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24 Questions to Use in Your Organizational Health Assessment

Oct 28, 2022| Reading time: 16min

BY Rich Rudzinski

CEO of Drivey, Tragic Media, and Oversight

Have you ever lied at the doctor’s office? Whether you’ve fudged the number of hours you sleep or how many cups of coffee you consume, most of us have fibbed a little when it comes to our health. 

But we ultimately know these fictitious answers don’t help us in the long run. Doctors, of course, provide better suggestions and arrive at proper diagnoses when they have a more holistic (and truthful) view of our health. 

Unsurprisingly, the same goes for your organization’s health. In short, organizational health is your company’s ability to cope with change while still effectively managing different aspects of the business. And just like a doctor’s visit, it’s critical to habitually schedule an organizational health assessment to ensure your company and people are equipped to respond to any challenges you may face in the future.

Ready to assess your organizational health? Below are 24 questions (housed under six themes) to answer regarding the ins and outs of your company.

Interested in learning the organizational health basics?

Read our 101 guide here

Theme 1: Leadership

Main Question: Are You an Effective Leader?

Being an effective leader means leading high-performing teams and hitting departmental OKRs. But to excel in these areas, leaders need strong interpersonal skills to motivate, inspire, and support employees.

It’s therefore necessary to evaluate your areas of strength – such as empowering others, communicating routinely and effectively, and recognizing colleagues – and noting areas in which you can improve. But, as we all know, self-evaluations are hard to complete and are sometimes prone to blind spots. That’s why sending out surveys to your team or adopting regular 360 reviews helps determine next steps as a people leader.


Upward review survey-01

You can create surveys within your people analytics platforms to help determine the next steps for you and your team. With the right permissions, leaders can create and modify surveys to glean information about their leadership style. 

For more specific insights on your leadership skills, consider the following. 

  • Do you develop great managers? It’s no secret that managers foster trust at all levels in your organization. In order to create a positive ripple effect, leaders need to prioritize manager training to ensure best practices are used throughout the organization. 
  • Are you transparent about your decisions and people data? “A transparent approach equips employees with concrete, accurate information that establishes an organization as a dependable resource,” says Emily Connery, former VP of People and Talent at ChartHop. Unfortunately, when an organization lacks transparency, employees often fill the gaps with their own assumptions. She explains, “Jumping to conclusions rarely generates positive outcomes. And it is more likely to happen when organizations hide poor numbers, deliver inconsistent messages on company goals, or engage in other deceptive behaviors.” 
  • Are you prioritizing diversity, equity, inclusion, and belonging (DEIB) on a daily basis? It’s not enough to make data-based decisions to create a more equitable workplace. Leaders also need to interrupt biases in day-to-day interactions to create a culture of respect and belonging

Theme 2: Processes

Main Question: Do You Have Clear Processes in Place?

A company with strong organizational health prioritizes team alignment, clarity of expectations, strong communication, and the employee experience. Every single item on this list ties back to the idea of clear processes.

It’s therefore crucial for your organization to have – and enforce – straightforward and equitable processes so your people can thrive, no matter what team they’re on. For your organizational health assessment, ask the following:

  • Is there standardization in processes across teams? While meeting cadences and communication styles may look different across departments, the big things – such as 1:1s, performance reviews, and OKR creation – should be standardized. Alternatively, if employees are having vastly different experiences at your company, they may begin looking for other roles where the employee experience is more equitable. 
  • Are projects continuously extended past their deadline? You know the saying: “Fool me once, shame on you. Fool me twice…we may have a process issue.” (Okay, we may have paraphrased a bit.) But if deadlines are often missed, it’s time to analyze just how transparent your processes and expectations are to ensure your people have everything they need to get the job done. In short, it may not be an employee issue, but a company issue.
  • Do your people know who’s who in your company? Rich org charts and employee profiles not only make for a more transparent organization, but also help streamline collaborative efforts. When your people can access your org chart with the click of a button – instead of trying to find a spreadsheet or asking HR – they’re able to reach out to the right colleagues at the right time.

an org chart with employee profiles helps people stay connected

Give everyone real-time visibility into your organization’s structure and teams with easily accessible, automatically-updated org charts. 

Theme 3: Professional Development

Main Question: What Professional Development Opportunities Do You Offer?

Gone are the days when professional development opportunities were simply for employees renewing their licenses or working towards promotions. Professional development is now a way to engage your workforce, close skills gaps, and help employees grow within their career paths. 

And it’s what employees want. In fact, over 35% of those who left their jobs in 2021 reported the cause as “lack of career development.”

It’s therefore critical to promote professional development opportunities and consider the following when assessing your organizational health.

  • Do you offer additional stipends for professional development? Beyond offering internal opportunities, consider granting professional development stipends to your workforce. For example, Indico offers employees $5,000 to spend on career development (such as conferences and courses). 
  • Has your organization created and shared professional pathways? It may be hard for employees to choose professional development opportunities if they don’t know what they’re working towards. By developing professional pathways, you help your people determine next steps for their career and skills development.
  • Is it a standard practice for managers to discuss professional goals with direct reports? Managers should discuss future goals with their employees often. Make sure this is a part of your continuous performance management strategy to ensure you support your people every step of the way.

