Conifer

Let's Make Interview Questions

We previously discussed the importance of consistency in interviews, not only ensuring that each interviewer covers different topics, but also that the interviews themselves are conducted similarly. Beyond training interviewers, one way to ensure consistency is by crafting a bank of questions for each area to assess, as well as recommended follow up questions. Interviewers should be able to exercise judgment to determine when they should go "off script" and probe for different areas than what's prescribed, but these types of resources can be valuable especially for newer interviewers building this muscle and folks newer to the organization that are less familiar with how your organization interviews.

In this post, let's talk through a few examples for how I would break down specific values and skills to craft interview questions. I've taken the time to think through the values I'd set for myself and an organization I'd like to operate at.

You may read the below and feel that I am cribbing Amazon's Leadership Principles. I remain inspired by them, no doubt, but I put my own spin and adjusted these to better reflect what matters most to me and the work environments I'd like to be part of. The exercise is designed to help me figure out what good looks like and craft questions that help me find this out.

Is this the best or only way to interview? I'm sure you could come up with a system that yields similar results in less time, but in my view, hiring is only one step of the process. It's the most important since it sets up everything further downstream, and taking the time to bring the best people in will have compounding benefits down the road. Regardless, the goal of the values gives us something to work back from and evaluate candidates against. Not only for hiring, but also how you make business decisions and operate as an organization. This cascades into how you train and develop employees. Assessing for these attributes upfront helps ensure you find people who are strong fits for the organization and have potential to grow beyond the functional role they will play when they first join the organization.

I boiled down my values into twelve discrete areas. The below includes a short description of how I'd frame these for my company to help show the world how we operate, what we care about, and what we look for in people who want to work with us. This gives us clarity on what "good looks like" in each area, which helps calibrate all interviewers around the same goal.

We want to make it easy to understand the purpose of each question and why this question is tied to the value. The quality of the answers we receive should tell us if the candidate has the chops to operate effectively in the environment and has potential for growth. The scope of the answers and the scope of the anecdotes will also reveal what we need to know about their seniority and their perception of "difficulty". Every organization will be different here, so you'll need additional calibration role by role depending on the seniority in your organization and how the team is structured.

Creating clarity here and calibrating the group ensures that good interviewers become a fungible commodity at your company, and that any random selection of trained interviewers will make similar hiring decisions that mitigate the risk of poor hires and consistently find strong candidates competitors would overlook.

With this, we can craft questions that assess candidate's alignment to these values we've set and their capabilities.

Value 1: Build Trust

Description: We operate ethically, are self-critical, focus feedback on the work not the individual, and speak with candor. Beyond words, we follow through on our commitments and aren't afraid to say "no", even when it's hard. This helps build trusting relationships that enable us to do our best work. Without trust, we can't go far.

Interview questions: 1) Tell me about a moment when you had to say "no" to something important.

Follow-ups:

How did you communicate your reasoning? What alternative solutions did you propose? How did the other party receive your response?

Why this question: We can gauge how the candidate prioritizes and communicates with their team members. We can see their rationale and how they approach delicate situations. In addition, we see what they gauge as an important decision.

2) Describe a time when you had to rebuild trust after a mistake.

Follow-ups:

What specific actions did you take? How did you demonstrate accountability? What would you do differently next time?

Why this question: We want to hire people who can reflect on their past actions, seeking to improve. This question not only shows their self-awareness and ability to reflect, but also being open and honest about issues -- critical for building trust.

3) Tell me about a time you had to give difficult feedback to a colleague.

Follow-ups:

How did the recipient respond? What was the long-term impact of that conversation? How do you prepare for challenging feedback discussions?

Why this question: We want to see what the candidate sees as "difficult" feedback, as well as how they communicate during sensitive situations.

Value 2: Take Responsibility

We own up to our faults and deliver on what we say we will. We treat customer problems as our own and work relentlessly to solve them together. We aren't afraid to jump in to help our team deliver in areas outside of our core responsibilities. We don't do this for personal glory, we do it because it's the right thing to do.

1) Share an example of going above and beyond to help your team deliver.

Follow-ups:

What challenges did you overcome? How did this impact the team? What was the result of your actions?

Why this question: We want to see how this person defines "above and beyond" and gauge their level of comfort going beyond the scope of their role. In addition, how do they speak about it? Some may come across as resentful they needed to do more, while others revel in the opportunity.

2) Describe a customer problem you treated as your personal mission to solve.

Follow-ups:

What made you so committed? How did you approach the solution? What was the outcome?

Why this question: We want to see if the candidate wants to own customer problems. If it's a problem they weren't initially tasked to solve, we can also see how they prioritize.

