213: Leading Others and Letting Go

Hello and welcome to another episode of the Working Without Pants podcast. Super excited today to dive into another episode about leading others and letting go. This one's near and dear to my heart, something I struggle with. So this episode is a little bit of my own therapy and also sharing with you guys some of the things I've learned about how to really let go and let others become leaders within your team.

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We pay out a 10% commission on any customer you refer our way. Just send an email introduction to jake at contentallies.com. So one of the hardest things that I have found about growing as an entrepreneur is that you have to eventually get to a point of letting go of things and letting others become leaders within your organization And I think this is a very different phase than hiring people and delegating and asking them to do things.

I think that that's, you know, there's like a level of leadership that's just delegation where you're saying, hey, I need you to do this thing. Please do this thing. Okay, cool. And then they give it back to you and you're like, okay, you did a good job.

You didn't do a good job. Like that's delegation. But where leadership comes into play is typically where you have someone who is overseeing a department or typically a team within your company. So someone who's kind of becoming a manager.

And this is really a challenging shift to go through because it takes, it's a lot more than just delegating something to someone. You're trying to give someone ownership over an area and saying, hey, when a problem comes up, you need to solve it. You need to figure it out. And this is kind of this level of like really giving them responsibility, giving them ownership is it's challenging and it's really hard to do.

And, you know, a lot of times this will typically what I found is, you know, with the natural growth of a company, you'll kind of promote someone who was maybe a doer in your organization into a management role. And that kind of tends to be the flow that I see among most small companies versus, you know, hiring in someone who's just some manager from the outside. That typically isn't quite as much of a thing that happens in small businesses. You know, most people, you know, start with a small team.

They grow a little bit. someone who was their best doer becomes a manager. And like that kind of is a common flow. And so what that is interesting about this is you actually hit the second kind of dynamic here where you have your challenge of letting go, but then you also have this challenge of these, the doers that you're promoting, they have to let go too, and they have to learn how to manage.

So you're, you're kind of moving to the space where you're trying to give people ownership, but then they also need to learn how to really kind of lead others as well. So it's just, it's really interesting challenge and dynamic and everything going on. But what I've found is a few things that are really helpful here. And one of which is an advice I got from my advisor, Anthony Tamboglio, was just like, you got to set the date and rip the bandaid.

And because what I will say is one of the biggest things to get to a point where you have someone like really having ownership over a role that you're not doing the work, you're not really like kind of micromanaging or Hawkeye-ing over it. At some point, you just got to be like, all right, at this date, you're on it. And if you need me, you can come back to me for questions. But at this date, like you've got it.

And you just got to kind of like rip that bandaid and make that happen to where you're saying, OK, at this point, like you're owning this. And if you need my support, you can come to me. Well, maybe you keep one on ones on the calendar. You keep supporting and developing them.

But after this point, like you are responsible. I did this when I went through trying to build out my guest scheduling team. And it was, you know, like a couple of months of shadowing. And then like there's this kind of scary thing where it's like, oh, God, like, is it my really ready to hand this off?

Are you going to screw it up? and at some point, it's just like, all right, like, you're going to take over on this date. We'll still keep doing our weekly check-ins. We'll go through questions.

I'll keep an eye on stuff. You know, we'll have some metrics that we can measure you by, and we'll have things we'll check in on each week, but at this point on, like, you're not going to, you're owning this. You are responsible for figuring out problems here, and again, just having that kind of set date where eventually you just set the date rip the band make it happen that definitely helps because I think one of the most toxic and not great spots to be in is to get in a spot where you just kind of keep hopping in and doing a little bit of the work because you don't feel like they're ready.

And that's super dangerous. And it's a super dangerous path to get into. It kind of wrecks their confidence and the ability to do the work. You're still not letting go.

You're doing the work. And it's just kind of a dangerous cycle that you can get in. You know, that is one thing. Just set a date, rip the bandaid on that.

Other thing I think that's really helpful, especially if you're kind of promoting someone is make sure that they have a job description, you know? So, um, one of my top, my head of production, she was honestly just like really one of our best kind of podcast managers. And now we're like, Hey, we need someone really overseeing the entire production team. So we're kind of promoting her to like this management.

And one of the things I think is really easy to do there is just be like, Hey, well now you're going to be responsible for all this, but like, that's not great. What you need to still do is if you're going to kind of promote someone into a leadership role from where they're at is they need a job description for what their new role is. And I think this is super easy to not do where someone just kind of gets hired and then you kind of just start shifting them around doing different stuff and not the most healthy thing.

