“If everyone on your team agrees with your decisions… you’re irrelevant as a leader.”

That was one of Ray’s biggest takeaways from his 2025 audit.

Many founders think leadership means alignment and consensus. In reality, leadership often means making the hard decisions no one else wants to make.

This episode explores “Management Debt,” a concept from Ben Horowitz—the compounding cost of avoiding tough conversations, difficult firings, or killing the wrong projects.

Left unpaid, that debt turns into stagnation, culture problems, and lost momentum.

The lesson: real leaders don’t avoid hard things — they sprint toward them.

If you’ve ever delayed a difficult decision to keep the peace, this episode will challenge how you think about leadership.

What You’ll Learn in This Episode:

1. Why leadership becomes irrelevant when every decision has consensus
2. The concept of Management Debt and how it compounds inside organizations
3. Why avoiding difficult conversations silently damages culture
4. How delaying tough decisions leads to stagnation and team attrition
5. Why firing, demotions, and killing projects are core leadership responsibilities
6. The difference between being liked today vs. respected long-term

Resources Mentioned

1. The Hard Thing About Hard Things by Ben Horowitz

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

==

This episode is part of the 2025 Audit series — lessons learned, relearned, and unlearned.

This podcast is where Ray thinks through hard decisions — especially when the usual playbooks stop working.

If that way of thinking is useful, that’s what continues here.

New to the show? Start with the “Start Here” playlist:

https://player.captivate.fm/collection/a7577a6f-15da-4521-b214-35e4e47f320b

If everyone on your team agrees with your decisions, you are irrelevant as a leader.

And that's.

That's not hyperbole.

Like, that is the actual job description.

And what I mean is the decisions that you make where everybody's happy, right?

Like, if you've got consensus, where nobody's pushing back, where it's obviously the right call, those aren't leadership, right?

Like, those.

That's.

That's just like, collective decision making.

And if that's all you're doing, what is the point for you?

And this was a really big lesson for me this year that I'm gonna.

I'm gonna dive into now.

Quick thing, actually, I break down frameworks like this in a weekly email newsletter that I send out.

You can subscribe if you want@raiseemail.com completely free.

I send it out every.

Every week.

Know, like, that I've changed my mind on.

And this one hit home really hard because it's not that I made a mistake or had to relearn something, but it was something that was reinforced from years ago that I.

That I had learned.

But because of the experience that I've had since then, I kind of saw it through a different lens.

The thing is, like, leadership isn't.

It's not the easy, teachable stuff.

It's not actually, you know, setting goals, getting KPIs, right, learning how to delegate, you know, writing a, you know, mission statement or, you know, vision statement like that.

Like, those are the obvious things.

And I'm paraphrasing a little bit of what Ben Horowitz talks about in an interview that he did.

He had been as the.

He's the author of Hard Thing About Hard Things, which, by the way, epic book, if you like.

If you read one business book this year, I. I recommend the Hard Thing about Hard Things.

I read it multiple times, and it's phenomenal every time.

And I'm actually.

I'll put a clip of him in the description, like the show notes below.

Okay.

If you want to dive into this further.

But he talks about these.

Like, he says people don't run into trouble with, like, the obvious leadership stuff.

Right.

Like, they run into trouble with the hard stuff.

Like the hard conversations with people that you actually like.

You know, how do you.

How do you handle a reorg and all the emotions that are involved in that?

And people are going to be losing power and all of that how do you handle demoting somebody?

How do you handle firing somebody?

Talking to, to someone about, you know, a project that they're really interested in and they're, you know, they're, it's almost like a passion project for them.

And you're gonna, you know, you're gonna kill it, right?

Like, you've gotta, you've gotta have that conversation.

And it's, it's like making the decisions where you're, you know, 60, 65% sure, but you're, you're not certain.

Maybe it's something that's unpopular with the team or it's unpopular with your, your, your customer base.

Like, those are the hard things.

