Episode 4 - Mastering The Art of Coaching Up | Situational Product Management Series

Plus Top 10 tips for Coaching Up and Manager's Corner

Welcome to Episode 4 of our newsletter – "Mastering the Art of Coaching Up" in our Situational Product Management Series.

As a product manager, 'owning your product' isn't just a part of the job—it's the job.

What does 'owning your product' truly mean?

It means being so intimately familiar with every aspect of your product that you can anticipate questions, prepare for changes, and have a plan for the next 6-9 months. It's about understanding the detailed mechanics—knowing the signals, levers, and triggers, and being able to articulate every part of the product process with confidence.

It's perfectly acceptable to have a strong grasp of the short term roadmap — being able to confidently forecast within 90% accuracy what will launch next month, 80% for the next six weeks, and anything beyond that is 50/50.

The key is to understand your path to these milestones, the associated risks, the macro environments impacting your product, and to ensure leadership is informed not just when there's bad news, but as part of a continuous dialogue. Show them how you prioritize your roadmap, get their input, and keep teaching them what you’ve learn along the way.

As product managers, we often find ourselves as the conduits between the ground-level details of our products and the high-level strategic vision of our leadership. Coaching up is an essential skill, enabling us to guide and influence the understanding and decisions of our managers and executive teams about our products.

No matter which organization I’ve worked for, every roadmap has ultimately been a dynamic one. This is one of the promises of being more agile and following an MVP approach, is that we can launch pilots, get the signals for whether it was helpful for the consumer or business, and either continue to put effort towards the initiative or pivot based on learnings.


With this ability to have a dynamic roadmap with pivots as needed, leadership at some organizations take this as an opportunity to inject net new ideas into the mix for product managers to take action on. When leadership injects new ideas, it's our cue to question, provide informed feedback, and manage up effectively.

Here are detailed tips for coaching up when you're tasked with incorporating unforeseen work into your roadmap:

Top 10 tips for Coaching Up

  1. Take a Stance with Diligence: "I'll champion this new idea, but let's ensure our due diligence doesn't fall by the wayside. For example, when we integrated chat functionality, we vetted several API providers to ensure scalability. Let's apply the same rigor here."

  2. Transparent ROI Forecasting: ""Integrating this feature could increase our quarterly revenue by 2%, based on current rates and past performance, adjusted for trends. However, it will require reallocating development resources, impacting other key initiatives. Let's consider the trade-offs."

  3. Clear Success Signals: "We'll consider this new search feature a success if we see at least a 10% increase in user engagement on our metrics dashboard. This aligns with our historical data, where enhanced features typically yield this uptick."

  4. Communicate New Assumptions: "While we pivot to include this feature, we're assuming a 15% increase in development resource allocation. This is based on our past three sprints where similar features were rolled out."

  5. Managing MVP Scope: "The MVP will focus on core functionalities to meet our timeline without compromising other critical roadmap items. This approach helped us successfully launch our mobile app's beta version on schedule."

  6. Impact Storytelling: "When we introduced one-click ordering, our narrative was about speed. With this feature, let's weave a story of discovery and personalization. It's about balancing speed with a rich, tailored experience."

  7. Data-Driven Decision Making: "The data from our A/B tests on the checkout process redesign clearly showed a 20% decrease in cart abandonment. We'll use a similar approach to validate the effectiveness of this feature."

  8. Educational Approach: "By sharing our analytical models with you, I hope to provide you with additional lenses to assess product initiatives. It's like giving you a Swiss Army knife for your strategy discussions."

  9. Strategic Compromise and Influence: "I understand the importance of this feature to our leadership. Let's align its development with our core KPIs to maintain product integrity and deliver on our promise of quality."

  10. If this then that: “I can see the through line to delivering this product with the scope we’ve discussed and the quality in which we deliver all of our products, since we only get 2 of the 3 (scope, quality, time); may I suggest that we work this new feature in parallel with our other features so we can progress across multiple feature development vs. stopping our progress on all items except this. I get it may take longer to deliver, but remember what our other investment ROI models predicted and how they relate to our goals of our website for the end of year. If that is not an option, please do know that we will need to adjust the goals of the team based on this new feature set. If we want to both hit the timeline discussed and continue progress on other items - we need to start hiring additional individuals to increase capacity by quarter end.”

Let’s jump into a case study

Recommendations in Onsite Search

Context: You are a product manager at an apparel company focused on optimizing the website to sell your core product (jeans) while also working to introduce customers to all the other clothing items you sell.

