Aug. 3, 2026

#086: Why Your Team Keeps Nodding and Nothing Changes

#086: Why Your Team Keeps Nodding and Nothing Changes

You've sat in that meeting. The slides are polished, everyone nods on cue, and by Monday it's like the offsite never happened — a kind of collective amnesia settles back in. In this solo episode, Dwight steps out from behind the usual guest chair to name something he's carried through years of designing gatherings for leaders and creatives alike: leadership, he believes, is its own creative journey — with the same doubt, the same awakening, the same hunger to be seen as real instead of just u...

You've sat in that meeting. The slides are polished, everyone nods on cue, and by Monday it's like the offsite never happened — a kind of collective amnesia settles back in.

In this solo episode, Dwight steps out from behind the usual guest chair to name something he's carried through years of designing gatherings for leaders and creatives alike: leadership, he believes, is its own creative journey — with the same doubt, the same awakening, the same hunger to be seen as real instead of just useful.

He talks about what actually breaks the spell: real check-ins instead of small talk, naming the tensions everyone's been quietly carrying, and commitments made in front of people who'll actually ask about them later. Not techniques. Permission.

Because underneath every job title is a person circling their own tender spots, wondering if it's safe to be honest here. Dwight's answer is simple and a little disarming — it usually is, if someone goes first.

This one isn't about running better meetings. It's about what becomes possible when a room finally stops performing.

This is Maddox & Dwight! More than anything, we want to connect and communicate with you. We don't want to think of you as listeners. We want to think of you as community. So, scroll to the bottom of the show notes and click the SUBSCRIBE link. Thank you!

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00:00 - Why Most Offsites Fail

03:43 - Real Check-Ins Not Small Talk

05:27 - Put Avoided Tensions On The Table

07:09 - Commitments With Witnesses

09:03 - Breaking The Slide Deck Spell

13:45 - Designing For Vulnerability And Momentum

18:21 - The One Conversation You Avoid

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Dwight: If you lead people, you've probably been in an offsite where everyone nods, the slides look great, And then…

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Dwight: Nothing really changes back at the office.

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Dwight: Hi, I'm Dwight with for the love of creatives.

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Dwight: I want you to think about the things that are at stake when you go to these offsites.

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Dwight: you have… time.

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Dwight: Money.

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Dwight: emotional energy.

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Dwight: In the head column.

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Dwight: And then there's the culture you're trying to build.

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Dwight: You you have your values, the safety, creativity, honesty.

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Dwight: Those are more in the heart space.

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Dwight: Today… I want to share what actually helps group.

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Dwight: Helps a group think together.

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Dwight: Be honest together and.

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Dwight: Have a gathering with commitments they're proud to follow through on.

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Dwight: Drawn straight from what we do at For the Love of Creatives.

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Dwight: Every leader in the room.

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Dwight: Is on a creative journey, too.

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Dwight: I'm a firm believer that leadership is a form of creativity.

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Dwight: and for that reason I can draw a straight line to my creative journey framework.

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Dwight: Some leaders are in doubt.

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Dwight: You know, they're the ones that ask, well, am I a real leader?

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Dwight: Am. Am I really up to this?

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Dwight: Some leaders are awakening.

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Dwight: They have the realization, my voice matters.

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Dwight: Some are an emerging voice.

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Dwight: They're sharing more, but they're still vulnerable, and some are more authentic.

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Dwight: They are rooted.

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Dwight: Leading from who they are.

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Dwight: If you don't design for that reality, most off-sites only reach a fraction of the room.

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Dwight: There are 3 things every meaningful offsite needs.

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Dwight: and I'll cover them here at the top, and I'll get a little more into them. First, st real check-ins, not small talk.

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Dwight: Next, the conversations that we're not having.

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Dwight: And finally, commitments with witnesses.

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Dwight: So let's unpack them.

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Dwight: a real check in instead of polite small talk. People need a way to arrive as humans, not job titles, not positions in the organization, not trying to figure out where they are in the hierarchy and figuring out how it is that they need to show up because they got to be really nice because someone could do something for them. No.

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Dwight: all of that has to stop. Do you have a meaningful gathering.

