5 Questions Every New Manager Needs to Ask | Lessons from Leveling Up by Ryan Leak

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Do you ever feel like a theme or lesson keeps showing up in your life on repeat—almost like déjà vu? That’s been me lately with words like honesty, integrity, and self-trust.

In this episode, I’m diving into Ryan Leak’s book Leveling Up. I thought it would be just personal development, but halfway through I realized: personal development and leadership development are the same conversation. This book held up a mirror and forced me to ask some hard questions I think every new manager needs.

We’ll cover:

• The Self-Awareness Question – “What is it like to be on the other side of me?”
• The Vision Question – “What is my definition of success?”
• The Humility and Integrity Questions – “What mistakes can I own?” and “Am I being honest with myself?”
• The Fun Question – “Am I enjoying it?”

I get really vulnerable in this one. From realizing I wasn’t being as honest with myself about small things (like tracking food) to admitting I wasn’t showing up as the mom or leader I wanted to be, this episode is all about how self-integrity connects directly to the way you lead your team.

Because leadership isn’t built on perfection. It’s built on honesty, humility, and the courage to ask better questions.

By the time you finish listening, you’ll discover:

• Why feedback is more powerful than grace when it comes to growth
• How to define your own version of success so you don’t climb the wrong ladder
• Why admitting mistakes builds more trust than pretending to be perfect
• How joy and enjoyment fuel culture more than toxic positivity ever could

Links & Resources Mentioned in This Episode:

• How to Set Boundaries, Unplug After Work, and Move Your Body Even When You're Exhausted 
  • Diving Into the Question around Rest 

Connect With Desiree on Linkedin
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Transcript

Desiree Petrich (00:01.44)
Do you ever get a feeling similar to deja vu where a pattern, a topic, a value, a lesson just keeps coming up over and over in your life and you know you're supposed to listen to it, but you're not entirely sure how or what the actual message is that's coming across? Well, this has been happening for me, but the words honesty and integrity and self-trust and the word lying have been coming up a lot for me in regards to what are the messages I'm telling myself?

What is it that I'm saying within my own head and why am I frustrated by things that I want that aren't happening? How am I getting in my own way? This is coming up a lot for me and I wanted to unpack it here. But not only am I going to unpack some of these questions, it's going to be directly relevant to you because we are going to talk about the book Leveling Up by Ryan Leake. It's another one of these episodes where I read so that you don't have to. And I'm really excited about this one.

I have been listening to Ryan Leake's podcast and if you don't know who he is, he is up and coming speaker, incredible, huge stages.

Desiree Petrich (01:15.756)
And Ryan has a way of holding a mirror up so that you can take on some of these really hard questions, some of these really hard personal growth conversations within your own head so that you can become a better person. And it's a definite style. I like to think that it's a style I kind of mirror because I never want to become complacent in my own personal growth. So I feel like the topics are sometimes a little bit heavy, but

I actually appreciate that about his podcast. And so I picked up his book leveling up thinking that it would be a break from some of the leadership development, a break from some of the culture conversations that I've been ingesting through podcasts and books. And I was really excited to just kind of let some of that go and have this be all personal development. And halfway through, I'm thinking to myself, well, that's dumb because I teach people on a daily basis.

what it means for leadership development and personal development and emotional intelligence and personal growth to all be synonymous with each other. They are all one conversation, not separate conversations. And that's what this book did for me. So we're going to cover just a couple of my favorite chapters, a couple of my favorite topics, the things that I found most impactful from this book. As always, I read so you don't have to, but I highly recommend that you do. So there is a link to the book in

The show knows there's also a link to Ryan's podcast if you want to listen to it. It's the Ryan Leake podcast. Super easy to find. But with that being said, I want you to understand one thing about this book. It is truly meant to hold a mirror up to you. Anytime I share something with you and I'm vulnerable with you, it is not so you can pity me. It is not so you can think, wow, she is doing so much or she's growing so fast. Anytime I talk about myself,

It is so that you can hold up a mirror to yourself and think, how does this apply to me? That is always my intention with this. So as we talk about these questions in Ryan's book, I want you to remember this quote, repetition will condition your mind to ask the better questions. Repetition will condition your mind to ask the better questions. In other words, it's not about just listening here today and thinking this is really interesting and then moving on. It is about

Desiree Petrich (03:34.647)
listening here today, journaling if that feels good, having a conversation with someone, sending me a message so that the conversation can keep going. And that will bring us to our very first question from Ryan in his book. It's chapter two, the self-awareness question. And the question is this, what is it like to be on the other side of me? What do your coworkers feel like to be on the other side of you? What does your family feel like to be on the other side of you?