Theme 4: Workplace Culture

Main Question: Have You Defined Your Workplace Culture?

Another major focus of your organizational health assessment is your workplace culture. Start by asking your leadership team if you’ve effectively defined your culture and have embedded it in every aspect of your company. You may even need to conduct a company audit with workplace culture in mind to see if departments and teams are aligned on expectations and experiences within your organization.  

When considering your culture, you should also ask:

  • Have you created a culture in which employees feel psychologically safe? When your people can show up to work as their whole self, they’re more likely to think, innovate, and be creative – leading to increased employee engagement and retention. Additionally, a psychologically safe environment respects employees’ feedback, and therefore allows people to answer honestly.
  • Do you proactively avoid employee burnout? Like any bad scenario, you want to prevent it before it happens. That’s why it’s so important to routinely collect feedback from employees to help identify risks and those struggling at work.
  • Do you provide opportunities for colleagues to connect? Whether it’s via happy hour or your employee resource groups, make sure you’re providing spaces for your people to develop positive relationships with their teammates to promote a collaborative working environment.

Theme 5: Employee Engagement

Main Question: Are Your People Engaged Across the Organization?

If you discover a weakness in one of the four themes above, you may have an employee engagement issue as well. That’s because leadership, processes, professional development, and workplace culture all help dictate whether you’ve created an engaged organization.

To easily visualize engagement across your company, use a people analytics platform with a variety of filters. Dissecting data enables you to better identify strengths and weaknesses, as well as develop appropriate plans as a response. 


Make sure you review data during your organizational health assessment. When you use a people analytics platform, you can filter your data to help you make the most strategic decisions possible.

Other engagement questions to ask are: 

  • What does employee engagement look like to your organization? Employee engagement is one of those phrases with nuanced definitions. Therefore, Sarah Diegnan, VP of Customer Experience at ChartHop, advises, “As a first step, your leadership team needs to define what employee engagement looks like at your company at an individual, team, and organizational level.”
  • Do your people have a voice in planning initiatives? If you want employees to be engaged, give them opportunities to do so. Extend invitations to plan events and holiday parties, as well as take part in company initiatives and focus groups. Not only will your employees feel more connected to your company, but you’ll also gather valuable perspectives in your planning process. 
  • Do you offer benefits that increase employees’ well-being? Gallup found that two major factors influence employee performance: engagement and well-being. And what’s interesting is that the two are cyclical. When employees feel supported in their well-being, they’re more likely to engage in their work, which – you guessed it – increases their well-being.

Theme 6: Customer Loyalty

Main Question: Are Your Customers Satisfied? 

Customer loyalty is an external health component, but one that directly ties to your organizational health. How so? Companies that prioritize internal structure and employee engagement actually see an increase in customer satisfaction.

Specifically, Jeff Cava, CHRO for Starwood Hotels and Resorts Worldwide, discusses the results of linking customer experience to the HR function. He explains:“Increased collaboration between departments in the hotel was very predictive of reduction of customer complaints and associated increases in occupancy rate. We intuitively knew that employees’ attitudes had a massive impact on client satisfaction, but [we also saw this outcome in] real data.”

And ultimately, customer satisfaction leads to better employee and customer retention, increased revenue, and more word-of-mouth marketing (all of which help your organizational health). To determine if customers are satisfied with your current product, look at your metrics, such as customer satisfaction surveys, net promoter scores, and online reviews.

And when it comes to increasing customer happiness, there’s more specific questions your leadership team can ask, including:

  • Do you act on customer feedback? You don’t want to just acquire customers; you also want to keep them. Therefore, a simple way to strengthen your organizational health is to respond to customer feedback. Use feedback to create your product’s roadmap (and make sure you communicate an external version so customers know you’ve acted upon their needs). If you can’t fix their current problems, always respond with empathy to maintain a positive relationship.
  • Is there consistent alignment between the Product and Customer Success teams? Simply put, you need to align your teams if you want a healthy organization. This communication is critical to Customer Success teams who are on the front lines responding to customers. Make sure your people know the ins and outs of your product – and any updates or bugs that may have occurred – to ensure they’re delivering the best support possible. 
  • Are there common reasons for customer churn? Analyze your recent customer departures to determine any themes between their decisions to cut ties. Since retaining customers is cheaper than acquiring new ones, you want to act on any common reasons that are causing customers to leave.

Final Thoughts for Your Organizational Health Assessment

There’s no time like the present to begin assessing your organizational health. If the process seems overwhelming, start by determining key metrics that will help your company reach its goals. From there, set a baseline measurement and then create a concrete plan – with a realistic timeline – to hold yourself and the leadership team accountable. 

In the end, when you prioritize your organization’s health, you’ll see short and long-term benefits for your company and your people.

Healthy organizations have processes in place to adapt quickly. If you’ve worked hard on creating a healthy culture that’s flexible, you want your HR tech to match. Download our infographic for four critical capabilities to look for in a best-of-class HR tech platform that will help your culture and business thrive. 

Learn more here

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