Top 20 Questions to Ask Staff in a Supervisor Evaluation

Discover the top 20 questions to evaluate a supervisor’s performance and improve leadership effectiveness in your workplace.

April 21, 2025
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There are 300 more icebreaker questions at the bottom of the article
How would you describe your job to a five year old?
What season would you be?
What is a weird food you have tried? Would you eat it again?
What is your favorite holiday tradition?
Would you go in the mother-ship with aliens if they landed on Earth tomorrow?
What is your favorite season?
Do prefer working from home or the office?
What is your earliest memory of this job?
What is the best thing you have bought so far this year?
What is the earliest book you remember?
If you had to move to another country, which one would you choose?
You are the best criminal mastermind in the world. What crime would you commit if you knew you would get away with it?
What is your favorite movie genre to watch?
What was the last thing you ate?
What person from history would you add to Mount Rushmore?
What is a weird fact you know?
What is your favorite part of working from home?
Were the Spice Girls a good team?
Imagine you can instantly learn any language. Which would you choose?
If you could live in any state, which state would you pick?
Which fictional team is the best team of all time?
What did you want to be when you grew up?
What do you usually eat for a quick lunch?
What simple food will you never eat?
Show us the weirdest thing you have in the room with you right now.
Would you rather stay at a hotel or an AirBNB?
What is your favorite movie genre to watch?
Are you more productive in the morning or at night?
Who is someone in your community that makes a difference?
Who was your most unique pet?
Choose one famous person from history you want on your team during a zombie apocalypse.
What is a good way to give back to the community?
Which song could you listen to over and over again?
Is Hugh Grant funny?
What is your favorite thing to eat for breakfast?
Would you want to have an imaginary friend today? Did you have one as a child?
What actor or actress would you want to play you in the movie about your life?
What is the best super power?
What is your New Years resolution?
You can only eat one food again for the rest of your life. What is it?
What is the best work holiday?
What is the first gift you remember receiving?
Would you rather join Metallica or Backstreet Boys?
What is the best example of a community you have seen?
What is an easy way to do something nice for someone?
Show us your phone background and tell the story behind why you picked this image.
What was your first job?
Pick any band to play at your funeral.
If you could have an unlimited supply of one thing for the rest of your life, what would you pick?
Which superpower would you give to your arch enemy?
What is the most obscure superpower you would want?
What emoji best describes how you are feeling right now?
If you could live in any country, which country would you pick?
Would you rather live in a city or a town?
What is your favorite holiday?
What is something you accomplished as part of a team?
What is your standard office lunch?
What is your most used phone app?
What is your favorite season?
Have you ever won something as a team?
Imagine you are a professional baseball player. What is your introduction song?
Beach holiday or ski trip?
Have you ever been to a funny comedy show?
Would you rather live at the North Pole or the South Pole?
What is your favorite song to sing?
If you could live in any state, which state would you pick?
Imagine you could teleport anywhere. Where would you go right now?
What is the most unusual job you have heard of?
What was the last thing you ate?
You can visit any fictional time or place. Which would you pick?
What do your family and friends think you do all day?
What movie do you wish you could watch again for the first time?
Show us your most-used emoji.
What was the most unique style or fashion trend you ever embraced?
What movie defined your generation?
You are stranded on a remote desert island. Are you alone or with your worst enemy?
What is your favorite knock-knock joke?
Have you ever told someone Santa is not real?
Do you know how to speak more than one language?
On a scale of 1 – 10, how much of a team player are you?
What is your #1 recommendation in this city?
What is your favorite holiday?
What bucket list item do you most want to check off in the next six months?
What is your favorite mythical creature?
What was the first way you made money?
If you could be great at any Olympic sport, which would it be?
Which song could you listen to over and over again?
When did you start liking/hating mushrooms?
Where is your favorite vacation spot?
Do you take your PTO all at one time, or another way?
Which show do you remember most from your childhood?
Which beverage goes best with pizza?
Would you want to have a personal assistant follow you around everywhere and do what you asked of them?
Have you ever met your idol?
What did you want to be when you grew up?
Would you rather live 100 years in the past or 100 years in the future?
What is your hobby?
When you are alone in the car, what volume is the music at?
Imagine you no longer have to work. How would you spend a Tuesday?
What is your favorite type of sandwich?

