Next time you find yourself in the Interviewer chair, this section might give you some better starter questions.
Converting Bad Questions to Great Questions
Converted to Relevant / Great
Role Play Questions That Good Interviewers Create
Role Plays incorporate whiteboarding, editing, debugging, demos, presentations, auditions, role playing
Role plays involve you, the interviewer, engaging the candidate in a real-world situation or scenario. It’s your chance to see them demonstrate their skills live, as they interact with you – who often plays the customer or manager – to work through the type of situation that they’d typically find on the job at YOURCO. In general, you want to be sure you’ve set up the role play really well – explain, in detail, who’s who, what the context is, and that your goal is not to embarrass them or trick them; you just want to see them demonstrate their skills in real time. Be sure to ask them if they have any questions before you dive in.
Good interviewers create these in advance, not on the fly.
Should be realistic, give a preview of our work, and be fair.
Remember the candidate has not been living with or studying the problem, so keep expectations in check.
Example Role Play 1:
Set up: I’m your manager, and I’ve just asked you to cut the (timeline or budget) down by ½ for the XYZ project, which is [explain the project]. Ask me any questions you need answered to be able to generate some creative ways to deliver on XYZ in ½ the time/for ½ the cost.
[Did they ask smart questions to understand the real constraints, and understand the tradeoffs if we cut budget or accelerate the delivery date?] [Did they generate a mix of big ideas and practical ideas to help deliver what’s needed?]
Example Role Play 2:
Set up: One of the typical problems we face in our group is… [Give example of a relatively complex problem that your group encounters].
How would you approach a problem like that? What information would you need before you got started? What is the typical root issue associated with problems like this? How would you solve this problem? What if we added this constraint? (Add 2-3 typical constraints, one at a time, and look for both practical and creative ways that they overcome barriers.) How would you solve this problem or pivot to solve it now? How do you know that your solution would work? (Did they run through test cases?) How would you know if the root issue was addressed? Have you ever solved a problem like this before? Walk me through it.
Example Role Play 3:
Set up: You’re the [job title] and I’m a [key partner/job title]. I’d like your help with problem X [example of problem your team typically faces]. Please dive in and help me. What questions do you have for me, to get things going?
[Did they ask to questions / seek to scope the problem before presenting solutions?] [Did they listen, incorporate your concerns, your needs, your ideas?] [Was their approach collaborative and iterative, building on the ideas you’re developing together, or did they come off as more of a one-way sales person, trying to convince you to do it their way?]
Example Role Play 4:
Set up: Here’s a high-level goal of X. Please build out a project plan, and tell me who else (what teams, what roles) you’d need to leverage to deliver X.
What specifically would you need from the other teams? How many people? Assume those teams are already at capacity. How would you decide if X needed reprioritization? What do you think are the major risks associated with this project?
Example Role Play 5
Set up: YOURCO is considering making a move away from [tech A] and towards [tech B]. Please walk me through the tradeoffs and potential impact that you think a move like that might have internally, across our teams, or externally, with our users.
“Who asked you to do that?” (to see how often they were “carrying out orders” versus initiating or working outside the normal scope of their responsibilities and demonstrating ownership.
Example Role Play 6
Set up: Here’s a high level, general problem you might face if you were in this role. I want you to imagine you’re my problem solving partner, and help me work through this. [Explain a high-level problem; don’t share all the details.]
First, what kind of questions do you have for me? [Then…Do you have enough information now to feel like you have a deep understanding of the problem? If not, what else do you need to know?] What do you think are possible root causes? What kind of data would you need to validate the root cause? How would you solve this problem? How would you know that solution would work?
Example Role Play 7
Set up: Here’s some data that highlights some of the activity in our department. We want to improve X. Take a few minutes to review this info.
What jumps out at you right away? What kind of questions do you have for me? What do you think is causing problems to the way we do X? Where would you focus first, if you were trying to improve X? What would it likely take to fix that? What are the dependencies that might exist – within or outside our department – that you think could also be impacting how well we do X?
Case Studies That Good Interviewers Create
Case Studies are usually best leveraged by sending the candidate some kind of pre-work ahead of the interview, so that they have time to review the situation in detail, and come to the interview prepared to share their analysis or recommendations. In general, these are used to give candidates the opportunity to work on a real-world problem that they’re likely to face on the job, and demonstrate their ability to dive in and work up a realistic solution.
