Speaking Truth to Power: How to Tell the Boss What They Don’t Want to Hear
- Stephanie Bickel
- 2 minutes ago
- 7 min read
Gravitas in real time
By Stephanie Bickel
“If I Say It, Do I Risk Everything?”
The higher you rise, the more you see things your leaders don’t: blind spots, risky decisions, toxic behaviors, or patterns that will quietly erode results.
And then comes the real dilemma:
If I don’t say anything, I’m complicit.
If I do say something, I might damage the relationship… or my career.
It's dangerous to criticize the boss.
Leaders tell me all the time:
“Speaking truth to power is the hardest thing to do.”
They’re not struggling with honesty. They’re struggling with risk management, emotion management, and power dynamics all at once.
This is where gravitas really gets tested. Not in a keynote, not in a town hall, but in that one quiet conversation where you tell someone above you that they are wrong, off, or becoming part of the problem.
This is the heart of executive communication coaching: helping leaders say the hard thing upward without burning trust.
Truth as an Act of Alliance
The theme I want you to hold onto is this:
“Speaking truth to power is an act of alliance, not rebellion.”
You’re not there to expose your leader. You’re there to protect them, protect the mission, and protect the team.
When you treat truth as an act of alliance:
Your tone softens, even when your message is sharp.
Your language shifts from “you did this wrong” to “here’s a risk to what we’re trying to achieve.”
Your leader feels your support and hears your challenge.
This is gravitas in motion:
Clear eyes on reality
Calm delivery
Deep care for the person and the outcome
Why This Is So Hard
If this feels difficult, it’s because it is. Here’s what’s working against you:
Power Imbalance: They control opportunities, budget, performance evaluations. Your nervous system knows that.
Emotional Load: You’re often delivering the message they least want to hear — that they made a mistake, missed something, or hurt their own reputation.
Fear of Being Labeled: Critical, disloyal, political, “not a team player.” Many people have seen others punished for voicing hard truths.
Timing Is Messy: Leaders are busy, stressed, and in motion. There is rarely a perfect calm moment to bring it up.
Style Mismatch: Some leaders say “Tell me straight,” but react badly when they actually hear it. Others shut down if you’re too blunt or too vague.
So we over-correct:
We say nothing and vent privately.
Or we wait until we’re frustrated… and then come in hot and blunt.
Both cost you gravitas. Neither grows your influence.
You Have Two Reliable Options
The good news is you don’t need a perfect script. You need a posture and a pattern.
There are two powerful options you can use in your executive communication coaching toolkit when you’re speaking truth to power:
Option 1: The Risk-Framer
Use this when the issue is a decision, strategy, or direction that worries you.
Core move: Anchor in their goals and shine a light on the risk.
Example:
“I hear your point of view on this decision. From where our team sits, there’s a risk I want to put on your radar. You’ll make the call, of course. I just want to make sure you see this piece clearly before we move forward.”
Why this works for power:
It honors their authority (“You’ll make the call.”)
It positions you as a strategic ally managing risk, not a critic judging them.
It protects outcomes and reputation, which senior leaders care about most.
You are saying: “I’m here to protect what you care about, not to win an argument.”That is gravitas.
Option 2: The Mirror-Holder with Warmth
Use this when the issue is behavior, impact, or reputation.
Core move: Hold up a mirror to how they came across — with warmth and belief in them.
Harsh version (what often backfires):
“In that meeting, you didn’t look good. You looked frustrated and dysregulated. People aren’t going to bring you ideas if you respond like that. It was not a good look.”
The content is accurate, but the energy is judging. Many leaders will armor up.
Mirror-Holder with Warmth version:
“Can I tell you something I saw in that meeting? When you reacted to that idea, it came across as really sharp. You’re usually great at inviting thinking, which is why people love bringing you ideas. In that moment, it had the opposite effect. I’m sharing this because I don’t want anything to chip away at your influence.”
Same truth. Different energy.
Why this works for power:
You link the feedback to the reputation they want (“You’re usually great at…”)
You’re on their side (“I’m sharing this because I don’t want anything to chip away at your influence.”)
You deliver a hard message with care, not contempt.
This is the kind of executive communication coaching most senior leaders crave but rarely receive.
Tips and Tricks: Helping It Land Well
Here are practical ways to build your skill (and your gravitas) in these moments:
1. Start with One Sentence of Truth
Before you speak, write it or say it to yourself:
“The truth I need to share is…”
If you can’t get it into one sentence, you’ll likely ramble, soften, or confuse the message.
