Five Early Signs Your Leadership Is Falling Behind

Even successful startups come across problems and challenges. In some instances, the leadership team is building silos that are slowing growth rather than accelerating it. If your startup is slow to recognize and amend those issues, it can have a profound and negative impact on the startup.

It’s important to remember that a leadership team falling behind doesn't announce itself with a crisis. The signs show up in patterns, not catastrophes. It shows up in small friction. For example, decisions that used to take one conversation now take three. Perhaps cross-functional work that used to flow now requires Founder/CEO intervention. 

It often takes four or five months until the founder starts to recognize that something is amiss. Yet, patterns that indicate an issue can usually be spotted at least two months earlier. Needless to say, that puts you at least two or three months behind in rectifying the problem. From working with dozens of startups in the $3M to $30M range, I have found five patterns that you can catch early to save your company from months of organizational drag.

Pattern One: Decisions Migrate Back to You

In the past, your VP of Sales used to run the full sales process. She handled comp plans, territory design, and pipeline reviews. But now she's asking you to weigh in on deal discounting thresholds. 

Likewise, your Head of Product used to own the roadmap. But now he's pulling you into feature prioritization conversations you thought you'd delegated eight months ago.

This isn't them getting lazy. It's them hitting complexity they don't have frameworks to handle. Creating those frameworks falls on the CEO.

Learn from This Example

I once worked with the founder of an $8M revenue company who noticed this issue with his Head of Engineering. Six months earlier, the department head was making architecture decisions independently. Then he started scheduling 30-minute "quick syncs" three times a week to talk through technical tradeoffs. 

The founder thought that he had the wrong person in the job. However, the actual issue was that the engineering team had grown from five to 12 people in just four months. The head of engineering wasn’t accustomed to managing other managers. He didn’t want to make decisions with incomplete information across multiple workstreams, so he wanted to check with the founder to feel safe.

What’s the Tell?

The tell to look for with this pattern isn't that department heads and other leaders are asking questions. The tell is that they're asking questions they used to answer themselves. This is a clear sign of regression, not growth.

Pattern Two: Your Weekly Exec Meeting Becomes Tactical Status Updates

Imagine holding a two-hour strategic leadership team discussion every Monday. Twelve weeks ago, you were debating market positioning and resource allocation. These days, you're reviewing ticket volumes and talking through individual customer escalations.

The format of the meeting has changed, but rather the cognitive load on your team. They started bringing problems to you that they should have been able to handle, instead of problems that require collective executive judgment.

Real-Life Example

I saw this situation once at a SaaS company doing $12M in revenue. Over the course of eight weeks, the weekly executive meeting shifted from being about strategy to being about status. The COO was reporting on support ticket SLAs. The VP of Product was walking through individual feature requests. The CRO was reviewing every deal over USD 50K.

The Founder just assumed the team wasn't preparing properly. In reality, the issue is that each executive leader was drowning in tactical work, which is why they brought tactical problems to the meeting. Since they were spending the majority of their time fighting fires, they lacked the capacity to think strategically.

What’s the Tell?

The tell that you want to notice for this pattern is when executive meetings become less strategic. If these meetings go from 70% strategic to 30% strategic over six to eight weeks, it means your team is falling behind the complexity curve. Areas that should be accelerating are slowing down because your leaders are drowning in tactical work and need to be thrown a life preserver.

Pattern Three: Cross-Functional Projects Stall Without You

The goal you set as a founder is for marketing and sales to become aligned on your ICP by the start of the next quarter. Unfortunately, six weeks later, they still aren’t close to being aligned. 

Naturally, when you, as the founder, get involved, things start to move forward. But as soon as you leave the room, things slow down. While this doesn't feel like a crisis because nothing is breaking, every week of stalled cross-functional work is compounding misalignment.

This Can Happen

I saw this problem at an AI startup doing $15M in revenue. The leadership team had experience, clear ownership, and good communication skills. Yet, cross-functional initiatives would stall for weeks. 

Marketing was waiting on positioning input from the product department, while sales was waiting on engineering for technical roadmap clarity. At the same time, customer success was waiting on everyone else for the expansion playbook alignment.