I think for the most part this question is probably pretty uncomfortable for people to ask because where 95 % of us think, well, I'm pretty self-aware, the reality is that only 10 to 15 % of people can actually answer that question with any real...

Desiree Petrich (04:34.018)
with any real confidence, what is it like to be on the other side of me? And the thing is, our family, our coworkers, maybe you are the boss, you are the leader and so it's your employees, they see our blind spots long before we see them. It's why they're blind spots. They are things that other people can see that we can't. So when it comes to self-awareness, when it comes to the things that other people see that we can't,

The only way that we're going to be able to get better in those areas is to ask people to define them for us, to ask people for feedback, even when it feels really risky. And it can feel scary and uncomfortable and people might not be genuine with us or maybe that's our fear that they won't be genuine with us because would you be? Would you feel the need to give grace to someone who's asking you for an opinion?

Would you feel the need to be kind because you don't want to be mean? You don't want to make someone feel bad about themselves? The answer is yes. I think we all have a desire to give some of that grace. We never want to be the blunt person. We never want to be that person who isn't giving someone the benefit of the doubt. But this is for giving feedback and receiving feedback. Feedback is our most underrated form of communication. We need to utilize it in a way that asks for sincerity from other people and honesty from other people.

and giving that ourselves. That is the only way that individuals, specifically leaders in this case, are going to get better. When I was 24 and asking my boss for feedback, he would always say, you're doing fine, you're new, you'll get better. That wasn't what I was asking. It felt good in the moment because it was validation that it was okay that I didn't know everything. But what I really needed was feedback on how I could get better. I needed someone to tell me what my blind sets were.

I knew they were there. could feel them in the after effects, almost like the aftershocks of what was happening in engagements with my team and interactions with them, but I couldn't put my finger on them. didn't know what they were. So feedback is always better than grace, especially when it comes to personal and professional growth. That covers a little bit of what's in chapter two, the self-awareness question. One of my favorite questions, something I talk a lot about, it's why I love personality assessments. It's why I...

Desiree Petrich (07:00.512)
really believe in having that vulnerable and transparent relationship with people and providing that type of trust maybe even before it's earned. I kind of give an innocent until proven guilty kind of framework with people that I meet. I will be transparent and vulnerable with people until they prove to me that I can't be. Might be the wrong approach. It's definitely the scarier approach, but I feel like it's a lot easier to get close with someone.

and it's a lot easier to learn more about yourself when you're being undeniably you. Question number one, self-awareness question, what's it like to be on the other side of me? Second question, this is kind of a myriad of different chapters brought into one question, but I thought it was a really important one to talk about, especially in regards to you as a new leader. The definition of success for you is gonna look very, very different than the definition of success.

for me. In this book, Ryan talks about how when he was a kid, he went to a private school and a lot of those people had what he would have thought of as success at that time, whether it was the type of car that they drove, the house that they lived in, if it was having a maid or something along those lines, that was his definition of success. But as he got older, he looked at that Volkswagen

which is what he thought was success at the age of eight because he saw it on a wealthier side of town, recognizing that that was only a sign of success if that was what it was you wanted with your success. It only counted as successful if it's something that you actually wanted and something you would define in it. So he uses this quote, You don't need to have mine. You don't need to have my version of success, but you do need to have yours.

My definition of success looks like a very boring life. My husband and I talk about this all the time. We watch movies or see drama on any social media and we say, am so glad that our life is boring. It looks like a very small house, zero debt, very somewhat repetitive schedules and that's okay with us. It's actually something that we had talked about wanting. That's our definition of success and you don't need to have mine, but you do need to have yours. So I'm going to ask you this question.

Desiree Petrich (09:17.664)
What is your definition of success? If we're looking at this from a spouse to spouse, what does that relationship look like? What does your spouse and yourself to your kids look like? What does your relationship with your family look like with your money? What does success look like for you in that personal sense? Now, in a work sense, what would success look like for you? Do you want to climb the ladder in a corporate setting? Do you want to start a

nonprofit and be the board of directors. Do you want to start an entrepreneurial side hustle so that you can use some of your creativity where you're not finding it at work? New managers, especially often borrow, I guess I would say the definition of success from their coaches, their mentors, the people that came before them, like work harder, stay later.

