Can you describe how the product management team participates in sales enablement?
An experienced product manager will embrace the responsibility for the success of the product or service. They will understand the needs of the marketing and sales departments and invest time to educate sales, systems engineering and marketing resources. A successful product manager should be able to discuss their role in supporting sales enablement. Listen for the key activities that support or drive the following activities:
- Sales onboarding: Tools, processes, contacts, references, online resources—the materials that will get a new sales team up to speed with your new product or service
- Sales training and workshops: Professional sales training for inside and outside sales; training incentives, certifications, customer communications training (customer success); center of excellence training
- Training library: Online quick video training (internal and external sourced)
- Coaching and recognition: “Buddy” programs for new sales professionals; inside campaigns (posters, contests, quarterly reviews, sales meetings)
- Spiffs and contests: Programs to incentivize deal acceleration
- Sales journey roadmap: Engagement plan and account plan support
- Process streamlining: Eliminate “order closure” roadblocks; simplify onboarding
- Order finalization: RFP/RFI response boilerplates, proposal templates, FAQs, exception management
- Sales repeatability: “Look alike” customer case studies
- Demo systems and executive briefing center (EBC) management: Logistics and customer experience; visual representation (videos, posters, catering, décor, etc.)
- Major account support (MVPs and VIPs): Processes and direct account support for major accounts
- Segments and vertical markets specialization: Content (messaging) and product adjustments for specific verticals (e.g., healthcare, finance, public sector)
- Online buying experience and online customer management: Blogs, social, chat, online support, etc.
- Customer interactions: Release description documents (RDDs), bulletins, notices, support, white papers, technical white papers, speaking engagements, events and tradeshows, thought leadership programs
- Channel programs: Supporting htird-party channel organizations (sell thru, sell with, embed relationships)
- Resource management: Documentation, people, demos, EBCs, executive engagements
- Deal desk support: Supporting the exceptions and negotiations for customer deals
- Sales scripts and vertical playbooks: Ensuring the messaging is factual and represents the product and/or company direction
- Prospect qualification identification: Support in identifying high-value prospects
If your candidate is able to describe at least three of these key areas, then they have demonstrated the real-life experience of working in a functional product management role. Strong candidates will focus their responses on the sales support, requirements, and feedback gathering in partnership with the sales and marketing teams. They will speak of their experience in terms of the KPIs including revenues, clients, customer lifetime value, time to revenue, conversion (prospect to customer) rates, and other business measurements.
Have you ever been in a situation where your team has let you down and you’ve had to take the blame?
A professional product manager will always manage the communications around “fault.” For a team effort, they would ultimately own the responsibility for the delay, taking the blame and need to learn from that experience to correct estimates and commitments for the future. If the delay was caused by malfeasance or lack of skills, then corrective action should be initiated by the product manager. Performing a root cause analysis for the delay is important and should be part of every continuous improvement initiative. In discussing this with your candidate, listen for the business approach to addressing slippages.
What are the identifiable differences between a project manager and a product manager?
A project manager will drive the day to day activities for every meeting, will be very detailed about who’s doing what, and will be responsible for the on-budget and on-time delivery of commitments. A product manager is also responsible for the delivery but they will act more as a business owner, responsible for the success or failure of the product or service in the market.
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Product managers will often have to manage personnel issues or conflicts. Can you describe a time where you had to deal with a personnel issue?
Listen for empathy and a willingness to listen. In some cases, an individual just might not be a fit, and that person—while they have great talents in certain areas—might need to rethink their professional goals. If it’s not a direct report, they may have coordinated with the direct manager. The product manager needs to manage the situation and make the changes that will get the team back on track.
An experienced product manager may have developed a performance improvement plan, or PIP, which they monitored and reviewed with the employee on a weekly or monthly basis. In larger enterprises, this might have included human resources. Termination or reassignment may have been required. Explore how they were able to deal with this type of situation and the result. Listen for concrete steps to get the team back on track.
What was your most successful product as product manager?
You’re looking for the qualitative and quantitative measures that can identify a strong product manager. What were the revenues or user count? Over what period? What was the value that they achieved? A professional product manager will be able to point to simplify their achievements in terms that relate to business results.