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Dwight: in our live gatherings, we do something that makes it really obvious that I take into my offsites.

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Dwight: We insist that everyone wears name tags, and that sends a subtle message that we are people first. And another way that we set the room is we get people to focus on something that isn't related to the enterprise, to what it is that they're doing directly.

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Dwight: because we want to get them out of that space of strategizing and

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Dwight: Interrupt the pattern and make it so that they show up as real people.

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Dwight: You'll see this if you listen to things in our podcast feed.

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Dwight: Where we talk to people and get them to name their fears, their hopes, talk about their internal weather. We get people to share a lot of the things that are the highs. So we stay on the surface there, but then we go deep into their valleys. We want to understand their pain and struggle.

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Dwight: Some of this translates in a way that for other creatives that might be listening, they get a sense that, oh, wait.

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Dwight: They're… they went through this, too. I'm not alone.

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Dwight: And we need that in the rooms where we bring people together as well.

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Dwight: moving on to the next thing which builds on the 1st we need those real check-ins and small talks to and not small talk to get to the conversations that we're not having. Create off sites. Put the avoided tensions on the table.

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Dwight: We actually point to the elephants in the room.

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Dwight: and we just drag everything out. We pull the skeletons out of the closet. We make it so that those things that are uncomfortable are given light, and they lose their power.

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Dwight: These can be things like just subtle, unspoken resentments, misaligned priorities, or just culture gaps.

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Dwight: If we look at the way that we approach these things with what you can see in this podcast feed.

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Dwight: you see how we talk about things that that make people uncomfortable in in many contexts. We get the feedback a lot of times that people share things in our conversations that they

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Dwight: I hadn't shared with anyone or hadn't thought about in years.

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Dwight: And it's because we talk about the real things that matter.

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Dwight: Whether you're a leader or a creative.

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Dwight: you are going to always have issues that are going to surround tender spots like your fear of judgment.

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Dwight: You're going to have to deal with loneliness, burnout, comparison.

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Dwight: And those are the things that really move the needle, the things that matter instead of just keeping it polite and talking about the things that are pretty on the surface.

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Dwight: So, with those two things, the real check-ins, not small talk, the conversations we're not having.

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Dwight: That brings us to a place where we can close meaningfully and talk about the commitments with witnesses.

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Dwight: Without specific commitments and relational accountability, offsites

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Dwight: Stay in the head. They they remain a nice little thing that happened and nothing of consequence changes there. There's a popular phrase making the rounds that's really cute, but also a little bit too truthful. If nothing changes.

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Dwight: Nothing changes.

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Dwight: When you look at what we do on the show.

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Dwight: and you look at some of the solo episodes where I get into the creative journey framework, I've asked our listeners to name the phase that they're in.

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Dwight: And tell one trusted person.

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Dwight: And ask for support if they want to advance beyond where they feel that they're stuck.

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Dwight: This is the same thing that I bring into rooms.

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Dwight: we get very practical and get in the weeds. We roll up the sleeves, and we do work that matters, and make it so that it's not just another

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Dwight: event that meant nothing.

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Dwight: Something that's a nice little memory, a little thing that people can talk about.

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Dwight: and have a shared experience and think it was something that happened over there. No, it's something that they are able to carry with them and build forward

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Dwight: To build the cultures that matter, to make the most of the time, money.

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Dwight: and emotional energy that they have once they're back in the trenches, And making stuff happen.

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Dwight: Now, I have been to a lot of off-sites myself, and conferences, and all kinds of gatherings, and I approach them as

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Dwight: An observer?

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Dwight: and I do my best to show up as a full participant as well. I wear both hats.

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Dwight: and there's a lot of bad things that happen in offsites, good intentions, but the execution can can just land in a way that is not optimal.

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Dwight: for one thing, People are prisoners to the culture, the prevailing culture that we have of not wanting to

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Dwight: Step outside of what would what would be considered the etiquette for that situation.

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Dwight: People want to be polite. People want to make sure that they hit all the notes. They do all the things that are expected. So there's a script that people follow.

