The Three Signs You Aren’t Ready to Hire

Founders are wired for growth. You see it in user counts revenue and headcount. The first two are good signals. The third is often a trap.

The desire to hire is powerful. It feels like progress. It feels like you’re building a real company. But hiring too soon is like pouring water on a spark. It doesn’t help the fire grow it just puts it out. Before you spend a month writing a job description and screening candidates ask if you are truly ready. In most cases the answer is no.

Hiring Solves Execution Problems Not Strategy Problems

The most common mistake is hiring someone to figure out what to do. You think “We need to grow so let’s hire a marketing person”. You hire them and ask them to create a marketing plan. This almost always fails.

An early stage employee is not a cofounder. They need a well defined problem to solve. They need a machine to operate not design the machine from scratch. If you cannot write a document that describes exactly what this person will do for their first three months you are not hiring for an execution problem. You are hiring for a strategy problem. And strategy is your job.

“Figure out marketing” is a bad directive. “Increase signups from our content marketing channel from 100 to 400 a month by executing the playbook we've already validated” is a good one. The first is a prayer. The second is a task. If your task list for a new hire is vague or full of discovery work you should do that work yourself. Adding a person to a situation of high uncertainty just adds communication overhead and burns cash.

You Haven’t Done the Job Yourself First

You should never hire someone to do a job you haven’t done yourself. Not the full time professional version but the scrappy manual version. Before you hire your first customer support rep you should personally answer every support email for a month. Before you hire a salesperson you should be the one doing demos and closing the first ten customers.

Why? Because it is the only way to understand what good looks like. You learn the nuances of the role. You learn what tools are needed what processes work and what the common obstacles are. This firsthand knowledge makes you a better manager. You can set realistic goals. You can tell if someone is doing a good job or just sounds like they are.

When you've felt the pain of the job yourself you can write a job description that attracts the right people.

A good job description isn’t a wish list. It’s a clear description of a real pain you have.

Without doing the job you’re just guessing what that pain is. You also often discover that you don’t need a person at all. Sometimes a better tool or a simpler process is the real solution. Doing the work yourself forces you to find these efficiencies. Hiring someone is the most expensive solution to a problem. You should exhaust the cheaper ones first.

The Cost Is More Than Just Salary

Founders often look at a hiring decision through the lens of salary. “Can we afford a $100k salary?”. This is the wrong question. The salary is the most visible cost but it’s often the smallest. The true cost of an employee is much higher.

You must account for three hidden costs.

First is the time cost. Hiring is enormously time consuming. You will spend time writing the role sourcing candidates interviewing them and making a decision. Once they start you will spend a huge amount of time onboarding them training them and managing them. For your first few hires a founder should expect to spend at least a quarter of their time directly on that person’s success. That’s time you are not spending on building product or talking to users.

Second is the complexity cost. Communication in a company scales geometrically not linearly. A two person team has one line of communication. A three person team has three. A five person team has ten. Each new person adds overhead. Decisions take longer. Alignment is harder to maintain. A startup’s biggest advantage is speed and simplicity. Every hire you make erodes that advantage. You should guard it jealously.

Third is the culture cost. The first ten employees don’t just join your culture they define it. Their work habits their attitudes and their values become the template for everyone who comes after. A great hire can elevate the whole team. A bad hire or even a mediocre one can be toxic. The stakes are incredibly high. This is why hiring your first engineer is so critical. You are setting a standard. The cost of getting it wrong isn’t just a wasted salary it’s a damaged foundation for your entire company.

So When Should You Hire?

This may sound like you should never hire. That’s not the point. The point is to hire deliberately. Hiring is an amplifier. It amplifies what’s already working. So you should only hire when you have something that is working and is being held back by a lack of manpower. You should hire when the pain of not having someone is acute and specific.

Here is a simple checklist. Do not hire until you can answer yes to all three questions:

1. Is the problem I’m hiring for a well defined execution problem? Can I write a specific 30 60 90 day plan for this person?
2. Have I personally done a manual version of this job? Do I know what success in this role looks like from direct experience?
3. Am I willing to dedicate 25% of my time to this person’s success? Have I accepted the true cost in time complexity and culture?

If the answer to any of these is no the solution is not to hire. The solution is to simplify the problem automate it or just do the work yourself. The best companies aren’t the ones who hire the fastest but the ones who hire the best. And that starts with knowing when not to hire at all.

Hiring should feel like a relief not a gamble. It should be pulling a specific lever you know will work not pushing a button in the dark and hoping for the best.

