Ask These Questions to Find a Good Boss

Woman in black jacket sitting at a desk and smiling

A client recently asked me how to ensure their next boss will be better than their last one. 

It was an excellent question to ask and one that many job seekers who are looking for a new job, in part due to their boss’s behavior, have on their minds.

A 2019 study by DDI Research showed that 43% of those surveyed quit a job because of their manager, with 14% quitting multiple jobs because of their manager.

There is a saying that people don’t quit a company; they quit their manager. These numbers show how true this can be.

A good boss can make or break your experience in an organization. When you work with a boss whose management style aligns with how you work, this can positively impact your job satisfaction, the effort you put in, and ultimately, your long-term success at this organization and in your career.

Many people have a significant roadblock with their boss when the employee’s values do not align with their boss’s. If what we hold dear is not reciprocated, no matter if the work is interesting or you are accomplishing great things, you will always feel something is off.

Eventually, you become disengaged and burned out.

Our values are our “why.” If the person you work closest with does not honor our “why,” we will never feel comfortable working there. Most people eventually realize they must go elsewhere to fulfill their “why.”

The Role of Values in Finding the Right Boss

Thankfully, there has been a change in how workers view their jobs. Previously, a good job was considered one with a good paycheck and benefits. Some only look at a job from that lens, but in my experience, most workers now look at the job more broadly. Is the job effectively using their talents? Does it align with their interests? And does it align with their values?

So, what are values? They are our core beliefs. They are deeply ingrained in us and essential to who we want to be in this world. They influence our decisions and actions.

Since humans are all different, we have different values. Therefore, it is important to understand what values are important to you.

For example, you could have a core value of authenticity. You present yourself honestly and transparently and may want others to reciprocate that. So, if you find your boss gaslighting you, manipulating, or denying your experiences or feelings, that violates your values.

Or let’s say you have a value of growth. You believe in continuous improvement, learning, and development. You value expanding your knowledge, skills, and capabilities. However, your value is being violated if you have a boss who resists change or fails to provide growth opportunities.

Knowing your values is important to understanding. Then, you can find out whether your prospective boss also upholds these values in a way that will help you thrive working for them.

Key Questions to Ask to Understand Management Style

An interview is always a two-way conversation. The employer is assessing you and your fit for the role/organization, and you should be doing the same. I am not a believer in asking questions to look “smart.” It would be best if you asked the questions that are important to you to assess whether the role/boss/organization is right for you.

One way to do this is to ask the hiring manager/team questions about their values. Below are 24 sample values and questions you might ask to understand whether they hold these values.

Authenticity

-Share a time when you had to make a difficult decision. How did you communicate it to your team?"

-What were some situations where you were transparent with the team and when you could not?

Achievement

-How do you measure success for your team, and do you measure success for individuals differently?

-What strategies do you use to recognize and reward high performance among your team members?

Autonomy

-Do you want your team to work a certain way, or do you prefer them to work how they choose?

-What level of independence do you give your team when working on projects?

Balance

-When it comes to work-life balance, what is your philosophy?

-What are your expectations around availability and working hours?

Boldness

-Have you made any bold decisions since working here?

-Has there been a time when you encouraged your team to challenge the status quo?

Compassion

-Can you do anything to encourage your team members to maintain their well-being?

-What actions have you taken to ensure a supportive work environment?

Challenge

-How do you ensure that your team is consistently challenged and growing?

-What types of stretch goals do you set for your team members?

Community

-How do you foster a sense of community and collaboration within your team?

-What strategies do you use to build strong relationships within your team?

Competency

-How do you support your team in continuously improving their skills and competencies?

-How do you ensure your team has the necessary skills to succeed?

Contribution

-How do you ensure that each team member feels their contributions are valued?

-How have you recognized and rewarded contributions that go above and beyond?

Creativity

-Have you encouraged creativity and out-of-the-box thinking within the team?

-Can you share an example of how you supported a creative solution in your team?

Fairness

-What are your thoughts on fairness in assigning tasks and recognizing achievements within your team?

