Questions to Ask Your Next Manager

Avoid surprises by asking these 7 questions before signing your next offer letter

👋 Hi, this is Akash with this week’s newsletter. I write about leadership in software engineering. This week we hit 1000 subscribers! Thank you for your readership.

This week I’m sharing 7 essential questions you should ask the hiring manager next time you interview. Hope you enjoy this edition!

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“Do you have any questions for me?” - how many times has this question startled you in interviews?

It’s not that we don’t expect it. Yet, it leaves us thinking, “What should I ask?”

The pressure is off the charts if it’s the hiring manager round. We want them to like us. At that moment, we don’t think about whether we like them.

But did you know that people leave their boss 5 out of 10 times, not the company?

It’s sad, but not surprising. Leadership is difficult, and there’s no right way to do it.

People have good intentions, it’s just not the right fit.

Have you ever started on a new role and soon realized it’s not going to work out?

What if there’s a way to avoid it?

Today, I will share 7 essential questions to ask your future manager before you make a decision. I wish someone had shared this with me sooner. I have made bad choices and later regretted them; you don’t have to.

⭐ Main Takeaways

• How to choose your next role carefully by asking questions

• Practical thought process to deal with emotional difficulties of asking questions

• Sample questions you can use on your next Hiring Manager interview

Let’s dive in!

🙋‍♀️ Asking Questions Will NEVER Cost Your Job

Do you feel uneasy asking questions to your potential manager?

I’ve always felt very uncomfortable. I’d tell myself, “it’s okay, I can adjust?” or when I notice some red flags, “they probably didn’t mean it that way”.

Many of us struggle to ask for what we want. We think, “What if they think of me as difficult to work with?” or “Is it the right time? I’m sure I’ll get plenty of opportunities to ask questions.”

If you feel like that, I’m with you. I’ve made the mistake of not asking enough questions. I always thought it’d hurt my chances if they felt interviewed.

The truth cannot be further from this. When you ask questions, the HM knows,

• You have a genuine interest in the role and the company

• You’re a dedicated person who cares

• You are looking for stability

Depending on the company you’re interviewing, you might have an HM interview round,

• at the very beginning of the process (Amazon, Meta)

• at the very end of the process (Google, OpenAI, Netflix)

• multiple times during the process (Apple, Anthropic)

(these are based on my experience interviewing at these companies, it may vary)

I appreciate having an initial conversation with the HM for a quick vibe check. But I prefer saving in-depth questions for later.

If you’ve only spoken to your potential manager once at the start, ask for another call before moving onto the offer stage.

You might want to wait till this stage because:

• Starting with hard questions might not be a great experience

• You can avoid this conversation altogether if others don’t go well

• Now your interview feedback is available, and you’ll get more personalized answers

It’s a personal choice though. The important thing is to ask and assess your match.

Let’s explore 7 questions that you MUST ask before signing your next offer letter.

⁉️ 7 Questions to Ask Before You Decide

🧭 1. What are your core leadership values?

Have you ever felt that your manager isn’t sharing important information?

Not a big fan of how feedback is communicated?

You and your manager have your own set of values. It’s okay if they’re not the same. But, it becomes a struggle when it’s completely opposite.

How do you deal with that?

If you ask someone if they’re a micromanager, you’ll only get a “NO”.

Asking an HM about their leadership principles is a great way to understand their style. You can ask them:

• “How have your leadership values evolved throughout your career?”

  • Tells you about the adaptability and growth journey of their own.

• “What are the top 3 values that guide your leadership approach?”

  • It’s a nice ice-breaker into this topic of core values.

• “How do you ensure that you strike the right balance between values?”

  • It tells you how they adjust their style depending on the situation.

The core idea here is to understand how they lead. And if that aligns with what you’d want from your next manager.

🏢 2. How are decisions made at the team or organizational level?

Engineers spend most of their time not coding. The majority goes into planning and designing systems, all requiring decision-making.

Wouldn’t it be great if you had clarity on how decisions are being made at your new team?

I’ve worked in both engineer-driven and top-down cultures. Some I like more than others. You should know what you’re getting into if you're making a switch.

Try asking these questions:

• “How transparent is the decision-making process?”

  • Tells you about overall company culture.

• “How much autonomy do individual team members have in making decisions?”

  • Know how much influence is with the team vs coming from executives.

• “If there's a disagreement within the team, how is it resolved?”

  • Tells you how escalations are used and handled.

Organizational culture plays an important role in your happiness. These questions can reveal a lot about internal culture and processes.

🚀 3. What are your career goals and aspirations?

If you’re particularly growth-minded, this is for you.