Case studies typically require you – the interviewers – to set up the problem you want solved, the business context, the key players, and possibly some constraints (i.e. needs to be done in 3 months, you have X budget to work with, existing technology can’t do X well). Be really clear on what you’re looking for from the candidate – do you expect a verbal walk through, a powerpoint deck, a one-page overview, footnoted research to support recommendations, a piece of software or a website or app that will work through a web browser? Also, be aware that top candidates are often in high-demand, and be sensitive to the time investment needed by a candidate – who may be actively interviewing and have other offers – to complete your case study. Additionally, ensure that what you ask them to do doesn’t come off as free consulting request; this should be very clearly linked to the job they’re interviewing for, and not a way for you to learn how they did something at their prior company, or get some free outside help J
Should be sent as pre-work for the candidate. Should require no more than 2 hours of prep time for the candidate. Be fair and be respective of their time and the stress and distraction that interviewing can create.
Example case study 1: Engineer
Set up: YOURCO is looking to replace X technology with something that will [do Y better]. What would you recommend, and why? What are the pros and cons? How would your recommendation change if we were optimizing for A instead of B?
Example case study 2: Recruiting Manager
Set up: We at are in hyper growth mode and recruiting needs to rapidly respond to the ever-changing requirements of the business. One of the biggest challenges is figuring out how we scale. To complicate the issue, we have international tech recruiting needs that need to either be supported locally or remotely. Lastly, our clients’ needs are in constant flux, which means constant changes to our targets.
Context for our fictional case study: • We need to hire 50 Engineers in Seattle in 12 months • To start the year, we have 3 recruiters & 1 sourcer in Seattle • Recruiters produce on average 5 hires per month and take 1 month to ramp. • Sourcers produce on average 3 hires per month and take 2 months to ramp. • We use agencies when necessary and are open to RPO.
Questions that we would like you to address: • How would you add capacity to hit these hiring targets? Feel free to add recruiters (perm or contract), sourcers, agencies, RPO or anything else that help you hit hiring targets. • How would you approach ramping recruiters quickly so that they are productive ASAP? • What key metrics would you rely on to assess the health of your recruiting team? • Tech hiring can be complicated at CompanyX as we hire engineers, designers and data scientists to support the Product Management (PM) organization but in most cases, these resource report into functional line managers. Given that our engineers, designers, and data scientists don’t report directly into PMs, how would you recommend ensuring that PM’s get access to the talent that they need to hit their product road maps and how would you go about providing transparency of pipeline and the progress against hiring plans of these individuals? • What are the major pitfalls that companies make when scaling too quickly? • Any other thoughts?
Example case study 3: Recruiting Manager
Set up: We've got a strong recruiting team at CompanyX that works extremely hard and hits extraordinary high numbers of hires on a monthly basis. However, hiring managers need more support than they are getting as our growth rate is unmatched. At the same time, we’re concerned about recruiter burnout as they work long hours and see no end to sight with very heavy hiring targets. We haven't had the time or luxury to focus on career development or coaching given how stretched the team is.
Questions that we would like you to address: • What are the most important Attributes for a recruiter in a hyper growth environment? What are best practices on coaching and developing recruiters to these? • How do you manage req load and overall load balancing to optimize productivity across the team? • Describe what the profile of a high potential, high performing tech recruiter looks like to you (can be more than one level – junior, intermediate, senior) • What are ways to introduce career development to recruiters in our intense, hyper growth environment?
Some Decent Functional Questions
Business Operations Leader (COO/GM/P&L Owner)
Development & Drive Forward
What are/were the critical components in developing and driving your business forward?
P&L and Driving the Budget
What is the largest product revenue you've driven? What was the growth (or turnaround)? Looking for % or market increase, etc.
Matrixed influence - Internal to business, Sales, Marketing, Field, Support, Services, etc.
Ambiguity and matrixed organizations... Tell me about the most complex organization with which you've had to navigate/influenced? → What you're looking for: are they successful only when everything is under them?
Leadership (CXO, VPs, Sr Directors)
Provides Dynamic Leadership to People
Tell me about your most effective (& ineffective) performance strategies. Another way to look at this... Rewards, what has worked, what hasn't and why? What would you do differently today?