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description: 'The Three Signs You Aren''t Ready to Hire' date: September 2025 created: 2025-09-25T17:27:01.000Z publish: true

Founders are wired for growth. You see it in user counts revenue and headcount. The first two are good signals. The third is often a trap.

The desire to hire is powerful. It feels like progress. It feels like you’re building a real company. But hiring too soon is like pouring water on a spark. It doesn’t help the fire grow it just puts it out. Before you spend a month writing a job description and screening candidates ask if you are truly ready. In most cases the answer is no.

Hiring Solves Execution Problems Not Strategy Problems

The most common mistake is hiring someone to figure out what to do. You think “We need to grow so let’s hire a marketing person”. You hire them and ask them to create a marketing plan. This almost always fails.

An early stage employee is not a cofounder. They need a well defined problem to solve. They need a machine to operate not design the machine from scratch. If you cannot write a document that describes exactly what this person will do for their first three months you are not hiring for an execution problem. You are hiring for a strategy problem. And strategy is your job.

“Figure out marketing” is a bad directive. “Increase signups from our content marketing channel from 100 to 400 a month by executing the playbook we've already validated” is a good one. The first is a prayer. The second is a task. If your task list for a new hire is vague or full of discovery work you should do that work yourself. Adding a person to a situation of high uncertainty just adds communication overhead and burns cash.

You Haven’t Done the Job Yourself First

You should never hire someone to do a job you haven’t done yourself. Not the full time professional version but the scrappy manual version. Before you hire your first customer support rep you should personally answer every support email for a month. Before you hire a salesperson you should be the one doing demos and closing the first ten customers.

Why? Because it is the only way to understand what good looks like. You learn the nuances of the role. You learn what tools are needed what processes work and what the common obstacles are. This firsthand knowledge makes you a better manager. You can set realistic goals. You can tell if someone is doing a good job or just sounds like they are.

When you've felt the pain of the job yourself you can write a job description that attracts the right people.

A good job description isn’t a wish list. It’s a clear description of a real pain you have.

Without doing the job you’re just guessing what that pain is. You also often discover that you don’t need a person at all. Sometimes a better tool or a simpler process is the real solution. Doing the work yourself forces you to find these efficiencies. Hiring someone is the most expensive solution to a problem. You should exhaust the cheaper ones first.

The Cost Is More Than Just Salary

Founders often look at a hiring decision through the lens of salary. “Can we afford a $100k salary?”. This is the wrong question. The salary is the most visible cost but it’s often the smallest. The true cost of an employee is much higher.

You must account for three hidden costs.

First is the time cost. Hiring is enormously time consuming. You will spend time writing the role sourcing candidates interviewing them and making a decision. Once they start you will spend a huge amount of time onboarding them training them and managing them. For your first few hires a founder should expect to spend at least a quarter of their time directly on that person’s success. That’s time you are not spending on building product or talking to users.

Second is the complexity cost. Communication in a company scales geometrically not linearly. A two person team has one line of communication. A three person team has three. A five person team has ten. Each new person adds overhead. Decisions take longer. Alignment is harder to maintain. A startup’s biggest advantage is speed and simplicity. Every hire you make erodes that advantage. You should guard it jealously.

Third is the culture cost. The first ten employees don’t just join your culture they define it. Their work habits their attitudes and their values become the template for everyone who comes after. A great hire can elevate the whole team. A bad hire or even a mediocre one can be toxic. The stakes are incredibly high. This is why hiring your first engineer is so critical. You are setting a standard. The cost of getting it wrong isn’t just a wasted salary it’s a damaged foundation for your entire company.

So When Should You Hire?

This may sound like you should never hire. That’s not the point. The point is to hire deliberately. Hiring is an amplifier. It amplifies what’s already working. So you should only hire when you have something that is working and is being held back by a lack of manpower. You should hire when the pain of not having someone is acute and specific.

Here is a simple checklist. Do not hire until you can answer yes to all three questions:

1. Is the problem I’m hiring for a well defined execution problem? Can I write a specific 30 60 90 day plan for this person?
2. Have I personally done a manual version of this job? Do I know what success in this role looks like from direct experience?
3. Am I willing to dedicate 25% of my time to this person’s success? Have I accepted the true cost in time complexity and culture?

If the answer to any of these is no the solution is not to hire. The solution is to simplify the problem automate it or just do the work yourself. The best companies aren’t the ones who hire the fastest but the ones who hire the best. And that starts with knowing when not to hire at all.

Hiring should feel like a relief not a gamble. It should be pulling a specific lever you know will work not pushing a button in the dark and hoping for the best.

Now try answering the prompt below for yourself.

