Three Powerful Checkpoint Questions to Level Up Your Leadership

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Welcome back to Leveraging Leadership, where we unpack the art of business leadership.
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I'm your host, Emily Sander, executive advisor to founders, CEOs, leadership teams, and chiefs of staff.
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This show is all about finding your points of greatest influence and leveraging them to better serve those around you.
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Tip of the day for you: set up important checkpoints for yourself How this topic came up was because one of my coaches recently retired.
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So I have a team of coaches and mentors and advisors and a board of directors for, me personally, all those different things, for personal growth, wanting to get better, push yourself, et cetera.
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And one of my longest-standing coaches, I've been with him for years and years and years, retired.
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He wants to spend more time with family and it's fantastic for him.
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And as we wound down our sessions and engagement, we worked on some questions that I could ask myself on a regular basis, and they were out of themes and patterns and topics that he and I had discussed repeatedly, and it was the n- natural extension or next extension of those themes, patterns, et cetera.
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So I'm gonna share with you the three questions.
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These are not the best questions or the only questions or anything like that.
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They're just the ones that happen to be the most appropriate and relevant for me right now.
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Can and will change, but for me right now, and you are happy to borrow them if, if you so choose.
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So, I have picked every other week just to run through these three questions, and I journal them.
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So super basic, super easy, nothing fancy schmancy, just I write it down, um, a sentence or two, and that's it.
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If it's longer, then it's longer, but a sentence or two and that's it.
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It literally can take five minutes.
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Um, it usually takes like ten-ish minutes on average.
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But it's a, it's a pit stop, it's a checkpoint, it's setting up this practice of me, pushing myself to get better, having a point of self-reflection to go,"Whoo.
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Okay.
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Let me just step out of it for a second, put my head up.
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Okay, let me check in." Three questions, boom, boom, boom.
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Sometimes I sit there with tea and sit there for like 20 minutes and think about these things.
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Sometimes I'm like,"Bullet points, baby, let's go." Boom, boom, boom, and we're done.
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On to the next thing.
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Cool.
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So here are the three questions.
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Question number one: Where are you getting in your own way?
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Where are you getting in your own way, Emily?
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So sometimes there's obstacles that are external, and there's actual things happening, and sometimes I get in my own way, and I fall over my own feet, and I put up obstacles that are not there, and I make stuff up in my head.
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And when I'm like,"Oh, wait, where am I, like, making this harder on myself unnecessarily?
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Do I need to do it that way?
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Or are there dozens of other ways or hundreds of other ways if I'm creative, if I'm open, if I don't have to do it that way?" all these different permutations of answers to that question.
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But where am I getting in my own way?
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Um, and sometimes you can add your name to that.
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I've...
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I know people who sometimes wanna make it personal, so they would be, like, looking at themselves in the mirror and saying, like,"Where are you getting in your own way, Emily?
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Where are you getting in your own way," into your name here.
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So that can be a question.
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Second question is, what's a middle way?
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So I tend to, getting a lot better, but I tend to or I have tended to see things in black or white.
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It's either this or that.
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It's all this or all that.
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It's 100% or 0%.
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and this has gotten me into trouble in many cases.
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It's appropriate sometimes, but most of the time there's a lot of gray, and you wanna find a middle way, and there's extreme avenues open to you, but then there's a whole ocean full of middle ways and middle options.
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And, oh, you could do this.
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You could do some of this and some of that.
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You could do this...
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You could do this, this time and then that the next time.
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Like, you can be flexible.
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You can, uh, be adaptable.
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So all these things like, all right, am I thinking in extremes?
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Am I putting an ultimatum on myself or others that doesn't need to be there?
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Am I thinking in black and white, or am I seeing the middle way?
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What's a middle way?
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Doesn't mean, by the way, I have to do the middle way or agree with the middle way or proceed with the middle way, but what is a middle way?
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Not the middle way, a middle way.
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One middle way out of hundreds, and just have the mental flexibility and fluidity to come up with,"Oh, yep, I am kind of in black and white mode there.
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Let me just come up with a middle way just as a thought experiment, just to get my mind moving in that direction," or just reminding myself,"Oh, yes, there is almost certainly a middle way here, Emily.
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Let's just name one of those things just to be creative or just to kind of get that, get that side of things going." Okay?
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So where are you getting in your own way, and what's a middle way, so a counterpoint to black and white or extreme thinking?
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And then my third question I ask myself is, who can help with that?
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So I have all these things that I wanna do, and all these projects, and all these initiatives, and all these, like, mover and shaker things that I wanna put out in the world, and, connections I wanna make.
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And sometimes I fall into the trap of trying to do it all myself.
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I know I'm not the only one out there, so if you're raising your hand or going,"Amen, sister," like, more power to you.
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But who could help with that?
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I, I need to do that, or better said, that needs to get done.
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So if I've gone through my, action steps or action items, or like, hey, like, to get from point A to point B here, I've gotta do these things.
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Um, better said, these things have to get done.
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So I'm pulling back the superfluous, and they're like, that's...
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Like, I'd like to have it.
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It's nice to have, but not in the MVP version.
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Or, you know, maybe, uh, I, I really am prone to that and I really would prefer that, but honestly, if we're gonna get it done, we just need these three steps, and that fourth step can wait till maybe later or maybe never.
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Okay, so once you've kind of stripped it down to like, okay, like, instead of these 17 steps, we really need these three to get it done.
