Strategic Execution, Negotiation & Full Mock Problems
Full Mock EM Interview Scenarios
Real EM interviews do not test one skill at a time. They give you a messy, multi-dimensional problem and watch how you break it down. The three scenarios below combine people management, delivery, org design, behavioral, negotiation, and strategic skills into realistic problems. For each one, study the prompt, understand what is being tested, follow the structured approach, and learn the common mistakes that sink candidates.
Scenario 1: The Team That Keeps Missing Goals
The Prompt
"You are hired as an Engineering Manager to lead a team of 8 engineers. The team has missed their last 3 quarterly goals. Morale is low, the VP is frustrated, and the previous EM left 2 months ago. Walk me through your first 90 days."
What Is Being Tested
| Skill Area | What the Panel Evaluates |
|---|---|
| People Management | How you diagnose people issues versus process issues, your 1:1 approach, how you rebuild trust |
| Delivery | How you stabilize execution before trying to improve it, your approach to realistic goal-setting |
| Managing Up | How you set expectations with the frustrated VP while buying time for a real diagnosis |
| Self-Awareness | Whether you resist the urge to make sweeping changes in week one |
Structured Approach
Days 1-14: Listen and Diagnose
- Conduct 1:1s with every engineer. Ask: "What do you think is the biggest reason the team has been missing goals?" and "What would you change if you could change one thing?"
- Review the last 3 quarters of planning documents, sprint retrospectives, and goal definitions. Were the goals realistic? Were they clearly defined? Did scope change mid-quarter?
- Meet with the VP. Do not promise a turnaround. Say: "I need 2-3 weeks to understand the root causes before I commit to a plan. I will share my findings and a proposal by Day 21."
Days 15-30: Identify Root Causes and Quick Wins
- Categorize issues into: people problems (skill gaps, low performers, unclear roles), process problems (poor estimation, no sprint discipline, excessive context switching), and external problems (unrealistic goals set by leadership, constant reprioritization, unclear product direction).
- Implement one quick win to build credibility. This might be canceling a recurring meeting that everyone hates, fixing a flaky CI pipeline, or clarifying on-call rotations.
- Present findings to the VP with data: "We missed Q3 because 40% of the committed scope was added mid-quarter. We missed Q4 because two engineers were pulled to incident response for 3 weeks."
Days 31-60: Restructure and Reset
- Set a realistic Q1 goal with 30% less scope than the previous quarter. Underpromise and overdeliver.
- Introduce lightweight estimation practices if they do not exist (story points or t-shirt sizing, not a heavy process).
- If there are underperformers, begin feedback conversations and document expectations. Do not delay this.
- Create a team working agreement: how you handle scope changes, how you protect focus time, how you escalate blockers.
Days 61-90: Deliver a Win and Build Forward
- Ship the reduced-scope goal on time. This single win resets the narrative with leadership.
- Begin planning Q2 with the team, using data from Q1 to calibrate capacity.
- Share a 90-day retrospective with the VP showing what changed, what improved, and what still needs work.
Common Mistakes
- Trying to fix everything at once. Panels want to see prioritization. You cannot fix morale, process, and hiring in the first month.
- Blaming the previous EM. It signals you look backward instead of forward.
- Promising the VP a turnaround in 30 days. Experienced interviewers know this takes a full quarter. Overpromising shows poor judgment.
- Skipping the listening phase. Jumping to solutions without diagnosis is the most common failure mode.
Scenario 2: Build an Engineering Org from Scratch
The Prompt
"The company is launching a new product area -- a developer platform. You are the first engineering hire. You need to design the engineering org, establish processes, and ship an MVP in 6 months. You will grow from 0 to 15 engineers. Walk me through your plan."
What Is Being Tested
| Skill Area | What the Panel Evaluates |
|---|---|
| Org Design | How you structure teams, define roles, and plan for growth beyond the initial headcount |
| Process | How you establish lightweight engineering practices that scale without over-engineering |
| Hiring | Your hiring strategy, timeline, and how you balance speed with quality |
| Technical Strategy | How you make build-vs-buy decisions and define architecture for an MVP |
Structured Approach
Month 1: Foundation (You + 2-3 Engineers)
- Hire 2-3 senior engineers first. They will help define the architecture and culture. Prioritize people who have built 0-to-1 products before.
- Define the MVP scope with Product. Use RICE scoring to cut features ruthlessly. A 6-month deadline with a growing team means you must ship with a small team and scale after.
- Establish minimal process: daily standups (15 minutes), weekly planning, bi-weekly retros. No heavy tooling yet.
- Make key architecture decisions early: monolith vs. microservices (lean toward monolith for MVP speed), language/framework choice, infrastructure (use managed services to reduce ops burden).
Months 2-3: Grow to 6-8 Engineers, 1 Team
- Hire aggressively but maintain a bar. Define a hiring rubric before the first interview. Every candidate meets at least 3 existing team members.
- Operate as a single team with one backlog. Do not split into squads yet -- you do not have enough people or enough product clarity to define ownership boundaries.
- Ship a working internal prototype by end of Month 3. Even if it is rough, it validates the architecture and gives Product something to test.
Months 4-5: Split into 2 Squads, Scale to 12-15 Engineers
- Split the team based on product domain boundaries, not technical layers. For example: "Ingestion & API" squad and "Developer Console" squad, not "Backend" and "Frontend."