For example, even for highly complex technological innovations, they should be able to convert it into business values. “Our team created and patented complex machine learning algorithm to predict traffic volumes” is a reasonable response. But this has not provided the “So what?” answer. “Our team created and patented complex machine learning algorithm to predict traffic volumes, reducing congestion by 30% and traffic accidents by 15%.” Drill down into the details of the project to confirm that they were actually driving the effort, not just part of the team.
How do you define market opportunity in a business plan?
An experienced product manager will be able to describe market opportunity in various ways, including the total dollar value available in the market. Often referred to as total addressable market (TAM), it represents the current and growing (future) total value of what everyone will spend on solutions of the same type.
The compound annual growth rate (CAGR) represents the speed at which the market is growing, and would often also be referenced when talking about a market size. A product manager should also be able to describe the portion of that whole value that would be available to them, which represents their potential market share (or
What are signs that it’s time to cut corners to get the product launched, and what would you cut?
An experienced product manager will recognize early that the are not going to meet their deadlines. It might be apparent when testing is failing, when sprints are not completing on time, or when UX design is falling behind.
An experienced product manager will be exploring different opportunities to meet their deadline. Explore some of the potential actions they took:
- Did they reduce functionality to a minimum for the first release?
- Did they re-prioritize their roadmap?
- Did they move ahead without an MVP?
- Did they soft-launch with selected customers and announce full commercial launch for a later date?
They should be able to explain how they determined that there was a problem and what actions they took to resolve the gap. Listen for the impact on sales, marketing, and support. How did they communicate the changes to manage the impact? Validate that the decisions were typically ancillary changes, not impacting the core of the product.
In the context of product management, how would you describe “low-hanging fruit”?
In the context of product management, low-hanging fruit often refers to a quick win. This might refer to a target market that is in dire need of a solution, or may be a feature/functionality add on that will drive exponential revenues. Explore how a product management candidate might be attuned to market changes that would suddenly create an opportunity for dramatic changes in results.
The 80/20 rule applies here—gaining 80% of the value with 20% of the effort. Or, from another perspective, addressing 80% of the market and treating outliers as exceptions.
What are the most exciting technology trends and why are they important?
A professional product manager will be on top of the latest trends in the industry. Listen for augmented reality, the growth of audio interactions in all systems, virtual reality, analytics, artificial intelligence, or blockchain. Ask how they might affect individuals as they become more prevalent and listen for automation, predictive analytics, and process automation. Explore their methods for staying on top of trends and how they may incorporate advances into the solutions they are bringing to market.
What are the important elements of a competitive analysis?
An experienced product manager should break a competitive analysis question into two parts—the first is the strength, weakness, opportunity and threat (SWOT) analysis that will be used internally by the company to develop strong positioning statements for the sales and systems engineering teams. It should cover both the technical and business aspects of the competitor. For example, if the company is financially unstable, this can be used in a “maturity and risk” discussion with a potential customer.
A second, more detailed technical analysis would do a feature-by-feature comparison, highlighting the gaps that the competitor has. It should be factual and presented in a professional, non-slanderous format. This may include actually downloading the competitive application and using it or calling their support lines to explore how they perform. Often, companies will have these comparisons completed by a third party to represent an independent assessment.
Listen for your product management candidate to have an understanding of both the business and technical aspects of a competitive analysis.
Can you explain the impact of GDPR on today’s products and services?
One of the most stringent regulations (in line with the complexity of HIPAA), the General Data Protection Regulation (GDPR) provides very stringent rules for how data related to personally identifiable information (PII) must be handled for any client in the European Union. Fines for non-conformance are potentially in the tens of millions of dollars.
A professional product manager will have a concrete understanding of what comprises PII data, along with the key concerns for management of the data. Of key importance is to listen for the collection process for data, what comprises PII data (anything that can be tied to a person) and the right to be forgotten. This last element implies that all records must be purged from any active or inactive archive and can have complex implications on historical analytics and machine learning solutions.
Furthermore, the product manager should be aware that if they are not compliant, they cannot operate, market, or advertise in the EU without potentially being in violation of the GDPR. In an internet commerce where apps can be downloaded from anywhere, explore their understanding of the risks.
What is your experience with shutting down a product or service? What are the key challenges in an end-of-life (EOL) process?
