How to Practice Loving Assertiveness

Not just read about it

Nov 04, 2025

Photo by charlesdeluvio on Unsplash

You don’t need to justify your love, you don’t need to explain your love, you just need to practice your love. Practice creates the master.
― Don Miguel Ruiz, The Mastery of Love: A Practical Guide to the Art of Relationship

I’ve been getting messages from people who’ve read the Substack, read the book, heard the intro.

The pattern is consistent: “This makes so much sense. I can see exactly where I need to use this. But when the moment comes, I fear I may freeze / I could default to old patterns / I fear that maybe I can’t quite make it land.”

This is the gap between knowing and doing.

You can read about listening for needs beneath words. You can intellectually understand that anger is a tragic expression of unmet needs. You can recognize the pattern of pseudo-community in your team.

When your teenager slams the door, or your business partner questions your judgment, or your direct report pushes back on feedback, or someone you love challenges your motivations—can you actually do it in that moment?—not remember to do it later, not wish you’d done it differently. But actually speak what’s alive in you in a way that lands, and hear what’s alive in them beneath the reactivity?

That’s a different skill. And it requires practice. It’s a practice we have to literally “embed” into our reflexes…ideally with supportive reinforcement.

Reading vs. Practicing

Here’s what I’ve learned over 30+ years: Frameworks don’t change behavior. Practice does.

You can study Non-Violent Communication and still make people defensive.

You can understand Transactional Analysis and still get hooked by your Parent or Child ego states.

You can know the pseudo-community → chaos → emptiness → community progression and still get stuck in the first two stages.

The gap isn’t knowledge. It’s muscle memory.

When someone criticizes your work, you have about 2 seconds before your nervous system decides: defend, deflect, or actually listen for what’s beneath their words.

Two seconds. That’s not enough time to consult a framework. That’s only enough time to act from practice.

You can wish you’d handled that conversation differently. You can replay it in your mind. But you can’t practice it. The only time you can practice is before the next difficult conversation, before the next moment when you need to speak truth or hear it.

Photo by Christina @ wocintechchat.com on Unsplash

What Practice Actually Looks Like

In November, I’m running the first Loving Assertiveness workshop. It’s deliberately for a small group—because this isn’t primarily about me lecturing. It’s about you practicing.

Here’s how it works:

You bring real communication challenges. Not hypotheticals. Not “imagine if...” scenarios. The actual conversation you need to have with your co-founder, your spouse, your teenager, your boss, your team, anyone you interact with.

We practice it. In real-time. With guidance.

You try the framework. You discover where you get stuck. You try again. You get feedback—from me, from the group. You refine.

Then you go use it, that week, in your actual life, with the actual person.

Next session, you report back: what worked, what didn’t, where did you freeze? where did it flow.

We troubleshoot. We practice the next layer. You go use it again.

Four sessions, two hours each, real scenarios, real practice, real transformation!

And if “one tough conversation” doesn’t loom large, pick a key relationship you’d like to rescue, refresh, extend, deepen. And let’s make that happen together.

Why Small Groups

I could run this for 50 people, and in time we almost inevitably will. But this was a response to a personal request for an intimate deep dive. It is possible to get “lost” in large groups, and the most vocal dominate, and those who are more tentative, can get cloaked

Here you are invited, welcomed, and supported throughout your exploration of this highly nourishing form of communication.

In a smaller group, everyone practices. Multiple times. With real-time coaching. Everyone can be heard. And something else happens:

You develop practice partners.

By session two, you know each other’s communication challenges. You’ve seen each other stumble and recover. You’re rooting for each other’s breakthroughs.

The group becomes a container for the vulnerability this work requires.

Photo by Harli Marten on Unsplash

The Four Sessions

Session 1 (Feb. 17th, 2026): Hearing Beneath the Words

Listening for needs beneath judgments, demands, and reactivity
Practice with your actual difficult conversations and interactions
Releasing toxic emotions
What to do when you get triggered

Session 2 (Feb 19th): Speaking What’s Alive

Expressing your truth without making others wrong
The continuum from observations to feelings to needs
The anatomy of a request vs. a demand
Practice: enriching the relationship you’ve been avoiding or ignoring

Session 3 (Feb. 24th): When It Goes Sideways

The magic of empathic listening
Navigating your ego states (Parent, Adult, Child)
The art of the repair

Session 4 (Feb. 26th): Integration & Mastery

Your toughest scenario yet
Building sustainable practice
From technique to way of being
Working with groups and on systems

What you’ll leave with

Not just understanding…capability.

The ability to:

Stay present when someone’s anger catches you off guard, by hearing the underlying needs
Express what matters most without making others defensive, reveal rather than cross-examine
Hear the longing beneath their frustration, and create a safe harbor for it, and help them set sail for better destinations from there
Navigate your own reactivity in real-time, learning to shift ego states, practice pattern interrupts, and even reclaim opportunity when it “seems lost”
Speak and hear “truth” in ways that deepen, enlarge and invigorate relationships

And something else: A small community of people who’ve practiced this work together. Who can call you on your patterns. Who will celebrate your breakthroughs.

That matters more than you might think.

Ready to dive deeper?

Loving Assertiveness workshops teach the frameworks that make this depth and breadth possible—how to move from strategies to needs, from shallow to deep, from jockeying to genuine connection.

->To explore this further, join us for the upcoming Zoom workshop Loving Assertiveness

The Details

When:

March 17th, 19th, 24th & 26th, 2026
https://lovingassertiveness.com/march-2026-live-workshop/
10:30 a.m. -12:30 a.m. U.S. Eastern Standard Time (7:30-9:30 a.m. Pacific)

Where:

Interactive online (Zoom). If you are unable to attend a session, all of the sessions are recorded; and you will be able to watch the recording of the missed session, and ask for a personal 10 minute “top up” so you will be fully ready for the next one.

Why Now

Here’s the thing about practice: You can’t practice in the past.

You can wish you’d handled that conversation differently. You can replay it in your mind. But you can’t practice it.

The only time you can practice is before the next difficult conversation, before the next moment when you need to speak truth or hear it.

This workshop starts March 17th, 2026, before whatever the rest of 2026 brings.

If not now, when?

Looking forward to practicing with you.

Omar

Questions? Please reach out to us at leslie@3-s-consulting.com

About the author:

Omar Khan is Founder & Principal of 3S Catalyst Consulting and author of Loving Assertiveness: A Framework for Authentic Communication. He has spent 35+ years working with organizations and communities across six continents, including post-conflict reconciliation work and organizational transformation. Recognized by Consulting Magazine as one of the top 25 consultants worldwide, he was mentored by Dr. M. Scott Peck and is an Oxford University alumnus. Find him at www.lovingassertiveness.com

3 S Catalyst Consulting:

https://3-s-consulting.com/

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Loving Assertiveness is how we bring ourselves back, to ourselves and each other, to connection, to community, to true collaboration, and forward to the triple win: I win/you win/the world wins.