Five Powerful Ways To Turn Your Software Development Organization Into a Learning Machine

Milo Todorovich
CodeX
Published in
2 min readJan 10, 2022

Let’s look at what it takes to create a learning organization that leads to the innovation all executives dream about.

Photo by ThisIsEngineering from Pexels

1. Lead with problems

Sharing problems with developers leads to happier users, improved quality, shorter cycles, and retention — all the things executives want from their development teams.

Apple has product managers who engage developers with problems, leading to beautiful software and amazing market success. Basecamp provides their developers with a problem to be solved and they story about why it’s important and where it came from; then pass over responsibility, agency, and autonomy. When President Obama brought a team together in Silicon Valley to fix healthcare.gov , he didn’t provide them with a list of features to build. Instead, he presented a problem: “Your country needs you.”

We are at a point in history that technologists need to be part of the decision-making process for nearly every important decision.
— Evan Cooke, Twilio co-founder

Providing autonomy to developers frees them do to their best work while minimizing the chances that they leave.

2. Socratic method

You can model a learning environment at work using the Socratic method, asking questions that let employees teach themselves.

As a leader, your position provides direction, context, guardrails and support for those around you. You don’t need to have all the answers. Asking the right questions lets your team arrive at better answers.

3. Low-stakes projects

Projects where an alternative also exists provide a path for upcoming leaders to learn by doing.

Look for projects that have a fallback solution, either another system or a potential vendor. Internal systems and low-usage features can provide this opportunity. Give your team some room to be creative.

4. Root causes in the system

Look for your root cause at the system level. People will make mistakes; this part is inevitable. Ask “how did our way of working get our people into this situation?”

Finding the root cause of an outage looks at the system of working to determine how that system allowed a team member to release a mistake that impacts customers.

5. Training and education

In 2018, Target invested 20% of their developers time in training and education.

This type of investment allows Target to continue as a viable player in the retail space. These investments have led to multiple in-house brands that exceed $1 Billion annually. They have adapted their big box format for the digital age.

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📋 About Milo

I am a tech executive, writer, speaker, entrepreneur, and inventor. I’ve been developing software since 1995 and developing teams for over a decade. 🚀

I write articles about software, engineering, management, and leadership.

You can also follow me on Twitter. 🐦

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Milo Todorovich
CodeX
Writer for

Coaching software engineers to more frequent software delivery | Software Engineer | Engineering Management | Leadership | PhD Candidate