How to Build Judgment and Decision Making Skills: A Free Workshop for Managers
Oct 30, 2026How to Build Judgment and Decision Making Skills: Watch the Full Live Workshop
I taught a workshop at From Day One Philadelphia to a room of senior HR leaders. I opened with this challenge:
Would you send this email?
Your boss wants you to send it to the entire department. No context provided. You can tell it was written with AI. You have 30 seconds to decide whether to send it.
Thirty seconds is generous, until you're unsure.
But many of your people are using making fast calls every day and often now they're blindly accepting the advice they’re handed from AI. Now you can teach them better discernment, judgment and decision-making using a tool that’s easy to learn, to remember & to implement.
We recorded the whole session. It's on YouTube as a Mini but Mighty℠ Leadership Lesson, and it's built for you to watch with your managers.
Why judgment and decision making matter more with AI at work
AI is very good at sounding sure. We lean towards automation bias (trusting the machine). meanwhile, even before the advent of AI, we’ve never been very good at decisions, because we don’t teach the skills.
The tools keep getting faster, but the accountability will stay human. So we've got to fix this. Your managers' judgment is the last check before a decision reaches your people and your customers.
The Sign-Off℠: a 30 second judgment tool
The heart of the workshop is The Sign-Off℠, three questions any leader can run before they commit to a decision:
- Blind Spots. What am I not seeing?
- Stakes. What or who is at risk?
- Signature. Would I put my name on this?
You'll learn to notice that flicker of hesitation, to recognize it as discernment, and why it's worth listening to.
Follow along with experienced leaders & practice judgment on real decisions
You'll watch the room work through 3 real scenarios and you can pause and try it, too.
- An email your boss wrote with AI
- Merging two teams six months after an acquisition
- An AI dashboard ranking which person on a team to promote
You hear how experienced leaders reason through each one, where they disagree, and what the tool surfaces that you might otherwise overlook.
How to use this workshop to train your managers
Watch it yourself first. Then put it on the agenda for your next manager meeting. Press play, pause at each scenario, and let your own team run the three questions before they hear the room's answer. Close by asking each manager to run The Sign-Off℠ on one real decision sitting on their desk this week. Pick a difficult decision the team is facing and work through it together.
A heads up: this one looks and sounds different from our usual lessons. It's a live recording of a real webinar, the video quality isn't fantastic and there are a lot less b-roll animations. But it's worth the slightly longer run-time because you get the whole session, real perspective from real leaders and you walk away with a tool that you can put to use immediately.
Watch the full workshop free on YouTube: How to Build Judgment and Decision-Making Skills (Live Workshop)
Subscribe for a new Mini but Mighty℠ Leadership Lesson every Friday.
Lead yourself. Then lead others. Be a Boss.
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Bringing judgment skills to your managers? One video starts the conversation. Building the skill across a team takes practice and accountability. We develop Human Intelligence skills like judgment across your managers through workshops, online courses, and The Helm Leadership Essentials℠ cohort program, grounded in the Helm Method℠ and tailored to how your company works. Let's talk: https://www.bossatthehelm.com/contact