What do I expect from my leadership in my tech startup?

One of the best questions a leader can ask people they are leading is “What can I do for you?”

Unfortunately, without a burning desire for a specific thing to happen this is a really difficult question for anyone to answer. So when the Lead Engineer on my team, the Engineering Manager, or the founders and executives of Infinicept ask occasionally what I expect from them, what is my answer? What do I expect from the leadership in my tech startup? These are very important questions that require some thinking before answering.

What do I expect from the leadership in my tech startup?

I served in the Marine Corps so when I think of good leadership I think of military leadership. But what can I translate from a large organization built to kill and destroy as efficiently as possible to a small, very non-violent, tech startup intent on responding to clients and changing the payments industry? More than you think.

I want to know that all levels of leadership in my tech startup are focused on my welfare as a software developer and as a person. I want them to be focused on making sure I have the time, tools and resources to do my job effectively and enjoyably so that I can focus on my tasks and my life.

I want clear direction from all levels of leadership and I want that direction to be the same from all levels of leadership. From the top down, each level of leadership should provide more detail of the implementation of the direction. From the bottom up, each level of leadership should be able to easily detail why the implementation details are related to our direction.

I want the option to be involved in thinking through administration and planning but I do not want to feel obligated to make those decisions. I don’t know how to run a tech startup and I don’t know how I want to develop software but I have opinions and I will feel more valued knowing that my opinions are heard.

I want structure that is defined, adaptable and receptive to feedback. Startups are defined by our desire and ability to grow and change rapidly but that growth cannot happen without some structure. This is likely the hardest thing I ask of my leadership.

Considering Welfare

Many of us think of the people above us in the chain of command as our boss and our boss’s boss and on and on until we get to the top person in the organization. Good leaders think of organizations in the exact opposite direction. They see the people below them in the chain of command as people they need to support more than as the boss of those people. A director is not a director without people to direct. Without care for our welfare, we will not do our jobs well.

Marine Corps Welfare

In the military, the term “administration” means the management of all phases of military operations not directly involved in tactics and strategy.

This includes things like feeding, clothing, equipping, sheltering, paying, transporting and maintaining the health and welfare of the unit as a whole and of its individual members.

“Administration” is maintaining the health and welfare of the organization as a whole and of its individual members.

In the Marine Corps, the three people who are directly responsible for administration as it concerns individual Marines are platoon commanders, company/detachment commanders and first sergeants. This attitude of servant leadership continues down chain of command to squad leaders who lead a group of 12 other Marines and their fire team leaders who are in charge of leading a group of 3 other Marines.

This servant leadership allows Marines to focus on their tasks because they know that their leadership is caring for them and giving them the resources to perform their duties.

This does not mean that the people in leadership need to do all these things for the people they lead. I have never seen a First Sergeant set up a mess tent by themselves, however it is common for a First Sergeant to coordinate the setup and operation of a mess tent by giving their Marines the resources, time and assignments to ensure that the mess tent provides food for the Marines. A commanding officer does not iron a Marine’s uniform for them but instead gives them training, resources and time to be ready for inspection.

Tech Startup Welfare

I expect founders and executives to provide pay, benefits, perks and deal with HR-type things and office logistics and employee appreciation.

I expect tech-related leadership to be in charge of things like defining the Software Development Lifecycle (SDLC), setting up environments, making testing resources available, defining deployment process and resources, defining the review process, etc.

This does not mean all this stuff has to be done for me by leaders. A leader who over-extends themselves for their team is not a good leader, they are a martyr. Instead I want to know that my welfare is something my leadership is always considering. This can be shown by doing things, discussing things and giving me time and resources to take care of these things.

Provide Direction

If there’s one thing the military is known for, it’s giving orders. However, clear direction is not just important in the military. Clear, well-communicated direction is important for any organization. And the more trust there is between leaders and subordinates on a team, the more collaborative this direction can be.

Clear, well-communicated direction is important for any organization.

Marine Corps Direction

After a squad leader has completed a plan of attack, they will issue the attack order. The format of this order is well-defined as the Five Paragraph Order.

The Five Paragraph Order:

  1. Situation: Description of enemy forces, friendly forces detachments and attachments. This ensures everyone involved is has the same situational awareness and the same understanding of the circumstances.
  2. Mission: The expectation of results. This is often framed in relation to the larger organization’s mission.
  3. Execution: Concept of operation, subordinate mission instructions and coordination instructions. This is the details of what subordinates are expected to perform to achieve the mission objective so that everyone is crystal clear about their role.
  4. Administration and Logistics: Details any extra equipment needed and how equipment will be provide and how administrative tasks will be handled. Even in attack orders, the welfare of subordinates is considered!
  5. Command and Signal: Communication and special signal instructions and the location of the commander. This is how the team will communicate and where to go for answers and support.