3) Tell me about a time you stepped in to help a teammate that was struggling to solve a problem.

Follow-ups:

How did you identify there was opportunity to help? What actions did you take to help them? What was the outcome?

Why this question: Good teammates help each other, and this question gauges if the person is willing to help their team members.

Value 3: Diverse and Inclusive

Not everyone looks like, sounds like, or has the same experience as us. It is the diversity of our team that makes us better and gives us a unique collective viewpoint. We ensure our products, processes, and solutions consider broad populations to ensure they are inclusive and accessible.

1) Tell me about a time your perspective was changed by an alternative viewpoint.

Follow-ups:

How did you gather this feedback? How did it change how you approached the work going forward? Why did this perspective change your own?

Why this question: Inflexibility in thinking can lead you down a path to ruin. Being open to other perspectives and ideas, even if not originally your own, shows flexibility and willingness to challenge assumptions.

2) Tell me about a time you built or modified a product or process to make it more relevant for a broader set of customers?

Follow-ups:

How did you identify this as an opportunity? Why was this the highest priority change? What results did you see from this change?

Why this question: We want to see if the candidate can evaluate how a product or process inadvertently is less accessible or relevant for a specific population that could benefit. How they identify and prioritize opportunities to make their work more broadly applicable is useful.

3) Tell me about a time you needed to balance diverging viewpoints and make a decision.

Follow-ups:

What were the opposing viewpoints? How did you evaluate the pros and cons? What did you do to align the team on a path forward?

Why this question: The best candidates are open to hearing diverse viewpoints and can make decisions that are easy to follow. This question shows how the candidate navigates conflict and forges a path forward. We don't want to be stuck in debate while the world turns.

Value 4: We All Are Interns

We may be experts, but work to maintain our beginner's mind. Everything we do is a learning opportunity. What worked yesterday may not work today: We continuously learn, challenge assumptions, and view every interaction as an opportunity to grow. We reflect on what we've done and think about how we'd do it better next time. What we do today will prepare us for what's next.

1) Tell me about a skill you've deliberately worked to improve in the last year.

Follow-ups:

What resources did you use? How did you measure improvement? How did you determine what you wanted to learn?

Why this question: We want to see how the candidate identifies their gaps, what they see as priorities for learning, how they go about learning, and if they pursue growth outside of their day job.

2) Describe a time you realized your initial approach was completely wrong.

Follow-ups:

What triggered your realization? How quickly did you adapt? What did you learn?

Why this question: We want to see how candidates pivot or adjust their approach as they test and learn. We want to see the candidate's ability to reflect and articulate what went wrong and how they improve.

3) Share an example of a time when something you were an "expert" in changed dramatically.

Follow-ups:

How did you stay current? What was your learning process? How did you help others understand the changes?

Why this question: For folks who have a narrow-but-deep skillset, this question helps us understand how they stay current in core area. We want to see how close team members stay to their functions and how they continue to develop expertise.

Value 5: Clarity in Thought

We take time to write our thoughts, plans, and concerns. We focus on making our ideas easy for the reader, whether that's team mates, partners, or customers. Our rationale should never be murky -- we explain how we got to our recommendation so others can offer their feedback and validate our thinking. We take time to break down complex topics so that they are easy for us to understand and reflect upon.

1) Walk me through a scenario where you needed to educate a stakeholder, customer, etc. on a topic they did not have strong knowledge in?

Follow-ups:

What mental model do you use for simplification? How do you verify understanding? What analogies have you found most effective?

Why this question: We don't want to hire people who cannot speak in a clear, easy to understand way. The best experts can break down the complex jargon and make it understandable for all.

2) Share an example of how you've helped a team understand a nuanced or complicated situation.

Follow-ups:

What visual or narrative techniques did you use? How did different team members respond? What was the ultimate resolution?

Why this question: Teams, especially leaders, are not always privy to the intimate details of a situation. There can be a lot of nuance and complexity to manage, so being able to articulate this clearly and succinctly is valuable.

3) Describe a time you broke down a complex problem into manageable components.

Follow-ups:

How did you identify the best way to break this down? How did you prioritize these components? What insights emerged from this process?

Why this question: First, I want to see what they see as a "complex" problem. Second, I want to see how they break up the project into manageable tasks, as well as how they organize and communicate it out. This question not only shows clarity of thought, but broader organizational skills.

Value 6: Foster Open Discussion & Limit Ego

We don't let our ego get in the way of doing what is best for customers. We create space for teams to communicate openly and honestly, working diligently to create psychological safety to let enable teams to communicate without fear. We foster diversity of thought and value spirited discussion, but don't let this stop us from taking action: instead, it sharpens our thinking.

