16 Lessons Learned From Five Years As An Enterprise Technologist, Part 1

By Moshe Karmel, Software Architect, Rocket Mortgage


Going from the classroom to the boardroom can be a scary experience. The larger the company, the more intimidating it can seem. I’ve compiled a list of tips and tricks that can help ease you into the enterprise software world. Most of these are lessons that I’ve learned the “hard way,” meaning I’ve made mistakes and I’ve grown from them. It only seems fair to pass this knowledge along to the world.

This is the first part in a two-part series. Once you finish reading, check out Part 2.

I just hit my five-year anniversary at Rocket Mortgage, and I’ve been reflecting on the past. In this article, I’ll share some of the tips, tricks and lessons I learned while creating software at a large fintech enterprise over the last five years.

A Few Disclaimers:

  • I’m not necessarily fully compliant with all these suggestions; I’ve just noticed them along the way.
  • Your experience may vary! These have worked well for me, but we’re all different.
  • Rocket Mortgage already has some really good ISMs — philosophies that give our enterprise and team members a solid foundation — and the below lessons are principles I’ve relied on in addition to those.

Feedback In Private, Praise In Public

“Praise in public, criticize in private.”
– Vince Lombardi

Although a team member may have screwed up, there’s never a good reason to call them out in a public setting. No one likes being put on the spot for their mistakes. On the other hand, when a team member does something great, shout it from the rooftops.

Talk To People — And Also Listen

“When people talk, listen completely.”
– Ernest Hemingway

Organizations are just collections of people, and you can learn a lot by talking and listening to them. Especially in a fully remote world, it’s important to take the time to communicate with other team members. Additionally, always keep a high level of awareness and an ear to the ground to listen out for things that are relevant to your team.

When people talk, listen to what’s between the lines. For example, “Hey, you’ve done this before, right?” might be their way of asking, “Hey, can you help me out with this?” (This is one of the lessons I’m still learning!)

Ask A Lot Of Questions, Specifically “Why?”

“Cake is the answer. What was the question?”
– Unknown

It’s always important to understand why you’re writing code for a specific project before you start, especially when talking with “The Business” or any stakeholders in a project. As I like to say, “Whys make you wise.” For example:

The Business (TB): Can you create a button that will close the ABC task? And then create a way to export the task data to Excel?

Developer: Why?

TB: Because we want to track if team members do X, and the way we do that is by opening an ABC task, closing it and pulling it out into Excel and filtering by Y.

Developer: Why not just have a database table that stores information about X, and then has a user interface that shows the data filtered by Y?

TB: Sure, that’ll work too.

You shouldn’t think about how you will do something until you clearly define what you’re doing and why you’re doing it. For example:

Engineer 1: Hey, we’re going to use Elixir and Kubernetes as the solution.

Engineer 2: Wait, what was the problem again?

A deep understanding of the problem will lead to choosing the right solution.

Processes Are Good, But Don’t Forget To Think

“If everyone is thinking alike, then someone isn’t thinking”
– George S. Patton

Enterprises have processes. Typically, they were created as a response to address specific problems. By definition, processes apply a broad-brush approach. Sometimes you can be so deep in the weeds on a process that you lose sight of why it exists in the first place. I often see this with work prioritization, where the process says X is more important, but deep down, everyone knows that Y is more important. So yeah, let’s do Y.

This also applies to those times that you know you can fix something in 30 seconds, but how it’s traditionally done says to create a story, get it assigned, etc. Don’t forget why we’re here — to make team member and client lives easier. You can’t go on autopilot. Use the process as a tool, but also use your common sense and do the right thing.

Help People And Develop Relationships

“Success comes in direct proportion to the number of people you help.”
Will Craig

If you see someone struggling and you have the capacity to help them, do it. It’s that simple. Side effects of helping people may include:

  • Becoming a kinder person.
  • Those same people being more interested in helping you in the future.
  • Your teammates having greater respect for you and looking to you for guidance.
  • An effect on your personal brand where other folks know who you are, thereby raising your credibility.

Everyone Is Different

“Different strokes for different folks.”
- Unknown

This is true in life generally, but it becomes much more pronounced at a large organization. Previously, I worked at a much smaller company where we all had the same quirky sense of humor. When I moved to an organization with thousands of people, I realized that I needed to be much more specific in my communication. While working with so many other team members, it became abundantly clear that not everyone thought like me. You can’t assume you have alignment just because you’ve said your piece. There may be some team members who deeply disagree but aren’t speaking up — yes, even after you ask “Hey, does anyone disagree?”

How can you solve this problem?

Keep in mind that we’re all different and communicate in unique ways. Reach out to quieter team members individually and try to get their perspective and keep them in mind in the future. Understand your title may be intimidating to some folks. Try to understand the different cultural nuances with the way people communicate.

Additionally, a good rule-of-thumb is the wider the communication, the more likely it can misinterpreted. In a one-on-one chat, speak differently than an email sent to 500 people.

Humor Can Break Barriers

“Laughter is the best medicine.”
- Unknown

Frustrating situations are inevitable at any organization. A change in requirements, a late-night tech incident, a mistake by another team, etc. Instead of feeding the tension with grumbling and finger-pointing, try diffusing it with humor. Everyone will be calmer and happier as a result.

(Unless of course, you’re in a situation where humor will get folks upset. In comedy, timing is everything. Knowing your audience is also key.)

Feedback Is A Gift

“Feedback is the breakfast of champions.”
– Ken Blanchard

If you speak up and give constructive feedback, good things will happen. Most people aren’t malicious. They may be doing something you don’t understand because it’s the only way they know. Teach them new, better ways to do things. Usually, they will be appreciative of good, targeted feedback. If they’re not, that’s their loss. You’ll be surprised how far quality feedback can go.

In return, when people give you feedback, listen to it. Swish it around in your head. Tell your ego to pipe down for a second and think about whether they may be onto something. They probably are.

Read Part 2 of this series for eight more lessons.

Questions? Thoughts? Leave some feedback in the comments below.

Moshe has worked in technology for more than seven years, often diving into new technologies and learning as projects evolve. He likes to think he’s an architect who is a “doer” and tries to keep coding whenever possible. When he’s not working on stuff, he can be found studying Talmud, making dad jokes and hanging out with his family.

We’re hiring! Interested in joining us in reshaping the fintech industry? Check out our technology openings.

These opinions are those of the author. Unless noted otherwise in this post, Quicken Loans is not affiliated with, nor is it endorsed by any of the companies mentioned. All trademarks and other intellectual property used or displayed are the ownership of their respective owners. This article is © 2020 Quicken Loans.



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