---

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description: 'The Three Signs You Aren''t Ready to Hire' date: September 2025 created: 2025-09-25T17:27:01.000Z publish: true

Founders are wired for growth. You see it in user counts revenue and headcount. The first two are good signals. The third is often a trap.

The desire to hire is powerful. It feels like progress. It feels like you’re building a real company. But hiring too soon is like pouring water on a spark. It doesn’t help the fire grow it just puts it out. Before you spend a month writing a job description and screening candidates ask if you are truly ready. In most cases the answer is no.

Hiring Solves Execution Problems Not Strategy Problems

The most common mistake is hiring someone to figure out what to do. You think “We need to grow so let’s hire a marketing person”. You hire them and ask them to create a marketing plan. This almost always fails.

An early stage employee is not a cofounder. They need a well defined problem to solve. They need a machine to operate not design the machine from scratch. If you cannot write a document that describes exactly what this person will do for their first three months you are not hiring for an execution problem. You are hiring for a strategy problem. And strategy is your job.

“Figure out marketing” is a bad directive. “Increase signups from our content marketing channel from 100 to 400 a month by executing the playbook we've already validated” is a good one. The first is a prayer. The second is a task. If your task list for a new hire is vague or full of discovery work you should do that work yourself. Adding a person to a situation of high uncertainty just adds communication overhead and burns cash.

You Haven’t Done the Job Yourself First

You should never hire someone to do a job you haven’t done yourself. Not the full time professional version but the scrappy manual version. Before you hire your first customer support rep you should personally answer every support email for a month. Before you hire a salesperson you should be the one doing demos and closing the first ten customers.

Why? Because it is the only way to understand what good looks like. You learn the nuances of the role. You learn what tools are needed what processes work and what the common obstacles are. This firsthand knowledge makes you a better manager. You can set realistic goals. You can tell if someone is doing a good job or just sounds like they are.

When you've felt the pain of the job yourself you can write a job description that attracts the right people.

A good job description isn’t a wish list. It’s a clear description of a real pain you have.

Without doing the job you’re just guessing what that pain is. You also often discover that you don’t need a person at all. Sometimes a better tool or a simpler process is the real solution. Doing the work yourself forces you to find these efficiencies. Hiring someone is the most expensive solution to a problem. You should exhaust the cheaper ones first.

The Cost Is More Than Just Salary

Founders often look at a hiring decision through the lens of salary. “Can we afford a $100k salary?”. This is the wrong question. The salary is the most visible cost but it’s often the smallest. The true cost of an employee is much higher.

You must account for three hidden costs.

First is the time cost. Hiring is enormously time consuming. You will spend time writing the role sourcing candidates interviewing them and making a decision. Once they start you will spend a huge amount of time onboarding them training them and managing them. For your first few hires a founder should expect to spend at least a quarter of their time directly on that person’s success. That’s time you are not spending on building product or talking to users.

Second is the complexity cost. Communication in a company scales geometrically not linearly. A two person team has one line of communication. A three person team has three. A five person team has ten. Each new person adds overhead. Decisions take longer. Alignment is harder to maintain. A startup’s biggest advantage is speed and simplicity. Every hire you make erodes that advantage. You should guard it jealously.

Third is the culture cost. The first ten employees don’t just join your culture they define it. Their work habits their attitudes and their values become the template for everyone who comes after. A great hire can elevate the whole team. A bad hire or even a mediocre one can be toxic. The stakes are incredibly high. This is why hiring your first engineer is so critical. You are setting a standard. The cost of getting it wrong isn’t just a wasted salary it’s a damaged foundation for your entire company.

So When Should You Hire?

This may sound like you should never hire. That’s not the point. The point is to hire deliberately. Hiring is an amplifier. It amplifies what’s already working. So you should only hire when you have something that is working and is being held back by a lack of manpower. You should hire when the pain of not having someone is acute and specific.

Here is a simple checklist. Do not hire until you can answer yes to all three questions:

1. Is the problem I’m hiring for a well defined execution problem? Can I write a specific 30 60 90 day plan for this person?
2. Have I personally done a manual version of this job? Do I know what success in this role looks like from direct experience?
3. Am I willing to dedicate 25% of my time to this person’s success? Have I accepted the true cost in time complexity and culture?

If the answer to any of these is no the solution is not to hire. The solution is to simplify the problem automate it or just do the work yourself. The best companies aren’t the ones who hire the fastest but the ones who hire the best. And that starts with knowing when not to hire at all.

Hiring should feel like a relief not a gamble. It should be pulling a specific lever you know will work not pushing a button in the dark and hoping for the best.

Now try answering the prompt below for yourself.