That's how you're going to get success. Not only are we borrowing the definition of success, we're borrowing the playbook to get there. And that's not always helpful because we might get to the end of the road. We get to the top of the ladder and look over to the house next to us and say, we got to the top, but it was on the wrong ladder. It was down the wrong road. And then we have to either backtrack or change direction. It's a lot easier to change direction in the moment as opposed to getting to the destination and having to turn back. So let me ask you this question.

What is your definition of success? Because without that clarity, without answering that question, you are going to end up chasing approval, someone else's definition instead of the real growth that it is that you crave. So write down what your version of success looks like as a leader. I want to know what does your version of success looks like? Maybe it's for this year. What do you want to accomplish in the next three months of this year? And it's not about what your company says success should be. It's not about what your

in-laws say success should be or that overbearing family member. It is what do you want it to look like?

Desiree Petrich (11:28.758)
Now, here's where we're going to get into these questions that I said the pattern was forming of integrity, self-trust, honesty. And this comes from two of the chapters, but I kind of mushed them into one because I see them as a little bit one in the same. The humility and integrity chapters are chapters five and eight from the book. And the question for humility is what mistakes can I own? You've heard me talk about the five dysfunctions of a team on here. One of the main

pieces of having trust within a company, which is that very foundational level of building a cohesive team is trust. One of the very foundational pieces of that is a vulnerability based trust. And if we break it down even further, what does it look like to not only be confident making mistakes, but admitting your mistakes and asking for help, asking for advice. That is a huge piece of the puzzle of building trust. It's where it's born. It's not in

perfection but in honesty and transparency and vulnerability. And I know those words sound a little bit overused like they're buzzwords, but they are buzzwords for a reason. I always say that. Honesty is where trust is built. Humility is where trust is built. Leaders who can admit their mistakes are honestly, they're respected more than the ones who try to act perfect because the ones who act perfect, A, we know that it's a mask. Nobody is perfect.

I tell that to my daughter all the time. I am raising a five year old perfectionist and it already worries me. putting on that mask as a purposeful way of getting through life, it's not genuine. It's not authentic. People will be able to see through that mask. And the other piece of it is you are going to burn yourself out. You are going to get to a place where that mask is too heavy for you to wear and you're going to break down and you're going to feel like you fell a million feet.

because you were so far from reality. It's okay to show that honesty perfection is not necessary. I was listening to the Liz Moody podcast, which is another podcast that I listen to every single week. And she was talking about self-confidence, how we are actually viewed as more confident by other people when we are vulnerable, when we're willing to make mistakes, like saying a dumb joke during a conversation with someone.

Desiree Petrich (13:52.321)
you are going to be viewed as more confident, not because the joke landed or didn't land, but because you were simply willing to make a joke. You are going to appear more confident. And it's not about the level of professionalism. mean, yes, that piece is important, but it's not about that. That's not the thing that's going to make you valuable to your bosses. It's not going to be the thing that makes you connect better with friends and family, your vulnerability and your willingness to be real.

is what's going to show your self-confidence. It's what's going to show that humility in you. Owning those mistakes out loud, it also creates a really psychologically safe environment because if you are willing to say that you made a mistake, if you're willing to share an example of when things were really hard for you and you overcame them, that is what is going to help the team feel safe to admit their mistakes and to ask for help and to ask questions. So you

owning your mistake is overall helping your team, your family and yourself to become more confident and to feel more.

Desiree Petrich (15:07.768)
capable of growth because they're going to be able to get further faster by not feeling like they have to do everything perfectly. Now here comes the integrity piece of this question. They say when you're taking a shower is one of the best times to have like new thoughts, new breakthroughs because your mind is taken off of the day to day things, the fire that's going on every single day. And it's brought to this place where you can just have a creative outlet.

That outlet for me comes when I'm working out. So my husband built me a shed in the backyard. I'm working out in my shed. And all of a sudden, all of the patterns, all of the questions around honesty and the word integrity, self honesty, self trust, all of these words and all of the instances that have been coming at me and forming this feeling of a pattern without being able to put words to it, it all culminated in this one message.

