ABOUT THIS EPISODE
Observation stops feeling like a threat when we treat it as a tool for learning instead of a surprise evaluation. We share how leaders can use quick, low-stakes moments of watching the work to coach with precision, build psychological safety, and help people improve faster.
• why “observation” triggers anxiety at work and how organizations create that reaction
• a simple story that shows why staying to watch matters
• how educators use observation to spot thinking, not just mistakes
• why “do you understand?” fails and performance becomes visible in action
• how to “watch the work” in real workflows and software struggles
• modeling as leadership development through seeing an experienced leader think
• psychological safety as the condition that makes observation useful
• language shifts that change observation from judging to learning
• making observation ordinary through small, frequent, low-stakes check-ins
Look at your calendar. Find the next formal observation or performance review that you have scheduled. Keep it. You might need it. But then ask yourself, why am I waiting until then to see the work? What if before the formal observation you had three or four much smaller moments of observation? Not evaluation or scores or documentation, but just curiosity, just learning.
SHOW NOTES 🔗
TRANSCRIPT 🔗
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Welcome to Lead with Learning.
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I'm Tess, and here we explore what happens when the science of learning meets the art of leadership.
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Let's get started.
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There are probably few words in the workplace that can make an employees sit up a little straighter more than this one.
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Observation.
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Because when we hear I'm going to observe you, most of us don't immediately think, like, great, a learning opportunity is coming.
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I can't wait to get this feedback.
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We think, what are they looking for?
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Is this going in my file?
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They're going to watch me do something wrong.
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And if we're being honest, a lot of organizations have trained people to have that reaction.
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Observation gets attached to performance reviews and compliance checks and formal evaluations and those lovely calendar invites with titles like performance observation.
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So today I want to make a case for something a little different.
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What if observation wasn't primarily about evaluating performance?
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What if it was one of the ways we actually help people learn?
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Because educators have been using observation for a very long time, not simply to judge whether someone is doing something correctly, but to figure out what the learner understands and where they're getting stuck and what they're trying and what kind of support would move them forward.
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And there's a version of that happening in the workplace that I think we're seriously underusing.
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It's the moment when a manager sits down next to someone and says, Show me how you're doing this.
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And not because they're conducting an evaluation, but because they're actually trying to understand the work.
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And that distinction and intention really matters.
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Let me tell you a story about an observation that I did with my 13-year-old daughter.
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My daughter was trying to put up command hooks in her bedroom.
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And she's a super smart girl, and she had already put up command hooks in her bathroom.
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And so she understood the process, right?
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And so she wants to put up these lights in her room.
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And so we got these little mini command hooks that she's gonna put across the wall to be able to string up the lights.
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So in my thought process, I'm like, she's already done the command hooks in the bathroom.
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She understands how to do it.
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I set her up and I said, okay, remember the process.
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You take off the one that says wall, you hold it onto the wall, and then you peel off the sticker, put on the hook, you're good to go rinse and repeat through 500 of these or whatever until you have as many as you need to hang the lights.
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And I was about to leave the room, but that's when the educator in me, the learning coach in me, thought, I just need to sit here for a minute and just give her a little bit more of my time.
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And so I gave her the instruction, she had already done it.
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We're applying it to a new situation, but very, very similar.
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And she goes to put the command hook on the wall, she puts it on.
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Then when she goes to peel off the sticker, she peels the sticker that's like the one that you're supposed to use to release it.
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And then she's like, Why did this fall off the wall?
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What is happening?
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Okay.
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So then, okay, no problem.
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Remember, that's the part you use when you're removing it completely from the wall.
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This is the part you have to pick it off of this one.
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Look how tiny it is, right?
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So we show her how to do that.
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Okay.
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So then she, I think, okay, she's good.
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She's got it.
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So then she goes and puts it on the wall, but here she's decided she's put it in the wrong place.
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She now understands the process, but she's done it wrong because she's put it up too high.
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So then she has to remove that one.
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Then she goes to put on another hook on the wall.
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And at this point, I can't even remember what went wrong.
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Something else went wrong.
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I sat there with her for four different command hooks that all did not attach to the wall correctly.
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And thank goodness I stayed and I observed a little bit so that I could give her the feedback.
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So many times we walk away from people.
