The 2011 Red Sox: legendarily dysfunctional

Our Team is Fucked, and So is Yours

About 6 years ago, in a private conference room of a Paris hotel, I sat silent as two grown men yelled business-oriented insults at each other. One of them — a bearded and bespectacled, seasoned and mostly soft-spoken executive — finally had enough and stormed out of the room.

As our team assembled the next morning, the executive quietly mentioned a family emergency that required him to return home to another country. Acknowledging nothing of the tension from the day before, he apologized to the nine other executives for missing the rest of our four-day offsite — and exited.

Just another ordinary day as part of the highly dysfunctional executive team of a $1b revenue company.


Early in my career, I always thought everyone else had it figured out. While my team’s dynamic might be unfortunate, others were operating with clarity, openness, communication and efficiency. They knew the answers. They listened. They were respectful. They promoted each other’s skills. They accepted failure. They challenged each other and loved it.

They — that company you’d always admired from afar — THEY were gods among men and women. They — the pedestal-quality, celebrity-like, media-worthy— THEY were out there.

But now that I’ve been part of dozens of teams, I’ve found that THEY are a myth. They are imaginary. The truth: Every team is a mess. Every team is totally fucked up. THEY are all dysfunctional in their own special way.


Let’s talk about the team I’m on now. This one is a venture-backed startup comprised of 8 people (Mylestoned), and I happen to be the CEO. Here are a few things that we’re working through:

  • SILO BEHAVIOR. Making choices without involving others, creating “insiders” and “outsiders”.
  • COMMUNICATION BREAKDOWN. Limited dialogue about what we’re doing and when, leading to confusion.
  • DISRESPECT. Ignoring communications, unintentionally or intentionally; silence tends to cause frustration.
  • ROLE CONFUSION. Shifting priorities leads to overlapping roles leads to people feeling stepped on or on the sidelines.
  • LEADERSHIP. A CEO (me) who finds it hard to trust, can be snappy and micro-manages when he feels a lack of control.

Am I worried? Sure, I worry every day — but I’m not paralyzed. From everything I’ve experienced, this is entirely normal. Every single team I’ve been on has had interpersonal issues and structural complexity.

The truth is co-workers are often like children on a playground: Taunting each other, creating tribes and cliques, choosing who gets to play and who doesn’t. They operate out of confidence and pride and fear and ego. Children or adults, no single human has perfected interactions with others to a point of no conflict.

At larger companies — where executives were often deified as internal celebrities — some senior executives ascend due to political navigation and effective networking, not because they were more skilled or adept at working well with others. At one team I was on, a peer was secretly labelled the “Brown Crusader”, because everything behind him turned to shit (and yet he was skilled at ensuring the mess wasn’t attributed to him). I can only imagine what they called me.

A Senior Executive: The Brown Crusader

Startups aren’t much better — in many cases individual contributors are thrust into positions as managers before they’re ready (see Intelligent.ly for help with that). At one of my startups, tears were a common occurrence due to teammates talking behind each other’s backs.

I’d argue, this is normal.

The fact is, a team isn’t static. Rather it’s like a wave in an ocean, sometimes rising to excellence — supportive, caring, delivering — and occasionally sinking to the bottom — confused, fraught, spent. At times your team may swallow a little water, but the key is to avoid drowning.

Lencioni’s 5 Dysfunctions Pyramid

In Patrick Lencioni’s 5 Dysfunctions of a Team, he highlights Fear of Conflict as a key dysfunction, and the result being “artificial harmony”: on the surface everyone is smiling, but inside, things aren’t so rosy. People aren’t saying what they’re really feeling, where they’re blocked, and that’s handcuffing results.

My mom always said to me, “If you don’t have something nice to say, then don’t say anything at all.” Maybe Mom wasn’t right about everything?


Ultimately, no matter what size, teams require constant, unrelenting attention; the team — for lack of a better way to put it — is a group of individuals who operate within the bounds their interpersonal conflicts allow for. Limit those conflicts, and you become high performing. Allow the conflicts to fester — trust to dissipate between individuals — and your chance of success is greatly limited.

The net is you need to maximize your teams capacity to perform— individually together. There’s no magic equation; I work on this every day. But here are three things that can help:

  1. Be religious about 1:1s. Actual problems can be obfuscated by the team dynamic. Spending time 1:1 is where the issues between people become clear. If you’re a manager, have them. If you’re an employee, ask for them and use them.
  2. Do not let interpersonal issues fester. Once you identify areas of friction, you have to address them immediately. Talk to people, try to get everyone to express their POV and what would help them perform better. If you’re a manager, help people talk to each other.
  3. have everyone read 5 Dysfunctions of a Team. It’s an easy read and a healthy tool for shining a light on bad behavior. Refer the team back to it when you need.

Nearly a decade ago our COO — my teammate — sat across from me, stone-faced, after a very combative internal meeting. Once everyone else had filed out of the room, he took a breath and asked me point blank,

“you know we’re on the same team, right?”

I’ve found it useful to reflect on that reminder often. If you’re on a team of any size, I hope you do, too.


People, if you got this far, please hit the ❤ below. We’re a team right?

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