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Instead of going, okay, gotta have these three things.
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No room to budge on these three things.
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Um, w- do you have more hours in the day so I can get these three s- things done?
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Like, I have a day job, I have kids to take care of, I've got this, I've got that, I've got commitments out the gazoo, and you're a- you're adding three steps to my plate.
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Um, or maybe I'm adding three steps to my own plate.
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But these have to happen and I...
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This is important, and I've gone through the exercise o- of my why and what's important, and what really has to happen.
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It's like, this is important.
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From A to B, I gotta hit these three steps.
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Who can help with that?
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Whoa.
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Whoa.
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Other pe- I can a- I can ask for help from other people?
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I need to be reminded of this.
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I'm probably not the only one with, with this one either, but like, who can help with that is a very powerful question.
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Like, oh, it opens up a whole new branch and channel of thinking for me, and it makes me think of like, okay, who...
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So you can, you can interpose what, like what can help me with that, if there's automation or a tool or a system, things like that, but you get the point.
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Like, who could help me with that?
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I'm not automatically the default for all this new stuff.
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I can very well identify this for myself, um, but it doesn't necessarily mean I have to do it.
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So if there's someone who can help with that, uh, I wanna look at all of those options.
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Very often, in my life anyway, there are loads of people better than me at these things.
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So it's like, I want your help with that because you're just better at that than I am.
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Um, and sometimes it's one of those cases where, hey, I could do that, meaning I'm capable, like I have the ability to do that, but so do, 10,000 other people, so why would I constrain myself to having me do it instead of someone else?
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So three questions.
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Where are you getting in your own way?
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What's a middle way?
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And who can help with that?
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So those three questions are just really nice checkpoints for myself, and, um, I've kind of given you a little inside baseball, like my tendencies and where I have come from and where I'm trying to, um, lead myself and trying to get to and the person I'm trying to become.
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So, I would really, really encourage everyone to have some sort of checkpoint, and again, play around with, method and cadence and things like that so it works for you.
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For example, if you're like,"Yo, Emily, I am not doing something every other week," fine, every quarter, every month, once a year.
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That's a regular checkpoint if you do it every year.
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But I, I would press it to at least once a quarter, maybe once a month.
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But up to you on cadence and method.
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I like writing, like handwriting on paper, so I just grab my journal and answer these questions.
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If, apps work for you or if mental check-ins work for you, um, those can be a little tricky, but if you can do them, great.
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If you need someone to actually ask you these questions, family, friend, colleague, coach, mentor, any of these things, AI can prompt you.
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It can automate the prompts for you at your, selected cadence, all these different things.
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If you, um...
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I have one person I know who does sticky notes, and she color codes her questions.
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She's got five she asks herself, and she color codes the questions.
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Um, so, like, one question, the answer is always green, one question, the answer is always, like, yellow, et cetera, et cetera.
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And then she'll stack the sticky notes on top of each other, and then she'll kind of flip through, like thumb through the previous questions, or the previous answers for that question in that, like, color stack.
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And that just, works for her, and it's kind of a cool, fun way for her to do this.
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But play around with it, be creative, make it work for you.
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But I would say, um, set up a- an ongoing practice for yourself.
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Make it super short.
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Make it super easy.
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Again, these check-ins for me take anywhere from, like, at the extreme, like 60 seconds to maybe 25 minutes to maybe 30 minutes, where I just sit with this stuff if I'm kind of in the mood, my schedule allows for it.
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I feel like I need to let these q- questions and answers and these prompts breathe a little bit, um, for this time period or whatever other reason I have.
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Sometimes I will think about them on a car ride.
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So for instance, if I'm driving, like, to the airport to pick someone up, and there's traffic and it's, like, a two-hour car ride, then I'll just think through these questions in sequence.
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And then when I get home, I'll kind of write down what I remember about the answers.
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So it could be one...
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something like that, where it's like,"Hey, I'm here in the car anyway, and I've got all this time, and I can't really do anything else on my computer or phone'cause I'm driving.
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And so this is a good time to kind of check in with myself." And then if you wanna capture that for later, um, you can write that down.
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So something like that.
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I would recommend this.
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You can do it for yourself personally.
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You could do this for yourself professionally.
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You could do this for your teams.
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So if your team is like,"All right, let's come up with, like, three questions we can ask ourselves as a team," that's another option you can work with too.
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I would say that you, you don't want questions that are softball questions, meaning that you can just lob over to yourself, and you don't really have to think about an answer, or it's an easy answer, or you'll always have a nice, tidy answer.
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Like, I would, um, I would push yourself, challenge yourself.
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I'm not sure that's the right word, but I would, I would make it so they're more relevant and helpful to you, is a way to say it.
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So sometimes you might ask yourself the prompt, and it might be, like, an easy, nice, tidy answer for that month, let's say.
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But sometimes, like, oof.
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Oh, that's challenging.
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That's hitting it on the nose.
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Okay.
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All right.
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Nope.
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I put these here for a reason, and now I have to think about this question and answer this question for at least five minutes.
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So it could be one of those.
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So I would pick the most useful and relevant, and you know where you are, and you know where you're trying to get to, and what are the prompts that would best help you get there.
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So anyway, have a think about that.
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hopefully, it's food for thought and something that can help you in this next week, in this next month, quarter.
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And with that, I will call it a wrap and catch you next week on Leveraging Leadership.
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