Debugging Difficult Conversations
Most advice about difficult conversations starts too late. It assumes you already know which conversation you need to have.
But what if you're debugging the wrong problem?
Robert Harris draws on 25 years of engineering leadership — and an earlier career in psychology and anthropology — to examine the human systems underneath the conversations leaders avoid, mishandle, or never realize they need to have. Using real stories from his career, from a production outage to a board asking, “How many developers do we need to fire?“, he'll show why the conversation that looks obvious on the surface is often very different from the real one underneath.
Because before you can have the difficult conversation, you have to find it.
This 60-minute session borrows the engineer's own mental model: debugging.
Humans won't show you their internal state, call stack, or debug log, so engineering leaders have to work from the signals the system actually gives them. Robert introduces three forces operating underneath difficult conversations - power, risk, and reward - and three signals that appear when those forces get out of balance: silence, conflict avoidance, and withdrawal.
Then he puts the model to work.
Through real conversations from his career, attendees will debug what happens when a leader accidentally teaches a team to stay silent, when a promotion changes relationships with former peers, when a boss makes uncertainty dangerous during a production incident, and when a valued employee has already decided to leave - whether either person is ready to admit it yet.
Each conversation becomes a debugging session: inspect the inputs, read the hidden signals, identify the strongest forces, and test the assumptions behind the apparent problem. Sometimes the assertion passes. Often it fails. And sometimes the first difficult conversation you need to have is with yourself.
Attendees will leave with:
- A diagnostic model for reading power, risk, reward, silence, conflict avoidance, and withdrawal during difficult conversations
- A debugging approach for separating the apparent problem from the real conversation underneath it
- Practical questions for testing their own assumptions before trying to correct someone else's behavior
- A better understanding of how every difficult conversation teaches the team whether the next difficult truth will be safe to say
Whether the conversation is with your team, your boss, or yourself, the goal isn't to become fearless about conflict. It's to stop solving the wrong problem because you never found the real conversation.
About Robert Harris
Robert N. Harris is the Founder of Coded2Lead, a coaching practice dedicated to transforming software engineers into emotionally intelligent leaders. A 4x software engineering executive based in Houston, TX, Robert draws on 20+ years of pragmatic leadership experience - alongside a unique academic background in psychology and anthropology - to tackle the toughest problems in technology: the human ones.
His claim to fame is helping small engineering teams punch above their weight. He’s helped companies shrink product cycles from months to weeks, launch new products in months instead of years, and scale revenue by 10x.
He’s mentored tech leads, managers, and founders across industries, blending technical rigor with surreal metaphors, visual storytelling, and deeply empathetic insight. Whether he's refining a brand identity or helping a developer navigate imposter syndrome, Robert’s approach is iterative, creative, and always human-centered.
When he’s not coaching, you’ll find him in the garden, under the stars, or behind the wheel - using race cars, astronomy, and nature as unexpected mirrors for leadership growth. His mission: to help engineers debug themselves, lead with courage, and build systems where people thrive.
If a business is willing to invest in software engineering, he’ll make sure they get the most out of that investment.
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