-How do you handle ensuring everyone feels heard on your teams?

Fun

-Do you incorporate fun and enjoyment into the team's work environment?

-Do you feel fun has a role in the workplace?

Growth

-How do you support your team’s professional development and growth?

-What opportunities for building skills and acquiring additional expertise do you offer within the team or organization?

Happiness

-How do you measure your team members' happiness and satisfaction with their work?

-What steps do you take to create a positive work environment?

Influence

-What actions should your team members take to influence decisions positively?

-What strategies do you use to ensure your team’s voice is heard at higher levels?

Kindness

-What are ways you promote kindness and empathy within your team?

-How is kindness demonstrated on your team?

Knowledge

-How do you encourage knowledge sharing and continuous learning within your team?

-How do you help your team stay informed and up-to-date with industry trends?

Leadership

-What is your leadership philosophy, and how do you apply it in managing your team?

-Who has been the most inspiring leader you have had, and what did they do?

Meaningful Work

-How do you see the work of the team as meaningful?

-Can you share an example of how you’ve helped a team member find meaning in their work?

Respect

-How do you ensure that respect is maintained within your team, both for you and among team members?

-What do you do to create a culture of mutual respect in your team?

Responsibility

-How do you ensure each team member knows their responsibilities, and how do you enforce accountability?

-Have you had a situation where a team member doesn’t meet their responsibilities? What did you do?

Security

-What is your process for letting people know they are not meeting expectations?

-What steps do you take to provide stability within the team?

Trust

-How do you build and maintain trust within your team?

-Have you ever had a time when you had to rebuild trust with your team?

Clues for Value Alignment

Okay. Now that you know what to ask, how should you interpret what was said?

Shared Language: Pay attention to whether the potential boss uses language or phrases consistent with your values. For example, if you value teamwork, listen for words/phrases like "collaboration" or "collective effort."

Questions About Your Values: A good prospective boss will also ask questions about your values to understand whether you can thrive in this environment. Pay attention to how they respond to your answers.

Respectful Interactions: How does the prospective boss interact with you? How are you being treated?

Look for Consistency: If the potential boss lives by this value, then their answers, with examples of their actions and decisions, should align with them. Are the values lived out in low-stakes and high-stakes situations? Expressing your values in low-stakes situations is easy, but there may be more personal risk to doing so in high-stakes situations.

Red Flags: Some obvious red flags are vague answers to your questions, answers that paint broad pictures but give no specifics, and a lack of empathy about your desire to find the right fit by asking these questions.

Beyond the Interview - Other Ways to Gauge Management Style

I would not rely on only what the prospective boss tells you to gauge their values. Gathering other information is best to lower the risk of finding yourself in a situation where your future boss may not have been entirely truthful with you. Here are other actions you can take.

Observe the Workplace Culture: If you have in-person interviews, observe how that prospective boss interacts with others and how they react to them. Does it seem friendly? Are people happy? Or is the mood dour?

Talk to Others: If you can, speak with people who would be your peers to understand how this manager interacts with people on and outside of the team. If this is not available, you may be able to speak with others with connections to the organization, like vendors, suppliers, and even clients.

Conclusion

Yes, if you have had a bad work relationship with your boss, you definitely do not want to repeat this in your next job. It is important to do your due diligence to lower the risk of finding yourself in the same or similar situation again.

It is important to ask good questions of your prospective boss that give you information to help you determine whether this person’s values align with yours. Take the time to understand your top values and develop questions (or take the ones I have here) to help you make this assessment BEFORE you accept an offer.

You deserve to thrive in your career. Working with the right boss can help you do this.

Shelley Piedmont is a Career Coach who focuses on understanding your unique skills, interests, and aspirations and provides personalized coaching to guide you toward roles where you can truly thrive. Whether you are stuck as to what your next career move should be or need help with resumes, LinkedIn profiles, or interview preparation, Shelley is here to help you. Please set up an exploratory call to find out how she can help you reach your career goals.