1) Tell me about a time you transformed a potentially combative discussion into a constructive dialogue.

Follow-ups:

What communication techniques did you use? How did you manage emotions? What was the ultimate resolution?

Why this question: There can be a lot of emotion in work, especially when things go wrong. We want to see candidates avoid the "blame game" and instead focus on solving the problem. How they navigate these kinds of tense situations will be telling.

2) Tell me about difficult feedback you received and how you responded.

Follow-ups:

What was the feedback? Why was this difficult? How did you get more insight to inform next steps?

Why this question: We want to see what they see as difficult feedback, how they drove clarity in expectations, and what they did to improve next time.

3) Describe a situation where you deprioritized personal credit for team success.

Follow-ups:

What motivated your approach? How did the team respond? What did you learn?

Why this question: Projects are complex and it's rarely ever a sole effort. But we also know it is easy for folks to look for ways to show they "owned" the work, even when it is collaborative. In healthy cultures, we want to see how team members share and lift each other up to deliver the best work and foster a strong environment.

Value 7: See the Big Picture

We may have different roles and team-level goals, but we all work for the organization to support customer problems. We invest time to build cross-functional relationships to help us understand the big picture and how our work contributes to it. This helps us build the best solutions to customer problems, not just what makes us and our teams look good.

1) Share an example of how you've helped align team goals with customer needs.

Follow-ups:

How did you gather customer insights? What data or methods did you use? What changes resulted?

Why this question: We want to see if the candidate looks beyond the core scope to work from the customer need and tie each of the teams' outputs to supporting that objective.

2) Describe a situation where you connected seemingly unrelated aspects of a business challenge.

Follow-ups:

What prompted you to look beyond immediate perspectives? How did you validate your connections? What was the impact of your insight?

Why this question: Perhaps more important in more complex environments, we want to see if the candidate proactively forges relationships across teams and can recognize opportunities to collaborate to deliver more value.

3) Tell me about a time you saw an opportunity to go bigger than what you and the team had done before.

Follow-ups:

How did you know there was broader opportunity? How did you get buy-in for a larger vision? What were the steps you identified to help get there?

Why this question: We want to see if the candidate has the capacity to think beyond their day-to-day or core scope, and if they can recognize when they can take a bigger swing. For example, how do they know when to double down or expand an initiative? This question can help also understand what they think "big" looks like and how that ties to your work.

Value 8: Think Long Term

Short-term gains and vanity metrics may make us look good today, but could set us up for ruin tomorrow. We think long term, establishing for a vision for what we want the future to look like, even if it makes today more difficult. We design solutions that create meaningful value not just for immediate stakeholders, but consider broader societal and systemic implications. We do this by embracing incrementality, working step-by-step towards our vision, and adjusting as we learn.

1) Share an example of a decision you made that sacrificed short-term gain for long-term benefit.

Follow-ups:

How did you measure the potential long-term impact? What risks were involved? How did stakeholders react?

Why this question: We want to see if the candidate can take the long view and balance the cost of going long. We want to see if the candidate is focused on their long term objectives and knows what is being compromised in the near term to achieve this.

2) Tell me about a time you anticipated a future challenge and proactively addressed it.

Follow-ups:

What signals made you recognize the potential issue? How did you build support for your preventative approach? What was the outcome?

Why this question: We want to see if candidates can "look around the corner" to identify the impact of their next action, and work to mitigate any risks. Thinking ahead is crucial to avoiding catastrophe.

3) Tell me about a time you needed to align a team around a vision to make incremental process towards a goal.

Follow-ups:

What was the goal? What were the steps needed to get there? How did you get buy-in?

Why this question: This one is about persuasiveness and painting a picture for the team. Is the candidate going to be able to articulate where they want to go in a clear and inspiring way? Can they also bring along the team on this journey?

Value 9: Sharp Focus

We don't chase trends. While we should know what's happening in the wider world, we shouldn't pivot based on what we hear in the news alone. We stay focused on the problems we are solving and adopt new technology and practices if it helps us solve problems, not because it's "the latest". We prioritize doing fewer things with a high degree of excellence, limiting the division of our focus.

1) Describe a moment when you said no to an opportunity that didn't align with core objectives.

Follow-ups:

How difficult was the decision? How did you communicate this? What alternative did you propose?

Why this question: We want to see if the candidate can stay on task and keep to the mission. Being able to say "no" is important to staying on task and delivering on time

2) Tell me about a time you needed to make a trade-off between competing objectives.

Follow-ups:

What were the priorities and how did you evaluate them? How did you communicate this? If you were in the same situation today, would you evaluate this differently?

