Business

I Watched a Company Keep Hiring to Avoid One Difficult Conversation. Here’s How to Know When You Actually Need More People.

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Published 10/19/2026 3:00:00 PM

Stop Hiring Around Problems — How to Know When to Add Staff

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

Before adding headcount, tie the decision to a specific metric, like billable hours, open tickets or pipeline volume, that proves demand has outgrown your team’s capacity.
Fix unclear roles, missing processes and unaddressed performance issues first, because hiring into chaos spreads it.

Several years ago, I worked with a company that had become trapped by one employee.

She was exceptionally good at a handful of critical responsibilities. She knew the systems, the customers and the history of the organization. Leadership viewed her as indispensable. Whenever concerns about her behavior surfaced, the conversation ended in the same place: They could not afford to lose her. The problem was that nobody wanted to work with her.

New employees joined the team and left within months. Managers spent significant time mediating conflict. Colleagues avoided interacting with her whenever possible. The organization kept absorbing the disruption because she handled a few functions that nobody else understood.

Instead of addressing the issue directly, the company started hiring around it. They brought in support staff. They shifted responsibilities. They created new positions designed to reduce friction. When one solution failed, they tried another. Every new hire was supposed to relieve pressure, yet the pressure never disappeared. At some point, leadership found itself asking a question many business owners eventually confront: Why do we keep adding people without making progress?

The answer had been sitting in front of them the entire time. They did not have a staffing problem. They had an accountability problem. Before you post the job, you need to know whether you are facing a people problem, a systems problem or a leadership problem.

Diagnose the real problem first

One reason business owners make poor hiring decisions is that they treat hiring as the first step in solving a problem instead of the last. When a team feels overwhelmed, the natural reaction is to add capacity. Stress is real, but stress is not a metric. Before adding headcount, leaders need objective evidence that demand has exceeded the team’s ability to deliver.

In my own business, we rely heavily on capacity planning and operational metrics. We track workload, pipeline activity, client growth and billable hours. Those measurements help us determine whether demand truly exceeds capacity or whether another solution would create a better outcome. Without that kind of data, hiring decisions become emotional. A manager feels overwhelmed, so the company assumes the department needs another person. A team is busy, so leadership assumes busyness equals productivity. A few deadlines slip, so the business adds another layer without understanding why the work is falling behind.

The better question is: What number proves we need another person?

That number will look different in every business. It may be billable hours, open service tickets, sales pipeline volume, client growth, production demand or response times. The point is not which metric you use. The point is that the decision should be tied to something more reliable than a feeling. Sometimes the data will show that you need to hire. Other times, it will show that the better answer is training, process improvement, technology, clearer ownership or a better handoff between team members.

The data creates clarity. Clarity produces better decisions.

Stop hiring around unresolved problems

One of the most expensive habits I see in growing businesses is the tendency to hire around problems leadership does not want to confront. A sales leader struggles to hold people accountable, so the company hires additional support. A customer service employee creates conflict throughout the department, so management adds more people to absorb the workload. An operational process breaks down repeatedly, so leadership assigns additional staff to monitor it rather than fixing the process itself.

Over time, the organization accumulates layers of workarounds. Payroll grows. Reporting relationships become more complicated. Communication becomes more difficult. Leaders find themselves managing a larger organization without seeing meaningful improvement in performance. The original issue remains untouched.

This is one reason growth can feel surprisingly difficult. Leaders believe they are investing in solutions when they are actually financing avoidance. Before you create a new position, ask one uncomfortable question: If I add another person tomorrow, what specifically becomes easier?

If the answer is vague, hiring is probably premature. If the answer is measurable, observable and connected to a specific business objective, you are much more likely to make a smart investment.

Build the system before you hire into it

Every employee brings value. Every employee also introduces complexity. A new hire requires onboarding, training, management, communication, feedback, technology and integration into the existing team. They need clarity around expectations. They need defined responsibilities. They need to understand how their role contributes to broader business objectives. When those foundations are already in place, adding a person can accelerate growth. When those foundations are missing, the organization gains another person trying to navigate uncertainty.

Before creating a new position, leaders should take a hard look at the environment that person will enter. Can you clearly explain what success looks like in the role? Are responsibilities documented? Do employees understand who owns which outcomes? Have expectations been communicated clearly? Are performance standards being enforced consistently? Can you identify the metrics that show whether the role is succeeding?

If those questions produce uncertain answers, there is work to do before hiring.

