If you ask me, entrepreneurship it is one of the most challenging roles you can ever undertake. The stress and burden of starting and building a successful business—not to mention the pressure of keeping people gainfully employed—falls squarely on your shoulders.

It can be very easy to get so distracted by increasing your revenue and sales to appease your investors that you forget to look at the health of your company. The bigger your company gets, the heavier that load becomes. However, for those who have the courage to take it on, it is an exciting and rewarding experience, full of daily joys and challenges.

Regardless of your type of business, every entrepreneur needs to take a step back from the day-to-day and assess where their company is and whether it is healthy. As an entrepreneur and venture capitalist, I always try to judge the overall well-being of a startup and focus on these five areas to make it a healthier company.

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1. How are my employees doing and how can I improve their well-being?

No healthy startup survives unless the people who keep it moving are healthy. If the pandemic has taught us anything, it's that providing support and resources for health and wellness can have a positive impact employee morale.

A startup's commitment to creating a supportive and healthy work environment can help reduce stress and improve employee motivation, increasing engagement and productivity. I am not talking about a blanket, one-size-fits-all approach that will simply be seen as a half-measure. Each person on your team is different and each person's health needs vary.

Improving employee well-being

If your startup is still small, don't be afraid to speak directly to your employees to ask them how they're doing and understand their wellness routines. These conversations will help you develop an informed strategy for the company to better support their needs.

For larger companies, contact an employee health consulting firm. Ask them to collect employee feedback, find out what your competitors are doing, and use these data points to build a customized plan for your workforce. Don't rule it out your health also in this field. As a leader, you must be at the top of your game, setting an example for others to do the same.

2. How are we handling failure?

Depending on your personality type, risking failure it can be the best or worst part of your startup life.

Most entrepreneurs understand that failure can be a good thing, but only if it is handled in the right way. While this can be difficult to measure, here are some probing questions to help get a clearer picture:

• Do I or my team dwell on failures too long?
• Are we repeating the same mistakes over and over again?
• Does fear of failure affect our motivation or creativity?

Strong leadership is critical

Ultimately, it is up to the leadership team to encourage a culture of learning from failure and implementing structures to capitalize on these lessons and prevent re-occurrences.

Encouraging managers and employees to think critically and assess where things went wrong is vital. Meet with your teams and discuss these questions:

• What was in their control versus out of control?
• Looking back, were there any early signs that now seem obvious that this was going to be a failure?
• What can we change in our process to better detect problems earlier?

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3. Are we attracting the right kind of people to hire?

There are generally two types of employees: those who work for a bigger paycheck and those who work because they believe in direction and culture. Is your business built for one type over the other?

It is vital that we focus on building a business where people want to work rather than those who will simply work there because they are paid above market rates. With younger employees, compensation is key, but role and company fit are just as, if not more, important. This is another challenging area to check for status, but a good sign is that you regularly receive leads on LinkedIn and directly from job seekers.

The most suitable employment for your startup

So where can you find suitable candidates?

Your employees are yours the greatest lawyers, and while you have to be careful, you often find high-quality candidates from their networks. Encourage your employees to take some ownership and let them be more involved in the hiring process, especially if your team is smaller.

4. How well do you understand where you are spending your money?

You'd be shocked how often companies don't know how much money they spend per month, quarter or year. If you find yourself in this category – and it's okay to admit it – or you want to understand your financial picture More specifically, here are some questions to ask yourself and your team:

• Do you have a budget and is it realistic? Have other people in the organization mentally checked him?
• How are you currently tracking against your budget?
• How well is spending aligned with your core strategy relative to new opportunities or potential distractions?

These are simple questions, but they can help you uncover important flaws in your financial process.

An early focus on finance

Building a strong financial function early in the company's life cycle may cost more initially. Still, it saves you and your startup pain and costs in the future, especially when you start dealing with investors and auditors.

If your company is more mature and making significant financial progress, it may be time to invest in a strong CFO if you haven't already. You'll want to bring in someone who can tie company strategy to your budget and expenses and support the finance team.

5. Do your employees take initiative?

Earlier, I mentioned the importance of hiring the right people for your organization. This aspect is strengthened when you consider how often employees are promoted and take ownership – and if you, as a leader, are encouraging it. While they experience the ins and outs of company life every day, your employees likely know the inner workings of your business better than you do. This is a good thing. It means they are deeply involved and invested.

However, it's essential to understand whether your employees are bringing you new ideas of their own volition or simply obeying orders. Do they voice their thoughts and opinions in meetings or do they sit quietly and just listen?

Promoting the culture of initiative

One of the best things you can do as a leader is to take the initiative and talk to your employees, encouraging them to be critical of operations and provide them with a safe environment to do so. In certain cases, this is best done through an outside firm or using an anonymous method. As an investor, I've found the most success talking directly to employees and communicating feedback to management.

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A healthy perspective

Assessing the overall health of your startup means paying attention to details beyond financial metrics. An entrepreneur must constantly assess the company's well-being and adapt as needed to ensure long-term success. These five questions are not all-inclusive, but they are essential to building a healthy and sustainable business.

All of these require a keen sense of self-awareness as a leader. Leaders often operate in isolation with “armor” in pursuit of their goals or revenue targets, sacrificing the broader foundation of the business and how it will impact future scaling. As a long-term investor, I'm a firm believer in building a solid foundation, even if it means taking things a little slower.