Why this question: We want to see how the candidate balances tasks against their goals and see if they are able to commit and make tough choices. We want to see the candidate reflect on these decisions and what they learned.

3) Tell me about a time you reduced complexity to move faster.

Follow-ups:

What made this situation complex? How did you prioritize what to remove? What was the result of the change?

Why this question: We want to see if candidates can recognize core benefit of what they are doing and work to make it easier to deliver. We want to see their ability to cut through the noise and get to the heart of the issue.

Value 10: Scrappiness and Grit

Business is constantly shifting. We need to remain adaptable and resilient to change. This means finding ways to move quickly and get things done. We find ways to deliver even in the face of adversity and aren't afraid to pivot if what we tried isn't working. Incremental progress is still progress.

1) Tell me about the hardest thing you've ever done.

Follow-ups:

Why was this difficult? What did you do to overcome the challenge? Knowing what you know now, would you do anything differently?

Why this question: This is important. Every environment offers a different level of comfort and difficulty. What the candidate sees as difficult, whether a personal or professional challenge, will reveal a lot about their character and their grit.

2) Tell me about a time when you delivered results despite one or more significant obstacles.

Follow-ups:

What were the specific obstacles? How did you break down the challenge? What support did you seek or create?

Why this question: Projects go awry and there are times we need to adjust our approach. We want to see how the candidate manages to deliver and prioritizes what they deliver to meet commitments.

3) Tell me about a time you found a creative way to deliver in a constrained environment.

Follow-ups:

What constraints were you dealing with? Why was this solution novel? What did you do going forward?

Why this question: Everyone wants to be able to spend more and increase headcount, but that's easy. We want to see how candidates get creative to deliver despite constraints, whether temporal or financial. We want to see if they are willing to plug in holes themselves to keep the ship afloat, or if they're the type to wait for the carpenter to show up.

Value 11: Artisan's Spirit

We don't serve slop. We are always looking to build solutions that are high quality, ethical, and straightforward to maintain. We use our judgment to invest time and resources into what matters most. It's great to move fast, but we aim to mitigate future debts by building things that can scale and change as our company evolves.

1) Tell me about a solution you designed with future scalability in mind.

Follow-ups:

What future scenarios did you anticipate? How flexible was your design? What assumptions did you make?

Why this question: We want to see how they think about future state and if they can recognize what they build can or cannot scale beyond its current implementation.

2) Tell me about a time you prioritized quality over speed.

Follow-ups:

Why did this situation call for this trade-off? What would've happened had you prioritized speed? What was the result?

Why this question: Quality vs. speed is a constant trade-off. We need to gauge if the candidate can identify when quality cannot be compromised.

3) Tell me about a time you needed to fix something that was broken.

Follow-ups:

How did you identify this was an issue? What did you do to improve it? What did you do to ensure this issue wouldn't happen again?

Why this question: We always inherit broken products, processes, and workflows. As businesses and teams change, so too must the way we do things. However, we need to see if people can fix and keep these items maintained.

Value 12: Measure and Verify

We measure everything we do, and we verify what we want to do is worth doing. If we can't measure, we hypothesize what we should evaluate and look for directional signals. This thoroughness keeps us aligned on what's most important and ensures we prioritize the deliverables that drive desired impact.

1) Walk me through how you've used data to validate a project's success.

Follow-ups:

What metrics did you choose? How did you ensure these metrics were meaningful? What surprised you in the data?

Why this question: We want to see how they use data to validate if they did the right thing, and how they tie back metrics to the work.

2) Walk me through how you interpreted data to make a decision on which path to take.

Follow-ups:

What metrics did you choose? What action did you recommend based on the data? Was this the right way to look at the problem?

Why this question: While the previous question provides a look back, this is looking forward: using data to decide what to do next versus evaluating what was done. We see how much research the candidate does to make a decision and how they evaluate using data.

3) Tell me about a time you wanted to use a specific data point to measure effectiveness, but it was unavailable.

Follow-ups:

What did you use to evaluate success? Were you able to work towards getting this metric? How did you verify the accuracy?

Why this question: It can be hard to get good data for everything, and sometimes we need to use rougher indicators to make decisions to keep things moving. We want to see how they adapt to different circumstances and data availability to make informed judgment calls on where to go next.

Closing Thoughts

I recognize this was a lot. You may also notice similar questions that assess adjacent areas, but from a different lens. This helps us get a fuller picture of the candidate.

The goal is not to be overly prescriptive -- these questions are not "battle tested" or a silver bullet designed to get you perfect candidates. This section, from the values to the questions themselves, are illustrative. You need to work back from what you want to get there. My goal with this is to show you how I'd do this exercise to inspire you to put in the same thought and rigor into this.