4 Imperative Skills for New Leaders or Managers | Ep 219
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What's up guys, welcome back to build and today I want to talk about four skills that are imperative to succeed as a new leader.

So when I say new leader, this means it could either be you're a leader of your own business or you're a leader of another person's business. You know, it really is applicable both ways. And the reason that this is top of mind for me, and actually, I don't really even have a script for this podcast. I'm just, it's been something I've been sitting here thinking about between meetings. And I really wanted to kind of crystallize my thoughts since I thought it would be helpful. The reason I want to talk about this is because I found myself this last two weeks, I put together quite a few development plans for people on my team. And development plan is really like

It's the things that I want somebody to work on or I would suggest they work on to achieve their goals. So if I know that somebody comes in and they're a operations manager and they want to become a director of operations or a COO, what I essentially do is I look at all the skills that they lack. And then typically what I do is I put together three that I think are the 80-20, like these three skills will get them 80% of the way. And then I write a document out with those three

And then with those three, I say what things would need to occur for me to know they have the skill or what things I think they should change to get the skill. And then usually what I do is I say, let's just focus on one until we've mastered it. And then let's move on to the rest, depending on the person and how anxious or, you know, like what their tendency is. Sometimes I give all of them to them at once. Sometimes I don't. It really just depends on the person.

But I found this to be something super helpful because if somebody comes to me who doesn't report to me and says, "Hey, I really want to know where to improve," I don't want to withhold information. And so what I do is I usually put together a document, I let their manager know, I usually run it past their manager to say like, "Are you aligned? Do you see anything that's missing?" And I hand it over to them. But I had quite a few people ask me in the last few weeks. And so, you know, it's probably with the end of the year coming up, people are reflecting and people are thinking like, "Where can I get better?"

I wrote down a few that I've just seen across the board are similar for a lot of people. And really it's just like, it's the people that are stepping into new leadership roles that I think these apply to. And what I realized is these are all things that I had to learn building my businesses over the last decade. And they're all skills that I had to acquire to be,

to be the leader that I am today to be capable of running my company. And they're not skills that I was born with. They're not skills that came second nature to me. They're actually skills that were really hard for me to learn. And I will tell you the reason for that is, you know, I don't really have anyone to model. I've never had, like, I've not had a lifelong mentor. I didn't have somebody telling me what to do.

I didn't really have anybody that was telling me and giving me feedback constantly. And so I've had a lot to learn a lot of this by reading books, by looking at aspirational figures, and then just asking myself, like, what's the gap between me and this person? Like, what would this person do that I'm not doing? Or what do I do that they wouldn't do, right?

You know, the four things that I wrote down are really skills that I think would help anybody, whether you're leading yourself and leading your company or leading a department and you are working within a company. The first skill is understanding that it's not about saying yes or no, it's about informing people of the cost of yes or no. When I was first in business and, you know, I obviously have my business partner, Alex, who I'm also married to, and we would be talking about decision.

Typically, all the departments roll into me. So I have the most context on most decisions. So when Alex is like, what if we tried this? What if we did this? You know, for me, it's sometimes he would say something and it'd be so obvious. They're like, well, no, like that's obviously not going to work. But here's the thing. He didn't have all the information to understand that.

And as I've grown my companies and they've gotten bigger, what I've had to understand is that now I have executives who don't have context on the whole business the same way I do. And then they bring ideas to me and say, we should do this. And I think to myself, well, what the fuck? No, like, of course not.

And what I recognize is that it's not about saying no. Nobody wants to be the person in the company who's known for saying no, because nobody wants to be like, oh yeah, he's a no man. She's a no girl. Like she'll just say no, no, no, no. Right. Nobody wants to be known for that. And I don't want to be known for that shit either. Right. I don't want to shoot down ideas for my team. I don't want to shoot down ideas for my business partner. I don't want to shoot down ideas for myself. Instead, what I realized is what it is, is that when you're the

closest to a problem, or I would say you have the most perspective on a problem, you tend to know what the cost of solving that problem or exploring an opportunity would be more than anybody else. But what that also means, and this is where a lot of people miss out, is that it's your responsibility to provide people who ask about it and who have ideas to solve it with the context.