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We say, okay, here's what you do.
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Here you go.
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I'm gonna go back to do all the things I have to do, right?
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Or we say, hey, they've done this before.
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It's exactly like that other task.
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It's so much like that other project.
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I'm gonna give them the new directions, and look, they're gonna be ready to go.
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I am not suggesting that my 13-year-old having issues with command hooks on her wall is the same thing as your multi-million dollar company and the employees that work for you needing to figure out the things you need them to figure out.
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But what I'm saying is there are times where we just walk away because we assume that that person can apply that knowledge into a very similar situation.
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And there's times that they totally can.
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But if we wait, if we give that moment of observation, if we stay for that extra two or three minutes just to help them get started, or to say, hey, let's get this started together, you can alleviate so many issues.
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If I had left, there would have been a lot of frustration.
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If I had left, it definitely wouldn't, the project definitely would not have gone well, right?
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So the idea is to just stay for a little bit and give some information, check in, find out what's going wrong, alleviate and give that targeted specific feedback to the exact thing that's frustrating, so that then, yes, they can continue to do the project and keep going just as it was intended.
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So if we go back into the education realm, observation in education is a lot more than just watching.
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If you think about a teacher who's working with a student who's struggling on a brand new skill, that teacher doesn't necessarily need to give the student another test.
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They might just need to sit beside them and watch.
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What does the student do first?
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What strategy did they choose?
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Where do they hesitate?
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What do they already understand?
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What mistakes are being made?
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And probably most importantly, what does that mistake tell me about their thinking?
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Because that's observation as assessment, but it's also observation as instruction.
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Because once the teacher understands what the student is doing, then the teacher can respond and give supportive, helpful feedback.
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Maybe the student needs another explanation, but in a different way.
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Maybe they need to see it modeled, or maybe they need more time to practice.
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The observation gives the teacher information that they couldn't get from simply asking, do you understand?
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And that's important because people aren't always particularly good at accurately reporting what they know.
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Sometimes we think we understand something.
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We we completely believe we get it until we actually have to do it.
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That's when the gap becomes really visible.
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Don't just ask people what they know, watch what happens when they use it.
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So let's take that a step further and put it back into the workplace.
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Because sometimes in the workplace is where observations go wrong.
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Some organizations have reduced observations to a very specific event, one that goes on the calendar and the employee knows it's coming, the manager has some sort of checklist, someone observes, someone writes something down, there's a conversation about it, and six months later it happens again.
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Now, there are certainly situations where formal observation is necessary and supportive.
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But if that's the only time that you're observing someone's work, you're missing an enormous space for learning opportunities.
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Because real learning doesn't happen in those anxiety-producing observations that happen twice a year.
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And performance doesn't suddenly become visible just because the calendar says it's the day to observe.
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In fact, the more we make observation a rare and high-stakes event, the more likely we are to create anxiety about it, which then changes behavior.
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And then you're observing someone who's on high alert and they're making more mistakes because they're anxious.
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You're not even actually seeing their real workflow.
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Think about how different you behave when someone says, I'm gonna sit here so we can work through this together, versus, I'm going to observe you do this and we'll discuss your performance afterwards.
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It's the same basic activity, but it's a very different psychological experience.
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An observation doesn't have to mean I'm watching you.
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This is where I think leaders can borrow something important from education.
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Imagine a manager notices that an employee is struggling with a new software system.
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The traditional response might be, have you completed the training?
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Yes.
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Did you watch the tutorial?
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Yes.
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Did you read the documentation?
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Yes.
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But yet they're still struggling.
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So the manager schedules a performance observation.
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But there's another option.
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The manager could say, Hey, let's sit down together.
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Show me what you're trying to do.
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And then they watch.
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You don't have to watch the person, watch the work.
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Watch the employee navigate the system and then explain their thinking.
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The manager can ask a question, employee might get stuck.
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Suddenly, we're discovering something.
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Maybe the employee wasn't resistant to the new process.
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Maybe there's a step that isn't clear.
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Or maybe the training demonstrated the process differently from how it actually appears within your work system.
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Maybe the employee developed a workaround because that original process doesn't fit with the reality in the job.
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Or maybe they understood the process perfectly, but they just haven't had enough opportunities to practice.