Strong systems create leverage. Clear expectations reduce friction. Documented processes shorten learning curves. Accountability improves execution. None of those improvements requires additional headcount. Many require leadership attention.

This matters especially when a business is growing quickly. Hiring into chaos doesn’t calm the chaos. It spreads it.

Know when hiring is the right answer

There comes a point when every healthy business needs more people. Growth creates demand. Demand requires capacity. Hiring should be part of a company’s evolution. The strongest hiring decisions happen when leaders understand exactly what problem they are solving and what success will look like once the role is filled.

A business is ready to hire when the work is clearly defined, the role has a measurable purpose and the organization has the ability to train the person entering it. Hiring also makes sense when existing employees are consistently operating at capacity, the demand is tied to real business growth and process improvements alone will not solve the gap.

That is very different from hiring because everyone feels busy. Busy is a signal to investigate. It is not enough by itself to justify another salary, another manager, another onboarding process and another layer of complexity.

Before you add headcount, take the time to identify what is actually broken. The answer may lead you toward a new hire. It may lead you toward a better process, a clearer dashboard, a difficult performance conversation or a handoff that should have happened months ago.

Either way, you will make a better decision than hiring first and diagnosing later.

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

High-performing entrepreneurs avoid constant reactivity by filtering distractions and focusing their mental energy on decisions that drive meaningful outcomes.
Build reflection and recovery into the workday. Create micro-pauses to question assumptions, reassess direction and examine whether momentum is still aligned with purpose.
Simplifying workflows, reducing friction and staying close to customers and operational realities help entrepreneurs make better decisions and sustain long-term results.

Spend enough time building companies, and in my case, navigating both medicine and entrepreneurship, and a counterintuitive pattern begins to emerge. The people who consistently deliver are not the ones operating in a state of constant visible intensity.

In fact, many of the highest-performing founders I’ve encountered appear surprisingly controlled. Sometimes even uneventful from the outside.

The separation happens in quieter ways.

It reveals itself in how they protect attention, structure decisions and preserve energy for moments that genuinely matter. These are not dramatic habits. They are small, repeatable behaviors that compound silently while nobody is paying attention.

Over time, I’ve come to believe that in high-pressure environments, habits become infrastructure. And entrepreneurs who consciously build that infrastructure create an advantage that is extraordinarily difficult to replicate.

1. I’ve learned that attention is a precious resource.

Earlier in my entrepreneurial journey, I believed responsiveness was synonymous with effectiveness. Every message deserved attention. Every meeting felt important. Every opportunity seemed urgent.

That instinct becomes expensive very quickly.

Over time, I developed the discipline of deliberate non-engagement. I let things pass. I delay responses. I opt out of conversations that do not meaningfully influence outcomes.

This is not simply about selectivity. It is about cognitive preservation.

Every input competes for mental bandwidth. When attention becomes fragmented, thinking loses depth. Decision-making becomes reactive rather than strategic.

Some of the most effective entrepreneurs I know are exceptionally disciplined about what they refuse to engage with. They understand that clarity is achieved by filtering aggressively and protecting attention with intention.

2. I integrate thinking directly into execution.

There is a common assumption that meaningful thinking happens away from work, during retreats, long breaks or isolated strategy sessions. My experience has been different.

Some of the clearest strategic insights I’ve had emerged in the middle of execution itself: between meetings, immediately after difficult conversations, during transitions between decisions.

I’ve learned to create deliberate micro-pauses throughout the day. Brief moments to question assumptions, reassess direction and examine whether momentum is still aligned with purpose. Without those interruptions, execution continues, but direction quietly deteriorates. Decisions become incremental. Activity increases while clarity declines.

In medicine, this distinction matters enormously. A clinician moving quickly without periodically reassessing the situation can continue executing flawlessly in the wrong direction. Entrepreneurship is not very different. The discipline is not in stepping away from execution entirely. It is in embedding reflection inside it.

3. I design my days to reduce friction.

For years, I optimized aggressively for output. More meetings. More calls. More visible productivity. It felt efficient. It was not sustainable.

The real shift came when I stopped asking, “How do I get more done?” and started asking, “How do I make important work easier to sustain consistently?” That subtle distinction changed how I operate. I simplified recurring decisions. I standardized workflows. I removed unnecessary complexity from my day. I became far more intentional about where cognitive energy was being spent. Over time, the day itself began to feel lighter, despite the workload remaining demanding.

