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Building a business shouldn't mean losing your mind.
Strategy, Solutions, & Sanity is the real-world business podcast for owners and leaders who are serious about scaling — but don't want to drown in chaos while doing it.
Host Samantha C. Prestidge cuts through the noise with practical insights on hiring, delegation, team building, operations, and leadership for family businesses and second-stage entrepreneurs.
(No vague "10x your mindset" fluff here — just the strategies, systems, and sanity moves you actually need.)
Each week, you'll get short, actionable episodes that help you untangle the bottlenecks, lead with more confidence, and build a company that runs smoother — without losing the heart, hustle, and humanity that made you successful in the first place.
Whether you're navigating early team growth or getting ready to finally step out of the daily grind, this podcast gives you the tactical tools and real-world advice to build your business the smart, sustainable way.
👉 Follow Strategy, Solutions, & Sanity for practical strategies to help you lead, grow, and actually enjoy your business again.
Let's talk about the trap of wanting to be the cool boss. I have been there. I have fallen down that hill of wanting to just be super fun and cool. And lemme tell you it's not helpful for you or your team. It ends up taking up way too much of your time and energy. It ends up taking up way too much money 'cause you have to overcorrect and it just leads to not a lot of awesome cool stuff for your business.
So I'm gonna break down what it looks like to be in that trap and how to get yourself out of it or just how to avoid it altogether. 📍
Welcome to Strategy Solutions and Sanity, the show for family run businesses and serial entrepreneurs who are done letting chaos run the show. I'm Sam, your business and team strategist and your no Fluff Guide to Making Business Simple and fun. This is a quick cast, a short, sharp dose of strategy and action.
'cause I know sometimes you just need that quick next step to get your sanity back. So let's get into it.
All right, so typically what happens, and this is talking in general terms, so we get a little, little stereotypical, obviously this isn't going to apply to each and every one of you, but typically what happens is business owners, even in small teams or in large teams, I've seen this happen in, in every industry and companies of all sizes.
You pendulum swing. So you start off wanting to build a great culture. You wanna be approachable and fun and flexible. You wanna have some kind of story that lets you write a super cool LinkedIn post where you're like, this person did this, but I still believed in them and this super awesome thing happened.
And that becomes your cool opening anecdote for your next TED Talk, right? And you wanna be friends with your team, but what ends up happening. Is that they don't exactly reach the awesomeness of what you want them to. Performance starts to dip. Accountability starts to slip up, and you're like, oh, well, maybe it's me.
Maybe I'm not being the great leader I'm supposed to be. Let me go read this leadership development book again, or, they were really great when I first hired them, they interviewed really well. Not totally sure what's happening. And then because performance and accountability is slipping, your trust in them also starts to slip.
And your trust in yourself, your confidence in your own leadership and management skills also starts to dip. And we pendulum swing and we overcorrect. Well, now we think we need even more structure and rules. Now we are doubting that there's any good person we can hire. So we get really funky with hiring.
You end up maybe micromanaging. Or you stop delegating and you wanna do a lot of the work yourself. That pendulum swing in business is super exhausting. It, uh, is not sustainable. It takes up way too much time and money, and it totally kills your team's momentum. So what exactly is the way out of this?
Well, if you know me, if you know any of my content, you know that I like super simple. Super easy to implement actionable steps when we're solving big problems like this. And the easiest thing I can break this down into is setting clear expectations. There's nothing that says you cannot be friends with your team.
When I have my check-ins with my VA every week, these are 15 minute check-ins, and we spend like seven to eight minutes catching up and talking about like. Her farm animals and like, what's the next thing? What's the next animal she's going to buy for their little homestead. Okay. So you can totally be friends with your team.
My husband has worked in large organizations. He's had team members where we've gone to concerts with them. These are the people that he manages and has to set big expectations for on an everyday basis. We've gone to concerts, we've been drinking for their birthdays, like we have a friendship with these people and the reason why.
We've been able to do that is because we've been able to set clear expectations for our team. I'm not saying you gotta be friends with everyone you work with, but I'm just saying it's possible if that's something you wanna do. So you can still be a fun boss, but also be a great leader and not fall into the trap of just trying to be cool.
Right? If you have not set clear expectations for your team and you're trying to be the cool boss, and you see performance, dipping, accountability, dipping, you feel like the trust issues coming on and like the want to micromanage, most likely what's happening is your team doesn't really know the outcomes that you want.
You're probably avoiding some tough conversations with your team, and we've just kind of got this conflict aversion happening. On the flip side of that, which isn't necessarily a pendulum swing, it's rather than just like the pendulum coming, is when you have set clear expectations, you're able to have like these really healthy conflict resolution skills because it becomes so much easier to have tough conversations when you know that you've given them a clear expectation.
If they have not met a certain KPI or a certain outcome on a project, a certain deadline, you can super easily then just say, Hey, we talked about getting this done by this state, or We talked about this project turning out this way doesn't seem like that's happening. Help me understand why. Break this down for me, and you can be direct and still be kind. You don't have to come off as a jerk, even though you're calling them out on something that they messed up on. So that clarity and expectations helps you then have clarity and kindness and dive into those tough conversations.
It also helps you understand who's actually performing, who's actually a high achiever and not just charismatic and coasting and helps you stop overcompensating for people who aren't the right fit. You can gain back trust in your interviewing and hiring skills. So when you have set clear expectations, there's a lot of other like leadership and management skills that you still need to have, like you still need to know healthy communication and, and conflict resolution and all that fun stuff. However, that's your step one, your simple action step to still leading a super fun yet high performing team, to still possibly being friends with your team members if that's your goal without falling into the trap of like cool boss.
It's only when you stop trying to be everybody's buddy and start leading the way that they need to be led, and with clarity and defined expectations that you can step into that fun, good leader role.
📍 Okay. That's it for today's quick cast. If you have a question around business and team strategy, operations, delegation, hiring, anything along those lines, then I'd love to answer it in an upcoming quick cast episode. You can find me on LinkedIn, Samantha Cordero Prestige, or you can email info at A-U-X-O-S-V-S .com. We will have that in the episode description so you can email me there or reach out to me on LinkedIn and I'll answer your question in an upcoming ask me anything quick cast episode.