As a result, the founder had to spend 15+ hours a week being the connective tissue between functions. To him, this felt like normal leadership, so he didn’t recognize the problem. He thought everything was fine because he was helping teams align. But if you took him out of the equation, cross-functional velocity would drop by 60-70%.

What’s the Tell?

The tell to look for is not making decisions at the end of conversations. Instead, you’re merely creating the forcing function that makes the conversation happen. That's a system problem, not a people problem. And system problems slow things down.

Pattern Four: Strategic Projects Keep Sliding

As a founder, you might set 3-4 strategic priorities with your leadership team for a quarter. Perhaps you’re building out the growth engine, redesigning the customer onboarding experience, and launching the partner program.

Unfortunately, every quarter, two or three of those projects don't come to fruition. It’s not because people aren't working hard. Instead, it’s because strategic work keeps getting displaced by urgent tactical work.

Your team tells you: "We're making progress, just slower than planned." However, what’s actually happening is that your team is already working at full capacity. This means when they have to choose between strategic projects and keeping current operations running, operations wins.

These Things Happen

I once saw this happen at a $9M services company. The leadership team wanted to build a formal sales process. They wanted it so bad that it became their goal for three quarters in a row. Each quarter, it got 30-40% done and then stalled. The VP of sales was too busy closing deals, while the COO was too busy handling delivery issues. 

The founder kept telling himself that they would have more capacity to get the project done next quarter. But the business was growing, so that never happened. It didn’t happen because the tactical load was growing faster than the team's ability to build systems to handle it.

What’s the Tell?

The tell in this scenario is that your strategic priorities failed to come to fruition two quarters in a row. Instead of hoping for better results next quarter, recognize that your team doesn't have the capacity or capability for the current complexity level. Don’t fool yourself into thinking that trying harder will fix it. Instead, you need to either reduce complexity or increase capability. Otherwise, you're choosing slowdown over acceleration.

Pattern Five: Your Team Starts Asking for More Headcount to Solve Every Problem

Consider a scenario in which your sales department says it needs two more AEs to hit its target. Meanwhile, marketing needs another demand gen person, product needs another PM, and Engineering needs three more engineers.

You might be tricked into thinking that headcount requests are the signal. But that’s not the case because the signal is that headcount is the primary solution that every team is proposing for every capacity or velocity problem.

This can happen when your leaders are solving for throughput instead of leverage. They're thinking linearly, assuming that if we need to do more, we must need more people. But they're not thinking systematically in terms of what process or decision-making change could double the output with the same team?

In Real Life

I’ve seen this problem at a SAAS startup with $11M revenue. The founder noticed this when her Head of Customer Success asked for two more CSMs to handle the growing customer base. On the surface, it seemed like a reasonable request. 

However, when they looked closer, the real issue was different. The CS team was doing manual work that should have been automated. They were also handling questions that should have been in self-service documentation.

What’s the Tell?

The telltale sign in this scenario is that every department is asking for more people. Yes, adding headcount can indeed solve a problem. But doing so can also hide an inefficient process, meaning adding headcount only solves the problem temporarily. Rather than assuming you need to hire when it looks like you need more people, look for a system-level fix.

What All This Means

These five patterns aren't performance problems. They're capacity and capability mismatches. Your leadership team is lagging behind because the business crossed a complexity threshold that your team has yet to cross.

Founders who catch this early should ask three questions:

1. Where is decision-making regressing? What decisions are coming back to me that weren’t coming to me before?

2. Where is coordination breaking down? What cross-functional work is stalling without my involvement?

3. What's the ratio of strategic vs. tactical work? Are my leaders building systems or just running harder?

If you're seeing two or three of these patterns, you're probably 60-90 days into a leadership team lag. The fix isn't working harder or hiring more people. The fix is upgrading how your team makes decisions, coordinates across functions, and creates leverage.

The companies that scale most effectively don't wait until the lag becomes a crisis. They spot the early patterns and act proactively while they still have 4-6 weeks of runway to course-correct. Unfortunately, the startups that don’t spot these patterns early end up with a crisis that could require 6+ months of organizational drag to repair.

To help get ahead of issues that could slow you down and help your startup shift to third gear, get in touch with the Midstage Institute.

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