"Screw You, Alessandra!"

On the cost of speaking up and why it's worth paying

"Look at you, stirring the pot on a Monday morning."

I recently received that message from a peer after putting a question out to a larger community of leaders about something that did not sit right with me.

Saying what I mean, meaning what I say, and standing for what I believe to be true and right aren’t aspirational qualities I’m working toward. The question I brought to this community is difficult and uncomfortable. Bringing it up could create potential discomfort, potential ill will toward me, and force a harder conversation no one was rushing toward.

The intention wasn’t to stir the pot. It was to address a concern I believe needs to be addressed openly.

That’s my responsibility as a leader.

None of this comes easy, but I believe it’s essential, so I do the uncomfortable thing anyway.

The Cost of Speaking Up

In my coaching work, I’m regularly called to do the same thing at a different scale: to ask the difficult questions, to name the patterns that are right there and that everyone can feel but no one has said out loud, to bring into the light what someone needs to see but has been working, consciously or not, to avoid.

Done properly, it might create a moment of genuine discomfort, maybe even a “screw you, Alessandra!” said straight to my face or silently in my clients’ heads. I’ve learned to cherish those moments rather than fear them. They’re proof I’m serving my clients deeply.

The tension at the center of leadership courage is this: the thing that most risks rejection is often the thing that creates the deepest connection. The moment you say what everyone else has been thinking but not saying is the moment you stop going through the motions of leadership and start practicing it. The leaders in my world have the most to lose by honoring this. They have reputations to protect, relationships to maintain, rooms they need to keep being invited into. The cost of staying silent, of navigating around the truth rather than through it, is always higher.

I Love You

Last week I had two separate moments with two different women where I called out something true and charged. One was a client, the other a inspiring biopharma leader; both responded with the same three words: “I love you.”

Speaking the truth, naming the pattern, raising the concern, it isn’t about being brave or showing tough love, it’s about caring deeply. My coach has a reframe for tolerating this level of discomfort: “Care so much you don’t care.” Care so much about your client and their success that you stop caring about whether saying the thing, highlighting the pattern, or showing up fully will get you fired. When you’re that committed to someone’s ambitions, dreams, growth, success, the fear of their disapproval loses its grip. That’s what’s required for deep transformation to occur.

The Question Worth Asking Yourself

When you speak the truth other people won’t say, raise the concern others are hoping someone else will raise, when you name the pattern no one has said out loud, you’re being of genuine service. It won’t always feel that way. In the beginning it’ll actually feel like you’re the one making things complicated, tense, heavy. The short-term cost of speaking up and acting in alignment with yourself can feel too high.

You might get a reputation for being the person who stirs the pot; I do. But you know better. You understand your motives, which are not to stir things up, but to shed light on what needs to be surfaced.

Ultimately, the real question isn’t whether you’re stirring the pot. It’s what’s worth stirring it for.

What value is so central to your identity, so woven into your sense of what’s right and wrong, that the people and rooms and relationships you’d risk losing still aren’t enough to make you let it go?

How does it show up in how you actually operate? Not in how you describe yourself, but in the room, in the conversation, in the moment when honoring it costs you something.

And where are you most tempted to let it go?

That last question is the most important one - because we’re all tempted, and we all give.