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Dwight: And I understand and appreciate structure, but when you keep it polite and when you just stay with what's in a slide deck, no matter how polished.

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Dwight: Then, you know.

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Dwight: It makes it so that you have a barrier that prevents you from connecting with people and having people connect with each other.

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Dwight: That's what leads to those situations where people are in the room.

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Dwight: Maybe it goes dark so that we can see.

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Dwight: the crisp text on slides that someone is just mindlessly reading and signaling to everyone in the room that they need to go into Powerpoint hypnosis and leave their bodies for the time that they're being silently

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Dwight: read to.

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Dwight: And then, when everything returns back to normal.

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Dwight: People are conditioned to make it to where

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Dwight: That thing, that event never happened.

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Dwight: They they literally have time loss. It's like they black out for

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Dwight: For that moment that they were held in, in that situation where they had to listen to someone drone on in front of them.

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Dwight: We've all experienced this, and we know that we can do better, right?

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Dwight: I am involved in…

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Dwight: all kinds of training all the time. I study the way that we are, that we actually work.

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Dwight: And I have an appreciation for the systems that are in place, the model that we have of having a person standing in front of a large group of people to disseminate information quickly.

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Dwight: That's something that was born out of necessity of the war effort in World War II. We needed to mobilize troops, and we needed to train a whole new factory workforce

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Dwight: In such a way, where things were…

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Dwight: automated or systematized is the better way to express it. We needed to make it to where we could deliver the same messaging to large swaths of people

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Dwight: In a way that…

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Dwight: Made the most of the resources and efficiently got the same thing in front of people.

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Dwight: Over and over, right?

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Dwight: And we did such a good job of that that we forgot that that was just an emergency effort.

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Dwight: And that just became normal.

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Dwight: It's not normal. People don't think like that.

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Dwight: There may be one or two people that are on board when you're in a large group like that, and they can listen intently.

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Dwight: But people naturally Don't sit still in…

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Dwight: don't just absorb everything that's coming at them when it starts to look exactly the same.

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Dwight: The brain's efficient, so it's going to protect us from having to expend the kind of energy that it takes to try to build

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Dwight: Something in her mind, from…

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Dwight: a packaged presentation, or when we see someone reading in front of us, the brain's smart. It's going to say, Oh, wait! They're probably going to give me this presentation later. I can check out now. I can think about what's for dinner. I can think about what I'm going to do for my kids. I can think about what I'm going to do this weekend.

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Dwight: And I don't have to be here, really.

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Dwight: You know what I'm talking about.

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Dwight: when… I try… when I'm in a room, I try to make it so that we…

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Dwight: Change the situation just enough to where, first of all, we're going to have fun.

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Dwight: Right?

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Dwight: We are not going to be trapped in that weird dance where everyone sits politely and pretends to listen while there's someone of the room. No.

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Dwight: No, that's garbage. We don't do that.

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Dwight: we invite people to say the unsaid. I told you about the levers that I pull where we have the the real check-ins.

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Dwight: And get people to… Talk about what's unsaid.

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Dwight: That can be really hard, and here's, here's the thing about doing that.

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Dwight: When you, when we force people to go inward.

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Dwight: All of a sudden.

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Dwight: where they would have just checked out to to reserve energy and and not make it to where they were wasting their time by listening to what they were going to get later.

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Dwight: They're suddenly activated because

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Dwight: They have to think about things that really matter. They are circling their own tender spots and thinking about those things that

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Dwight: are important to them.

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Dwight: They show up, and they… They're able to get vulnerable because they see it being modeled.

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Dwight: And it's a beautiful thing.

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Dwight: And here's the… here's the deal. When you are fully activated, That's something that carries beyond just that moment.

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Dwight: It's something that sticks with you and it's something that invites transformation because instead of putting all of those uncomfortable things in the locked compartments in your head where you only visit them when you absolutely have to.

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Dwight: It brings light to them, and makes it so that

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Dwight: We can work on them, and they aren't as tender.

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Dwight: We are able to show up a bit more, and be a bit more real.

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Dwight: and actually be a bit more effective because we're we're not just trying to tiptoe around the tulips and and make it so that we are are just being as polite as possible and not trying to step on anybody's toes. We

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Dwight: Create a situation where we can show up more fully the people that we are.

