Of every 10 coaching sessions, 7 or 8 of them wind up at some version of this:

You’d be shocked how often these “difficult conversations” stand in the way of achieving our goals or getting to where we want to be.

You know what else is shocking?

These conversations we avoid aren't generally in our personal lives: conversations with a partner or a friend.

MOST of them fall into the “work life” category: conversations with coworkers, a manager, a direct report, a contractor.

Have you ever wanted to have a conversation with someone at work and backed off because you weren’t sure how to go about it?

You’re not the only one.

Why do you think conversations are so much harder at work?

Because we’re less free to be honest about our feelings in a professional setting — and feelings are part of every single conversation, especially the difficult ones.

Let's dig into how to fix this.

Today, you'll learn:

• Why having learning conversations at work is difficult for us, but also super important to master
• How the highest performers approach challenging conversations to make them successful, in terms of tangible wins AND relationships
• Step-by-step guide you can follow to have better conversations with anyone in your life, but particularly at work

Meet Caitlyn.

One of Caitlyn’s direct reports, Mike, had poor performance for months, mostly due to his difficulty collaborating with teammates on other teams. But Caitlyn was struggling with how to handle it. She’d tried talking to him about it various times, and Mike would promise to do better, to try harder, but things were just getting worse quarter after quarter.

In a coaching session, Caitlyn and I walked through a new approach, moving from a conversation full of concerned reprimands to a conversation focused on curious learning. We discussed how she might bring her feelings to the table, invite Mike to do the same, and then collaborate around how to best meet everyone’s needs.

We practiced and role-played the scenario a few times, until Caitlyn felt confident to try this new approach with Mike.

The next week, she reported back:

The conversation had gone surprisingly well, with just a bit of awkwardness at the start. Once she got through that, she’d been able to hear Mike out on a deeper level and discovered a potential obstacle (and it's solution): Mike needed help navigating his own learning conversation with the teammates he collaborated with most often. He didn't know how to approach them, and thus working together was tense and not very successful.

With the training I’d given her, Caitlyn was able to coach Mike through how to approach his own conversations, and sent him on his way to repair his work relationships.

A few months later, Mike was collaborating smoothly and his overall performance was better than ever. Because of it, Caitlyn (and everyone involved) felt a profound sense of relief.

All because they both learned how to have better conversations.

Why is it so difficult?

We all know communication is at the heart of our interactions, but we somehow forget that it’s just as important at work.

You may be focused on your heads-down work as a marketer or engineer or designer UNTIL a thorny situation pops up, and then the frustration and awkwardness starts taking a toll.

Whether you're writing code of designing a brand, the success of your career also hinges on your ability to communicate successfully, especially when what you have to say isn’t necessarily super easy.

Just like Caitlyn and Mike, you can learn to have those conversations that matter in a better way.

And in true Marcella form, I’ll ask you:

What happens if you DON’T?

If you don't learn to have these conversations, you’ll pass up growth of all kinds:

• External growth: promotions, relationships, collaborations, leadership, clients, better project outcomes, etc.
• Internal growth: peace of mind, connection, boundaries, etc.

That’s why my approach to coaching deals not just with maximizing performance but also boosting how you feel.

Both matter.

Because YOU matter.

We are human beings, not human doings, after all.

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How to turn difficult conversations into learning conversations

You must be asking yourself, how do I have better conversations, then?

This is the part where I tell you how.

I’ll share the full framework in my upcoming online course (you can sign up to be notified when it's live) but right now I’ll walk you through the first part of what I did with Caitlyn:

• Establish rapport to make it clear your intentions are good. When you care personally, the person is way less likely to be defensive about any guidance you give them.
  • Try starting with something like, "I really admire the way you..." (but make sure you mean it.)
• Define your feelings and needs with clarity. Moving into the challenging part of the convo, use the formula "I'm feeling ___ because I'm needing ___." You can even ask the other person to share their own feelings and needs, so you can then collaborate on how to meet everyone's needs more successfully.
  • The feelings and needs that come up will likely surprise you. Speaking about them helps you gain clarity and find new solutions you hadn't considered.
• Take a beat to self-regulate when things get tense. It's inevitable to have emotions and thoughts running amok, but you can take deep breaths and pause before replying.
  • Pausing has two benefits: gives you a chance to relax any tension that comes up and also helps you come across as thoughtful and caring.

There are more steps, of course, but this should get you started in thinking through how to have those conversations you’ve been fretting over (and maybe even putting off).

I’ll share the next few steps in the next edition of the newsletter, so watch out for that in 2 weeks.

(If you can’t wait that long, reply to this email and we can run through your particular situation in a session.)

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Always be practicing

You’ll never be done having conversations that feel challenging and tense because you’re surrounded by humans with different perspectives, beliefs, and agendas.

That’s totally okay, and it’s what brings color to our world.

But you’ll get better every time you practice turning the conversations into learning conversations where everyone can walk away feeling heard, collaborative, and respected.

Here's a recent example from my life:

Last week, I had a very challenging conversation with someone in a spiritual group I’m a part of, and I’m so happy with how it went. There were moments of tension, and I definitely had to self-regulate HARD a handful times, but the conversation ended on such a high note with the person thanking me for helping them gain clarity on the situation. They even expressed feeling much lighter and at peace. Days later, I received a follow-up text repeating their appreciation for me taking the time and effort to discuss things directly and bringing things to a productive, peaceful win.

(The coach in me is a switch I can’t easily turn off in my personal life. 🤷‍♀️)

Whether it’s me or someone I coach having these conversations, I see again and again just how powerful it can be to learn to have challenging conversations in a collaborative way with a focus on listening and learning.

Dare I say humanity would be better off if we all learned and used some of these skills more often?

Get on the waitlist for the Learning Conversation course

In just a few weeks, I’ll be releasing the full course on how to turn awkward, difficult conversations into better, learning conversations.

The investment will be $47 for the full step-by-step framework you can follow to make your conversations more successful and way less tense.

Through videos and worksheets, I’ll walk you through exactly how to prepare, what to say, what NOT to say, and how to guide the conversation toward a collaborative win for everyone involved.

And exact scripts you can use to make your conversations foolproof.

I’ll be letting 10 people in at a time, so run don't walk to sign up for the waitlist:

That's all for this edition

I’m wrapping this email from the skies as I fly home from my 15th Boston College reunion.

It was so nice to bask in the memories, friendships, and places that hold such a special place in my heart.

But wow running to catch the BC bus in the biting cold and pouring rain really took me back to the stresses of student life, as well. 🫠

Now I’m looking forward to wrapping my arms around my family as soon as I land.

Not to mention put the finishing touches on the course, so you all can start improving those conversations sooner rather than later.

(The holidays are a hotbed for awkward and tense convos, am I right? Don’t fret, it’ll be ready before Thanksgiving. 😉)

Until next time, friends.

You got this. ✌️

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All the best vibes ✨

Marcella Chamorro

Mental Health Coach + Executive Coach

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