Scarlet Ink

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Resolve Risk First - Why Complexity and Ambiguity Not Effort Should Dictate Your Focus
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Resolve Risk First - Why Complexity and Ambiguity Not Effort Should Dictate Your Focus

Too often we resolve the hardest work first, instead of the riskiest. A walk through of why that's a mistake.

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Dave Anderson
May 12, 2025
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Scarlet Ink
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Resolve Risk First - Why Complexity and Ambiguity Not Effort Should Dictate Your Focus
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Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice.

Free members can read some amount of each article, while paid members can read the full article. For some, part of the article is plenty! But if you'd like to read more, I'd love you to consider becoming a paid member!

At Amazon, like other big companies, there is an informal performance management process, where you can gently give hints and feedback and suggestions. That’s where most employees and their managers operate.

My wife in Death Valley National Park. Photo credit: Me

And then there’s a formal process, where you fill out paperwork, and officially notify an employee that they’re in trouble. That formal process is certainly scary for employees - but it’s also stressful and scary for their managers as well.

“Gabriel is still dragging his feet on every task.” Lauren said. “The last four standup meetings, he’s said he’s still working on that same two hour task. The rest of the engineers on the team have no more patience for him.”

“Ok, we talked about this last week. Have you talked to him about how he’s going to go into the official coaching process?” I asked. Lauren was Gabriel’s manager, but she was also dragging her feet on the next step.

“Well, I wrote up the coaching doc. And I created a spreadsheet for all the milestones of his deliverables.” Lauren said. “I’m getting closer to ready.”

I shook my head.

“The most important thing right now is that Gabriel gets clear feedback that his performance needs to improve immediately, and that he is going to go into our coaching process. Nothing else should happen until you do that. That needs to happen immediately. Today.”

Everyone procrastinates. We put off doing our taxes, mowing the lawn, and writing that novel I keep wanting to write. The more mental and physical energy a task will take, the more we avoid it. We are particularly good at avoiding complexity, uncertainty, and risk of failure.

In our private lives, it results in a family neglecting to put together a will, or a planned kitchen remodel languishing.

At work, it can result in a project being delayed, a great employee quitting, or a poor employee sticking around.

I know I didn’t provide all the context of the above story, but Lauren was dragging her feet. She was fine giving Gabriel polite and nice manager feedback that he really needed to get his work done. But when it came time to tell Gabriel that his career was in jeopardy, she did everything in her power to put off the work.

She decided she needed to write a better document, with better task explanations. She needed a spreadsheet of due dates to make certain the deliverables were clear. In other words, she wanted to do all her time consuming tasks, before she got to the single complex task.

Except that complex task was the meat. The most important thing was that Gabriel got harder feedback, so that he could either pick up his performance, or at least he’d know that his time here was short.

For a lot of our work, our temptation is to look at the long list of tasks we need to finish, and decide that it doesn’t matter which we do first. Perhaps we’ll just do the most time consuming task first. Except it does matter. Choosing to address the risk up front improves outcomes.

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