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Managing Difficult People

2 Sep 2026 · 15m · 6 chapters

Episode artwork

Allow Consequences: Let People Own Their Choices

In short

Let people own their choices by setting boundaries, replacing “should” with “could,” guiding with questions, and allowing consequences instead of rescuing.

Guest backgrounds

No guests mentioned; episode is hosted by Adam Holbrook.

Key claims

Over-helping creates dependency and prevents growth; advice works better as suggestions (“could”) than commands (“should”); boundaries are “doorways” that protect mental health; covering for others (missed deadlines, lateness, excuses) erodes your credibility and self-respect.

Notable examples

Adam’s friend “Al” (houseless, not homeless) rejected being “saved” and later died; Adam withheld emotional padding when a grant proposal was late; he required a mother to replace ink-damaged shoes; he stopped covering for repeated no-shows and late work, using clear, minimal expectations.

Written by AI. May contain mistakes.

Chapters

0:45

Purpose of the Podcast

Adam discusses the purpose behind starting the podcast and its focus on leadership.

“in, gain the awareness of what's holding them back in their own lives and have a pathway forward through my stories, my failures, my triumphs, my guest stories.”
1:44

The Savior Mask Concept

Explaining the savior mask and the importance of letting people grow through their own experiences.

“We put this mask on because we want to help everyone, me included, always want to help other people.”
4:12

Advice vs. Suggestions

The difference between giving advice as commands and suggestions, using the word 'could'.

“we use the word should, as in you should do this or you should do that.”
5:05

Consequences and Personal Growth

The importance of allowing people to face their own consequences and set boundaries.

“Asking questions to guide the person in the right direction is key.”
9:50

Setting Boundaries for Healthy Relationships

How setting boundaries helps maintain personal well-being and accountability.

“If they showed up late for work, you don't have to cover for that.”
11:28

The Role of Critical Thinking

The significance of developing critical thinking skills in the context of job security and personal development.

“And these boundaries, we've talked about this before in past episodes.”
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Transcript

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0:00Adam Holbrook: If you've ever worked with someone who creates chaos, plays the victim, and blames everyone else, then this podcast is for you. So here's your host, Adam Holbrook.

0:19Welcome to the Managing Difficult People podcast. I am your host, Adam Holbrook. The reason I created the Managing Difficult People podcast, I was noticing teams and leaders not leading themselves well, sabotaging themselves, not leading their team members well. And I said, maybe I can create a place, a safe place where team members and leaders can listen in, gain the awareness of what's holding them back in their own lives and have a pathway forward through my stories, my failures, my triumphs, my guest stories. I consistently work with schools and organizations that want to change culture. Because here's the thing, when you stop talking about culture and actually do something about it, that's when teams show up and excited to work and excited to grow and connect with one another.

1:16And yes, the bottom line increases too. And I do this a variety of different ways, including executive coaching, workshops, connection exercises. It could be a variety of other things, dispersonality assessments, and many, many more ways. Today's episode, I'm excited about it. I write about it in my new book coming up this fall called You're Not for Everyone. And chapter five is about allowing people to face the consequences they deserve. It's the savior mask. We put this mask on because we want to help everyone, me included, always want to help other people. But when you do that, they rely on you.

2:02They keep coming back for more and they never actually grow into the person that they're meant to be. Now, don't get me wrong. There's a gray area with this. And there's sometimes that we need to be helping people. And I agree with that 100%. But we have to look at this line today. And sometimes it's about giving people advice and telling them what they should be doing. And I'm to blame as well. I want to tell you about a homeless man that I started becoming friends with. Each night on my walks, I would run into this homeless man. I started giving him money. I started to make conversations with him, brought him food, He even brought him a blanket when it started getting colder.

2:46And one day, I'm in a conversation with Al. And I said, Al, you're so smart. You can get any job you want and get off the streets and get a house of your own. And he said to me, it blew my mind. He goes, Adam, do you have a job? I go, yeah, I got a job. He goes, so you have a house. I got a house. So you have a car. I got a car. so it sounds like you got a whole lot of stress. Look at my life. And he raises his hands to the sky. At that moment, I recognized that Al wasn't homeless. He was houseless. I had been trying to get him to live a life what I thought he should be living. But he was completely content living that life and being on the streets and being free.

