How to Work with Complicated People

Leak identifies four options when facing complicated people:
1. Avoid them (61% do this constantly or often)
2. Change them (manipulation by another name)
3. Cancel them (write them off entirely)
4. Understand them

Only the fourth option produces lasting results. A coworker named Lucy was labeled "rude" for eight years because no one knew she was deaf in one ear. When she finally shared her story, the label dissolved overnight — she wasn't complicated, just misunderstood. Understanding doesn't mean agreeing. It means engaging authentically, asking questions without judgment, and recognizing that the word "with" in the title is the linchpin — a connecting word that puts you on the same side.

An expectations detox means honestly evaluating what you think people should do — and why reality keeps falling short. Leak describes Baron, a pharma exec whose superhero standards left his team walking on eggshells. When Baron started expecting human imperfection instead of demanding miracles by Monday, creativity flourished and colleagues began sharing ideas they'd hidden for years.

Practical resets Leak recommends: accept that meetings will be messy, that not everyone will agree with your pitch, and that someone going through a divorce won't be emotionally balanced daily. Before interactions, tell yourself: "This probably won't be easy. They probably won't agree. But it's okay if it's complicated." Something can be awkward and still be productive.

Your brain is an unreliable narrator. It casts you as the hero and fills in blanks about others' motives — usually with villain-level assumptions. Leak applies Brené Brown's hypothesis of generosity: what's the most charitable interpretation of someone's behavior? Maybe that curt reply had nothing to do with you. Maybe their crappy attitude hides a personal crisis.

Try relabeling their traits: "combative" might mean "honest," "indecisive" might mean "analytical," "loud" might mean "passionate." An NBA coach who dreaded working with a notoriously "difficult" player eventually discovered the player's intensity came from relentless drive. His one-line epiphany: "He's grown on me." Leave room for people to grow on you.

Leak's collaboration mindset rests on four self-check questions:
1. What is it like to be on the other side of me? (self-awareness)
2. What is my part to play? (ownership)
3. What is it like to be you? (curiosity)
4. What brings us together? (connection)

After a speech, someone asked Leak if Kobe Bryant seemed "in a hurry" during their conversation. Kobe wasn't — but Leak realized he often was, making people around him talk faster as if they were on a shot clock. That blind spot was costing him connection. His survey also found executives report 48% positive conflict resolution while employees report only 27% — suggesting leaders routinely misjudge their own effectiveness.

William Wrigley Jr. pivoted from soap to baking soda to chewing gum — each time because customers and employees told him he was wrong. He preferred workers "with backbone" who would challenge his ideas. His philosophy: when two people always agree, one of them is unnecessary.

Research confirms this. A landmark study on collective intelligence found that a team's c factor — its group smartness — wasn't strongly predicted by individual IQ. What mattered most was social sensitivity (reading each other's cues), equal conversational turn-taking, and the proportion of women. Connection quality trumped raw brainpower. Complicated people who see differently aren't obstacles to great work — they're prerequisites for it.

Leak introduces the DQ connection — decency quotient — measuring your ability to connect through kindness, empathy, and genuine care. It's the fifth of his People Qs, alongside intelligence, emotional awareness, adaptability, and tech savvy. A Harvard Business Review article argues DQ ensures that IQ and EQ are "used to benefit society, not tear it down."

Does being decent cost you career advancement? UC Berkeley researchers ran two fourteen-year studies and found that selfish, combative, and manipulative individuals gained no more power than generous, trustworthy ones. The bullies intimidated their way upward but destroyed relationships that offset any advantage. Nice guys don't finish last — they just have fewer bodies under their bus.

BlackBerry owned the smartphone market — then watched it evaporate. One root cause: their board consisted entirely of finance people who thought alike. Groupthink killed their ability to hear dissent. Meanwhile, a Fortune 100 leader discovered that his team's "complicated" colleague Richard — an empathetic questioner who slowed meetings down — consistently produced better outcomes. They began inviting him into rooms specifically for balance.

Leak offers five rules for productive conflict:
1. Fight fair — no manipulation or intimidation
2. Fight fast — don't let resentment brew for months
3. Fight factually — stick to data, not ego
4. Fight focused — keep it about the task, not personalities
5. Fight forward — treat disagreement as a stepping-off point for exploration

Some people put the "nearly" in "nearly anyone." They're uncoachable, unapologetic, and uninterested in meeting you 10% of the way. For them, you need boundaries — but Leak distinguishes between a castle wall (defensive, isolating, moat with crocodiles) and a picket fence (delineative, marking where your territory begins while still allowing conversation).

Start with small wins: headphones to block interruptions, Do Not Disturb after hours, scheduled focus blocks, hard stops for phone calls. Boundaries aren't about controlling others' behavior — they're about controlling your response. Crucially, good boundaries keep you connected, not isolated. They define terms for ongoing collaboration. If someone repeatedly violates them, that data tells you when a relationship may need to end.

Pre-forgiveness is Leak's term for a one-time life decision: you will forgive people before they've offended you. When an insult lands or a colleague steals credit, you don't deliberate whether to forgive — you already decided. It's not naivety; it's preparation. Since you can't plan around complicated people, plan your way into forgiveness instead.

The data supports this approach. Leak's survey found 59% of workers experienced anger or bitterness from complicated colleagues in the past year. Research shows workplace forgiveness leads to higher job satisfaction, greater engagement, and lower burnout. One practical technique: pick a calendar date by which you want to be over a specific grudge. Give bitterness an expiration date — then work toward it through processing, therapy, or honest conversation.