2. Put Their Worry on the Table First
Ask yourself:
“What are they most afraid of in this situation? Missing a number? Looking unprepared? Losing credibility?”
Open with that:
“I know one of your biggest concerns is how this will land with the Board. That’s exactly why I’m worried about moving this forward without naming X.”
You’re not adding stress; you’re protecting them from the very thing they fear.
3. Use “We” Language to Signal Alliance
Shift from:
“You’re making a mistake.”
To:
“We’re increasing our risk of X if we move forward like this.”
“We may be sending a signal we don’t intend.”
“We” says: I’m in this with you.
4. Match Directness to the Relationship
If you have strong trust, you can be more direct:
“This doesn’t look like you at your best. I’m telling you because I’ve seen you lead at a much higher level.”
If trust is fragile, go slower:
“There’s something I noticed that I’m not sure we’ve fully acknowledged yet. Can I share it?”
Either way, you are signaling respect, not superiority.
5. Soften the Edges with Voice and Face, Not the Message
You don’t have to soften the content. You soften the delivery:
Steady, calm voice
Open posture
Curious expression
A hint of warmth or a small smile when appropriate
You can absolutely say, “That moment was not your best look,” with kindness. The body carries as much meaning as the words.
6. Tie Feedback to Their Aspirations
Link the truth to the leader they want to be:
“You’ve said you want a team that will bring you bold ideas. That’s why I need to tell you this. The way that conversation went could make them hold back next time.”
You’re not critiquing them; you’re closing the gap between their stated goals and current behavior.
Now we transition into the sequence you asked to keep as-is:
How to Prepare to Speak Truth to Power
Here is a simple Speak by Design sequence from our executive communication training programs that you can use before your next hard conversation upward.
1. Clarify the Truth You Need to Share
Ask yourself:
What is the one sentence of truth they must hear?
Is it about a decision, a behavior, or a pattern?
If you can’t say it in one sentence, you’re not ready yet.
2. Decide Your Role: Risk-Framer or Mirror-Holder
For strategy or decision risks, start as a Risk-Framer:
“From where I sit, here’s the risk I see that could hurt our outcome…”
For behavior or reputation issues, lean into Mirror-Holder with Warmth:
“I know your intention, and I saw something that doesn’t match the reputation you’ve built.”
Both are examples of speaking truth to power. They just serve different purposes.
3. Read the Room — But Don’t Wait for Perfect Timing
One participant mentioned “catching them at a good time” as a go-to strategy. It’s smart — and also imperfect. Senior leaders are rarely relaxed and available when you most need to deliver hard news.
Instead of waiting for perfect timing, aim for:
Containment: not right before a major presentation
Privacy: not in front of peers or their boss
Sufficient time: enough to say the one sentence and answer a question
Then trust yourself.
4. Anchor in Their Biggest Worry
Before you speak, ask:
“What is the thing they are most afraid of in this situation?”
Open with that:
“I know one of your biggest concerns is X. That’s exactly why I’m worried about this path, I think it increases the chance of X happening.”
Now your truth is helping them with their fear, not adding to it.
A Few Phrases You Can Borrow
Use and adapt these to your own voice:
“I’m sharing this because I want you and the team to win.”
“From where I sit, there’s a risk I don’t think we’ve fully named yet.”
“This might be hard to hear, and I’m telling you because I have your back.”
“That moment in the meeting didn’t look like the leader you usually are.”
“You can absolutely decide differently — I just want to make sure you see this piece of the picture.”
Become A Leader Your Boss Can Truly Trust
Imagine being known as the person your leader can count on to:
Surface the risks others are afraid to say out loud
Tell them when they have become part of the problem
Admit your own mistakes early, with a plan
Do all of that with calm, care, and composure
That’s what speaking truth to power, Speak by Design style, really is.
It’s not about being the bravest person in the room.
It’s about being the most useful, the person who can hold both truth and relationship in the same sentence.
And the next time you feel that nervous energy before you speak, try this quick reframe:
“I’m not here to criticize.I’m here to protect what we are building.”
That mindset will change your words, your tone, and your impact — all the way up the org chart.
If you’re ready to lead with more gravitas, clarity, and authority, here is your next step.
Speak by Design University is currently closed as we prepare for the next cohort.
Enrollment will reopen on Cyber Monday.
Join the waitlist below if you want to strengthen the skills that help you motivate teams, create clarity, and lead with confidence. You’ll be the first to know when doors open again, and you’ll receive early access to resources to support your growth in the meantime.