So the cost of a change, the cost of a solution, the cost of yes or no means providing people with context. So for example,

If an executive comes to me and they're like, you know, I think we need to roll out this new software for the whole company. It's going to track all of our goals and it's going to do this and it's going to do that. We really need this. Right. And they're like, why do you not think this is a priority? It's like, well, if I were like, that's an amazing idea. However, these are the other six things in the department that we're doing right now. And here's how these six things are actually going to solve that problem before we even deploy that solution.

That's me informing somebody of the cost. And so what I'm doing is I'm telling them the reason why, the logic as to why it would make sense to go with a different solution, right? Another one for that would be if somebody comes to you and they're like, here's what I think we should try doing. And you're like, oh my gosh, that would take forever.

All of this time from these four leaders and these four leaders are working on these six initiatives and these six initiatives are driving 90% of our revenue. Why on earth would we deploy them into this other thing that's going to not, it definitely won't match that much revenue.

then your job is to say that. And sometimes that means telling people that you as a resource don't have capacity and that you would have to reorganize your priorities. And so what I've had to explain to a lot of people recently is like, it's not about saying no, it's about explaining the cost. Especially if I, for example, ask somebody, I'm like, hey, I would love to do this thing. It's not like say no to Layla and you're like doing a good job protecting your team. It's inform Layla of the costs that she can decide if it's worth it.

When you're bringing this stuff up to somebody that's above you, if you have someone above you and you're working in a company, it's about informing them of the cost and giving them context on all the other things that are going on so that they can make the best decision. And so what you have to learn to do is inform key stakeholders of the cost.

If you have teammates bringing to you solutions, right, and they don't know the true cost, then as their boss, it's also your responsibility to give them context on the situation, which will allow them to calculate the cost themselves.

So if somebody who runs a sales department comes to me with a solution that's going to completely drain my customer success and likely just completely diminish my renewal system or my renewal strategy, then I need to inform them, hey, I don't know if you know this, but over here in customer success, if we were to use them for this, here's what would happen to our renewal strategy. And they're like, oh my gosh, wow, I didn't know that. The difficulty is like, we want people to make decisions like owners without having all the same context as an owner.

It's the same goes for like, we want people to make decisions for the business or for our department, but they don't have all the information. And so what I see happen with a lot of new leaders, including founders, it is not like isolated to just people that work in a company, is they're just really bad at informing of costs

Usually they get like emotional. They think, oh my gosh, I can't believe you would ask this. I can't believe they're asking this. It's like, well, they wouldn't believe it either if they knew the cost, right? But they don't. And so it's your job to communicate and advocate that cost. It's like if you have a boss and that boss is saying, hey, I want you to go work on this. And you're like, oh my God, does he not know I'm doing all this other stuff? It's like, well, what if he doesn't?

Seriously, I mean, like companies are not perfect. Your boss does not always know all the other seven things somebody else has asked you to do. But your boss is responsible for helping you prioritize once you make them aware of the other demands on your plate.

There's so often that I just see people miss out on this because they don't communicate context to others. They don't give context and they don't give the cost. And so the two things that you want to do if you're stepping into a leadership position and you're moving up in a company or you're a founder and this is your first time is you want to think about informing people of cost and giving people context.

This is why companies have a hard time coming to decisions unanimously is that it's often just because people have different context. And then people who have the context don't do the best job sharing the context.