This principle is deeply connected to behavioral science. Human beings consistently underestimate the effect of friction on execution. Even small amounts of unnecessary complexity quietly drain decision quality over time.

When execution becomes smoother, energy is preserved. When energy is preserved, judgment improves.

The entrepreneurs who sustain performance over long periods are often not working less. They are operating inside systems designed to reduce unnecessary resistance.

4. I stay uncomfortably close to reality.

As organizations grow, abstraction becomes seductive. Dashboards replace direct observation. Summaries replace raw information. Layers absorb operational complexity. Distance begins to feel efficient. I’ve learned to resist that instinct deliberately.

Even today, I make it a point to stay close to customer conversations, unfiltered feedback, operational friction points and the realities of execution on the ground. In healthcare, distance from reality can become dangerous very quickly. Clinical decisions made from incomplete or abstracted information carry consequences. I’ve found the same principle applies to leadership and innovation.

The founders who remain closely connected to what is actually happening tend to make fewer unforced errors. Their judgment sharpens because it remains grounded in reality rather than interpretation. As companies scale, proximity becomes uncomfortable. But it also becomes incredibly valuable.

5. I protect energy through deliberate, short resets.

Burnout is often discussed as a function of long hours, with recovery framed primarily as vacations or extended time away. I think the issue is more immediate and more physiological than that.

Over the years, I’ve become increasingly deliberate about building short resets into the middle of demanding days. A pause between meetings. A brief walk before a major decision. A few minutes of silence after an intense interaction. These moments appear insignificant in isolation. Their cumulative effect is substantial.

Without resets, cognitive residue accumulates. Attention narrows. Emotional regulation weakens. Decisions become rushed without us fully realizing it. Harvard Business Review says that it’s important to “create several moments to pause over the course of your workday. By doing so, there will be a cumulative benefit, as you’ll be able to more effectively manage your energy and capacity, helping you to be more resilient.”

I’ve found that a few intentional minutes of recalibration can restore clarity more effectively than pushing through another uninterrupted hour.

The advantage few people talk about

None of these habits is particularly complicated. They do not require sophisticated tools, large teams or dramatic lifestyle overhauls. That is precisely why they are often underestimated.

Most entrepreneurs search for leverage in strategy, funding, technology or talent. Those variables matter immensely. But daily operating behavior quietly determines how effectively those advantages are ultimately used. Over time, the divergence compounds.

One founder operates in a state of constant reaction. Another operates with protected attention, preserved energy and deliberate clarity. Across decisions, across quarters, across years, that difference becomes profound.

Where I would start

If my own journey across medicine, innovation and entrepreneurship has taught me anything, it is that meaningful change rarely begins dramatically. It begins precisely.

Ignore one unnecessary input. Remove one source of friction. Create one intentional pause inside the day. Then observe what changes. Small adjustments, repeated consistently, reshape how we operate. And ultimately, how we operate shapes what we build.

Entrepreneurship celebrates visible milestones, funding rounds, launches, acquisitions and public wins. But the foundations of those outcomes are usually far less visible.

They exist in the quiet architecture of the day. In the systems that either preserve energy or quietly deplete it. The entrepreneurs who separate themselves over time do so because they learn to operate differently, long before anyone notices.

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

Reflecting on a decade of experience as a CEO, offering insights gained from building and growing a successful business.

On the heels of my business’s 10-year anniversary, I’ve been reflecting on the journey and the many lessons I’ve learned in my decade as CEO. Below, I’ll share the ten most profound takeaways — the ones I wish I’d known in the early days of entrepreneurship. Apply them to your journey if you’re on a similar path!

1. Have clear expectations and consistent accountability

In my mind, these two factors are the foundation of successful leadership. Without clear expectations, your team members might not understand what you actually want from them, and their definition of success may not align with yours. Without consistent accountability, they won’t meet those expectations and will have a harder time learning how to improve.

Establishing clear, consistent communication ensures everyone is on the same page and moving towards the same goals.

2. Understand evolution vs. revolution for leadership hires

When it comes to hiring for leadership roles, make sure you understand the roles you actually need. My best advice is this: Hire a manager when you need evolution and an executive when you need revolution.

I’ve learned (the hard way!) that all leadership hires are not created equal. A growing organization will eventually need both, but understanding whether you’re looking for evolution or revolution will help you make more strategic hiring decisions.