I feel like I should be further. I feel like I should be better and doing more and having better relationships. But am I being honest with myself? And I started to reflect on this. was doing a challenge, a physical health challenge with a friend and kind of complaining, full on complaining to him that I felt like I was doing everything perfect for three months, but I didn't lose any weight. And yeah, I wasn't napping anymore during the day and I didn't feel the need.

blah, blah. There was good things, but the weight hadn't gone down. And he asked me, how closely are you tracking your butter? And I just, I kind of stopped in my tracks and I'm thinking, what a strange question. But I said, well, I think I'm tracking it pretty, pretty closely. And he said, because I find myself trying to put one tablespoon and tracking one tablespoon when in reality it's probably more like three. And it's not an obvious

and blatant disregard for the truth. It's a, don't want to be completely honest with ourselves because it would mean that we either have to track said butter. If we're staying with this analogy, we're going to track that butter and recognize why we're not losing as much weight as we want to. Or we're going to have to be honest and change what it is that we're doing with intentionality and only use one tablespoon. And maybe your food won't taste as good, but you are going to be able to say, I am actually doing

Desiree Petrich (17:30.927)
everything that I say I'm doing. I'm actually doing everything perfect and I was not. There was definitely pieces of the puzzle that I was either just not doing and saying that I was doing or I kind of felt like I was doing but maybe not to the level that I needed to be doing. I put a lot of things into this health and wellness perspective because I think that's where a lot of lessons come in. But another way that I look at a lot of leadership lessons is through parenthood.

And I was having a conversation with my husband and I said, I don't feel like I'm as patient as I want to be. I don't feel like I have as much desire to play with my kids and get on the floor as I want to. And I don't know what to do. I think I literally said, I don't know how to want to do those things more. And I was sitting watching TV one night with the kids. I'm sitting in a recliner with my feet up, my bowl in my lap.

They're sitting at this little kid sized table in our living room. We're watching a baking show. It's 100 % kid friendly and we all enjoy it. But I'm thinking to myself, I always complained that we didn't sit down for family dinners enough when I was a kid. That was always something that I wanted. And yet I was getting into the same pattern. And I was lying to myself saying that I was doing everything I could to have the level of patience.

and connection with my kids that I wanted and that I thought I was working for, but was I really? And so within a week, we kind of gave my kids their three and five, we gave them a warning that the table was going to be going away and to enjoy it while it lasted. And we brought the table over to his parents' house and we have sat at the dining room table every night since then. And my joy has gone up, my desire to ask my kids how their day went. And I realized that makes me sound

Like kind of a, I don't want to say a bad mom, but maybe a less attentive mom, or I'm not going to even put words in your mouth or in your mind, but I'm sure all of us at some point in time have felt this way or felt some sort of way about our relationship with our spouse or our kids. And the reality is, are you being honest with yourself? If you say that you're trying as hard as you are, what can you?

Desiree Petrich (19:53.739)
look a little bit deeper at? What can you truly do in your situation to make things better? I know it can feel like we're doing everything we can, but there's usually a deeper level that we just have to hold the mirror up to ourselves and truly look and truly say, okay, I could do more. So that was a lot for this question, but it's the one pattern that's coming up over and over and over again. And I think this book and this particular question around humility and integrity really got to me. So

When you are at a networking event as a young leader, as a new leader, even maybe as a seasoned leader, and you feel like you don't belong in a space, maybe you don't feel like you earned it, maybe you feel some of that imposter syndrome, it's not because you don't belong there. And it can feel like as you're telling yourself, I don't belong here, I'm not up to level with these people, I'm not as confident as I should be, I'm not as good of a speaker, et cetera, et cetera. Be.

honest with yourself about why you're feeling these feelings. What is truly behind that thought inside your head and how can you ask a better question? How can you ask the better question around why you're feeling the way you're feeling in regards to your health, your family, your work, whatever it is, how can you ask a better question and be more honest with yourself about the things that you are feeling? Hopefully,

You can appreciate the honesty and vulnerability and transparency that I just shared with you and I hope that you relate to it in some way, shape or form. But it's a really important topic that a lot of us are not sharing with each other. And I think that it makes it really hard to relate to one another sometimes because what we see on social media and the perfect weekends of things that are going on and nothing went wrong, we all have those moments of honesty that feel a little bit hard to share sometimes. But

What mistakes can you own and how can you be more honest with yourself? Here's the last one. Here's the last question that I want to cover. This is from Chapter 11. This is the fun question. And the question is, am I enjoying it?