Each level of command should be able to give a 5 paragraph order to their immediate subordinates until everyone is on the same page and knowledgeable of their role in achieving the mission objective.

Tech Startup Direction

Take away references to “attacking” and “enemy forces” and the 5 paragraph order is a great model for communicating direction for any organization.

When a direction is decided by my leaders I want to know why the direction is desirable, the expected results, the role of my team and myself and to know that we have the support required to reach that expected result.

If we compare a Marine Corps rifle squad or fire team to a development team then the Situation and Mission is given as part of sprint planning and task descriptions. Execution, Administration and Logistics are handled by grooming tasks and by engineers discussion implementation. Command and Signal is handled with Kanban boards and work agreements.

If we can make Epics, Stories and Acceptance Criteria consider all the things that are considered in a 5 Paragraph Order, then we can ensure that everyone is moving in the same direction.


The more that members of a team trusts each other, the better we will be by collaborating with each other and with our leadership. While the military is known for giving orders, collaboration is key to military success. A leader who does not listen to the people they are leading is not a good leader. Also when things are constantly changing, as they happen in combat and in tech startups, it is impossible for a leader to make all the right decisions on their own. When a leader knows they will get good information from their subordinates and subordinates know that their leader will pay attention to the information they provide, good things happen.

When a leader knows they will get good information from their subordinates and subordinates know that their leader will pay attention to the information they provide, good things happen.

Marine Corps Collaboration

In a combat situation, Marine Corps leaders send Marines out to patrol and scout to find information about the current situation. When reporting information on enemy units, Marines are encouraged to consider the acronym SALUTE to report the enemy’s Size, Activity, Location, Unit, Time and Equipment. Marine Corps leaders trust the information provided by their Marines and use this information to plan their strategies.

This trust and comfort with collaboration do not just happen. It takes time to build trust between leaders and subordinates. This trust is tested in everything from training to living together to going out and having fun with each other.

This trust and ability to collaborate are vital when things do not go as planned. A bedrock of trust allows a Marine Corps unit to adapt and overcome obstacles because they’ve trained enough to make the feedback loops between leaders and subordinates quick, open and honest. The best military units have the most collaboration.

Tech Startup Collaboration

A tech startup, obviously, deals with much lower stakes but the need for information, ideas and trust stays the same. It is on the leaders to ask good questions and trust our answers and it is up to us to give good, honest, open answers.

Much of the collaboration in a tech startup happen in agile ceremonies but the gist is the same. Leadership provides goals and asks for information. Subordinates provide information and opinions. The better each is at giving good, open, honest information and acting on the words and trust, the better the team performs.

Good leaders encourage collaboration and trust in their team by listening to feedback and making decisions based on that collaboration.


I work best when I know my role in a team and I know that the role I’m in is important. This structure is engrained in the military but it has to be invented in a startup and constantly involved. When members of an organization are confident of our role, feel valued and know of the resources available to us, good work gets done in a more enjoyable way.

Marine Corps Structure

Each unit in the Marine Corps has a well-defined Table of Organization (T/O) that lists the different billets (roles) and the requirements for each role. Leaders can use this to place Marines in different roles to make the unit work. Each Marine knows their role and the roles of other Marines which makes it easier to accomplish missions. This T/O allows all Marines in a unit to know the resources available to them and gives leadership an idea of their capabilities at a glance.

Tech Startup Structure

In a tech startup, near constant grown and change requires constant restructuring and constant communication. This makes creating and communicating the structure of the company very difficult. Tech startup employees also enjoy working with less structure and feel a sense of freedom and ownership in a flattened hierarchy.

Regardless of how the startup is structured, there still needs to be some structure otherwise employees will be unsure of their role, their value and unsure of the roles and resources available to them. Structure in a startup should not and cannot be rigid. This is why asking my startup leadership to provide structure is one of the biggest things I will ask of them.


Good leadership is good leadership regardless of the organization. If a leader can show care for their subordinates, provide direction and structure, and show value of collaboration, they will provide good leadership. What qualities do you expect from a good leader?

One thought on “What do I expect from my leadership in my tech startup?

  1. I could not agree more. To add to your list, a leader should be a jack of all trades, especially in a tech startup, so as to provide proper direction regardless of the challenges.

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