Key Metrics you’ve been asked to drive are Conversion, Average Order Value, and Taps per Task (how many taps or clicks it takes to go from initial visit to checkout complete)

Imagine your VP requests a prototype for adding personalized jean recommendations in the search bar, hoping to capitalize on the high engagement with the search function.

As a product manager, you need to quickly convene UX and Dev to flesh out a feasible prototype, ensuring it's a true representation of what can be delivered. You spend days refining the design, conscious of the trade-offs.

The Feature: You build a capability that as the consumer types “mens jeans” in the onsite search bar, recommendations show up directly in the search box before you submit your search query. See an example below of what this could look like (for example purposes)

When the VP expresses satisfaction with the prototype, you recommend a scoped MVP that allows for technical agility, thus maintaining momentum on other roadmap items. You are able to reduce scope in order to maintain quality and a timely schedule.

After launching, it's time to analyze the data. You find some interesting facts.

Similar to why a grocery store puts the milk in the back corner, ensuring customers walk the aisle and hopefully find additional items that they didn’t intend on purchasing (or didn’t know you sold!), this feature removes that type of experience from the customer. For this eCommerce site, after the customer lands on the search page - they are not only introduced to the products that relate to search, but it is also a way of introducing the customer to all the other clothing items that are sold (“Customers also shopped for”; “Customers also searched for”; etc)

You saw the numbers: out of every 100 searches, 20 were concluding at the recommendation and adding the item to cart—forgoing the journey through the rest of the website. This shift had a ripple effect. Typically, a stroll through the search results yielded 1.3 add-to-cart actions, with each cart addition averaging $45. But now, with 20 fewer shoppers per 100 making that journey, we were missing out on those extra 0.3 add-to-cart moments.

The story unfolds—a story of trade-offs. It's the classic tale of the balance between convenience and exploration, between the immediate satisfaction of finding 'jeans' verse the discovery of the perfect 't-shirt' or 'hat' that complements it.

It's about understanding that our customers value discovery, and our search results page is more than just a list—it's a narrative of choices and opportunities.

So as Product Protégé Guide taught you, you wait 2 weeks post launch to ensure you have statistically significant data before scheduling time with the VP to review your findings.

So, you brought this story to your VP, not just with data points and graphs, but with the human elements of our customer journey. Our MVP is a testament to our agility and innovation, but it's also a new chapter in our ongoing story of customer experience. We've observed, we've learned, and now it's time to decide on next steps—bringing back the richness of discovery while also maintaining the goal of increasing add to cart rate for the site.

The compromise?

You decide with the VP aligned that while the feature was effective if it were a silo experience, it did impact the AOV and add to cart rate of the site. While it is decided not to move forward, you recommend how search term based recommendations could work really well on the home page and product detail pages - using this type of approach in other areas of the site that will further reinforce the strategies to drive add to cart rate and conversion on the website.

Example on a Product Detail Page - “Customers who search “mens jeans” ultimately purchase <product recommendation 1> ; <product recommendation 2>; product recommendation 3> etc.
You are able to reuse the development approach and most of the designs the UX team put together.

Coaching up requires a blend of data-driven storytelling, a deep understanding of your product, and the finesse to navigate the delicate dynamics of leadership and innovation.

It's about painting a picture that's compelling not just in its aesthetics but in its ability to capture the true essence of customer behavior and business impact. By doing so, we empower our leaders with the insights and foresight to make decisions that resonate not just on the balance sheets but on the user’s screens as well.

Manager’s Corner:

I've been on the other side of these conversations, where I'm the one requesting changes and meeting with the product management team that reports to me.

The last thing I want is for them to simply say, "Sure thing, we're on it." Instead, I'd prefer them to push back, to help refine the idea, to educate me on why it may or may not be a good idea, and to coach me on the signals they're monitoring and how this change could affect those.

As a manager, you might wonder, "Shouldn't you already know all this?" However, I recommend discussing with your manager what their typical day entails. A manager's daily responsibilities cover a wide range—spanning product details, team dynamics, politics, strategy and vision, and even sourcing funding for the team. Given that product features and sets can change dynamically, it's crucial to recognize that your manager may need some coaching to ensure they're aligned with your thinking.

Until next week, keep nurturing your product management skills, and may your efforts lead to impactful and empathetic product development.

P.S. If you found this newsletter insightful, consider sharing it with your team. Let's grow together in our product management journey!

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Episode 5: Leveling Up from Associate Product Manager to Product Manager

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Situational Product Management Episode 3: Mastering the Human Dynamics of Product Management