What to Do When You Don’t Want to Hold Back Anymore
Recently, a client who was newly hired to a very senior position called me. She had just gotten the offer letter and it didn’t reflect her expectations.
On the one hand, she was talking herself into backing down and accepting it. She started with thoughts like, “well, equity is very complex.” But clearly she was disappointed.
I explained that an offer is a negotiation. The hesitation she felt probably wasn’t about the offer itself, but about whether she’d earned the right to push back on it. With seven patents to her name and a stellar leadership record in her industry, she needed to learn to speak up about her expectations. Her new boss would want her to, as holding back at this moment risks damaging the relationship and her trust in the company.
Still, I cautioned her not to go in too strong, which can backfire. Besides, it wouldn’t have felt authentic to her anyway. Instead, I gave her a few techniques for how to come in soft, make her feelings known, and push back in an acceptable way.
She called me two weeks later to say she had doubled her equity stake.
If you find yourself holding back what you actually mean — or saying too much, too forcefully, and losing the room — this webinar is for you. In this session, I’ll walk you through exactly what I gave her — and what’s worked for clients like her since.
Join me for a leadership workshop, Wednesday Nov. 4 at 3 PM ET on how to speak so others actually listen — and grow your influence in the process.
Note: registration will open 30 days before the event.
This communication workshop will explore how to communicate in leadership moments when the stakes are high. A longer course about leading through an inflection point is coming next year.
This is the second session in a series for leaders at an inflection point.
Are You Too Soft — Or Too Sharp?
It happens to all of us. You’re negotiating something that matters, or you need to say something hard to a colleague or your boss, and you either soften it so much the point gets lost — or you come in so direct it puts people on the defensive.
Here’s what surprises most of my clients: those aren’t two different communication styles. They’re the same instinct — to protect yourself — just showing up in opposite directions.
Once you can see that, you can catch it in the moment, and choose something better than either extreme.
Before You Join
In the days before the workshop, I’m asking everyone to do one small exercise: keep a short journal of your emotions as they shift. This shouldn’t take more than 5-10 minutes.
Notice: What made you feel bad? What made you feel better? Bring what you notice — we’ll be building on it live.
You’ll get a downloadable tracker for this exercise when you register.
What We’ll Cover
This is a live, interactive session — not a lecture. Come ready to keep your camera on and unmute.
A leadership styles framework that illustrates the effects of how you communication
Daniel Goleman’s research reveals how your leadership style is shaping what you say (and what people hear).
Communication is a two-way street
Why the words you choose only account for half the equation — and what the other half actually is.
One real story
How Jim learned that communication fundamentals — starting with listening first — were what actually built his leadership presence, not the other way around.
You’ll leave with specific, practical communication techniques to help you say what needs to be said — in negotiations, in feedback, in pushback — in ways that build trust and influence, regardless of how the conversation goes.
Who This Is For
This session is for you if you’re at an inflection point — newly promoted, navigating rapid growth at your company, or positioning yourself for what’s next.
One of these may feel familiar to you:
- You soften hard truths so much that the message doesn’t land
- You’ve gone in too strong in a negotiation or disagreement and watched the other person shut down
- You know what you want to say, but the words come out wrong — or don’t come out at all — in the moment that matters
- You’re capable and know it, but something about how you communicate is still getting in your way
Details
📅 Wednesday, November 4, 2026
🕒 3–4 PM Eastern Time
💻 Live on Zoom — workshop format, seats are limited
💲 $34
If you don’t leave the session with at least one thing you can put to use right away, I’m happy to refund your registration fee.
Hope to see you there.
Note
This is a leadership workshop designed to allow time for reflection and discussion.
Seats are limited.