---

---

description: 'The Three Signs You Aren''t Ready to Hire' date: September 2025 created: 2025-09-25T17:27:01.000Z publish: true

Founders are wired for growth. You see it in user counts revenue and headcount. The first two are good signals. The third is often a trap.

The desire to hire is powerful. It feels like progress. It feels like you’re building a real company. But hiring too soon is like pouring water on a spark. It doesn’t help the fire grow it just puts it out. Before you spend a month writing a job description and screening candidates ask if you are truly ready. In most cases the answer is no.

Hiring Solves Execution Problems Not Strategy Problems

The most common mistake is hiring someone to figure out what to do. You think “We need to grow so let’s hire a marketing person”. You hire them and ask them to create a marketing plan. This almost always fails.

An early stage employee is not a cofounder. They need a well defined problem to solve. They need a machine to operate not design the machine from scratch. If you cannot write a document that describes exactly what this person will do for their first three months you are not hiring for an execution problem. You are hiring for a strategy problem. And strategy is your job.

“Figure out marketing” is a bad directive. “Increase signups from our content marketing channel from 100 to 400 a month by executing the playbook we've already validated” is a good one. The first is a prayer. The second is a task. If your task list for a new hire is vague or full of discovery work you should do that work yourself. Adding a person to a situation of high uncertainty just adds communication overhead and burns cash.

You Haven’t Done the Job Yourself First

You should never hire someone to do a job you haven’t done yourself. Not the full time professional version but the scrappy manual version. Before you hire your first customer support rep you should personally answer every support email for a month. Before you hire a salesperson you should be the one doing demos and closing the first ten customers.

Why? Because it is the only way to understand what good looks like. You learn the nuances of the role. You learn what tools are needed what processes work and what the common obstacles are. This firsthand knowledge makes you a better manager. You can set realistic goals. You can tell if someone is doing a good job or just sounds like they are.

When you've felt the pain of the job yourself you can write a job description that attracts the right people.

A good job description isn’t a wish list. It’s a clear description of a real pain you have.

Without doing the job you’re just guessing what that pain is. You also often discover that you don’t need a person at all. Sometimes a better tool or a simpler process is the real solution. Doing the work yourself forces you to find these efficiencies. Hiring someone is the most expensive solution to a problem. You should exhaust the cheaper ones first.

The Cost Is More Than Just Salary

Founders often look at a hiring decision through the lens of salary. “Can we afford a $100k salary?”. This is the wrong question. The salary is the most visible cost but it’s often the smallest. The true cost of an employee is much higher.

You must account for three hidden costs.

First is the time cost. Hiring is enormously time consuming. You will spend time writing the role sourcing candidates interviewing them and making a decision. Once they start you will spend a huge amount of time onboarding them training them and managing them. For your first few hires a founder should expect to spend at least a quarter of their time directly on that person’s success. That’s time you are not spending on building product or talking to users.

Second is the complexity cost. Communication in a company scales geometrically not linearly. A two person team has one line of communication. A three person team has three. A five person team has ten. Each new person adds overhead. Decisions take longer. Alignment is harder to maintain. A startup’s biggest advantage is speed and simplicity. Every hire you make erodes that advantage. You should guard it jealously.

Third is the culture cost. The first ten employees don’t just join your culture they define it. Their work habits their attitudes and their values become the template for everyone who comes after. A great hire can elevate the whole team. A bad hire or even a mediocre one can be toxic. The stakes are incredibly high. This is why hiring your first engineer is so critical. You are setting a standard. The cost of getting it wrong isn’t just a wasted salary it’s a damaged foundation for your entire company.

So When Should You Hire?

This may sound like you should never hire. That’s not the point. The point is to hire deliberately. Hiring is an amplifier. It amplifies what’s already working. So you should only hire when you have something that is working and is being held back by a lack of manpower. You should hire when the pain of not having someone is acute and specific.

Here is a simple checklist. Do not hire until you can answer yes to all three questions:

1. Is the problem I’m hiring for a well defined execution problem? Can I write a specific 30 60 90 day plan for this person?
2. Have I personally done a manual version of this job? Do I know what success in this role looks like from direct experience?
3. Am I willing to dedicate 25% of my time to this person’s success? Have I accepted the true cost in time complexity and culture?

If the answer to any of these is no the solution is not to hire. The solution is to simplify the problem automate it or just do the work yourself. The best companies aren’t the ones who hire the fastest but the ones who hire the best. And that starts with knowing when not to hire at all.

Hiring should feel like a relief not a gamble. It should be pulling a specific lever you know will work not pushing a button in the dark and hoping for the best.

Now try answering the prompt below for yourself.

