Your largest customer is loudly advocating for a new feature which is not in your prioritized roadmap. Sales, eager to please, have gone straight to Engineering to see if they can drop everything and get this done. What do you do?

This question aims to assess your leadership, decision-making abilities, and prioritization skills in a high-pressure situation where developers, salespeople, and customers are involved. The interviewers want to understand your approach in managing conflicting demands among stakeholders and sticking to a predefined roadmap.

Key points to address when answering this question:

1. Understanding the earnestness and the potential positive impact of the proposed feature.
2. Raising and discussing the issue with all the relevant stakeholders.
3. Making the final decision based on a detailed analysis of development resources, the product roadmap, and customer expectation.

In this situation, my initial approach would include understanding the urgency and benefits of this feature that the sales team and customer are advocating for. Given that the largest customer is pushing for this, it has to have substantial weightage. However, a hasty decision can be detrimental for the entire project.

Next, I would arrange a meeting with stakeholders from engineering, sales, and product management to understand the development feasibility, potential impact on sales, and compatibility with our long-term product roadmap. If the feature complements our product vision and adds significant value to our user base without causing disruptions in the roadmap, I would consider reprioritizing our roadmap.

However, if it compromises our existing roadmap and resources, I would stick by our current plan, and communicate the reasons for our decision to the customer, along with some alternative solutions, if possible. This ensures we maintain great customer relations and are transparent with them.

If I were faced with this situation, my first step would be to understand in detail from the sales team about why the customer insists on this feature and how it's perceived to bring value. It's critical to quantify the benefit - is it something that just satisfies the largest customer or could be beneficial for the wider customer base as well?

Subsequently, I would involve key leadership stakeholders - including product, sales, and engineering heads - for a discussion and present a balanced view of the situation. This would help us analyze and brainstorm the pros and cons of incorporating this feature as opposed to sticking to the existing roadmap.

If we all decide it's worthwhile despite the disruption, I would then work closely with the product and engineering teams to redraw our roadmap, ensuring that important feature developments are not overly compromised.

But if we conclude it would cause more harm than good based on our analysis of cost, time, manpower, and other projects on the pipeline, I would let sales communicate this professionally to the customer. It's key we emphasize our commitment to satisfying the customer needs but not at the expense of disrupting our overall product development strategy.