughts from the author and that may listening to it more enjoyable.
Profile Image for Mwenzie.
121 reviews2 followers
October 18, 2025
No matter who you are, someone out there finds you to be the complicated person they have to deal with. Fundamentally, this book is about developing empathy towards other human beings. Lots of good thought-provoking nuggets and frames for communication, approaching conflict, and collaboration. I think it’s particularly relevant, and hopefully equally relatable and accessible, to individuals fairly new on their professional journey or in leadership roles.
Profile Image for Julie M..
179 reviews
May 4, 2025
I got to hear Ryan Leak speak at my company’s leadership event. He was excellent. This book is engaging, easy to read, and full of great nuggets of info on working with complicated people (which we are ALL complicated!!). I found this helpful not just for work, but for doing life with all manner of people.
Profile Image for Danielle Lynn.
356 reviews3 followers
June 23, 2025
Honestly a lot of good things here. We don’t and actually shouldn’t agree with everyone on everything, that ends up being an echo chamber which is damaging. Also, expect that people did things with the best of intentions instead of assuming the worst. Forgive the grievances you feel have affected you and move on, it’s not helping anyone.
Profile Image for Molly Bruning.
109 reviews2 followers
July 10, 2025
Everyone works with complicated people. If you don’t, then, well, maybe you’re the complicated person 😂

Entertaining but didn’t gain any new knowledge or tactics other than forgiving people, remembering everyone has a life outside of work, and setting boundaries for yourself. The author had a humorous voice so I enjoyed hearing him read the book, but not one of my top self-help books.
Profile Image for Sara.
272 reviews4 followers
August 8, 2025
It feels paradoxical but this book is a light read about a complicated topic (getting along with difficult people). I read this after hearing Ryan Leak speak, and he writes in such a conversational style it was like being back in his audience. The insights aren’t necessarily earth-shattering but it was full of good reminders and easy to read.
Profile Image for Miranda.
607 reviews15 followers
May 24, 2025
4 🌟

I love Ryan Leak!

I mean, who hasn't worked with a difficult person before?! I think Leak does a good job showing us to look in with dealing with difficult people. There are definitely some nuggets I will use moving forward.
Profile Image for Mare.
111 reviews8 followers
August 5, 2025
4.5 stars - I love self-improvement books that have clear, actionable recommendations that make sense. This one does that and is also enjoyable to read/listen to (the audiobook is read by the author). Highly recommend for anyone with… interesting coworkers :)
Profile Image for Julia Pearce.
1 review
December 4, 2025
I coach a team of ten people how to build relationships with their clients. To help them be successful in their sales. This book not only helped me see that part of my job in a new light but also how I interact with my boss and the leadership teams that’s I work along side.
9 reviews
December 30, 2025
First self help book I have actually finished in awhile, which is why I gave it 3 vs 2.

Basically, we are all complicated. Deal with it. Ryan's mannerisms when speaking were sometimes hard to listen to.
Displaying 1 - 30 of 46 reviews

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