And from personal experience and working with, with other leaders, those are the things that people tend to avoid, right?

And as a leader, you are better off sprinting to those things instead of avoiding them.

So you can actually handle them instead of trying to dodge them.

But the defaults typically is avoiding the hard decisions, the hard conversations, the hard things.

And the thing is, if you don't sprint towards those things, they're going to find you one way or the other, right?

Like they're going to hunt you down.

You're going to have to deal with those things no matter what.

And if you don't, what you end up with is what Horowitz calls like management debt, which is basically all the decisions you should have made, all the conversations you should have had, all the changes you should have implemented, but you didn't.

You avoided them.

And then they accumulate in the background, right?

They just start to compound like, just like a, just like financial debt, like management debt compounds in the background, it accrues just like, just like money debt.

And there's a real compounding impact of not making the decisions or not having the conversations or not doing the things that you need to do as a leader.

Because if you, if you don't fire the person who should be fired, if you don't demote the person that needs to be demoted, if you don't change the behavior that needs to be changing, your business continues to operate with that inefficiency.

It keeps adding up in the background and it actually accumulates like it's not just that specific problem, because as that problem permeates within the organization, within your team, you end up with impacts to your culture.

You, you get good people leaving, so you've got attrition in, in your team.

Your, your business stagnates.

Like you, you start to plateau.

That's management debt.

And you've got to deal with it, because you don't want to accrue that, that debt the same way that you acre an unhealthy financial debt.

That, because that, like I said, like, the compounding is real.

And the longer those things go, the more they add up and the harder it becomes to actually unwind, the harder it becomes to fix.

And if you wanted to avoid it in the first place, as it accumulates and as it grows, you're definitely going to want to avoid it later on.

If you're avoiding the things like trying to make everyone on the team happy or because you know, you, you know that people are going to disagree with your decision, you're basically avoiding your job as a leader because your job as a leader is basically making unpopular decisions.

If you're not willing to make unpopular decisions, you are irrelevant.

The point where you add value as a leader is literally when you do things that people don't like.

When you have the conversation other people won't have, the one that, you know, the person at the other end of the table may not want to have.

When you make that decision that, like, you're confident and, but you're not.

Like, I'm not certain.

Like, I, I'm, you know, I feel pretty good about this, but we operate in uncertainty.

Like, that's what leaders do and we've got to make decisions.

And when people push back, that's you doing your job, right?

Like, it's where you add value.

Because again, if all you're doing is making decisions and, and looking for what everybody is going to collectively do anyway, what's the purpose of you?

Right?

Like, that's why it, like, leadership takes courage.

It's, that is the essence, at least in my mind.

Like, that is the essence of leadership is, is courage.

And it's not about whether you're light and respect in the short run, it's about whether you're liked and respected in the long run.

And that's like a direct pull from, from Ben Horowitz.

And that lesson, like, the, the elements of those lessons really hit home this year, like, particularly in some decisions that we made about my own business where, like, where we're going, how we're building the team, what kind of business model we're running, how we're approaching growth, what we're going to do with the, the culture, how intentional we're going to be, what that's going to look like, whether we're focusing on sales growth or whether we're going to focus on product improvements, whether we're doing like full service white glove stuff or we're going to be doing more scalable, low touch, lower ticket stuff.

Like, these are all decisions.

And I've, I've been working through with the team, working through with advisors, and there, there are things that people disagreed with, right?

Like, I, I'm not in the business of making everyone happy.

That is, at the end of the day, that is my job.

And that is your job as a leader.

And it, it takes some courage.

But we don't want to avoid it.

Right?

Like, it's, it's negligence to, to avoid the tough stuff.

So, yeah, big lesson for me.

2025, I'll put Ben's clip in the show.

Notes the description below.

Highly recommend checking that out.

And again, hard thing about hard things.

Could not recommend that book more if I tried.

So hope this helps.

Adios.