The EOL process can be complicated, and a professional product manager should be able to describe the key elements, including:
- EOL decision-making: What drives the decision to EOL?
- Sales notifications: How to prepare Sales for an EOL situation with their customers
- Customer migration plans: What alternatives are possible, how can they migrate?
- Returns, rebates, upsell policies: Are there alternatives? What would the financials look like?
- End of life, end of support, end of availability: The timing of stopping selling, stopping availability, and stopping support
- Contracting: For large customer and/or channel notifications and meeting any contractual obligations as it may relate to notification periods, service-level agreements (SLAs), and penalties
Explore whether they have had the experience to make the decision and manage the complexity without damaging the company brand or losing large customers.
They should be concerned how the EOL might affect future sales or create litigation and need to have a good handle on the risk/reward analysis.
What was the hardest decision you had to make as a product manager? How did you handle it?
Product managers must make strong complex decisions. You’re looking for the analysis that went into the decision, the research that was done, and the result or impact that happened as a result of the decision. A hard decision is driven by recognizing that a recommendation is going to impact a lot of people, and the business overall. It might be a personnel decision or perhaps a dramatic change in product direction.
Hard decisions imply having to convince a lot of people of a point of view. Listen for the process that was employed to get agreement from the company to proceed with the decision.
Can you describe a scenario as a product manager where you failed? And what did you learn from it?
You’re looking for someone with experience. Challenge any product manager who could not find fault with a decision or outcome within their realm of responsibility. The learnings are key, as they will identify an individual who has taken the experience to heart and improved.
The type of failure they encountered should be material to the results of the product or service that they were working on. Listen for an admission of failure to identify the customer properly, or perhaps the product or service was too early for the market.
Perhaps they were trying to compete in a saturated market where differentiation was hard to identify or did not have enough value. Other challenges might be internal to the company operations.
Perhaps they did not price it effectively, or the pricing model was too complex. If the solution was too complex for onboarding, then perhaps the churn rates were too high. If there was not marketing and sales team to get the word out, then perhaps they were unable to make the case for a strong business plan.
How do you monitor performance and success?
A professional product manager will have a strong set of key performance indicators (KPIs) that they will monitor in order to understand their position, growth, progress and success. There are four key categories to listen for, including business metrics, product usage metrics, product development metrics, and product quality metrics. Listen for a solid selection of the following KPIs:
- Revenues or bookings: Top-line dollars that have committed to in conjunction with the sales team
- Funnel: Sales in process
- Retention, attrition, churn, customer lifetime value: Track the movement or flow of customers
- Customer counts: Current customer base
- Velocity, time to revenue, onboarding times: Looking to accelerate revenue recognition and customer adoption
- Margins, gross margins, costs of goods sold (COGS), and operational costs of goods sold (OCOGS): Understanding the cost basis on which to calculate profitability
- Net promoter score (NPS) or customer satisfaction (CSAT): Subjective analysis of customer feedback
- Number of users per feature or transaction volumes: Can track feature importance for prioritizing sprints, and can highlight value for marketing or competitive positioning
- Time to execute: Records of time that functions take to perform, possibly indicating infrastructure or complex calculations which will result in customer complaints for poor performance
- On-time delivery: Managing the roadmap and creating credibility—the integrity of the team will depend on delivering as expected, on-time
- Team velocity: Monitoring team performance against sprint calculations using story points
- Resource availability: Monitoring critical resource availability and planning appropriately for coverage
- Support tickets and escalations: Monitoring the quality of the released product
- Testing or QA: Monitoring the quality of the code going into test
As a follow up, ask them what they did when they found a KPI that was not moving in the right direction. Listen for an action plan that would include common sense root cause analysis, and some creative thinking to solve for an unexpected KPI.
Product managers should also be using KPIs to plan for growth, perhaps in their NetOps environments or of onboarding resources to meet more demand. Likewise, if the support and maintenance metrics are reducing, look for an adjustment of engineering resources as an appropriate data-driven management decision.
How do you gain credibility from the development/engineering teams as a new product manager?
Product managers should be comfortable with jumping in and providing leadership to a team. Listen for their ability to listen and respect opinions and suggestions of the team. How did they initially engage with the team? Did they engage in a workshop or webinar session with the team to get feedback and new ideas?