Supervisor evaluations are crucial for fostering growth and improving workplace dynamics. These evaluations provide insights into a supervisor's effectiveness, helping organizations nurture leadership and enhance team performance. 

According to recent studies, effective feedback can boost employee engagement by up to 30%. This guide offers a comprehensive approach to supervisor evaluations, complete with 20 thoughtfully categorized questions to ensure meaningful feedback. 

Why Supervisor Evaluations Matter

Supervisor evaluations are not just about assessing performance; they are about fostering growth, enhancing communication, and building a stronger team. Effective evaluations can lead to improved leadership skills, better team dynamics, and increased employee engagement. 

By focusing on key areas such as communication, leadership, and support, organizations can ensure that their supervisors are equipped to lead their teams successfully.

Benefits of Regular Evaluations:

  • Improved Leadership Skills: Feedback helps managers understand their impact and develop their abilities. For instance, a supervisor might learn that their team values more frequent check-ins, leading to better time management and increased visibility.
  • Enhanced Team Performance: Better leadership directly correlates with improved team outcomes. Teams with effective supervisors often report higher productivity and better project completion rates.
  • Increased Employee Retention: Staff who feel heard are more likely to remain with the organization. A study by Gallup found that employees who receive regular feedback are more likely to stay with their company.
  • Stronger Company Culture: Open feedback channels foster transparency and trust. When employees see that their feedback leads to action, it builds a culture of continuous improvement.

Moreover, regular evaluations can help identify potential issues before they escalate, allowing for proactive measures to be taken. This not only saves time and resources but also contributes to a more positive work environment.

Preparing for Supervisor Evaluations

Before conducting evaluations, it's essential to set clear goals and encourage honest feedback. Supervisors should reflect on their performance, and employees should prepare specific examples. This preparation ensures that discussions are productive and focused on growth.

Best Practices:

  1. Ensure Anonymity: Anonymous feedback encourages honest responses without fear of repercussions. Tools like anonymous surveys or third-party platforms can facilitate this.
  2. Establish Regular Intervals: Conduct evaluations consistently, whether quarterly, bi-annually, or annually. Regular evaluations help track progress and maintain accountability.
  3. Use a Mix of Question Types: Combine rating scales with open-ended questions for comprehensive feedback. This approach captures both quantitative and qualitative data.
  4. Act on Feedback: Demonstrate that input leads to meaningful changes. For example, if feedback indicates a need for better communication, supervisors can implement regular team meetings.
  5. Close the Loop: Share aggregated results and action plans with the team. This transparency shows that the organization values and acts on employee feedback.

To further enhance the preparation process, consider providing training for both supervisors and employees on how to give and receive feedback effectively. This can include workshops on active listening, constructive criticism, and conflict resolution.

Key Areas to Focus On

To make the evaluation process more organized, we've categorized the questions into key areas of supervision:

Communication Skills

  1. How clearly does the supervisor communicate goals and expectations?

Clear communication is essential for team alignment and productivity. Employees should understand their roles and responsibilities without ambiguity.

  1. Does the supervisor encourage open communication within the team?

Open communication fosters trust and collaboration. A supervisor who encourages team members to share ideas and concerns creates a more inclusive environment.

  1. How well does the supervisor listen to feedback and concerns?

Active listening is crucial for understanding team needs and addressing issues effectively.

  1. Does the supervisor provide timely updates on project progress and changes?

Keeping the team informed helps maintain momentum and reduces uncertainty.

Leadership and Management

  1. How effectively does the supervisor lead by example?

Leading by example is crucial for gaining respect and setting a standard for the team. Supervisors who demonstrate the behaviors they expect from their team members foster a culture of accountability.

  1. Does the supervisor demonstrate adaptability in changing situations?

Adaptability is key in a dynamic work environment. Supervisors who can pivot strategies and remain calm under pressure inspire confidence in their teams.

  1. How well does the supervisor delegate tasks and responsibilities?

Effective delegation empowers team members and ensures workload distribution is fair and efficient.

