Trailhead Thoughts
“When we avoid difficult conversations, we trade short-term discomfort for long-term dysfunction.”
- Peter Bromberg
Trail Map - Learn. Think. Act. ™
Tough Conversations? Start Here.
Some conversations feel heavy.
Giving feedback.
Receiving criticism.
Clearing the air.
Why do they go wrong so often?
Because what’s said, what’s heard, and what’s remembered are rarely the same.
Let’s fix that.
📚Learn
When feedback gets hard, three things are usually happening:
Walls go up.
We care. We care about our work. We care about the people we work with. We care about ourselves. As a result - we get defensive.
Noise gets in the way.
Stress from outside work follows us inside.
Trust is shaky.
Without trust, everything sounds like an attack.
Here’s the simple fix:
Ask, “What did you hear me say?”
Take ownership: “I didn’t communicate that clearly.”
Align on goals: “What are we trying to accomplish together?”
Be objective. Share observations, not accusations.
End with clarity. Who will do what by when?
Trust. But verify.
Small changes over time create big results.
🤔Think
Before your next hard conversation, pause and ask yourself:
Am I trying to win or improve the relationship?
What might be going on in their world right now?
Is this a skill issue, a motivation issue, or an opportunity issue?
Do I have a clear next step in mind?
Most people want to go good work.
But they find themselves distracted, unclear or unsupported.
Grace + clarity = progress.
💪 Act
Before your next feedback conversation:
Write down your objective.
Write down the shared goal.
Decide the one behavior that needs to change.
Plan one clear next step.
During the conversation ask:
“What did you hear me say?”
Then confirm:
Who will do what by when
Better communication leads to stronger trust which leads to faster results.
Beyond the Trailhead
Difficult Conversations
We find that most difficult conversations don’t go sideways because of what’s said. They go sideways because of what’s heard.
What’s heard is usually filtered through stress, ego, distraction, and a whole lot of “stuff” that walked into the room before you did.
That’s part of the issue and disconnect.
You think you’re addressing behavior. They think you’re questioning competence and the walls immediately go up.
Said. Heard. Remembered.
You already know this: there are things that said, things that are heard, and things that are remembered and rarely do they match.
There are things that are Said. There are things that are Heard. There are things that are Remembered. Rarely are they the same.
This is where strong leaders separate themselves.
Instead of explaining more, they verify.
Ask: What did you hear me say?
This question does three things:
Slows the emotion
Surfaces distortion.
Builds trust
If you find that there’s disconnect, it’s not “you misunderstood.” It’s “I didn’t communicate that clearly enough.”
Ownership lowers defenses and fast.
Here’s another perspective. Let’s say someone is communicating something to you. Use this phrase, and get aligned on what is being communicated.
“Here is what I heard you say…”
Before correcting behavior, reconnect to objectives.
What are we trying to accomplish?
What does good look like?
Why does this matter?
When you anchor to shared outcomes, feedback feels like alignment, not an attack.
Actions You Can Take This Week:
Before your next hard conversation, write down:
Your objective.
Their objective.
The specific next step you want to leave with.
And be ready to ask, “What did you hear me say?'“
That’s it.
Clarity. Ownership. Follow-through.
Voices from the Trail
Meet Heli Nehama-Ozery
Heli Nehama-Ozery, an expert in leadership development and organizational design, dives into the transformative power of feedback in leadership. From strategies for giving and receiving feedback to using it as a catalyst for growth, Heli shares her insights on creating cultures that thrive on learning, reflection, and effective communication.
Listen to this episode on Spotify
Hitting the Trail
Mike works with GTM and revenue leaders who know their teams are capable of more, but need space to think, recalibrate, and align at a higher level.
Through executive retreats, leadership offsites, strategy sessions, and curated peer discussions he creates the room senior teams rarely give themselves. Room to surface assumptions, name the friction, and make decisions that move their teams and business move forward.
Honest dialogue. Strategic focus. Clear next steps.
If your leadership team needs space for real strategic thinking, let’s talk.
Announcements
Are you struggling with the basics around AI and the application of it in work? If you’re into emerging and enablement tech, check out Brent and Mike’s live session on all of Mike’s social channels (Youtube, LinkedIn, X) Monday - Thursday mornings at 5AM Pacific / 8AM Eastern.
If you’re curious about how emerging and enablement tech can help you in your role, join them live Monday - Thursday morning.
That’s it for this week.
Keep putting one intentional step in front of the other - the view gets better and better as you climb.
We’d love if you would share this with someone who is ready to build their sprints for the new year.
The Find My Catalyst Team