Desiree Petrich (22:12.704)
This can be brought back to every single area of our life. Am I enjoying it? I just listened to an episode of the podcast with Shawn Johnson, the gymnast, the Olympic gymnast and her husband, and they were talking about kids sports. I've always been one that really, really struggles with the idea of youth sports simply because of all the time that is taken. And I'm not even going to get into this because this could cause an entire argument. But as as they were talking about it, they were saying, are you asking your children?

Do you enjoy this? Are you having fun or are you doing it to try and make mom or dad proud? Are you doing it to prove something to your friends or to yourself or are you enjoying it? And when I bring this back to a leadership perspective, it's if you're not enjoying it, if you are not genuinely enjoying what you're doing, at least to some extent, how can you expect your team to find joy in what they're doing? How can you expect them to have an attitude of gratitude to be as cliche as possible?

We have to find what it is that we love. In the book by Marcus Buckingham, Love and Work, he says, truly only need to love, like capital letter love, 20 % of what you're doing in order to find joy and fulfillment and decrease the risk of burnout, et cetera. 20%, that's all that's needed. How can you ask the right questions to find what am I enjoying? Am I enjoying it? How can you celebrate small wins so that you can actually remember and remind yourself

What is it that you love? Are you having meaningful and vulnerable conversations with people and sharing your progress and your wins and your losses with them? Not just the outcomes, but the actual how you did it, how you got there, what you're thinking in the moment.

Desiree Petrich (24:10.446)
Because when it comes to culture, the fun and the enjoyment and the positive attitudes, as much as we don't want it to be a toxic positivity type situation, that fun and enjoyment, actually fuel culture. They fuel that desire for people to want to be there on a Monday morning and still not wish for a Friday afternoon. If we can show up with that energy and gratitude and we can answer the question, are you enjoying it with a yes,

It's gonna give your team permission to do the same. It's gonna give the environment, the overall feel of that environment, an opportunity for people to find that for themselves. If you're asking the question, are you enjoying it? And your team says no. If they feel safe enough, if they have that psychological safety enough to say no, you get to then work with them and ask them the right questions, help them become a little more self-aware to figure out how can we make sure you're enjoying it? Because it's such a huge piece of the puzzle, it's kind of the point.

So with that, I want you to listen to this again. If and when you feel like you are stuck or maybe you're feeling frustrated about something, if you want to go pick up Ryan's book, Leveling Up, there's one conversation in here. It's the rest conversation. It's the question around, I?

Desiree Petrich (25:41.785)
The rest question is, do I have to do it all? And I was going to cover that in this, but first it would get a little long. And second, I covered it in another episode. So I am going to put that in the show notes so that you can go back and listen to that episode if you want to hear a little bit more on the conversation of rest, both for your mind and for your body.

What this book did for me was it helped to hold up a mirror. Sometimes I feel like I'm trying to hold up the mirror for other people so much that I forget to do it for myself. And so I appreciated the ability to do that, especially because so much of the conversation did come back to work and relationships, which is what leadership is. Leadership is influence, nothing more, nothing less. And you get to decide if you're doing it on purpose and with a purpose or if you are

just kind of letting things happen as they happen. So I want to fully encourage you to take responsibility for the things that are happening in your life right now and to make a change if you don't like what you see. But it all starts with the ability to ask better questions, to elevate your personal and your professional growth, which is the subtitle of Ryan's book. I hope you enjoyed this episode. I have four additional books that I've finished within the last month that I'm needing to do episodes on these. So let me know, do you love these episodes?

where we cover books. Please, please, please leave a rating and review if you are on.

Desiree Petrich (27:12.91)
Spotify, the three dots at the top, just hit rate this podcast on Apple, scroll all the way down to the bottom, leave a five star rating and review. Tell me what you love, which books you want me to cover. I can't tell you how much I appreciate and how big my smile comes across when those

Desiree Petrich (27:38.7)
I get an email every time a rating and review comes across. I got three just this weekend and I had to share every single one with my husband because they make me so excited to know that you guys are listening and that you're enjoying and hopefully that you're learning. So thank you so much for those. I will also put a link for you to rate the review right at the top of the show notes if you want to make the process really easy from your mobile phone. And just thank you again for being here. Thank you for taking leadership seriously because it is a responsibility.

and a privilege and I'm so thankful for you for stepping up and taking those on and you're the boss now. You get to decide what you do with it.

Desiree Petrich (28:26.69)
because leadership is a privilege, but it is also a really big responsibility and you're the boss now. So what are you gonna do with it?