How the Military Scales a Technology Leader

First Round Capital recently shared advice from Adam Pisoni (co-founder of Yammer) about how to scale oneself as a technology leader. He gave five tips, including one he learned from General (Ret.) Stanley McChrystal. This made me wonder what the military solution equivalent would be for Adam’s other 4 suggestions. After a bit of research, here is what I discovered:

  1. Roles & Responsibilities

According to Adam, “Without clearly defined accountabilities, it’s easy for companies to become paralyzed by decision debt and arguments.” The military uses something called the “G-staff model” to help define roles and responsibilities. Each branch of the military uses this model to define one leader as responsible for each of the roles below:

G1 – Deputy Chief of Staff for Personnel, G2 – Deputy CoS for Intelligence, G3 – Deputy CoS for Operations, G4 – Deputy CoS for Logistics, etc.

From there, they have a team to support the execution and function. The U.S. Army Material Command does a good job of explaining it here.

  1. Monitoring Progress

Adam covered this one well by using lessons from General McChrystal. Adam credits McChrystal for “creating a process where every single day for 90 minutes, thousands of people from all over the world would dial in to a rapid-fire update meeting. Each group had 90 seconds to say what they did, what they’re doing next and what the risks or blockers are.” By holding a weekly standup, McChrystal was able to ensure that everyone possessed the appropriate amount of baseline information to execute missions quickly and effectively.

  1. Retrospectives

The major lesson here is that members of the tech industry should aim to “stop repeating mistakes.” The military uses After Action Reports (AARs) to evaluate the success or failure of missions and learn how to improve for the future. I tackled how the Navy uses AAR in a previous post about development, and Craig Mullaney does an excellent job explaining the AAR in more detail here.

  1. Planning and Prioritization

Adam outlines a strategy for how to best create plans, but I think the most interesting part is how he concludes: “based on your new priorities, decide what you’re going to STOP doing.” To accomplish this, the military uses the appropriately named Military Decision-Making Process (MDMP). The MDMP is a 7-step process that is explained in detail in this textbook, but essentially comes down to understanding the mission, developing appropriate Course of Actions (COAs), war gaming the COAs, and then executing.

  1. Managing Tension

As Adam points out, tension between employees is inevitable. Evidently, the military agrees. They have a position – the executive officer (XO) – who helps to resolve tension within a unit. Going into each new project/initiative, the XO will convene all relevant parties/stakeholders to identify issues, allocate decision-making space, and hash out solutions. Adam agrees with this process and says, “instead of digging in and trying to resolve tensions as a leader, your only goal should be to make tensions public.”



Three Military-Tested Techniques for Improving Your Team’s Decision-Making

This was originally published in Fast Company:

“Captain, to the bridge.”

Mike LeFever, captain of the USS Destroyer, was abruptly awoken to these words at 3 a.m. to learn that a newly appointed officer had nearly crashed a $100 million cruiser into a fishing boat. As LeFever approached the officer, he could see a bead of sweat running down the young man’s neck. First, LeFever asked a set of rapid-fire questions: “What happened? Is anybody hurt? Is the ship okay?”

The officer answered concisely but still braced for the worst. Instead, he heard, “What did you learn? Let’s talk about this in the morning. You have three more hours on watch duty.” Then LeFever returned to his quarters.


Unlike in many—or even most—organizations, the military is relentlessly focused on developing the decision-making abilities of its personnel through empowerment. “If you take care of the people,” LeFever, who retired as a vice admiral after a more than 30-year Navy career, told me when we spoke recently, “the people will take care of you and perform the mission.”


In this view, people—their skills, expertise, and judgment under pressure—are inseparably linked with the success or failure of every undertaking. LeFever defines empowerment as delegating responsibility, and then allowing people broad freedom of action—permitting them to succeed or fail.

LeFever could have decided to use the interaction with the young officer on the bridge to dress him down in front of his subordinates. But he recognized that that served little purpose. The incident had already occurred. What mattered now was to make sure that the officer learned from this experience so he could prevent it from happening again.

The idea of empowerment is challenging enough when failure means missing a product deadline, but handing off that kind of decision-making when failure could mean a loss of lives? That takes a different level of trust altogether. Yet the military faces many similar challenges that organizations do when it comes to investing that trust in individuals:

  • Constantly changing teams, as military units are continually created and disbanded
  • Geographic separation, with personnel on almost every continent and teams varying in size from two people to tens of thousands
  • Rigid promotion requirements and dismissal protocol

The military still manages to enable individual decision-making not despite these challenges, but in order to counteract their potentially detrimental effects. In other words, only by cultivating leaders at all levels is such a large, complex organization able to maintain its effectiveness at scale.

“The hardest part of being a leader,” LeFever says, “is allowing other people to do that job, because they probably won’t do it the way that you want it. My goal was to provide guidance and boundaries.”

The military’s rigid organizational systems are designed to create the boundaries that are most likely to enable decisive action, not prevent it. These are a few of them.


After every mission, the Navy conducts an “after action report.” The process is designed to determine what happened in a given incident and why. Officers across different continents scrutinize events, debate and defend decisions, and resolve conflicting understandings of the scenario in order to learn how better to approach similar ones in the future.


The Navy’s mentorship program epitomizes the organization’s way of creating empowerment through clearly defined working processes. Not only does the Navy assign formal mentors, it also encourages sailors to seek out informal mentors on their own. These mentors then set quantifiable milestones for young officers to work toward short- and long-term goals.

The concept of a formal mentor is foreign to most entrepreneurs—especially during startups’ early days. When a company has three people and a product nobody’s ever heard of, where would a formal mentor even come from? You have to seek them on your own. When my cofounder and I first began to target film studio partners for our startup ReelSurfer, neither of us had ever worked with one. So I cold-emailed everyone from our alma mater’s alumni list who had entertainment experience. From one of these emails we formed an amazing relationship with a Hollywood producer, who then helped us start conversations and negotiate deals we’d never have been able to do on our own.

Not only can a mentor help guide you in our own decision-making, giving you the confidence to take action in difficult circumstances, they can also help create the situations that allow you to exercise (and, over time, improve) your judgment in the first place.


How a team is put together also has an impact on how empowered its individual members can become to make tough calls effectively.

When LeFever first joined the Navy, its personnel strategy revolved around skill requirements, commonly referred to as “Fill.” Finding that strategy wanting, LeFever proposed a new policy, “Fit and Fill,” which combined skill requirements and team chemistry.


This is an area many entrepreneurs and business leaders struggle with when forming new teams. It isn’t always easy to balance cultural fit and expertise. Startup founders are often overzealous simply to hire the smartest people they know. But sometimes the most brilliant people clash with each other or scoff at doing some of the less glamorous work. Members of poorly composed teams might not hesitate to make decisions, but they’re more liable to do so independently, less effectively, and without enough regard for the team’s unifying goals.

Truthfully, before speaking with Captain LeFever, my understanding of leadership development in the military stretched about as far as the drill sergeant scene in Full Metal Jacket. I thought of the military as a rigidly hierarchal, top-down organization. We like to think of the tech world as the complete opposite. But in reality, it’s a focus on leadership development through empowerment at the lowest possible level that allows the military to operate at the scale and excellence that it does. That’s a lesson more businesses would do well to take to heart.