3:42And it was mind-blowing to me. As much as I wanted to tell him the life he needed to live and save him, he didn't want to be saved. Over the winter, this past winter, Al died of sickness and the cold. But I didn't save him. I offered my assistance to get him off the streets. But here's the thing. is sometimes when we want to try to save people, we use the word should, as in you should do this or you should do that. And that's what I was doing with Al. And the best way we can give people advice is by replacing that word should, which I think the worst word in the dictionary, and replacing it with the word could, as in you could do this or you could do that.

4:32Because when you use the word could, it's a suggestion. It's not a command. It's not a shutdown. You could try this out. For example, if your wife's birthday is coming up and somebody suggests to you, or say it's my friend's birthday, and I say, you should buy your wife flowers. Instead, replace it with the word could. You could buy your wife flowers. Or you and your parents are fighting. You could write a letter and apologize instead of you should write a letter and apologize. Do you see the difference? There's a big, big gray area. And here's the thing. Asking questions to guide the person in the right direction is key.

5:13Because when was the last time you actually ever gave someone advice and they actually took your advice? It's probably never, to be honest with you. But when you ask them questions, you guide them to figuring out the problem on their own. And it's so important because it might be clear as day what the answer is. but to them, they need to figure it out on their own. But we have to allow people to have their own consequences based on their decisions in their life. And if we're gonna constantly be saving people, we're never gonna let them grow. And there's never gonna be any boundaries around us.

5:51They're gonna be constantly pushing. And I've been on the other side of that as well. I wrote a grant for New York City. I was bringing on five team members to run this grant in New York City to help empower school districts to personal development and leadership. And I had five people, and I said to them, one requirement, I need a brief overview of the workshop that you're going to be providing by Monday. Monday came, I had four of them. I didn't have one. Tuesday came, nothing. Wednesday came, I finally got it. And I was angry. I was like, this was like the perfect scenario. This person seems so interested in this.

6:36And I knew that they were interested in this. But instead of getting angry, I just said clear expectations. The proposal was due on Monday. I had to submit it without your proposal. No deep explanation needed. The fewer the words, the better. I'm not going to feel bad about somebody else's decision that they, all the excuses that they are going to make with that. And I used to like pad things and make people feel better about it. Oh, that's okay. You know, one of the situations that happened at my daughter's school this past year is she got these brand new Ugg shoes and they're so cute. And her first day wearing them to school, some boys are joking around and they bust open their ink on their pen and their ink gets all over my daughter's brand new shoes.

7:31Now, in the past, I would have accepted that and let myself, ah, no big deal. We'll take care of it. But this is not my responsibility. I didn't create this mess. So I emailed the mother and the mother paid for new shoes because I have to let other people face the consequences that they did. Accident or not, it's not how we're going to move our lives forward. Now, that said, that's not saying that we shouldn't help other people if they're in a jam. If other people are in a jam, but here's the thing. The gray area is if they've given it a fair shake and they've tried their best and they can't figure it out, helping people is great.

8:12But when you become a crutch for people, they're just going to keep on pushing and they're going to keep on draining your energy and sucking you in. So the difference is clear that if they've already attempted something, and I've made this mistake a lot of times and be like, can you help me? Can you help me? Can you help me? But now I honestly give everything a shot. And if I can do it, which is 90 something percent of the time I can do it on my own, it's done. But if I need somebody, I will ask for them and they'll know I'm asking not as a crutch, but because I truly need their help. And if you need help from someone and I can't do it, sometimes I have to pay for that service.

8:51It's something that I look at. Things are happening always around us. And you hear every excuse in the book, my tire got flat. I had Zoom meetings with people and people wouldn't show up. And then they would reschedule with me the following week and they wouldn't show up again. And then they're like, oh, I forgot all these excuses. but when these excuses pile up or when these things happen, I still love them but I love them at a distance because you don't have access to me anymore. You don't have full access to me like you had prior and I start off and I give everyone a 10 on their forehead. I give everyone a 10.

9:26I believe in them. I trust them. I think that they're amazing and then when something happens like this, I still love them but I love them at a distance. You're not going to get into my inner circle. You're not going to be able to get more time with me if you take advantage of my time. And that gray area for me is just understanding what we can do on our own and not trying to save people from the consequences that they're facing. If they showed up late for work, you don't have to cover for that. You know, I hear people saying that they signed people in to work because the other person's late. You're risking your own job.

10:01You're risking your own credibility by doing that. Let people face those consequences on your own. It's not up to you to save them. Now, there's a cost to saving other people. It erodes your self-respect. You find yourself surrounded by dysfunction that you didn't ask for. And yet somehow you recognize the responsibility is on you right now. Because you put yourself there. And as soon as you stop saying yes and saying no and setting those clear boundaries in place, that's when things start to change. Compassion is great. And listen, when you set these boundaries and when someone comes to you with all the stuff that you can't take on, you can empathize with them.