  1. Does the supervisor set realistic and achievable goals for the team?

Setting attainable goals motivates the team and helps prevent burnout.

Support and Development

  1. How supportive is the supervisor in helping team members achieve their career goals?

Professional development is vital for employee satisfaction and retention. Supervisors who invest in their team's growth create a more engaged workforce.

  1. Does the supervisor provide constructive feedback regularly?

Regular feedback is essential for continuous improvement. It helps employees understand their strengths and areas for development.

  1. How accessible is the supervisor for one-on-one discussions?

Accessibility fosters a supportive environment where employees feel comfortable seeking guidance.

  1. Does the supervisor encourage and facilitate professional development opportunities?

Providing resources and time for learning shows a commitment to employee growth.

Problem-Solving Abilities

  1. How effectively does the supervisor resolve conflicts within the team?

Conflict resolution skills are crucial for maintaining a harmonious work environment. A supervisor who can mediate disputes helps keep the team focused on their goals.

  1. Does the supervisor encourage creative problem-solving?

Innovation drives progress. Encouraging team members to think outside the box can lead to better solutions and increased engagement.

  1. How well does the supervisor handle unexpected challenges?

The ability to manage crises effectively is a testament to a supervisor's leadership skills.

  1. Does the supervisor involve the team in decision-making processes?

Involving the team in decisions fosters a sense of ownership and can lead to better outcomes.

Team Dynamics and Morale

  1. How does the supervisor contribute to team morale?

Positive morale leads to higher productivity and job satisfaction. Supervisors who create a positive work environment see better team performance.

  1. Does the supervisor recognize and celebrate team achievements?

Recognition is a powerful motivator. Acknowledging hard work and success boosts morale and encourages continued effort.

  1. How well does the supervisor foster a sense of teamwork and collaboration?

A collaborative environment leads to better problem-solving and innovation.

  1. Does the supervisor create an inclusive and diverse work environment?

Inclusivity ensures all team members feel valued and respected, leading to a more cohesive team.

Implementing Effective Supervisor Evaluations

To implement a successful supervisor evaluation process:

  • Use Digital Tools: Platforms like Assembly can streamline the feedback collection process. These tools often provide analytics to help interpret the data.
  • Provide Context: Explain the purpose and importance of the evaluation to staff. This helps them understand the value of their input.
  • Train Managers: Help supervisors understand how to receive and act on feedback constructively. Training can include workshops on effective communication and leadership.
  • Create Development Plans: Use feedback to create specific improvement plans for managers. These plans should be actionable and measurable.
  • Monitor Progress: Track changes in evaluation results over time to measure improvement. Regular follow-ups ensure that feedback leads to tangible outcomes.

Additionally, consider involving HR or a similar department to oversee the evaluation process, ensuring fairness and consistency. This can also help in aggregating feedback and providing actionable insights to supervisors and the organization as a whole.

Key Takeaways

Supervisor evaluations are a powerful tool for enhancing leadership and team dynamics. By using these categorized questions, organizations can gather comprehensive feedback, leading to improved performance and employee satisfaction.

Encourage open communication and use these insights to foster a supportive work environment. Remember, effective feedback is key to unlocking potential and driving success. By asking the right questions and following best practices, you can gather valuable insights from your staff members and create a positive, productive work environment.

Use Assembly to optimize supervisor evaluation. Assembly empowers employees to provide feedback in real-time. Book a free demo today.

FAQs

Why is it important to evaluate a supervisor’s performance?

Evaluating a supervisor’s performance ensures that leadership aligns with company goals and employee needs. It helps identify strengths, areas for improvement, and potential gaps in leadership effectiveness. Regular evaluations lead to better communication, increased employee satisfaction, and a more productive work environment.

What are common mistakes to avoid in a supervisor evaluation?

Common mistakes include lack of confidentiality, vague or biased feedback, focusing only on negatives, and failing to follow up on results. Effective evaluations should be structured, constructive, and solution-oriented, ensuring that feedback leads to meaningful improvements.

How can employees give anonymous feedback about their supervisor?

