Leaders don’t struggle to speak up because they lack courage. They struggle because somewhere between what they know needs to be said and the actual moment of saying it, something gets in the way.
Sometimes that something is the eleven rehearsals they’ve already had, alone. Sometimes it’s a very old story about what happens when someone in a room disagrees. Communication tends to live along a continuum, a pole of sorts. On one end is direct communication, the kind that can come across as hard, edgy, or aggressive when it’s under pressure. On the other end is indirect communication, the kind that can look like silence, like meekness, like not standing up for yourself or for the people you’re responsible for. Most leaders I know have a home base somewhere on that continuum, one they’ve probably occupied for most of their career.
And it worked, until it didn’t. That’s usually the season a leader ends up in my office: not because their default approach was wrong, but because it stopped producing what they needed it to.
Here’s what happens next, in almost every case. Once a leader can see that their pole isn’t working anymore, they start experimenting with something different. And that something different often looks like the opposite end of the continuum. The direct communicator suddenly holds back. The one who’s held back for years suddenly says too much, too fast. It’s disorienting, for them and for the people around them who are used to a certain version of them showing up. But it’s not a failure. It’s proof that the pole was a habit, not a life sentence.
There’s a third option, though, and it isn’t the opposite pole. It isn’t hardened words, softened. It isn’t edged words, filed down. It’s something else entirely, and it has a name. Assertive communication is the practice of being clear about what’s true for you while staying respectful of what might be true for the other person. And here’s what I’ve noticed after nearly twenty years of coaching senior leaders: almost no one was taught it. We were taught to be nice, or we were taught to be tough. Very few of us were taught to be clear.
The two extremes that cost the same
Aggressive communication protects your position at the other person’s expense. Passive communication protects the relationship at your own expense. Assertiveness protects both, which is why it builds trust where the other two erode it.
You already know which end of that continuum you tend to live on. What’s worth naming is what it’s protecting. What both patterns share is that the words are being driven by something other than a conscious choice.
And notice what’s absent from that definition: volume. I’ve watched accomplished leaders prepare for difficult conversations by rehearsing intensity, stronger words, a firmer tone, as though the problem last time was that they weren’t forceful enough. In my experience, the problem is almost always earlier than that. We try to shape how to say it before we’re clear on what’s actually ours to say.
The story underneath the silence
Your relationship to conflict didn’t begin in this job.
It began a long time ago, in rooms where disagreement meant something. For some of us it meant danger. For others it meant silence for three days, or someone leaving. We carry that history into every hard conversation at work, usually without realizing it’s in the room with us.
That’s why a communication framework, on its own, rarely resolves this. The framework addresses the words. The difficulty lives underneath the words, in what conflict came to mean to us before we ever had a title.
So before any technique, I invite leaders to get curious. When a hard conversation is on your calendar, what happens in you first? Does your chest tighten? Do you start rehearsing? Do you find reasons to postpone? None of those responses is a flaw. Each one is information. And awareness of what’s driving you is where choice begins.
Two questions that take the edge off
When something needs to be said, I offer leaders two questions to sit with before they say it.
What is true here?
What else could be true?
The first keeps you honest. It separates what you actually know from what you’ve concluded, and after a week of silent rehearsal, those are rarely the same thing. The second keeps you humble. It makes room for the other person’s reality before you’re standing in front of them, and that tends to change your tone more reliably than any script.
Write your answers down if you can. Leaders are often surprised to find that the sentence they planned to say changes shape once both questions have had their turn. What drains out is the charge. What remains is the truth.
One more thing worth saying, sometimes literally out loud: if you’ve been carrying something for a while, name that when you raise it. “I’ve been sitting with something, and I care about getting it right.” That sentence lets pressure out of the room, and out of you.
When restraint is the wiser service
Speaking up isn’t always the answer, and this distinction matters most for leaders who see what every project needs before anyone else does.
The language I sometimes offer is this: you may be wonderful at being a wedding planner. Truly gifted at it. And sometimes you’ve been invited as a guest. Showing up with the clipboard anyway isn’t a service to anyone, least of all you.
Before you speak up, there’s one honest question worth asking: is this mine? If it is, say it with clarity and respect. If it isn’t, your restraint might be the more generous contribution, because it leaves the ownership where it belongs.
What your voice teaches the team
There’s a pattern I see on teams more often than open conflict: the meeting ends in agreement, and then the real meeting happens afterward, in direct messages and hallway conversations, where people say what they actually think.
Leaders can usually feel this, even when every dashboard says the team is fine. The research affirms the feeling. Google’s multi-year study of its own teams, Project Aristotle, published in 2015, found that psychological safety, the shared belief that you can speak up without punishment, distinguished its most effective teams more than any other factor. Harvard Business School professor Amy Edmondson, whose research created that field, has shown across decades of studies that teams where people withhold questions and concerns learn more slowly and make more preventable mistakes.
What you’re sensing on a team like that is a gap, the distance between what people expected and what they’re actually living. That gap is measurable. In our work we use the Team Alignment Survey, part of the Trust Within Assessments, to give it shared language and data, because the data becomes the doorway to the deeper conversation.
And measurement follows modeling. When you speak up with clarity and respect, you make it a little safer for everyone around you to do the same. It’s more than a personal skill. It’s a culture being shaped, one conversation at a time.
A place to begin
This week, don’t change anything yet. Just notice what happens in you when a hard conversation approaches. Then, before the next one, sit with the two questions and see what they surface.
And if you suspect the real obstacle isn’t the conversation but a belief running underneath it, that’s what my free guide is for. You’re Not Off Your Game… You’re Playing Someone Else’s walks through the ten mindsets I most often see undermining capable leaders’ confidence, including the ones that keep us silent or send us in too hot. [Internal link: You’re Not Off Your Game opt-in page]
If this stirred something for you, I’d love to hear what it brought up. You can reach me at Jenna@JennaStoliker.com, or if you’re ready to explore it together, I’d be honored to sit with you in a discovery conversation. You can schedule one here.
Frequently asked questions
What’s the difference between assertive and aggressive communication?
Assertive communication holds your truth and the other person’s dignity at the same time. Aggressive communication defends your position at their expense, and it usually shows up in absolutes, blame, and volume. The practical test: after an assertive conversation, the relationship is intact or stronger. After an aggressive one, you won compliance and lost trust.
How do I speak up in a meeting without my emotions taking over?
Create spaciousness before you speak, even a single breath. Then anchor to what you prepared with the two questions, what is true here and what else could be true. If the emotion is still strong, name it simply and honestly rather than pushing through it. Saying “I feel strongly about this one” is steadier than pretending you don’t.
Why do I rehearse conversations instead of having them?
Rehearsing feels like preparation, and often it’s pressure-building. Each silent rerun adds charge, so when the words finally come out, they carry the weight of every version you swallowed. If you notice yourself on the eleventh rehearsal, that’s usually the signal to have the conversation, imperfectly, rather than perfect it privately.
Is it ever better to stay quiet?
Yes, when the thing you’d be speaking up about isn’t yours to own. Restraint serves when your input would take ownership that belongs to someone else, or when your goal is being right rather than being useful. The question that separates the cases: is this mine?