3. Know that company culture runs deeper than “fun”

Fun is an element of company culture, and I do believe you should invest in it — whether that’s through team breakfasts, team outings or other activities beyond just work. But true culture is about creating an environment where everyone feels valued and supported, and that goes beyond just having a good time together.

If you want to foster a company culture that doesn’t rely on throwing parties or catering lunches, be mindful of the little things, too: how your leadership team answers hard questions, how you balance transparency with protecting your team from hard truths and how you treat people day-to-day. Your employees will notice all of these details, and they really add up.

4. Expect everything to cost twice as much and take twice as long

Over the years, I’ve come to expect everything — from new projects to hiring decisions to new products — to take longer and cost more than I expect. And even when I try to apply this lesson ahead of time, I’m still likely to underestimate.

Planning with this principle in mind can help manage expectations and reduce frustration when things don’t go exactly as planned. A buffer is a good thing!

5. Hire a coach

My two co-founders and I started working with an executive coach about eight years into running the business, and I wish we’d done it sooner.

Coaches help you find your leadership blind spots, offer an impartial sounding board when you face challenges and help other members of your team level up alongside you. It may take time to find the right person for your needs, but in my experience, it was worth the effort.

6. Co-founders are everything

Co-founders are the people with whom you can share your truest experiences: your deepest fears, your most outlandish concerns and your greatest triumphs. A strong co-founder relationship is crucial for enduring the highs and lows of entrepreneurship.

Find the right people to hold you accountable, balance out your skill set and make the experience of running a business a little less grueling.

7. It sucks, but it gets better

In Lemonlight’s early years, I was regularly working 14-hour days, putting out constant fires and feeling like my to-do list was never-ending. Today, the company runs pretty smoothly with the structures and people we have in place, allowing me to focus on big-picture thinking and finding areas where my expertise is helpful.

I won’t sugarcoat it: Starting a business is hard. But if you just take it one day at a time, it really does get easier.

8. A little progress every day is impactful

Speaking of taking it one day at a time, little progress every day adds up. We’ve had days where the wins and milestones were especially noticeable, but most of the last 10 years has just been moving the needle forward a little bit at a time.

Ten years later, somehow that amounts to 20,000+ videos, 5,000+ clients and 150+ team members. The progress isn’t always noticeable, but it’s always there. Consistency is powerful!

9. Financial acumen is important

Having solid finances is a major component of entrepreneurship, and while it’s important to find experts you trust to support you, it’s also essential to have some personal understanding of your business’s finances.

Being able to read and understand your primary financial statements, track your key performance indicators and move the needle towards your financial goals is invaluable. Don’t just trust someone else to get it right, especially early on when you probably can’t afford world-class help.

10. You don’t save money if you spend it elsewhere

In the early years at Lemonlight, we were conscious of every dollar we spent, but we had a bad habit of “saving” money in one area only to spend it in an unproductive way elsewhere. We’d pat ourselves on the back for cutting costs, but that money wasn’t actually helping our bottom line.

If you find an opportunity to save money, make sure those savings stay saved — or, at the very least, they’re spent on something with real value. Don’t fall into the trap of thinking you’ve done a great job just to waste that money somewhere else. Real savings should strengthen your business, not just get shuffled around.

Entrepreneurship may be framed as a solo effort, but the reality is you don’t have to figure everything out on your own. I hope these lessons from my business can help you skip some of the uncertainty in yours, making progress without quite as many roadblocks.

Opinions expressed by Entrepreneur contributors are their own.

Entrepreneurship is a wild ride, and it’s not for the faint of heart. If you are reading this article, you were born to shake things up and pave your own way. And as some of the most successful entrepreneurs in history have said, the key to success is to just start. Here are 15 inspiring lessons from legendary entrepreneurs.

Need more than inspiration? Book a one-on-one session with the founders of some of the most successful startups like Reddit, Drybar, Nextdoor and more.

1. “Just start.” — Eric Ries, author of The Lean Startup

The hardest part of any journey is the first step, so why not just take it and see where it leads? Don’t wait for the perfect moment or the perfect idea. If you don’t start, you’ll never finish.

2. “What would you do if you weren’t afraid?” — Sheryl Sandberg, COO at Meta

Turn fear into your motivation. Strive for more.

3. “The biggest risk is not taking any risk.” — Mark Zuckerberg, founder of Facebook

Taking risks is like jumping into a cold plunge—it may be uncomfortable at first. Ultimately, it will help you achieve your goals.

