Thank you for Subscribing to CIO Applications Weekly Brief
A featured contribution from Leadership Perspectives, a curated forum for enterprise technology leaders, nominated by our subscribers and vetted by the CIOApplications Editorial Board.

Little Caesars Pizza
Jim Mason, Vice President of Software Engineering
Streamlining Technology Execution Through Concise Communication


In an interview with CIO Applications, Mason discusses execution discipline, communication clarity and the value of shared leadership insight.
A Glimpse into a Tech Leader’s Daily Routine
A day in my life starts early in the morning with a rollout, where we implement new updates. We do release every day or at least a couple of days each week. Once the rollout is complete and everything has been tested, we call the day good and move on to the next level of information—tracking and reporting on a wide range of technology.
We monitor numerous stores and various support mechanisms across all of them, both domestic and international. Additionally, we have innovation projects and the teams under my leadership are responsible for rolling out those innovations.
I use a principle I call life at 255. The name comes from the early days of Excel and text messages when character limits forced people to make their points clearly. In those situations, you had to get to the point because the space did not allow for anything else.
Today, we often over communicate by leading with explanations and context instead of just saying what we need. If I ask for a decision, I say what I want first and include two or three bullet points explaining why. If someone wants more background, it can be provided separately.
A common mistake is writing long messages that cause confusion instead of solving it. Many times, I have seen people respond to an email only to find out that the answer was already included in the message thread. That happens when the core message is hidden too far down.
Tools like Teams and WhatsApp are useful when they are used to finalize answers instead of explaining everything. Communication works best when it starts with a clear statement of need and assumes the recipient already has enough knowledge to respond.
Leadership Advice on Sharing Expertise Effectively
My biggest advice to other leaders is to share your tech, skillset and leadership knowledge openly whenever possible. I’ve always believed in working side by side and comparing notes. When I talk to someone from another company, I want to know how they do things and how we do things. The goal is to find commonality or figure out whether what they do is better or what we do works better for us.
-
Be concise in communication, stay specific and drive decision processes with consistency by starting with what matters most
I’ve been fortunate to work in four or five different industries. Food is different from telecom, which is different from cars and elections. The differences are clear, but what stays consistent is the importance of software development, lifecycle support and anticipating issues.
One way I look at it is through what I call right-to-left thinking. Start by asking what the system is supposed to do when it’s done, then work your way backward. That way, you’re trying to think it through and whatever you learn along the way becomes a bonus, not something you should’ve already known or happened without planning.

