- Leading by Design
- Posts
- Stop Asking for Permission
Stop Asking for Permission
The Strategic Questions That Get You a Promotion (Without Causing Conflict)

UnsplashPhoto by Christina @ wocintechchat.com on Unsplash
Welcome to Leading by Design!
Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.
⏱️ Today, in 5 Minutes or Less
You’ll learn the three strategic pillars of alliance building: how to elevate your visibility, the exact strategic questions to forge trust with your cross-functional partners, and why alliances are indispensable to your executive safety net.
🔎 Alliances as Insurance Against Political Risk
Failing to cultivate proactive alliances is the number one reason high-potential leaders are sidelined. In leadership roles, your reputation is often shaped not solely by your actions, but by how others interpret and communicate them to organizational leaders. If people are unaware of your value to the business, their ignorance becomes a barrier to your progress—effectively keeping you from asking for, and getting, what you want.
A study by the Corporate Executive Board found that executives who actively build a broad, strong network of internal allies are 2.5 times more likely to report career satisfaction and feel they have a "safety net" to navigate political resistance and organizational change.
Using Strategic Inquiry Questions at Work
Building a strong alliance begins with strategic inquiry—structured, short, open-ended questions that move beyond small talk to uncover your partner's true priorities, pain points, and definition of success. These questions, which often start with "What" and "How," are the keys to building trust and securing influence. If you’ve ever witnessed a user experience researcher conducting an interview, this is how they will be asking their questions. Short less than 12 words, and asked with genuine curiosity.
1. Build Rapport First: Focus on Their World 🧭
Start your meetings by showing genuine interest in their strategic goals. This builds the foundational relationship before you make any asks.
Goal | Strategic Questions |
Understand Priorities | What are your biggest priorities right now? How will you measure success this quarter? |
Assess Perception | How well do you feel our design decisions are contributing to key product metrics? What is one thing design usually misses during planning? |
Discover Opportunities | Where do you see the biggest opportunities for design to elevate our product strategy? |
2. Address Potential Problems Openly: Partner, Don't Blame 🛠️
When a project hits a roadblock, use inquiry to understand their perspective on the root cause and align on a path forward. This positions you as an ally.
Goal | Strategic Questions |
Diagnose Root Cause | What do you see as the root cause here? |
Align on Solution | How can we best fix this? How can we align our teams' success metrics? |
Get Clarification | What support do you need from my design team? |
When a project succeeds, use the opportunity to document and scale that success together. This reinforces the value of your partnership and increases your collective visibility.
Goal | Strategic Questions |
Identify Best Practices | What made this project's process so effective? |
Plan for the Future | How can we scale this successful collaboration? How could we make our processes even smoother? |
Increase Visibility | How could we share our team's success more broadly? |
The Short of It Is
In tech leadership alliances aren't a luxury; they are your safety net and your springboard to achieving your career goals. To ask for what you want and keep your job, you must actively forge supportive, trustworthy relationships with your cross-functional peers. Do this by making your team's work visible and by using strategic inquiry to understand their world.
Cultivate trust through transparency, accountability, and consistent delivery. By consistently translating your principles into the language of business—data, logic, and predictable growth—you solidify your reputation as a dependable and trustworthy leader, expanding your influence and impact without needing to resort to demanding or political behavior. To learn more about this topic, please buy my book “Leading by Design: The Insider’s Playbook for Tech Leadership”
What is the one strategic question you'll commit to asking your most critical cross-functional partner this week?
That's it for this week!
PS: Would you like to receive more leadership strategies?
Here are a few ways I can help:
Schedule a free coaching strategy call
Buy my book
Subscribe to this Newsletter

With ❤️ from Sally