4. “You must do the things you think you cannot do.” — Eleanor Roosevelt, former First Lady

Reach beyond our perceived limitations and strive for greatness.

You are capable of achieving more than you think is possible. You are probably operating at a 3/10 when you realistically can ramp to an 8/10. With hard work and determination, you can push through any barrier and come out stronger on the other side. So dream big and never give up!

5. “You don’t learn to walk by following rules. You learn by doing, and by falling over.” — Richard Branson, founder of Virgin Group

You’ll learn to take the right risks and be prepared for the occasional stumble. After all, there’s no better way to learn than by doing and getting back up again.

6. “If you’re not stubborn, you’ll give up on experiments too soon. And if you’re not flexible, you’ll pound your head against the wall and you won’t see a different solution to a problem you’re trying to solve.” — Jeff Bezos, founder of Amazon

Flexibility and stubbornness are both essential traits for entrepreneurs, so make sure to keep them in balance. With the right combination of boldness and patience, you’ll be well on your way to achieving success!

7. “If you can’t fly then run. If you can’t run then walk. If you can’t walk then crawl, but whatever you do you have to keep moving forward.” – Oprah Winfrey, media mogul

You should never give up, no matter how hard the journey may be.

Regardless of the challenges and obstacles that stand in your way, you can find a way to move forward. You all have the power to keep pushing, no matter what.

8. “My life didn’t please me, so I created my life.” — Coco Chanel, fashion icon

You can do anything you set your mind to. Don’t let life just happen to you—make it happen.

9. “Fail often so you can succeed sooner.” — Tom Kelley, IDEO partner

Failure and success are tied. More at-bats will help you iterate faster and learn more. Failing often will help you get closer to success – no matter how small the success, it’s still a step in the right direction.

10. “The way to get started is to quit talking and begin doing.” — Walt Disney, co-founder of the Walt Disney Company

Put Walt’s words of wisdom into action — stop talking and start doing! Success is within reach if you take the first step and learn from your mistakes along the way.

11. “In the modern world of business, it is useless to be a creative, original thinker unless you can also sell what you create.” – David Ogilvy, advertising executive

We’ve heard this before. Spencer Rascoff preaches that all entrepreneurs need to be salespeople. Able to sell your business, your product, and your company vision.

12. “The best way to predict the future is to create it.” — Abraham Lincoln, former US President

Abraham Lincoln is a man who knew a thing or two about making history.

Don’t wait for life to happen to you, make it happen. It’s a reminder that we’re all capable of creating our own destiny and that the future is ours to mold.

13. “Fearlessness is not the absence of fear. It’s the mastery of fear. It’s about getting up one more time than we fall down.” —Arianna Huffington, editor-in-chief of The Huffington Post

Don’t shy away from fear. Face it head-on.

It’s an ongoing battle of getting up even after life knocks us down.

14. “Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” – Steve Jobs, former CEO of Apple

Let’s face it, work takes up a big chunk of our lives, and the only way to make that time meaningful is to do something that you truly believe in.

15. “In whatever you do, you’re not going to stand out unless you think big and have ideas that are truly original. That comes from tapping into your own creativity, not obsessing over what everyone else is doing.” —Sophia Amoruso, founder of Nasty Gal

Making an impact requires more than just following the status quo; it calls for embracing your own innovative ideas. To truly stand out, you must be willing to take risks and unleash your creative potential.

The key is to focus less on what others are doing, and instead aim to generate unique solutions that can make a real difference. Only then will you be able to make a meaningful mark on the world.

16. “Be patient with yourself. Self-growth is tender; it’s holy ground. There’s no greater investment.” — Stephen Covey, author of “The 7 Habits of Highly Effective People”

Not an overnight success? Then, you are not making the headlines. It can take time to get things up and running and that is OK.

Don’t be too hard on yourself.

17. “Your most unhappy customers are your greatest source of learning.” — Bill Gates, co-founder of Microsoft

From my time pre-IPO at Uber, Instawork, and Intro, I’ve learned that your customers build your product roadmap. Listen to them.

18. “The best time to plant a tree was 20 years ago. The second best time is now.” — Chinese Proverb

In life, it’s best to take action as soon as possible.

The best time to plant a tree was 20 years ago because it would have had time to grow and mature by now. However, the second best time to plant a tree is now, even though it won’t be as mature as it would have been 20 years ago.

The same goes for any goal or task, the earlier you start, the better the outcome will be, but it’s never too late to start, and the present is always the second-best time to start.