Now, here's the key. If you're not a leader, I don't expect you to just naturally share context with people because you're probably like, well, that's not my job. Correct. I'm talking about leaders in a company. So if you're a leader in a company, it is absolutely your job to share context. Whether your boss verbalizes that to you or not, there is no way, shape or form, that is going to hurt something if you share context and share the cost, right? And say, hey, I would love if you help me prioritize so I can help us accomplish these goals. So that's the first thing that I've seen a lot of is just

you know, instead of informing of cost, we say yes or no, and we just shoot something down, or we just do it with like impulsively, right? And we don't want to do either of those things, like acting out of impulse without thinking something through isn't good for the company. Neither is just saying no to every single thing that's not on your list for the last three weeks. The second thing I see is people not knowing how to manage up. Now,

Now, what does it mean to manage up? It means to manage the person above you. It means to manage your boss. Now, some bosses make it really easy to manage up because they're easy to talk to. They don't get annoyed when you bring them bad news. They might thank you for bringing them bad news. They're pleasant to work with. You genuinely get along with them.

Not every boss is like that. Like some bosses are a little scarier. Some bosses, you know, are a little less filtered. Some people are just a little rougher around the edge. What I see is that when somebody doesn't feel comfortable at all times bringing something to their boss, they just tend to keep it to themselves instead of advocating something to their boss and trying to accumulate the skills of doing so. They just say, well, my boss is a dick and never is going to listen. And so I'm going to keep it to myself and I'm just going to be miserable in the corner over here.

Now, I want to caveat this. There are a lot of people who are shitty bosses. You guys, if you listen to my content, I'm fucking aware of this. I have had terrible bosses. But there's also bosses that are reasonable once you provide them with the information. A discussion I had with my team the other day was, you know, we had a project that we rolled out. That project had deadlines and it was all leaders that were involved in hitting these deadlines and quite a few did not hit them.

And what I explained is that it's not the fact that you didn't hit the deadline, even though I would like this team to hit their deadlines. It's actually the fact that if you knew you weren't going to hit the deadline, why didn't you communicate it ahead of time?

And if you didn't hit the deadline, you just kind of like did it in the dark. People who miss deadlines in the dark, they're just like hoping that you don't see. That actually makes you look so much worse. The best thing that you can do if you're going to miss a deadline, right, is advocate to your boss. Let them know, hey, I don't think I'm going to make this deadline and here's why. Now, if you wanted me and this is the most important deadline to hit, here's what I would need to do to hit it.

and you explain what the cost of hitting the deadline is, and you advocate for yourself by saying, here's what I think I should do, here's what I think my priorities are, do you agree or disagree? Again, guys, remember, this is if you're a leader in a company, because if you're a leader in a company, then you are a leader reporting to a leader. And if you're a leader reporting to a leader, then I would bet my bottom dollar that your boss expects that you have the skill to do this.

And even if they're not verbally saying, hey, I would like you to advocate for yourself, they are expecting it of you. And so if you're a first time leader, this is a difficult one for people to do, but it is absolutely imperative to do because if you can't communicate to your boss when you have too much on your plate, when you don't know what the priority is, when you think you're gonna miss a deadline, when you don't know how to tackle a project, how can they help you, right? Like it's like one of those people that's like, we're expecting people to mind read and people do it in business all the time. It's like when you're like,

God, I wish my husband would just get me this necklace for Christmas that I really want. It's like, well, did you tell him you want the necklace? And it's like, well, no, he should know. As much as we would like to think when we're leaders in a company, like, oh, I hope my boss understands everything on my plate. Here's the other thing that you should understand. If you're a leader reporting to a leader, you might have individual contributors that report to you and you know everything on your plate. But if you're a leader in a company, oftentimes your boss, who's also a leader, doesn't know every single thing on your plate.

And they expect you to be able to communicate all the things that do get put on your plate and communicate them back to them so they can help you prioritize and say, actually, I don't want you to focus here. Here, tell this person this. Yes, you should focus here. Let's reprioritize this. And so that is definitely a shift of what I see like first time leaders make that is difficult for them, which is like, how do I, you know, go from having somebody prioritize everything for me and know everything I'm doing to like learning how to do that myself?