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Dwight: and feel good about it.

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Dwight: I'm not saying that I'm inviting people to be rude, No, quite the opposite.

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Dwight: I'm inviting people to be vulnerable

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Dwight: In such a way that's safe.

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Dwight: So that they can show up more authentically in the spaces that matter.

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Dwight: And be a bit better at getting things done.

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Dwight: Because instead of trying to.

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Dwight: get at the edges of how it is that things need to improve. We're able to get to the point and and say what needs to be said.

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Dwight: and do it in such a way that's respectful and meaningful.

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Dwight: I mentioned before that I am always in the process of trying to build on what I have on board and make it better.

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Dwight: Right now, I'm involved in…

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Dwight: a certification effort through a group called Exchange. I'm a believer in the Exchange approach, and

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Dwight: this is… I normally try to keep things evergreen with what we do on the podcast, but

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Dwight: I'm confident that no matter when you find this, I will probably be involved in many different certification efforts through exchange as well as others. There are lots of great teachers that I draw from, and I try to approach every experience I'm in as an opportunity to learn.

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Dwight: Sometimes I learn what not to do.

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Dwight: But, for the most part, I am always trying to be the observer, the constant student.

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Dwight: As well as someone that's fully engaged, I want to play full out and always show up in a way where I get the most out of what it is that's put in front of me.

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Dwight: I would like to leave you with one thing to chew on.

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Dwight: As… You, you think about… This… Whole program, that.

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Dwight: we've had together.

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Dwight: And it's simply this.

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Dwight: A great offsite is less about what gets presented and more about what finally gets said.

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Dwight: Think about that for a moment.

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Dwight: It doesn't matter how slick things are in the presentation. It doesn't matter what kind of trickery they do or how it is that they make it so that it's…

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Dwight: a delightful experience. What really matters is the meat of the message that what really matters is how it lands. What really matters is how it changes you.

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Dwight: Now, I'd like to… leave you with a bit of reflection.

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Dwight: Think about this, and this is going to be… something that's… unique to you.

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Dwight: But seriously consider this question.

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Dwight: What's the conversation your team, your circle, your community?

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Dwight: isn't having yet.

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Dwight: Let's get one better. What would change if that conversation were on the table?

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Dwight: If you could bring that one honest question to your next meeting, your next Stand up. You're next. Staff.

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Dwight: Meeting, your next huddle What could change for you?

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Dwight: What could change for the…

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Dwight: the… the group.

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Dwight: And my goodness, let's be bold. What could change for the world?

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Dwight: If you want to hear how I hold, These kinds of conversations.

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Dwight: You can get a sample if you listen to some of the solo episodes that I've done in the feed.

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Dwight: And you can also get a flavor for how Maddox and I.

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Dwight: Try to get at

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Dwight: the things that really matter in the guest episodes. With our featured guests, we engage them in a way that

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Dwight: recognizes the the great things that they've accomplished.

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Dwight: but also get them to share from that raw place of the scrapes on the knees, the things that have been hard, those struggles.

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Dwight: that we know that everyone has had their own flavor of at some point.

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Dwight: And it's through that raw excavation that people can show up in a way that is more real.

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Dwight: That is a way that Is the fertilizer that grows.

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Dwight: the the things that become the the blooms of of tomorrow. You know the We can look at.

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Dwight: The the things that we're carrying.

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Dwight: As stepping stones to get us to the places where we want to be.

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Dwight: The things that that may be the hardest for us to deal with.

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Dwight: could be the very spark that leads to us reaching our full potential.

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Dwight: I design and facilitate gatherings for creatives and heart-centered leadership teams.

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Dwight: who want connections, honest dialogue, and clear commitments.

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Dwight: If you'd like to engage with me, I'm very easy to get a hold of.

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Dwight: There will be links in the show notes, and I'm very easy to find on socials.

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Dwight: It's been great spending this little bit of time with you on this episode of Community and Becoming for the Love of Creatives.

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Dwight: And I hope to see you in another episode on the feed.