An Engineering Manager at Smartsheet plays a pivotal role in driving the development of collaborative work management solutions that empower millions of users globally. In this position, you are not just a technical leader; you are a people-focused strategist responsible for building, mentoring, and scaling high-performing engineering teams. Your work directly impacts the platform's reliability, scalability, and enterprise-grade features, ensuring that organizations can seamlessly manage complex workflows and real-time data analytics.

At Smartsheet, the engineering organization is structured around high collaboration and cross-functional alignment. As an Engineering Manager, you will lead teams focused on critical problem spaces, such as core application features, cloud infrastructure, or advanced analytics platforms. You will collaborate closely with Product Managers, UX Designers, and business stakeholders to translate strategic product visions into robust, maintainable technical architectures.

What makes this role exceptionally compelling is the scale and complexity of the platform. You will guide your team through the challenges of modernizing legacy systems, optimizing high-throughput data pipelines, and maintaining high availability for enterprise clients. Strong leadership in this role requires a balance of technical depth, operational excellence, and an empathetic, people-first management style that aligns with the collaborative culture of Smartsheet.

The questions you will face during the Smartsheet interview process are designed to evaluate your technical leadership, people management philosophy, and execution capabilities. These representative questions, drawn from real candidate experiences, highlight the core patterns you should prepare for.

People Management & Team Leadership

These questions assess your ability to grow engineering talent, resolve interpersonal conflicts, and build cohesive, high-performing teams.

• How do you approach mentoring and growing mid-level engineers into senior roles?
• Describe a time when you had to manage a high-performing engineer who was exhibiting toxic behaviors within the team.

Preparing for an Engineering Manager role at Smartsheet requires a structured approach that balances your technical expertise with your leadership philosophy. You should be ready to demonstrate not just what you have built, but how you led the people who built it.

People Leadership & Calibration – Interviewers will look closely at your ability to recruit, retain, and develop engineering talent. Be prepared to discuss specific frameworks you use for career development, performance calibration, and conflict resolution.

System Architecture & Technical Depth – While you may not write code daily, you must prove you can guide architectural discussions. Focus on demonstrating your understanding of scalability, system boundaries, data modeling, and modern cloud infrastructure.

Operational Rigor – You need to show how you run a disciplined engineering process. Be ready to explain your approach to agile methodologies, sprint metrics, post-mortems, and continuous integration/continuous delivery (CI/CD) pipelines.

Collaboration & Ambiguity Management – Smartsheet values leaders who can navigate cross-functional partnerships smoothly. Show how you align engineering goals with product, sales, and executive stakeholders, especially when requirements are fluid.

The interview process for an Engineering Manager at Smartsheet typically moves quickly, often wrapping up within two to three weeks. It begins with a standard recruiter screen to align on your background, followed by a deeper conversation with the hiring manager. From there, you will move to a comprehensive loop consisting of four to six rounds, which may be spaced out over a few days or conducted in a single virtual onsite block.

While the process is designed to be highly conversational, candidates have noted that the structure can occasionally feel decentralized. You may find yourself speaking with a diverse group of stakeholders, including peer engineering managers, product partners, and direct reports. Because the interviews are highly collaborative, the company places a significant emphasis on personal alignment, team chemistry, and cultural fit.

The visual timeline above outlines the typical progression from your initial contact to the final offer stage. Candidates should use this timeline to pace their preparation, ensuring they focus heavily on behavioral scenarios and system design concepts before reaching the intensive loop phase.

To succeed in the Smartsheet loop, you must understand the specific competencies your interviewers are calibrated to assess.

People & Team Management

This area is the cornerstone of the Engineering Manager role. Interviewers want to see that you are an empathetic, structured leader who can build high-performing, psychologically safe teams.

Be ready to go over:

• Performance Coaching – How you identify high potential and guide career progression.
• Managing Underperformance – Your step-by-step process for executing Performance Improvement Plans (PIPs) with empathy and clarity.
• Team Topology – How you structure your teams to minimize cognitive load and maximize ownership.
• Advanced concepts (less common) – Scaling teams through rapid organizational growth, managing managers (for director-level loops), and handling cross-geography team dynamics.

Example scenarios:

• "Tell me about a time you had to deliver critical feedback to a senior engineer who disagreed with your assessment."
• "How do you handle a situation where two senior team members have a fundamental disagreement over architectural direction?"

System Design & Platform Scale

You must demonstrate the technical credibility required to lead senior engineers and make high-impact technical trade-offs.

Be ready to go over:

• Data Architecture – Designing scalable data warehouses, BI integrations, and analytics pipelines.
• API Design & Integration – Building robust, versioned APIs that support enterprise integrations.
• Resiliency & Recovery – Designing systems for high availability, fault tolerance, and disaster recovery.
• Advanced concepts (less common) – Multi-tenant isolation strategies, real-time stream processing, and cost optimization in cloud environments.

Example scenarios:

• "Design a real-time notification system that can scale to millions of active enterprise users without degrading platform performance."
• "How would you design an ingestion pipeline for a business intelligence platform to handle highly unstructured client data?"

Execution, Delivery & Product Partnership

This competency evaluates how you turn product requirements into working software while managing stakeholders and operational risks.

Be ready to go over:

• Agile Delivery – Your approach to sprint planning, backlog grooming, and removing development blockers.
• Risk Mitigation – How you handle scope creep, resource constraints, and slipping deadlines.
• Product Collaboration – How you partner with product management to define roadmaps and negotiate technical debt.

Example scenarios:

• "Describe a time you had to convince a Product Manager to delay a feature launch in order to address critical technical debt."
• "How do you manage stakeholder expectations when a critical dependency from another team is delayed?"