Jonathan Cutrell

Work With Me

8/28/2024

I've decided to publish my "Work With Me" doc in a place I own as I generally believe my working style largely remains the same across job roles. That said, this "work with me" doc is subject to change as my role shifts.

In general, my roles tend to be in some kind of engineering leadership position, and usually I have people that report to me. So, this document will be biased toward that perspective.

Leadership Style

I believe that leadership starts with clarity. Clarity in goals, motivation, expectations, and situation. If there is a lack of clarity, the primary job of a great leader is to find or create that clarity. Clear is kind.

What values do I represent as a leader?

  • Trust - I believe trust is the foundation of all positive working relationships. By default, I "trust but verify." When we lose trust, it becomes the top priority to resolve that.
  • Communication - the conduit of our work together is communication. This is the medium of clarity; if our communication is breaking down, all of our work will follow. Good communication is necessary to maintain trust.
  • Responsibility - The hallmark of a good leader is the ability to accept responsibility in any scenario. Responsibility does not mean "accepting the blame for someone else's mistake" - it is forward-facing. Responsibility in almost all circumstances means stepping into a situation and owning the next step.
  • Proof over gut - great leaders don't just trust their gut. They take it into account, along with a bunch of other checks and balances that are observations of reality. Going with your gut is usually a tradeoff of efficiency. For big decisions, or for repeated processes, the more we can integrate our intuition with observed measurements, the more accurate and informed our decisions can be.
  • Action and Grit - In every circumstance, I imagine I am in the pilot seat. I'm not along for the ride; I make things happen, I am a part of the solution, and life doesn't just happen to me.
    • Note that when you see a lack of this, it is often because of fear. Inaction comes often when psychological safety is lacking, because people are afraid that failure in their actions might result in negative outcomes for them. This is a disabling state that returns to the governing factor: trust.
  • Humility - Humility means being honest about the reality of our own limitations. This is at an individual level as well as a team level. The best leaders I've worked with were the first to say "I don't know", and the first to admit "I screwed up." In every case, humility worked in their favor and did not undermine their leadership; I aspire to this level of transparency.
  • Confronting Reality - Much of our jobs as managers is to find and manage the reality of a given situation. (Pro tip - This is really just an extension of humility.)
    • For example, we have a major delivery due at the end of the month, but based on our performance data we are trending to deliver end of next month, and we just lost one engineer to attrition. The reality of this situation is that there is a very slim chance we will deliver on time. Trying to get around this by using poor management tactics or rhetoric is the hallmark of an immature leadership culture.
    • The best working environments are the ones where we can observe truth together and decide what to do about it - not ones where we try to spin the situation to look better for us.

What do I expect from other managers?

  • High integrity - say what you mean, do what you say.
  • Focus on what you can do - It's often easy to see what's wrong. It's harder to decide what to do about it. But that's what a great manager does!
  • Clarity - if you need something, ask for it! If you are concerned about something, make it known.
  • Human spirit. - we don't have to approach most problems like we are saving the world. Yes, it's important to focus and do good work together, but sometimes the best thing we can do is laugh together. Managers set the tone for the workplace, and if all people see is seriousness, challenge, demand, and cold calculation, they will leave their own humanity at home when they come to work.
  • When data is available, us it. - Ignoring data is like putting your head in the sand. Backing up your decisions with data is a part of what it means to confront hard truths.

What do I expect from engineers?

  • Do the right thing. Often this means doing what you feel is the best option in the scenario; not cutting corners. However, sometimes the "right thing" can be ambiguous or dependent on the situation, which is when we talk about it as a team. Doing the right thing also extends to our moral and ethical considerations as a team.
  • Make your work visible. Work that isn't documented is hard to track. The organization and you benefit from making your work visible, both because it is shown to help with productivity and clarity, and because it provides a history of contribution.
    • Note: this isn't just about tracking tickets in Jira (though that's part of this) - it's also about making clear what your decisions are, and providing a paper trail for the soft parts of your work that don't fit in a ticket.
  • Learning mode is always-on. The industry changes quickly. What you need to know to be successful is always evolving. It is critical for engineers to pick up new hard and soft skills to grow their careers.
  • Focus on impact. We don't bike shed over unimportant details. When we disagree, we focus on what it will take to move forward, not on bolstering arguments further. "Impact" means different things in different circumstances; part of this skill is learning how to identify what impact matters in a given situation.
  • Adaptability. Every organization I've been a part of has undergone some kind of major change. Being able to ride through the changes is an important part of what it means to be a successful engineer.
    • Note that I'm not telling you you have to agree with every change; rather, that organizations will always be changing, and holding on to previous notions of an org produces friction that may not be useful to you, and instead may hinder your growth in that org.
  • Commit to your team. We win and lose together. We build our agreements, we stick to commitments, we support each other. We are not individuals working near each other - we work together.
  • Take responsibility for aligning your work with your career goals. Your biggest opportunities will come because you are ready to grab them. I am a good advocate for your success, but ultimately you are your greatest advocate.

I bring my personal values into my work; you can expect those values to drive my own behaviors. Not all of them translate in every context, which is why I'm keeping them separated for the sake of this document, but the discussion below may have some significant overlap with those values.

Overall, you can expect me to be people-first in my approach. This is an easy thing to say (and lots of people claim some version of this), but in practice what does this mean? Below I cover a handful of examples of how this plays out.

Humans are not machines. We are organic, head, heart, and soul. Our goals of working together are ultimately subordinate to our individual humanity, our personal search for meaning, our own full experience. Our emotions - fear, excitement, joy, loss, anticipation... all of these are more powerful than any OKR or Jira board can capture. This means that predictions about humans are less reliable than predictions about machines. Over the course of many humans, predictions become more reliable, but individual outliers are not only possible - they are fundamental to what it means to be human.


Written by Jonathan Cutrell, Engineering Manager at Guild Education and podcast host at Developer Tea. You can follow him on Twitter at @jcutrell.