10:53You can still, I understand how you can feel that way. Wow, that really must suck. That really must not be good. but when you start taking on that responsibility on your own, you're now absorbing their consequences and they're never going to be able to grow. And here's the thing about that is that same problem is going to come up time and time again for them until you say no and allow them to face the consequences so they can grow and they can learn from that. And then they can grow and learn from the following things that are going to follow that. But we're not going to be consistently saving people from the consequences that they did.

11:28And these boundaries, we've talked about this before in past episodes. Boundaries are not walls to keep people out. They're doorways, which we choose when to open them and when to close them. So it's not about shutting people out, but it's allowing space so you can work on your own mental health. You could say it a lot of different ways. I understand how you could feel this way, but this isn't something that I want to take on right now, using an I statement. But if you attack them and say, you've come at me and you've told me this, you've asked me to do this a thousand times, like that person coming at me with their proposal two days late.

12:09If I said to them, clearly, you didn't do what you were supposed to do, and I would have attacked them, what would that have done? That would have not fixed the problem. I just was clear, used as few words as possible. The deadline has passed. I had to move forward without you. I love you. I care for you, but this isn't for you. And I know that this is a tough pill to swallow sometimes. And sometimes we just want to be rescued. And I understand some people have had a tough life. And I understand that some people have gotten more breaks than other people. but we're not going to sit here and be jealous about other people.

12:48Instead, say, how can we move our life forward? And moving our life forward means taking responsibility for ourselves. And replacing that word should, that command word should, you should do this, which is the worst word in the dictionary, with the word could, and asking questions to guide people, figuring out the problem on their own. Because when they figure out the problem on their own, they're learning, they're growing. And here's what I'm noticing is that I'm hearing time and time again that AI is going to eliminate a lot of jobs. And that is true. I do believe that that is going to happen.

13:26And that's going to happen very quickly. But what is going to be needed is people that can critically think, problem solve. And if we're constantly bailing people out of that, we're going to be constantly living in dysfunction with them. And you're not even going to be able to concentrate on growing your life because you're so concentrating on their life and you're in a spiral out of control. I am excited to be with you guys here today on the Managing Difficult People podcast. And if you are looking to grow yourself, I am so excited about my new book that's coming out this fall, You're Not for Everyone.

14:05And one of the chapters is allowing people to face their consequences, loving people, but also allowing them to face the consequences that they created, accident or not. Till next time. Thanks for joining me. We'll see you again.

14:23Adam Holbrook: So that's it for today's episode of the Managing Difficult Pupil podcast. Head on over to Apple Podcasts or iTunes, wherever you listen and subscribe to the show. One lucky listener every single week that posts a review on Apple Podcasts or iTunes will win a chance in the grand prize drawing to win a$10 ,000 private VIP day with Adam Holbrook himself. Be sure to head on over to managingdifficultpeoplepodcast.com and pick up a free copy of Adam's gift and join us on the next episode.

15:02Thank you.

From the publisher

Are you helping someone, or are you accidentally keeping them from learning how to help themselves?

In this episode of Managing Difficult People, Adam Holbrook tackles what he calls the “savior mask”, our instinct to step in, fix problems, offer advice, make excuses, and protect people from the consequences of their own decisions. While it may come from a place of compassion, constantly rescuing someone can create dependency and prevent real growth. 

Adam shares personal stories that forced him to reconsider what helping actually looks like. He explains why replacing “you should” with “you could” can transform advice from a command into a choice, and why asking the right questions can be more powerful than simply giving someone the answer. 

He also explores the importance of clear expectations and consequences. When someone misses a deadline, repeatedly wastes your time, or creates a problem, you don't always have to step in and make everything okay. Sometimes the most valuable thing you can do is allow them to experience the outcome of their choices. 

Most importantly, Adam explains why boundaries aren't about shutting people out. They're about deciding what you will and won't take responsibility for while protecting your own time, energy, and well-being. You can still care about someone without carrying the consequences that belong to them. 

The takeaway: Stop confusing rescuing with helping. Give people room to solve problems, experience consequences, and grow, while giving yourself permission to stop carrying what was never yours to carry.

Stronger leadership starts with better communication.

Learn how to manage conflict, set boundaries, and lead with confidence.
Listen now: https://managingdifficultpeoplepodcast.com/

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