---

---

description: 'The Three Signs You Aren''t Ready to Hire' date: September 2025 created: 2025-09-25T17:27:01.000Z publish: true

Founders are wired for growth. You see it in user counts revenue and headcount. The first two are good signals. The third is often a trap.

The desire to hire is powerful. It feels like progress. It feels like you’re building a real company. But hiring too soon is like pouring water on a spark. It doesn’t help the fire grow it just puts it out. Before you spend a month writing a job description and screening candidates ask if you are truly ready. In most cases the answer is no.

Hiring Solves Execution Problems Not Strategy Problems

The most common mistake is hiring someone to figure out what to do. You think “We need to grow so let’s hire a marketing person”. You hire them and ask them to create a marketing plan. This almost always fails.

An early stage employee is not a cofounder. They need a well defined problem to solve. They need a machine to operate not design the machine from scratch. If you cannot write a document that describes exactly what this person will do for their first three months you are not hiring for an execution problem. You are hiring for a strategy problem. And strategy is your job.

“Figure out marketing” is a bad directive. “Increase signups from our content marketing channel from 100 to 400 a month by executing the playbook we've already validated” is a good one. The first is a prayer. The second is a task. If your task list for a new hire is vague or full of discovery work you should do that work yourself. Adding a person to a situation of high uncertainty just adds communication overhead and burns cash.

You Haven’t Done the Job Yourself First

You should never hire someone to do a job you haven’t done yourself. Not the full time professional version but the scrappy manual version. Before you hire your first customer support rep you should personally answer every support email for a month. Before you hire a salesperson you should be the one doing demos and closing the first ten customers.

Why? Because it is the only way to understand what good looks like. You learn the nuances of the role. You learn what tools are needed what processes work and what the common obstacles are. This firsthand knowledge makes you a better manager. You can set realistic goals. You can tell if someone is doing a good job or just sounds like they are.

When you've felt the pain of the job yourself you can write a job description that attracts the right people.

A good job description isn’t a wish list. It’s a clear description of a real pain you have.

Without doing the job you’re just guessing what that pain is. You also often discover that you don’t need a person at all. Sometimes a better tool or a simpler process is the real solution. Doing the work yourself forces you to find these efficiencies. Hiring someone is the most expensive solution to a problem. You should exhaust the cheaper ones first.

The Cost Is More Than Just Salary

Founders often look at a hiring decision through the lens of salary. “Can we afford a $100k salary?”. This is the wrong question. The salary is the most visible cost but it’s often the smallest. The true cost of an employee is much higher.

You must account for three hidden costs.

First is the time cost. Hiring is enormously time consuming. You will spend time writing the role sourcing candidates interviewing them and making a decision. Once they start you will spend a huge amount of time onboarding them training them and managing them. For your first few hires a founder should expect to spend at least a quarter of their time directly on that person’s success. That’s time you are not spending on building product or talking to users.

Second is the complexity cost. Communication in a company scales geometrically not linearly. A two person team has one line of communication. A three person team has three. A five person team has ten. Each new person adds overhead. Decisions take longer. Alignment is harder to maintain. A startup’s biggest advantage is speed and simplicity. Every hire you make erodes that advantage. You should guard it jealously.

Third is the culture cost. The first ten employees don’t just join your culture they define it. Their work habits their attitudes and their values become the template for everyone who comes after. A great hire can elevate the whole team. A bad hire or even a mediocre one can be toxic. The stakes are incredibly high. This is why hiring your first engineer is so critical. You are setting a standard. The cost of getting it wrong isn’t just a wasted salary it’s a damaged foundation for your entire company.

So When Should You Hire?

This may sound like you should never hire. That’s not the point. The point is to hire deliberately. Hiring is an amplifier. It amplifies what’s already working. So you should only hire when you have something that is working and is being held back by a lack of manpower. You should hire when the pain of not having someone is acute and specific.

Here is a simple checklist. Do not hire until you can answer yes to all three questions:

1. Is the problem I’m hiring for a well defined execution problem? Can I write a specific 30 60 90 day plan for this person?
2. Have I personally done a manual version of this job? Do I know what success in this role looks like from direct experience?
3. Am I willing to dedicate 25% of my time to this person’s success? Have I accepted the true cost in time complexity and culture?

If the answer to any of these is no the solution is not to hire. The solution is to simplify the problem automate it or just do the work yourself. The best companies aren’t the ones who hire the fastest but the ones who hire the best. And that starts with knowing when not to hire at all.

Hiring should feel like a relief not a gamble. It should be pulling a specific lever you know will work not pushing a button in the dark and hoping for the best.

Now try answering the prompt below for yourself.

— Rishi Banerjee
September 2025