Without going into the “engineers can better manage engineers” debate, I can say an ambitious person is more likely to support your accelerated career goals.

It’s purely based on my experience, but I wish someone had told me this sooner.

Growth is much more than just promotion. Increase in scope, influence are all growth. A leader with very high ambitions for themselves can create spaces for you to grow with them.

But, it sounds a bit intrusive and awkward, right?

Here’s how you can reframe this question,

• “What aspects of your role keep you motivated?”

  • Know about their interests and passions.

• “I'm impressed by your accomplishments so far. What are some of your future aspirations that you're most excited about?”

  • A subtle way to ask the questions is by praising their current position first.

• “How do you see the team's success contributing to your overall career goals?”

  • Tells you about their career goals.

It’s always an interesting conversation with the HM. It’s also one of the questions that can catch them off guard. Try to understand how they see themselves growing into their dream role.

🌱 4. How would you support my growth objectives?

It’s time to turn the table. Understanding how the HM thinks about growth should play a key factor in your decision.

We’d want to avoid joining a company only to realize there’s no growth trajectory.

As a TL at Google, I led a team and multiple impactful workstreams. This was not the case when I transitioned to Apple. They don’t have formal TL roles.

If I hadn’t discussed this clearly with my current manager, I wouldn’t know that Apple works differently.

Here’s what I asked (well, along the same lines),

• “How does performance evaluation work at [Company X]?”

  • Tells you about the process and frequency.

• “How often do you have career development conversations?”

  • Hear how seriously they invest in the team's development.

• “I’m very interested in growing as a leader, what opportunities will be available if I join this team?”

  • Understand the available opportunities and how they support growth in general.

The more context you can provide, the better. You’re trying to gauge potential opportunities and see if they align with your expectations.

🛠️ 5. What is your strategy when someone on your team is underperforming?

“The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy”

- Martin Luther King Jr.

How your manager handles difficult times can determine your job satisfaction.

Going into a job, underperforming is likely not on your mind. I wish my performance were always under my control. However, many external factors can affect how you perform.

Sometimes letting go is the right, yet hard decision a leader must take to protect the team (read more in this article from

Anton Zaides

). 

To understand the HM’s response to a crisis, try these questions,

• “What kind of support and resources do you offer to employees who are struggling?”

  • Tells you about how they provide support to members.

• “What steps do you take if an employee's performance doesn't improve despite your efforts?”

  • Learn whether they can make hard decisions if needed.

• “How do you balance providing feedback with maintaining a positive and supportive environment?”

  • Know how they treat feedback.

Knowing that you’ll get all the support helps with psychological safety.

🤩 6. What excites you the most about this team?

We have many opportunities to learn more about the team’s work. But getting insights from the leader on their vision reveals a lot more.

The lack of a vision is dangerous. Trust me, you don’t want to work there!

You can ask the following questions,

• “What are some of the ways the team is currently innovating or pushing boundaries?”

  • Innovation is a good indicator of a solid vision.

• “How do you think the team will evolve and grow in the coming years?”

  • Clarity in the team direction is important for a leader.

• “Where do you see [Project A] going?”

  • Demonstrate their technical abilities as a leader.

If you decide to chat with the HM last, it generally means your interviews went well. Make sure you’re sold on the vision, not just other things. It’s hard to survive work if you’re not interested at all.

❤️ 7. What do you care about?

The last one is a miscellaneous category. Topics around remote work, expectations, and work hours.

A few of the good managers I’ve worked with say, 

“I don’t care where you work from, what time you’re working, as long as you get sh*t done”.

It’s important to me. Trusting me with the work and offering flexibility is important in today’s world.

Managers have different work ethics. To get to know them more, inquire about things you care about.

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🌟 🔍 Parting Thoughts

I used to interview often, not to change jobs, but to stay current and prepared. I always hesitated to ask hard, meaningful questions.

I felt I might not get an offer if I offended them somehow.

I’ve joined companies only to realize, it was never going to work out. Since I started being more vocal about my needs, asking questions was never the reason for any of my rejections.

Don’t take chances. Start asking questions that fulfill your needs. Interviews are a two-way process, use it.

Tell us about your favorite questions to ask your potential manager.

Share them in the comments!

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🐦‍🔥 This Week’s Favorites

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  Perspectiveship
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• Secrets behind 10x engineers from

  The Hustling Engineer
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👋 💬 Get In Touch

Want to chat? Find me on LinkedIn.

If you want me to cover a particular area of leadership, you can reach out directly to akash@chromium.org. 

If you enjoyed this content, please 🔁 share it with friends and consider 🔔 subscribing if you haven’t already. Your 💙 response really motivates me to keep going.