You Have To Fight

Enjoy The Work blog post. You Have To Fight.

“The aim of argument and of discussion should not be victory, but progress.” Joseph Joubert

Companies face thousands of choices. What do customers need? What will they buy? How do we build it? How do we create some attention? How do we sell it? How do we build a team?

Sifting through the available data to make an informed choice is an exercise most well-run startups can tackle. But what separates the great from the not-so-great businesses is the team’s capacity for a good scrap. I mean it. High-quality teams fight, and they fight all the time over nearly everything.

I’m being figurative, of course. Actual fisticuffs (while potentially energy-releasing) will not hone strategy or reveal optimum tactics. Great teams fight as part of the recruiting process, during staff meetings, and during strategy sessions.

The fragile need not apply. Startups are pressure cookers designed to reveal the character of those brave (or masochistic) enough to join. Startups operate on a clock relentlessly ticking towards one of four outcomes — profitability, funding, exit, or death. To survive the gauntlet requires incredibly rapid feedback loops. Great founders marry empathy and kindness with directness and decisiveness. It is critical to have team members both with the humility to want feedback and the fortitude to hear it.

But just as the rules are different for boxing versus professional wrestling, the rules of engagement differ depending on which ring our combatants enter.

Fighting in recruiting

You’re not here to develop the emotional maturity of your people. You’re here to run a startup. Find people sufficiently mature to join you, and you’ll never have to coddle. The delicacy with a potential candidate is finding the balance between conflict and courtship.

Ask candidates about their career, specifically why s/he joined and departed their prior companies. A candidate’s examples may include reasons such as:

  1. Dissatisfaction with role/responsibilities.
  2. Passed over for promotion.
  3. Lack of belief in the company’s direction.
  4. A gap between expectations for the role and reality.

In every case, it’s easy to invent a reason to disagree. If they were dissatisfied, did they communicate that to their boss? If not, why?

If they got passed over for a promotion and chose to leave, ask about the person’s qualifications who eventually received the role.

If they claim lack of confidence in their prior company, ask if they communicated their opinion to senior leadership. If not, why?

Lastly, if a prior job failed to live up to what had been promised, ask about what diligence the candidate might have done prior to joining to avoid the mistake.

If somehow there are no obvious openings in the candidate’s job history, ask them to demonstrate their skill in some fashion — write some code, build a 90-day plan, participate in a role-play. Easy opportunities to create some conflict.

As a last resort, turn to philosophical arguments. Questions might include: “Describe your management philosophy,” or “What is the difference between management and leadership,” or “What constitutes a great culture?.”

Fighting in staff meetings

Typically, every week leaders gather to share metrics, progress, and roadblocks on key initiatives. It is entirely normal during these meetings to discover that critical projects or metrics are off-target. If you’re the CEO, I highly recommend that you master five simple questions. I promise that you will more quickly unpack root causes and nurture more (healthy) fighting among your leaders.

  1. Why is (project/metric) underperforming?
  2. If the response begins with “I think,” immediately challenge with “how do we shift from ‘I think’ to ‘I know?’
  3. What is the plan, and how quickly can it be implemented to recover our performance (project/metric) and hit our target?
  4. After hearing the plan, respond with, ‘How might that plan be a really bad idea?’
  5. Once the contrarian view has been explored, finish with ‘What help do you need to hit our agreed-upon target?’

Fighting over strategic topics

Red teams are a good idea. The military thinks so. As do journalists. The concept is simple. One team researches the hell out of a topic, determines the options available, assesses them, and then prepares a recommendation. The second team (the red one) is provided zero color commentary nor any of the conclusions. They are then provided the raw data to see if they reach the same recommended action. Put these folks in a room together, and if there are gaps between them, fireworks will follow. Fireworks are loud and explosive but, IMO, also very satisfying.

When the use of a red team is not feasible, then the next best is a simple method recently popularized by Amazon. Require meeting materials to be sent in advance and outlaw in-meeting presentations. When one person presents, everyone quietly listens (insert boredom, staring at the phone, and meeting fatigue). When materials are sent in advance, recipients can form independent conclusions and come prepared with questions. The attendees arrive at meetings as informed and willing combatants rather than spectators to a show.


Please fight. But remember, you’re on the same team. Great teams passionately debate getting to the right answers. And great leaders provide the ring, boxing gloves, and motivation. Go ahead, take a swing.

“It’s not the size of the dog in the fight; it’s the size of the fight in the dog.” Mark Twain

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