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And you wouldn't know that from a training completion report or from a performance review.
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And you might not even know it from asking, how's that new system going?
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But you can see it when you sit down and work through it together.
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That's observation as learning.
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And there's another powerful thing happening, and that's modeling.
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Observation doesn't only allow the manager to see the employee, it allows the employee to see the manager think, which is so powerful when you're developing people.
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Let's say you're working with a new manager who's struggling with difficult conversations.
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You can give them a training module on difficult conversations or a framework, you could give them a book, but if you have them sit in on a conversation with you, now they're observing how an experienced leader navigates the actual situation.
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How did you open the conversation?
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What questions do you ask?
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How do you respond when the employee becomes defensive?
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When do you pause?
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What do you say when you don't know what to say?
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That's not just information transfer, that's learning through observation and modeling.
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And workplace learning research continues to point towards the value of learning embedded in authentic work, including observation, practice, reflection, coaching, and role modeling, which gives us a pretty compelling sequence.
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Watch, try, reflect, try again.
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That's way different from attend a training, check a box, hope it transfers.
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So how do we make observation feel safer?
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This is where leadership really matters, because if every observation has consequences attached to it, employees are gonna protect themselves.
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And honestly, it makes sense.
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If I believe that everything you see could eventually be used against me, I'm gonna show you the safest version of my work.
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I'm gonna choose the easiest customer.
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I'm gonna ask fewer questions, I'm going to avoid trying something new, and I'm gonna hide.
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I'm gonna hide all the spots where I'm struggling.
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And that's exactly the opposite of what we need if the purpose of observation is learning.
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Research on psychological safety consistently points to the importance of creating environments where people can disclose uncertainty and ask questions and raise difficulties and engage in productive learning behaviors without fear of negative judgment.
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So if you want people to become better through observation, leaders have to change the message around observation.
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Instead of I'm observing to see how you're doing, you could try, I'd like to see how this process is working in practice.
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Or instead of, I want to see if you're following the process, try, walk me through how you're approaching this.
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And instead of I'm gonna sit in on your meeting, try.
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Would it be helpful if I join the meeting so that we can debrief after?
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The language isn't softer, it changes the purpose.
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So, one of the biggest shifts that I would encourage leaders to make is to stop making observation an event.
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Make it just part of ordinary life.
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Make it part of how you lead.
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Sit beside someone while they work through a problem.
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Ask a new manager if you can sit in on a team meeting, not to grade it, but to understand what they're experiencing.
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Have someone share their screen and walk you through a process.
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Shadow someone for 20 minutes.
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Ask an employee to show you what the new workflow actually looks like.
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And then talk about it.
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It's not here's what you did wrong, but tell me what you were thinking or what were you trying to accomplish?
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Where did you get stuck?
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What could I do to make this easier?
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Because now observation is becoming a conversation about learning.
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And here's the interesting part: the more frequently these low-stakes observations happen, the less threatening observation in general becomes.
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Because employees understand my leader isn't only watching when something is wrong.
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My leader isn't waiting for the annual review to tell me what they noticed.
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My leader actually wants to understand the work.
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That creates a very different relationship between observation and performance.
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So, what could this look like on Monday morning?
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Here's a simple challenge.
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Look at your calendar.
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Find the next formal observation or performance review that you have scheduled.
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Keep it.
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You might need it.
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But then ask yourself, why am I waiting until then to see the work?
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What if before the formal observation you had three or four much smaller moments of observation?
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Not evaluation or scores or documentation, but just curiosity, just learning.
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Sit with that person for 20 minutes, watch them handle a task, ask them to walk you through our process, join in on a meeting, look at a piece of work together, and then ask, what are you noticing?
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Because that's the shift.
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Observation doesn't have to be something we do to employees, it can be something we do with them.
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And when we make that shift, observation stops being a spotlight that people dread.
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And it starts becoming a tool that people can actually use to get better.
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Because the goal isn't to catch people doing something wrong.
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The goal is to understand the work well enough to help people do it better.
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And maybe that's another thing businesses can steal from education.
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If you want to help someone learn, sometimes the best thing you can do is sit beside them and watch.
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Thanks for listening to Lead with Learning.
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I hope you're walking away with something you can put into practice.
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Until next time, let learning change the way you lead.