How to Partner with Our Bosses with Authenticity and Compassion
Wendy Tan, PhD, CSP
Author, Keynote Speaker & Managing Partner of Flame Centre | Human Skills Institute
Feb 2025
Have you ever sat in a meeting, locked eyes with a powerful executive, and thought, "If I say this, I’ll be fired?" Or perhaps you’ve found yourself in a recurring work problem that everyone talks about but no one dares to address with the person who can actually change it?
You’re not alone. Every consultant, internal or external, and every professional who’s ever tried to "speak truth to power" knows this gut-wrenching moment. The question is, what do you do?
In Flawless Consulting®, we’re taught that the real work lies in human connection, and sometimes that connection needs to extend to the "gods of power"—the executives, decision-makers, and authority figures whose influence can make or break your effort. It’s daunting, yes. But navigating this territory is not about professional suicide—it’s about calculated risk, courage, and strategy. Let me walk you through it.
Power and Anxiety: It’s Real
Let’s face it: powerful people intimidate us. They hold the authority to approve, reject, or derail initiatives, and they often seem distant, preoccupied, or unapproachable. The anxiety you feel when facing these "gods" isn’t imaginary—it’s baked into organizational culture. But anxiety doesn’t mean inaction. It’s a signal to pause, prepare, and approach thoughtfully.
Here’s the truth: stepping into that room isn’t about being reckless or throwing your career to the wind. It’s about managing risk wisely. It’s not political suicide; it’s strategic courage.
Step One: Contract with Your Boss
Before you knock on the Big Boss’s door, don’t go alone. Contract with your immediate manager. Share your observations, your concerns, and why the issue at hand matters so deeply to the work, the organization, and to you. Be clear about your intention: “Boss, let’s talk to the Big Boss together.”
By bringing your manager along, you not only spread the risk, but you signal alignment. If your immediate boss is unwilling to join you, that’s a signal to pause. The work of consulting is not a solo act. You’re not there to be a martyr. Instead, build alliances and gather support.
Step Two: Take the Risk to Tell the Truth
Here’s the thing about powerful people: they’re not omnipotent. Behind their confidence lies their own anxiety about the organization, their role, and the outcomes they’re responsible for. They may not even be aware of the problem you’re seeing. Or worse, they may see it but have no idea how to address it.
If you care about your work—if the recurring problem truly matters to you—it’s worth the risk to tell the truth. But do it carefully:
Speak to the issue, not the person.
Be specific about the problem and its impact.
Offer to co-create solutions rather than criticize.
As Flawless Consulting® teaches us, truth-telling isn’t about confrontation; it’s about invitation. Invite the powerful person into the conversation. You might be surprised by their response.
A Real-Life Example: Lily’s Leap of Courage
Lily, a mid-level leader, faced a problem that had plagued her department for months. It was the kind of issue everyone whispered about but no one dared address with the Big Boss, a senior leader four levels above her. But Lily cared. She knew that if nothing changed, the problem would persist—and so would her frustration.
She decided to act, but not alone. Lily spoke with her immediate boss, outlined the problem, and gained his agreement to approach the Big Boss together. With their plan in hand, they walked into the Big Boss’s office.
What happened next surprised her. The Big Boss didn’t react with anger or dismissal. Instead, he shared his own concerns and challenges. For the first time, Lily saw the human behind the authority. Together, they co-created a solution, addressing not just the surface problem but its root causes. Lily left the room not only with a better plan but with a new partnership.
We Can’t Guarantee Success, but We Can Offer Options
Here’s the truth: no one can guarantee that speaking truth to power will always work out in your favor. But we can give you the tools to sense what’s appropriate and how to act. Flawless Consulting® is not about guarantees; it’s about navigating ambiguity with courage and clarity.
Every situation is different. Sometimes you’ll feel ready to take the leap. Other times, the risks may outweigh the benefits. What matters is that you approach these moments with intention and care—not recklessness, but deliberate action.
Finding Your Own Courage
So, how do you find the courage to act when the stakes are high? Here are some questions to guide your thinking:
What is my struggle, and where is it coming from? Is your fear rooted in the potential reaction of the powerful person, or is it tied to your own doubts about your readiness? Naming the source of your fear is the first step in addressing it.
What unproductive behaviors am I relying on? Are you avoiding action, making excuses, or waiting for someone else to fix the problem? Recognize these patterns and challenge yourself to step beyond them.
What is the worst that can happen? Often, our fear of catastrophic outcomes is exaggerated. What’s the real worst-case scenario, and how would you handle it?
What question, if answered, would set me free? Sometimes, we’re stuck because we don’t know the right question to ask. What’s the key question in your situation that, if answered, would give you clarity and courage?
What’s the answer I’m searching for? Deep down, what outcome are you hoping for? Define it clearly. If the possibility of achieving that outcome outweighs the risk, you’ve found your reason to act.
The Bottom Line
Flawless Consulting® is about making human connection the cornerstone of your work—even when dealing with the "gods." It’s about taking calculated risks, telling the truth with care, and partnering with others to create meaningful solutions. The road isn’t easy, but the rewards are worth it.
So, the next time you face that intimidating moment, pause and ask yourself:
What really matters to me?
What’s the risk of doing nothing?
What’s the risk of speaking up?
And remember: You’re not alone. Contract with your allies, take the risk, and move forward—step by step.
The courage to tell the truth must be matched with the wisdom to know when and how to share it.
How will you find your courage today?
If you're curious about:
How to build trust with clients, help and add value.
How to discover client needs, provide support and effective recommendations.
How to develop a collaborative relationship and give feedback.
Check out the Flawless Consulting® framework, tools and skills.