Jonathan Roemer

10x Orgs or: How I Learned to Stop Worrying and Build Leaders


High performers are enabled, not found. Our organizations are awash in talented, intelligent individuals who can complete the tasks ahead of them. A subset of these individuals stand out as top performers. These folks hold junior to principal, tech and non-tech roles, but they all have a disproportionate impact relative to their position at the organization. They create shadow org charts, working behind the scenes to bypass traditional hierarchy and accomplish their goals. We consider them to be unique, born with an intrinsic leadership capability and sense of ownership.

This is a misguided assumption which prevents us from building the sorts of organizations that enable every individual to be exceptional. Everyone at your company has the capacity to be a high performer. To enable this, culture and incentives must align to enable the intrinsic motivation and high-trust environment required for individuals to prosper.

What does this look like in practice? The following cultural expectations and practices will build the foundation to support this personal growth in your organization.

Understand and communicate risk

Create an organizational understanding of risk exposure, risk capacity, and risk appetite. Is your organization in a highly regulated industry, where compliance and auditing is your largest risk exposure, or are you most exposed to market forces? Are you highly financially constrained, limiting your capacity to make bets on technology investments that might not pay off? Are you approaching an IPO, and the organization needs to “stay the course” for a period of time? Without risk understanding, it is impossible to tell how far the organization can flex. Understanding and communicating this ability to flex allows for informed decision making. Without this, individuals have no sense of what “big bets” may or may not be feasible to take on.

"Know the why" or, "What is the problem we are trying to solve?"

Everyone, at all levels, must understand the goals the organization is trying to achieve.

Organizational goals do not exist in isolation. They are a distillation and distribution of complexity into understandable objectives. Without this, we increase confusion and ambiguity. With these goals, we increase clarity and organizational alignment.

This becomes more critical as you scale, as a decreasing percentage of individuals at the organization have the necessary context to make good decisions.

Psychological Safety and Incentives

Ownership and empowerment necessarily come along with a degree of latitude in execution. For this to work, individual incentives must align to operational outcomes. If performance reviews will be based on OKRs defined a year ago that no longer reflect the operational reality, are folks incentivized to work on the right projects? Is appropriate risk-taking rewarded, even if a project does not pan out? Exploratory opportunities as allowed by the organizational risk profile are a necessary precondition for growth, both individually and for the business. Investigate mistakes in a way that focuses on the process and situational aspects of the failure state and the decision-making process behind that failure, not individuals or teams. Stakeholders must not fear punishment or retribution.

Policies and procedures are written to enable, not prevent

Policies and procedures must be written such that we enable a distributed command mentality, giving individuals a framework for decision making within the constraints of our organization. They must not be solely written as punitive, documenting what must not be done.

From an engineering standpoint, this means incorporating compliance and security deep into DevSecOps pipelines and making the compliant, secure way of working the easy, convenient way of working. Balancing tactical and strategic work, depending on a given team’s need to be proactive or reactive, may mean that scrum is abandoned in favor of Kanban for some subset of Engineering.

Shoe-horning in policies without consideration for how they will impact workflows hinders velocity. Attempting to prevent every failure with policy, especially manually enforced policy, is misguided. This is an opportunity to instead analyze ways of working and triage the root causes of potential failure. Nurture an operational standard of blameless, continuous improvement, open to feedback from stakeholders anywhere and everywhere in the organization. Artificially imposing ways of working simply because it is “how we do things” reduces the organization’s ability to execute.

Be clear

In all aspects, be clear in intent and outcome. Document decisions in writing, use clear and precise language, and over-communicate when decisions are made, especially when changing a previous policy.

Make the implications of the decisions clear for those impacted, and have a single source of truth that is easily accessible to the entire organization. When written decisions are the norm, teams default towards reading and asking for clarification when necessary, instead of guessing and amplifying confusion.

Use lightweight processes for decision making so individuals always know the status of a proposal.

The criticality of this only increases with the fanciness of your title, as you have a disproportionate downstream impact on the rest of the organization.


With these cultural factors in place, you do not ensure that everyone will shine. You build a foundation that allows as many individuals as possible to flourish within an organization that supports independent, informed decision making. Employees are oriented towards a shared vision of desired outcomes, and understand the organization’s ability to execute.