They should represent the team with honesty and integrity and set reasonable expectations to the business outside the team (sales, marketing, finance, ops, support).
From a technical perspective, their ability to review proposals and recommendations should reflect their technical knowledge of the environments. Team members will expect the product manager to make timely choices and reflect recommendations, and remain confident in their data-driven decisions.
Listen for explanations that describe their decision-making acumen, their communication skills, and respect for the team. They should represent that credibility means honest, clear communications with results that match the commitments that they set.
Please describe the “…ilities”—the foundational elements that are required for a SaaS-based enterprise offering. For example, scalability would be one.
Primarily in the context of enterprise-grade offerings where a SaaS or cloud infrastructure element exists, listen for functional descriptions of the following:
- Securability: The ability to protect/secure the environment; meet regulatory requirements, preparation for a high-availability (HA) or disaster recovery (DR) situation; and everything in between (authentication, access controls (RBAC, VBAC), data management, encryption, archiving); and compliance reporting—this can be driven from following a 5x9’s consideration (prevalent in the telco world) to meeting regulatory definitions (GDPR may be mentioned).
- Scalability: The ability to manage peak performance and/or growth demands without impacting the production environment; managing any kind of migration, or cloud environment must not impact existing customers. This is a core requirement—especially necessary when dealing with high growth potential. This may also include multi-tenancy.
- Reliability: Critical KPIs for uptime and performance—24/7/365 systems have to be working at peak performance, so peak load conditions must be planned, designed, and tested. Often, having a failover or backup strategy leveraging in-house or external cloud providers can support these situations.
- Manageability: The ability to support customer/user policy controls/access to the systems and the network is critical, so consideration must be taken to simplify provisioning and management of entitlements to shorten the sales cycle and deal with change in the customer organization.
- Billability: The system design must consider the potential for different billing meters—whether it be subscriber-based, usage-based, transaction-based, or via other meters. They must be able to be easily adjusted (from one meter to another) to capture usage counts. Reporting of usage must be simplified and automated for simplified revenue recognition and auditing purposes. Further, when there are layers of responsibility (e.g., vendor selling through channel to enterprise with employees that need access); then the structure of the meters (and security) must allow for distinct reporting and policy controls at each level.
An experienced product manager will have a handle on each of these elements in an enterprise setting.
What is the Gartner Magic Quadrant, and why is it important for many software vendors?
An experienced product manager should be able to explain that Gartner is an analyst firm in the IT sector. Gartner has defined a methodology for identifying leaders, visionaries, niche players, and challengers in an industry. The ability for a company to have their product in a specific quadrant on the Gartner Magic Quadrant can have a dramatic market impact on revenues, and on acquiring investments. Explore whether they have experience in moving the position of a product on the Gartner Magic Quadrant, and if they have, how they accomplished it.
There is more to interviewing than tricky technical questions, so these are intended merely as a guide. Not every “A” candidate worth hiring will be able to answer them all, nor does answering them all guarantee an “A” candidate. At the end of the day, hiring remains an art, a science — and a lot of work.
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Submitted questions and answers are subject to review and editing, and may or may not be selected for posting, at the sole discretion of Toptal, LLC.
Connie Kwan is a storyteller and fractional chief product officer from Silicon Valley who works with B2B SaaS companies. Her 17 years of product leadership experience spans AI, crypto and blockchain, digital health, energy, hard tech, and software (Atlassian, MSFT, CY, SPWR). Connie's held CPO roles in multiple companies and she advises CEOs on becoming product-led. Think of her as your fractional CPO and sounding board for areas of design, marketing, product, and engineering.Show More
Greg is a seasoned product strategy consultant and trainer with nearly 20 years of experience shipping digital enterprise products at IBM, Microsoft, and SAP. He is also a global expert on delivering complex products and solutions at an enterprise scale.Show More
Laurens has six years of product experience, from product sprint workshops (product design, road mapping) to defining product strategy with management teams and feature definition and Agile development with engineering. He primarily works with companies that build complex technical systems, including Waymo and Google. The fields he’s been involved in include self-driving, aerospace, mobility, climate, data science, and eCommerce.Show More
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