How to Manage Your Manager (Without Them Realizing It)

Three approaches to align with leadership and produce better products

As product managers, we often find ourselves caught between our vision for the product and the realities of organizational constraints. While it can feel frustrating when leadership doesn't immediately embrace our ideas, there are ways to navigate these dynamics. This week, we're exploring strategies to create alignment and drive change, even in challenging environments.

The concept of "managing up" can be tricky, often seen as political maneuvering. However, in my experience leading product teams at companies like Pearson and SimplePractice, I've found that thoughtful approaches to leadership communication can create better outcomes for product teams. It's not about manipulation, but about finding common ground and shared objectives. The following strategies aim to improve collaboration and your ability to drive better products, while acknowledging the very real challenges product managers face.

The best part? These are skills you can start applying today, no matter your level.

1. Align on Product Direction Through Collaborative Problem-Solving

When faced with seemingly impossible mandates from leadership, it's easy to feel frustrated or powerless. However, by reframing the challenge and bringing a collaborative, data-driven approach, it's possible to find solutions that work for everyone.

At SimplePractice, we faced a classic product challenge. Execs mandated launching a revised billing product with an impossible timeline. Sound familiar?

Instead of simply pushing back or trying to escalate the resource constraints (which rarely produces good results), we tried a more collaborative approach:

• Anticipated leadership questions by spending an hour brainstorming what our C-Suite might ask.

• Collaborated across teams by involving Design, Engineering, and Product leads from other priority projects to identify tradeoffs.

• Backed everything with data by involving Customer Success and Data Science to analyze feedback and trends.

This preparation allowed us to present a strategic alternative that addressed leadership's concerns while proposing a more feasible path forward:

We brought together teams from our top three priorities – Pricing, Insurance, and Billing – to create a unified resource allocation plan. Our data revealed a surprising trend: while desktop was still the top platform, mobile usage for complex tasks like Billing was on the rise. Interestingly, neither Pricing nor Insurance had mobile on their roadmaps, but our Billing customers found both desktop and mobile equally frustrating.

By reallocating mobile resources from TeleHealth and the Customer app to Billing, we could retain the current Billing team (essential to maintain momentum) and accelerate mobile development.

Outcome: We progressed all three priority projects by shifting to a mobile-first strategy for Billing instead of the traditional desktop approach. Leadership felt heard, and we found a path forward that worked for everyone.

The key was not simply accepting constraints or fighting against them, but working collaboratively to find creative solutions that addressed both leadership's goals and on-the-ground realities.

2. Use Thoughtful Questions to Refocus Discussions

When faced with leadership decisions that seem misguided, many individual contributors feel powerless. However, the questions you ask can be a powerful way to steer the conversation and influence outcomes.

At Pearson, I faced an Exec frustrated about a bug in our Live Response platform. They viewed it as an unacceptable mistake and were berating the team who were already working extra hours (which was likely causing the bugs in the first place).

Instead of getting defensive or passively accepting blame (which rarely improves the situation), I tried to reframe the conversation using "what" and "how" questions aimed at problem-solving:

• "What's the biggest risk we face if we continue operating this way?" (This forced leadership to consider the hidden costs of burnout)

• "How do we optimize for success—speed or impact?" (Leaders often default to "both," but the bug showed the reality of prioritizing speed)

• "What's one small change we could experiment with to improve efficiency without slowing us down?" (This opened the door to solutions without assigning blame)

These questions helped shift the focus from blame to problem solving. The SVP, now more open to discussion, asked for recommendations. This gave us an opportunity to propose experiments aimed at improving both efficiency and team morale.

Working with Engineering and Sales counterparts, we identified a time intensive and chaotic process that team members had been putting off addressing. We proposed a lightweight discovery approach to test the new model with select customers. Leadership approved because they saw it as prioritizing "both" speed and impact.

Result: We freed up 20% of the team's bandwidth without reducing output, increased customer satisfaction, and renewed the team's energy to tackle complex integration work.

While this approach doesn't solve every leadership challenge, thoughtful questioning can help reframe discussions in a more productive direction. It's not about manipulation but finding common ground and shared objectives.

3. Navigate Challenging Management Styles

While the previous techniques work well for general leadership scenarios, sometimes you're faced with a specific challenge: the micromanager. This situation requires a tailored approach.

Dealing with a micromanaging boss can be incredibly frustrating and demotivating. While there's no guaranteed fix, I've seen some strategies help coaching clients navigate this challenge more effectively.

One client had a new VP who was well-respected in the company but an absolute micromanager:

• Required exact repetition of their words

• Overcomplicated technical concepts despite lacking technical knowledge

• Went deep into details, forcing my client to spend time "training" them on tactical concepts

• Their SVP had already advised them to "reel in" their critical communication style

My client was ready to change roles, but moving to another group wasn't realistic due to their specialized knowledge.

We developed a two-pronged approach:

Immediate tactical changes:

• Record meetings and use AI for summaries to create alignment

• Create a 6-month roadmap to show proactive thinking before crunch time

• Partner with a new Program Manager to reduce micromanaging

• Connect with peers who worked with this boss before

Strategic approach:

• Put yourself in their shoes: Micromanagers often treat their team like a system they can diagnose and adjust. This approach may have worked for them before.

• Seek to understand their why: Most micromanagers operate from fear, insecurity, or control issues. Instead of getting upset, asking "tell me more" helps identify what's driving their behavior.

• Preempt their concerns: Send updates before they ask. A quick "here's where we are" email reduces the number of tedious "do XYZ" messages.

• Document everything: Using AI to record meetings and send summaries with "Just confirming we agreed to X by Friday" helps keep micromanaging in check.

The key insight? By proactively addressing the manager's underlying concerns and creating more structure around communication, my client was able to reduce some of the micromanaging behavior. The situation wasn't perfect, but it became more manageable, allowing my client to focus more on meaningful work.

Steps Towards Better Collaboration

While organizational challenges can feel overwhelming, small changes in how we approach leadership interactions can lead to better outcomes. You don't have to wait for sweeping organizational changes to start improving your working relationships and product outcomes.

This week, try one of these tactics and see how it shifts the conversation with your manager:

1. Anticipate questions and bring solutions, not just problems

2. Use strategic "what" and "how" questions instead of "why"

3. Lead with curiosity to understand what's driving your manager's behavior

I'd love to hear how it goes! Drop a comment below or reply to this email to share your experience.

What's your biggest challenge with managing up? Let me know, and it might become a future newsletter topic.

Until next time!

P.S. Found this helpful? Share it with a colleague navigating a tricky manager relationship. Sometimes, a fresh perspective is all it takes to transform a challenging work relationship!

If you're looking for more ways to build confidence and move forward in your career, I have some exciting things in motion:

• Connect over LinkedIn with a note: Diana Stepner

• Curious about coaching? Let’s talk.

• Get notified about my Maven course on applying soft skills as a product manager

• Learn more about me on my website or pick up my book.