- Promote one senior engineer to Tech Lead per squad. Consider whether you need a second EM or whether you can manage 12-15 direct reports through the TLs temporarily.
- Establish cross-squad coordination: a weekly sync between TLs, shared on-call, and a single deployment pipeline.
- Begin hardening the system: add monitoring, alerting, and incident response procedures.
Month 6: Ship MVP
- Feature freeze at Month 5.5. Use the final 2 weeks for testing, bug fixes, and documentation.
- Plan the launch with Product and Marketing. Engineering's role: deploy, monitor, be on-call.
- Write a post-launch plan: what is the roadmap for Months 7-12? What did you learn? Where do you need to invest in platform stability?
Common Mistakes
- Hiring too junior too early. The first 3-5 hires must be senior. Junior engineers need mentorship infrastructure that does not exist yet.
- Over-engineering process. Agile ceremonies, OKRs, and design documents are important -- but at 3 engineers, a whiteboard and a shared doc are enough.
- Splitting into teams too early. Teams of 2-3 create coordination overhead without enough throughput. Wait until you have 6-8.
- Ignoring the hiring timeline. Hiring takes 6-8 weeks per engineer (sourcing, screening, onsite, offer, notice period). You must start hiring in Month 1 for engineers to arrive by Month 3.
Scenario 3: Retention Crisis Meets Scope Cut
The Prompt
"Your best engineer just told you she is considering leaving for a startup that offered her a CTO role. The same week, your VP informs you that due to budget constraints, your team's scope is being reduced by 40% and two headcount will be moved to another team. How do you handle both situations?"
What Is Being Tested
| Skill Area | What the Panel Evaluates |
|---|---|
| Behavioral | How you handle simultaneous crises with composure and prioritization |
| Negotiation | How you negotiate to retain the engineer and how you negotiate the scope cut with your VP |
| Strategy | How you replan your roadmap with fewer people and less scope |
| People Management | How you protect team morale when delivering bad news |
Structured Approach
Handle the Retention Risk First (Same Day)
This is more time-sensitive. Once she accepts the startup offer, she is gone.
- Have a private 1:1 immediately. Listen first. Ask: "What is drawing you to this opportunity?" Understand her motivations. Is it the title? Equity? Impact? Autonomy? Boredom?
- Do not counter with money immediately. Match the underlying need. If she wants more ownership, propose: "What if you led our new platform initiative as the technical founder internally? You would own architecture, hiring for your sub-team, and present directly to the VP."
- If compensation is a factor, work with your VP and HR to explore a retention package: equity refresh, promotion timeline acceleration, or a spot bonus. Be honest about what you can and cannot offer.
- Acknowledge the opportunity: "A CTO role at a startup is a legitimate career move. I will not try to guilt you into staying. I want to see if we can create something equally compelling here."
Handle the Scope Cut (Within the Week)
- Meet with the VP. Use the Pyramid Principle: "I understand the budget constraint. Before we finalize the plan, I want to propose which 40% we cut and which 60% we protect, to minimize business impact."
- Score your current projects with RICE. Present the bottom 40% with rationale for why those are the right projects to defer. Protect the highest-impact work.
- Negotiate the headcount transfer: "I understand we are losing two people. Can I have input on who transfers? I would like to keep my senior engineers and offer two mid-level engineers who will benefit from growth opportunities on the other team." Frame it as a win for the receiving team.
- If the scope cut affects the retention conversation (less interesting work), address this head-on: "I want to be transparent -- our scope is being reduced. Here is how the remaining work actually increases your impact: you will own a larger percentage of a more focused mission."
Communicate to the Team (Within 2 Weeks)
- Do not hide the scope cut. Address it directly in a team meeting: "Our scope is changing. Here is why, here is what we are keeping, and here is why the remaining work matters."
- Replan the roadmap publicly. Let the team see how RICE scores determined what stays and what goes.
- Protect morale by being honest: "This is not a reflection of our team's performance. The company is reallocating resources. Our job is to deliver maximum impact with our new scope."
- Watch for follow-on attrition. When one person considers leaving and scope shrinks, others get nervous. Increase 1:1 frequency for the next month.
Common Mistakes
- Treating the two crises as separate. They are connected. The scope cut affects the retention pitch. The retention risk affects how you negotiate the headcount transfer.
- Counter-offering with money only. At the EM level, the best engineers are motivated by impact, autonomy, and growth -- not just compensation.
- Accepting the scope cut without negotiation. The VP expects you to push back with data, not accept silently.
- Hiding the scope cut from the team. They will find out. If you hid it, you lose trust permanently.
- Panicking visibly. The panel watches your composure under compound pressure. Take a breath, structure your response, and prioritize.
How to Practice These Scenarios
- Time yourself. In a real interview, you have 35-45 minutes per scenario. Practice answering each one in 10-15 minutes of structured monologue, leaving time for follow-up questions.
- Use a framework, then get specific. Start with the structure (first 30 days, then 60, then 90) and fill in concrete actions. Vague frameworks without specific actions score poorly.
- Practice with a partner. Have someone ask follow-up questions: "What if the VP says no?" "What if two more engineers want to leave?" These curveballs are where top candidates separate themselves.
- Record yourself. Listen for filler words, long pauses, and circular reasoning. The best answers are linear and build on each point.
Congratulations on completing this module. You now have the strategic, communication, negotiation, and integration skills needed for EM interviews. Complete the module quiz to test your understanding. :::