And I think sometimes it just has to be said like, hey, you're now expected to actually do this for yourself. And it's like, whoa, I don't actually know if I can. I don't actually think I've done that before. I've always had someone telling me what my priorities are, right? And that is a muscle that you have to develop. However, if you don't communicate to your leader, you don't let them know, you don't advocate for something, you're never going to get there. Now, the third thing, and I think one of my, like the most important things, and I think I'm working on this with quite a few people right now,

Having the emotional resilience to make the right decisions, even though you know that you will be disliked. This is one that plagues companies. Plagues. And I promise you, it is something that I have dealt with myself. And I have just had to accept the fact that I'm going to make decisions and people aren't going to like me for them at times. And it is what it is. I would love if everybody liked me, but the reality is that's just not going to happen. Now, what this looks like is...

People being afraid to hold their boundaries. People being afraid to make the right decision. People being afraid to advocate their position in a company because they're afraid that they're going to piss other people off or people are going to dislike them. Now, caveat here. This doesn't mean that people dislike you because you're an asshole. If you're an asshole, of course people dislike you and

I am not an advocate for acting like an asshole. I am an advocate for you expressing your opinion, for you telling people what you think we should do on a project, for you saying where you think your priorities lie, for you expressing if you disagree. Those are all super appropriate things to do in a business, especially if you're a new leader. Acting like an asshole is not on that list, right? However, what I see is that so many people

What happens is they are so reliant on the approval of their peers and boss that they won't make the best decision and they won't protect their time, they won't make the best decision, they won't do the right things in their role because they're too busy getting approval of others. Needing to have approval from your coworkers and have them like you at every point in time

is lethal to a leader, lethal. If you feel like you can't rest assured, you can't focus on a project, if you don't think that somebody loves the decision you made or you don't feel like they absolutely like you at 11 out of 10 right now, you are going to have a very hard time in leadership

Because I can't tell you how many times I've made a decision that I know people don't like. I know they're not like stoked to talk to me at the moment, but I know it's the right decision and I'm okay with it. And I know that it's going to subside and they're going to feel okay in like an hour, two hours or a day at most. And it is what it is. We have to make decisions that are best for the business, even if it means it's uncomfortable for us personally.

And when I see this, what I see is that so many people, they keep themselves stuck in a certain level of leadership because they're so focused on getting the approval of others and making sure that everyone understands every little thing they did and every person likes everything they did and everyone approves of every decision they make.

It's like, well, did the right key stakeholders approve? Did you get the right buy-in from the right people? And if there's people that you don't need that buy-in for or who are naysayers, that's always going to happen no matter what. There's a lot of people who aren't going to think anything's going to work, aren't going to think any decision is good if it doesn't come from them and if they don't see a result. And that is just part of business.

And so what I see is like with a lot of new leaders, and this is founders and leaders and companies included, is that they slow themselves down so much because they're just seeking the approval of others. I used to feel this way. I will admit in the beginning of my business career, it was like I had the hardest time making decisions when I knew that people were not stoked with my decisions.

And it was really difficult for me when people were like, "Hey, I don't agree with you there, and I just need to like step out for a second." And I would be like, "Holy shit, like, do you hate me?" And the thing is, it's like, it's not like they hate me or dislike me personally. They don't like the decision that I made or maybe the direction I wanted to take something. And that's okay. Here's the thing. If everybody agrees with you all the time, you're probably not super effective because you're probably waiting until something is so obvious to make any sort of decision.

that it's like not actually that important of a decision anymore. It's just like the obvious common sense move. If you're stepping into this position, you know, something that I like tell people is I'm like, hey, I need you to be okay being disliked. I need you to be okay with ruffling some feathers. Now, again, I want you to understand this does not mean delivering things in a snide manner. This doesn't mean having an attitude with your coworkers. This doesn't mean being mean to people or, you know, raising your voice on calls. It does not mean any of those things.

It would sound something like, hey guys, I really appreciate everyone's input on this decision. Here's what I've decided to do. I understand some of you guys do not agree with this and I completely understand. I respect your opinions, but I'm gonna go with this as the decision. That's what we're gonna do moving forward. I appreciate everyone's input. And if you have any other follow-up questions, you can follow up with me privately.