Attain/Retain diverse key talent
What is your current action around this? Look for how they motivate, coach, select key talent, etc.
Resource Allocation - Makes wise leadership investments, determines proper resource allocation to ensure business needs are met.
How did you align your groups/organization and allocate resources according to strategic priorities. Have them give specific examples.
Team building across functions
How do you ensure your product managers are leveraging &/or are in sync with their development partners?
Communication - consistent, all levels, ensuring everyone is in sync with deliverables, goals and overall vision
How did you translate broad strategies into clear objectives and practical action plans? Get specifics.
Think about; How good do we think this person is at judging people. Do they know which buttons to push to get the most out of people and create a productive work environment for them? Do they know which people they should keep and which they shouldn't? How do they manage change? Do they know which to hire?
Industry Influence - analysts, press, standards committees, Government (i.e. legislature), etc.
What is your current participation? Why? → What you're looking for; participation & to what level (i.e. is it education or are they really making changes or giving appropriate visibility in the domain industry)
Technical Vision & Strategy
How are you currently identifying critical goals & success factors throughout different business situations?
How are your strategies different than others, what sets them apart? à You're basically looking for evidence that they can develop distinctive strategies to achieve and sustain competitive advantage during any climate (economy changes, etc.)
How did you anticipate risks? Did they devise contingency plans to manage them?
Proven record on focusing the organization on efforts that add significant value
Successfully shipped commercial product
Managed full cycle of product
Describe the last product you shipped? Clarify; was it beginning to end, cross functions? How did you keep everyone on target to meet ship dates? What was successful? What did not go well and how would you change (if you owned it again today). Can they turn troubled situations around?
Managed multiple functions include dev
Have them describe the functional team (dev, test, etc.) - how they managed, etc.
Ideally - have directly been involved with architectural decisions
Scenario... Tell me about a time when you were in a room of distinguished engineers and architects. They are mapping out a new vision for your product line. How did you... Influence them in a different direction if needed (because it's important to company, customer, bottom line cost, architecturally doable, timing/ship schedule, etc.)
What you're looking for 1) Can she/he get dirt under their fingernails... can they really roll up their sleeves and get very, very close to a problem to get the right solution 2) What is their blend of technical excellence
Product Marketing / Management
Before diving into the questions below – first understand key areas of the role
strategy verse tactical
partners/relationship building & owning
influencing technology acquisition
pricing/licensing; features; promotion- launch shipped.
Vision & strategy for Product in market
Tell me a little bit about the market (domain or product), when you joined "company x," what was your share? What changes did you make? How did you influence (drive, direct, own, etc.)? Where is it today?
Customer Satisfaction - How did you stay in touch, influence, be assured they're satisfied with what we have to offer?
Key components (& why) necessary for a strong/successful strategy?
Define value propositions -ask for a specific example
Acquisition (technology or company)
What was the end result? Revenue Increase? ($$, %, etc.)
Can they connect dots/pattern match between industry trends (partner and competitor), customer needs, and Company investments/capabilities on which dimensions (technology and/or business)?
Connected Market (for candidates with experience at larger companies)
How did they make sure subs & main entities of a company are leveraging/influencing each other?
How did they tie their marketing plans across businesses? How did they tie them all together?
Global understanding of the competitive landscape
Who are our competitors in this space? Why are they more successful/less successful than we are. What will you do coming into this role to evaluate our strategy? How will you stay abreast with what is happening in Europe/Asia etc. in terms of software or technology innovation?
What company (outside the tech industry) does product management really well? Why? (this is to gather insight as to the breadth of their experience or their knowledge)
Depending on the scope of the position, you may ask questions about marketing to different cultures and different countries
Global understanding of competitor strategies, successes, and failures
Can you discuss a particular strategy that you have been following? What type of strategy - product strategy, customer strategy etc.? What has worked, what has not, why not? How do you see this market developing in the next x years?
Get them to talk more about their successful and not so successful strategies at other companies
Ability to collaborate on complementary product marketing strategies with other divisions of Company as demonstrated by previous experience
How was product marketing/management structured at your current company, previous companies? Who did you have to collaborate with/how?
How have you avoided disparate marketing strategies in the past? What are pros and cons of running disparate strategies? When would you, when wouldn't you?