And a lot of times people get in the spot where they're kind of like half doing work, half managing, and then they start doing a poor job on like everything. And that's not good, not a good place to be. And so if you're going to shift someone into a different role, you want to define that role. You need to define like what is success.

Just go in it and write a job posting like you're hiring a new person. So even if you're promoting someone up into a new leadership thing, make sure there's a clear job description. They know what they're doing. They know what they're responsible for and they can go out and then finalize and execute on that.

Cause if they don't have clarity on that, then it's super toxic and it's going to get in a bad situation for everyone. They won't be happy. You're not going to be happy with her for performance, anything like that. Other thing I find is really helpful with a job description is like this defined success for them in one sentence.

And so for like our podcast managers, it is your responsibility is to make sure that your podcast, all podcast episodes get published on time and error free. Like that is your job. That is your responsibility to make sure that things get through production and everything that happens in production. You're on time error free.

Like that is your, your job. And so getting really clear on that, we know we have someone in guest scheduling is that like we always have guests a backlog of guests scheduled for every single one of our podcasts like that is success for you um recently hired a new enterprise client um strategist someone to help kind of do account management on the enterprise accounts and success for them is success for you is is making sure that our enterprise clients achieve their business objectives and so getting really quickly into like defining one sentence like what is success for them that is super helpful and it gets to like the core of it because otherwise they can easily just kind of be focused on all the wrong stuff so you want to make sure that they know what it is and you're just going to keep hammering that home so that they would that that becomes like a filter for all of their activities to go through other kind of thing i'll add in there is just again when problems come up it's really easy for you to want to just jump back in and solve them or tell them what to do and i think it's a really a thing when a problem comes up to just be like hey how would you solve this Or just let them handle it Or sometimes if someone comes to me and they like have a problem instead of solving it it like well what would you recommend doing Or how would you go about solving this And just turning that question back around on them and don't solve problems for them.

That's really enabling and it kind of makes it where they don't own their job and they keep kind of relying on you. And it's so crazy, but if sometimes a lot of people just don't have the confidence initially, especially when they're kind of transitioning into something new. And if literally, if you just ask like, well, how would you solve this? Or what would you recommend doing?

They'll come back with something. You're like, yeah, well, that's pretty much what I would have said. And it just kind of gives them that confidence there. Or maybe, you know, maybe they go down the wrong path and you correct them a little bit and it's a coaching moment.

But make sure you just get to the point where you're not solving problems for them and you're letting them solve problems. And last hack and really thing with leading others and letting go is go book yourself a vacation. I would say it's literally one of my favorite productivity hacks. I did a whole episode on this in the past.

I just got back from a three week vacation where I worked 10 hours over about three weeks. And it was just amazing because people had to step up and figure out things while I was out and nothing really went horribly wrong, you know, while I was out. And it was really cool to see at that spot and see the company be able to run like that. And it takes, I think you stepping away sometimes for people to be like, well, he's out.

So I'm going to have to figure this out because I don't want to bug him when he's on vacation, you know, And, and then people just will step up and figure things out and they'll own it. And, uh, you know, you need to make sure you set your clear criteria that everyone's, you know, set up for success. They know criteria, like what is succeeding for them, what they need to accomplish while you're out, but then go and just let it happen. And, and you'll be amazed.

I always feel like I'm way more ingrained. I'm like, God, how am I going to take this vacation? How am I going to do it? Like, I'm just, I'm so, I got too much work on my plate.

And then I take the vacation and I'm like, wow, like it really is working. Like I can step away. Like, that's awesome. And so just really can't speak highly enough of that approach.

Highly recommend. Once you got some of those leadership positions, you get them up there. You just get them owned. Get them prepped.

Spend time with them. Do one-on-ones. That's another thing I didn't mention, but I also do a lot of one-on-ones with people while I'm developing them into these leadership roles. Some of those are weekly for my really high-level team members.

Some of those are monthly for people that are a little more removed. But all of those together just really helps you get to a point of leaning and others letting go, which ultimately creates freedom, lets you get to the point where you can take vacations and hardly have to work while you're on them. And it ultimately lets you get to a point where you are freed up to work on more valuable, higher value problems in the business. So that's what I've got for you today on leading others and letting go.

Again, I'll mention here that I am still looking for about one or two more, which is really actually one or two coaching clients that I can work with, just on an ongoing basis, someone that I can just meet with twice a month, have a great conversation with, try to impart some wisdom, teach some of the things I've learned. I've got a ton of value from my coach, Anthony Tobolio, and looking to give back to some others as well. So reach out to me if you have a question, if you're looking for someone to work with as a coach.

And until next time, I hope you are working without parents. Thank you.