Like you hear the tone of my voice, it's not like I'm being snide or being malicious or being catty. I'm just like, hey, it is what it is. Like I appreciate everybody, but like I made a decision that like not everyone's going to be on board with. And the reality is, is like if everyone's on board with the decision, it's probably too late. Just remember like when you're stepping into a leadership role or when you're a first time leader and it's your first company, like not everyone's gonna like every decision you make.

But the thing is, if you try to make every decision to please everybody, one, decisions will take four fucking ever. They will take so long to make. It will be a painful process, and you will have so many hoops you have to jump through to get, quote, approval of everybody on the team. This doesn't mean that you don't want feedback from people. Like, that's completely missing the point. I'll do

I can probably make a whole piece of content on that. Like you should always be asking for feedback, but that doesn't mean that you're going to act on every piece of feedback. And it doesn't mean that you're going to take every feedback into consideration as if it is the word of God. Now, the fourth thing that new leaders tend to overlook or like have a gap in their skillset that I think is incredibly important is the ability to prioritize. Okay. My favorite tool to use for prioritization is the Eisenhower matrix. Right.

That's understanding what's urgent, what's important. Things that are urgent and important, we do now. Things that are important but not urgent, we do later, but we do. Things that are not important but are urgent, you delegate to somebody. And then things that are neither important or urgent, you get the fuck rid of. You figure out a way to eliminate it, outsource it, whatever you can do, delay it, just get it out of your plate. A lot of people that step into a leadership position for the first time, whether it be their first company and they're leading their first team,

or they are the first, you know, a first time leader on a team.

and they've never been in a position so high before is they have a really hard time prioritizing. And a lot of times it's because of a couple of things that I just mentioned, which is like, one, they have a hard time letting their boss know the things they work on. But two is they're so used to somebody else doing it for them that they don't actually formally prioritize their tasks or responsibilities. So when I say formally prioritize, I mean, like they don't sit down and be like, yo, what do I need to focus on for my priorities? What am I focusing on right now?

Is this aligned with my objectives? Is this moving the ball forward? Do I spend my time on the right things? And what I've noticed is that a lot of first time leaders, they do not block time to think and reflect. And so because they don't block that time to think and reflect, they never gain the insights that thinking and reflecting gets you, which is often knowing what to prioritize. Something that I have done every Sunday

since I started in business is I have time where I look at last week, I look at the coming week, and usually actually I look like a week or a month behind and a month forward,

And I ask myself, like, did I spend my time on the right things this week? Did I move everything forward I want to this week? And I reflect, like, how do I need to alter next week so I can actually be more effective or prioritize better? Because every week there's almost always, I mean, I've had perfect weeks, don't get me wrong, but like most weeks there's like, oh gosh, I wish I'd gotten this done. I wish this had happened. And then I'm like, okay, how can I change for next week so that going forward I can accomplish more with my time?

The issue is that to prioritize, in order to prioritize, right, which is deciding what you do when and in what order, you have to have time to do that. And so what I've seen is like a lot of new leaders have just so much frenetic energy and they're constantly in this reactive mode which prevents them from ever being in a proactive mode. So because of that they stay stuck in this like cycle of being reactive because they never give themselves a chance to even be proactive because they don't set aside even an hour a week to get ahead.

I will say this, I've said it so many times, but I will say it again, which is like planning your week on Sunday. I'm gonna be really honest. I don't know many fantastic leaders that plan their week when the week starts. Like they all know Friday, what they're gonna be doing the next week, or at least by Sunday. If you're a new leader, if you're stepping into a role that you've never been in before, or if this is the first time that you've run a company and had a team beneath you, these are four things that I would focus on and I would figure out

which one I needed to focus on first, that would give me the most bang for my buck. With that, I hope you guys have a good rest of your whatever day of the week it is, doing whatever you're doing. And I will see you on the next one.