Recently, my daughter had an important mission - at least by teen standards. She headed to the mall to fulfill a rite of passage: getting a "birthday month free gift" at Sephora. Not for herself - but for me, her mom - because it was my birthday and she wanted to surprise me.

A store employee made a quick judgment call that made my daughter’s day - and reminded me why it matters to give team members some leeway. In the video, I share what happened (and how it could’ve gone very differently). Watch below, then keep reading for tips for your workplace, no matter what it looks like.

The Power of Judgment Calls

Whether you're leading a retail team, a hospital unit or a group of remote engineers, the people on that team are constantly making decisions that impact others - customers, coworkers, vendors and your organization’s reputation.

When those judgment calls go well, they build loyalty and trust. When they don’t, they break it.

But we can’t expect people to make good decisions unless we’ve helped them understand how to do that. Being clear isn't micromanaging - it builds confidence.

5 Questions to Help Your Team Make Better Decisions

Want your team to get better at making judgment calls? Here’s a conversation you can start today - or at your next team meeting. (Pro tip: if you put unexpected time on the calendar, call it something like “How to Make Work Easier” or “Sharing Our Best Tips” so it feels helpful, not stressful.)

These five questions can work whether you're hosting a team meeting, onboarding new hires or just checking in 1:1.

1. What are decisions you have to make at work that impact someone else - like a customer, colleague or another team?
   (Example: Letting a customer get a free gift for their family member or friend, offering a refund, saying yes to a schedule change, handling a customer complaint.)

2. What would make that other person want to work with us? What would turn them away?
   (Example: Feeling understood might bring them back. Feeling brushed off might push them away.)

3. What are you afraid of by doing what makes them want to work with us?
   (Example: “Will I get in trouble if I do XYZ?” “Will everyone request this?”)

4. What would the costs be? What about the benefits?
   (Consider time, consistency, willingness to work with us and actual business impact - not just the dollar amount.)

5. What guidelines would be helpful so you feel confident taking action and making a difference, even when I’m not available?
   (This is the key step, so I'm expanding a bit here)

This does three things:

• Opens the door to real discussions about trust, autonomy, and decision-making.

• Highlights practical needs like tools, training, or clarity on what decisions they can own (and sometimes conversations with your own leadership on what guidelines would be helpful).

• Reduces hesitation - your team doesn’t need to check in for every little thing when the boundaries are clear. That makes a real difference - for your customer, who hears “Absolutely, I can help with that,” instead of “Hang on, I need to track down a supervisor,” and for your team member, who can handle things with confidence instead of thinking, “I just don’t want to mess this up and get in trouble.”

How to Make It Work:

• Create “go for it” zones: Outline what they can decide or fix without needing approval.

• Be clear about the exceptions: Be transparent about what still needs a check-in or higher-level decision.

• Give examples: Walk through common scenarios and where the line is (e.g., “If a customer is upset, you're good to offer X without asking me.”)

• Reinforce it regularly: Revisit and adjust guidelines as your team and business needs evolve.

When your team knows where they have room to act, they’re more likely to speak up, solve problems faster and feel like their work actually moves the needle.

What This Looks Like Across Different Workplaces

It's important to give your team applicable "how to" examples - so here are a few to start:

Retail:
A server notices a guest has barely touched their meal and looks disappointed. Instead of saying, “Well, we can't give refunds” orv“Let me talk to my manager,” they say, “This doesn’t look like a hit - would you like to try something else, or maybe grab a dessert, on us?”

Healthcare:
A receptionist sees a patient confused about the next steps for their testing. Rather than rushing, they pause to explain who they'll hear from and when - because they know how much trust is at stake in every interaction.

Tech or Remote Teams:
An employee jumps in to help a teammate who’s underwater, even though the project isn’t “theirs. Because they know it matters, they've been cross-trained on what to do and know they can count on their teammates to do the same when the roles are reversed.

Hospitality:
A hotel staff member notices a guest had a long travel day and offers a free drink or late checkout. It may be small - but it’s memorable.

Teach It Before You Expect It

Great judgment calls happen when:

• People understand the bigger picture

• They’re given permission to act within boundaries

• They’ve been taught how to think through the impact

• They feel trusted - not micromanaged

In all of these situations, you’ll need to be real - talk about what happens if someone starts taking advantage or relies on the team more than is fair - but don’t build your whole approach around the lowest common denominator, or you’ll end up holding back the people who are ready to step up and make a difference.

That Sephora employee didn’t just give great service. She showed exactly what happens when someone knows they’re allowed to make things better - and chooses to do it.

That’s the kind of energy we want in every workplace. And you can create it.

If you liked these tips, check out Manager Method - a leadership platform with blended learning courses, ready-to-use materials for HR teams to track progress, run live cohort sessions and have practical tools to make the training stick. It’s all created by Ashley Herd, a former lawyer and HR leader, LinkedIn Learning instructor, and co-host of the HR Besties podcast.

To get a feel for our approach, join my upcoming August 19th webinar: Scaling Leadership Efficiently – Build a 2026-Ready Workforce That Drives Real Results.