Organizations can use confidential surveys, third-party feedback tools, or HR-managed evaluation forms to collect anonymous input. Ensuring anonymity encourages honest feedback and helps companies gain genuine insights into a supervisor’s leadership style and effectiveness.

How often should supervisor evaluations be conducted?

Supervisor evaluations should be conducted at least once or twice a year, with ongoing feedback encouraged between formal reviews. Regular assessments help address concerns in real time and ensure that leadership remains aligned with company objectives and employee expectations.

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Frequently Asked Questions

Is Assembly SOC 2 compliant?

Yes, at Assembly, security is a top priority. Each quarter, we have ongoing security work that is everyone’s responsibility. While we maintain a strong security posture, it was important for us to prove to our customers that we do everything we claim to do. This led us to pursue a SOC 2 Type II report that would provide evidence of our compliance with industry gold-standard security practice.

What's the ROI for employee recognition?

There is study after study showing that employee recognition leads to increased engagement. This in return creates an environment where employees are happier and more motivated which increase productivity and reduces voluntary turnover significantly. In order to filled critical roles, companies tend to spend nearly twice the value of an annual salary. Assembly is an investment in your employees that supports your bottom line.

Does Assembly offer longer-term contracts?

Yes, we will offer contracts for companies with longer-term agreements to help larger customers have more certainty around future costs.

The minimum agreement term is a 12-month subscription.

Does Assembly offer onboarding support?

We do and for FREE! Any new customer needing further support to get started with Assembly to ensure you're set up for success can request custom onboarding support. Improving your employee experience is about much more than just using our amazing software; it’s about transforming your business to create a workplace that people love. That’s much easier to do with the personal support and advice from our passionate people experts.

How much do rewards cost?

At the time of redemption (when your employees exchange their points for a paid reward) you'll pay face value. If a reward is a $10 Amazon gift card, your cost will be $10. All paid rewards are billed for on a monthly basis.

The good news is that you don't have to pay for rewards upfront because we only charge you when points are redeemed, not when they're earned.

Does Assembly offer discounts?

We offer discounts or educational or charitable organizations. In order to secure a discount, you'll first need to book a demo with a customer support specialist.

For all other organizations, we are willing to consider longer-term agreements in exchange for discounts. To set up annual plans or longer, you will need to book a demo with a customer support specialist.

How do I cancel my plan if needed?

If you're on a month to month plan, you can go here and cancel anytime. If you're having concerns or need help setting up your account for success, you can always book a demo with a customer support specialist.

If you're on a longer-term custom plan, you'll need to reach out to your customer support specialist to cancel your account or email us at support@joinassembly.com.

What customizations are available?

Great question! You can customize your core values to match your organization's to boost and track alignment. You can change your currency from the 🏆 emoji (our default) to any emoji of your choice. You can swap our logo for your own. You can also set up company culture rewards such as, "Lunch with the CEO," "Buy a book on us," and so much more!

Who can give or receive recognition?

While we recommend a peer to peer set up where anyone in your organization can give or receive recognition, you can set up Assembly however you want. If you need to limit the people who can give or receive recognition, that's perfectly fine and can be done from your Admin, here.

What integrations are available?

Assembly connects to the tools your employees use every day to offer an easy, seamless experience with minimal change management.  

Assembly has integrations with HCM/HRIS systems like ADP, Google, Office 365, and Slack. We also integrate with communication tools like Slack and Teams so you and your employees can access Assembly wherever they work now.

What's your average adoption rate?

That depends on the company's permissions set up. That said, over 90% of the employees on Assembly's platform are recognized on a monthly basis. That means nearly every employee across all of our customers are receiving regular recognition from their peers, managers, or leadership. We're extremely proud of this.

Must rewards be set up to use Assembly?

They are not required. You can use Assembly without having rewards set up. However, we don't recommend it if you intend to have a high adoption and usage rate. You can always keep the costs down by offering internal culture rewards that are fulfilled by you internally.

Are points required to use Assembly?

No, you can remove allowances from anyone or everyone. It's up to you but we do recommend using points whether they're worth a real dollar value or not. Companies that use points have a much higher engagement rate even if those points don't exchange for real dollars.

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