1/18/26 - Documentation Feels Awkward—Until You Need It

Most leaders don’t avoid documentation because they’re careless. They avoid it because it feels uncomfortable, formal, or unnecessary—especially when things are “mostly fine.”

The problem is that documentation usually becomes urgent after something has already gone wrong. By then, leaders are trying to reconstruct decisions, conversations, and expectations from memory—often under pressure.

January is a good moment to reset this habit.

Focus Area 1: Documentation Isn’t About Distrust—It’s About Clarity

One of the most common misconceptions is that documenting issues signals a lack of trust. In reality, documentation creates shared understanding.

Clear documentation answers questions like:

  • What was expected?

  • What actually happened?

  • What support or guidance was provided?

  • What changed—or didn’t—after that conversation?

When expectations are documented, employees are less likely to feel surprised or singled out later.

Focus Area 2: Memory Is Not a Reliable System

Leaders often believe they’ll “remember the details” if they ever need them. But stress, time, and emotion distort memory—especially months later.

Even brief notes taken at the time of a conversation are far more reliable than trying to reconstruct events after a complaint, resignation, or dispute.

Documentation doesn’t need to be perfect. It needs to be timely and factual.

Focus Area 3: January Is the Safest Time to Start

If documentation habits have been inconsistent in the past, January offers a clean reset point. Expectations can be clarified without it feeling reactive or punitive.

This is a good time to:

  • Align on performance expectations for the year

  • Clarify attendance or conduct standards

  • Begin documenting coaching conversations consistently going forward

Starting now prevents the appearance that documentation only happens when someone is “in trouble.”

Focus Area 4: Good Documentation Protects Everyone

Well-written documentation doesn’t just protect the business—it protects employees too.

Clear records help ensure:

  • Consistent treatment across employees

  • Fair decision-making

  • Transparency around expectations and outcomes

When documentation exists, fewer decisions feel arbitrary, and fewer conversations escalate unnecessarily.

How This Ties Together

Documentation isn’t about creating paperwork—it’s about creating clarity before conflict.

The goal isn’t to document more. It’s to document better, earlier, and more consistently—so decisions feel grounded instead of reactive.

Looking Ahead

Next week, we’ll look at why performance conversations tend to get delayed—and how waiting often creates bigger problems than addressing things early.

New Bear Briefs are published weekly.

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1/25/26 - The Conversation You’re Avoiding Is Probably the One You Need to Have

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1/11/26 - January Slumps Are Normal. Mishandling Them Isn’t.