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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.
📍 📍 if delegation doesn't feel relieving for you, then you're not actually delegating. You're just assigning tasks and hoping for the best.
We've worked a lot of clients through this issue of feeling like they think that they've handed something off, yet they still feel overwhelmed or uncertain, and they're not really getting the full power of their assistant.
Now sometimes it's a wrong person in the seat issue. Usually not on our team, but sometimes that's the case when you're first delegating to somebody and we need to just put somebody else in that seat. But oftentimes it's how someone is approaching delegation.
I'm not hating on my clients here. Most of them haven't had an assistant before, and so it's a totally new routine for them. But this is a super common issue that we have to address. And so I figured, let me give the tools and strategies so you can avoid this if you ever hire an assistant on your own.
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.
First I want you to know that relief is the very first and most important indicator that delegation is working for you. It's not just about having more time in your day to day, it's also about having less things circling in your head.
More head space. Even if you've had bad team members in the past, or specifically just a poor hire in this role before, and your trust has been broken and you feel like you're gonna go down that micromanaging ramp of darkness. Even if that's happened to you before, you're still gonna feel relief if you've hired the right person and you're approaching delegation effectively.
If it's not working, then you should really quickly feel these warning signs. And there's three particular warning signs I want you to look out for . The first one is that you still feel like you mentally own the task. So if it's still circling in your brain, if you still feel like you need to check on the status of the task, is it gonna get done?
If you're still worried about it, then that's a really big warning flag. If delegation's working effectively, you do not feel the need to double check on it. You know that person's got it. You don't gotta worry about it. You're not wondering if it got done. The second warning sign is that you don't feel confident handing new things to them.
So you should have a kind of basic routines that a tasks this person is responsible for, but that, that job description should evolve and you should be able to add new things to their plate even if you don't have a process and structure for it. If you don't feel confident, if you hesitate and you're thinking, ah, they're just not gonna get this.
That's a warning flag. It's different than the feeling of like, it'll take too long for me to explain this. I'll just do it myself. And it's really that feeling of like, they're just not gonna get this, or they're not gonna do it the way I want it to get done. That's a warning flag.
The third warning flag is gonna go back to that to-do list. So if you feel like maybe you've got a shorter to-do list, but your head is still busy with stuff, that's a warning flag that you're really not delegating effectively. Because when you're able to get things off of your plate, you have more white space to be more strategic, creative, impactful in your business.
So it's not just about being less. Busy. You should be increasing your strategic capacity in business. So those are your three big warning signs. Now let's look at, is it a you problem or them problem. And this isn't meant to make you feel bad, it's just meant to really highlight, do you need to just fire this person because I believe in hire slow fire fast.
Do we need to fire them or do you just need to take a step back and really evaluate how you're gonna collaborate with them moving forward? Alright, and there's four signs here. So sign number one is that you're delegating low leverage tasks. This is super common. Most of the time when you look at what can I get off of my plate?
You're just thinking of those little things that just take up like two, five minutes, 10 minutes in your day. Those are like the low hanging fruit you can pass them on to somebody else. The problem with that though, is that that still leaves a lot of high impact challenging stuff on your to-do list. So I would shift your mentality here
if you've got a, a capable assistant, I want you to look at what are the high impact tasks that don't require your expertise. These are the things that you can hand off and you're actually gonna feel relief about someone else doing them, and it still moves the needle and makes progress on business goals.
The second sign is that you haven't really built a real runway of context. So if you want someone to take initiative, they need to know big picture. They've gotta know your goals. They've gotta know what really matters in the business.
A great way to give that context, which also builds up to that like proactive, someone being able to be inside your head kind of relationship with an assistant. A great way to do this is to just drop voice notes, so all those ideas that you get when you're driving from client meetings or job sites, all those ideas that you get, put 'em voice notes, even if it's not a task, just, Hey, I'm thinking about this, I'm thinking about this.
Those brain dumps and sharing your why go a long way with an assistant. The third thing is that you are giving unclear expectations. if you want someone to meet your standards of excellence, you've gotta let them know what that standard is. This is the difference of saying. I needed the numbers on X, Y, Z to instead saying, Hey, I need these numbers by end of day tomorrow because I present them the next day and I need time to analyze them so I feel confident on this presentation or something like that.
The more context you give on the why, but then also the more clarity you give on expectations helps that assistant really take ownership of a task. And then the fourth thing that it might be a you thing is just realistic expectations about the timeline. Alright, let me break this down. The first four to six weeks is really about you and the assistant getting into a rhythm and then proving that they're reliable.
Then that next six to 12 weeks, that's where I'd expect an assistant to start providing some suggestions and saying like, Hey, I think we can clean this up, or Would you like me to do X, Y, z? But then the next three to six months, that's where True Proactiveness really shows up with an assistant.
So I just wouldn't expect Strategicness when they are still learning where your folders are, who all's on your team and who your customers are. Give them that realistic timeline, but still look for the shot. Look for those signs that they're meeting, your standards of excellence and expectations.
So if you've handed something off but you still feel burdened by it, run through this checklist, run through, is it a you or them problem? What can you shift in how you collaborate with them? And are they truly just not meeting up to expectations and they're the wrong person? Or are there some things that you can look in the mirror a little bit and shift to improve how they show up for you?