In The Making

In The Making

Share this post

In The Making
In The Making
How to master uncomfortable conversations (fast)
Paid Section

How to master uncomfortable conversations (fast)

The quick way to win at the hardest and most impactful skill in Leadership

Heather Elkington's avatar
Heather Elkington
Oct 17, 2023
∙ Paid
4

Share this post

In The Making
In The Making
How to master uncomfortable conversations (fast)
Share

How to master uncomfortable conversations (fast)

Todays headline chapters are…

  • WHY do I need to be having these conversations? They’re scary

  • If I could go back in time

  • The 5 things you need to know to get good at uncomfortable conversations… (FAST) Including the words I say to myself before any uncomfortable conversation

  • The full method in HOW to deliver them

WHY do I need to be having these conversations? They’re scary

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”
Tim Ferris

In the world of work (or otherwise) it's easy to fall into the trap of being ‘nice’.

We love to shy away from difficult conversations to avoid hurting someone's feelings or creating conflict.

But in the long run in your Leadership journey, this niceness will lead to HUGE issues for yourself and your team. Gossip, surface level relationships, and it’ll put a cap on how successful you truly can become.

To foster a positive, fulfilling and healthy work environment that encourages personal growth and the entire team pushing toward your companies goals, we need to shift from being NICE into being KIND. By delivering the hard truths and having the uncomfortable conversations.

“Uncomfortable conversations aren’t fun … However, stepping into them is an essential ingredient for effective leadership and a hallmark of a successful career.
By being transparent with the other person you open yourself to deeper, stronger connections in life and at work.”

Michelle Gibbings, CEO Magazine

If I could go back in time…

Rewind 7 years, I’m an assistant manager at Harrods in London with a direct team of 8 people. Uncomfortable conversations were my biggest fear. Telling someone about their unacceptable lateness, delivering difficult feedback about the standard of their work, or god forbid firing someone.

But fast forward to 2023 and I am and feel like an expert in these conversations, I’m addicted to having them. Why? Because I see how KIND they are. I see how much it strengthens the humans in my team and the relationships I have with everyone around me.

So if I could go back a few years, these are the few key things I’d tell myself, the secret sauce, to becoming an expert in uncomfortable conversations (and FAST)…

I’ve been testing and mastered these over the last 7 years, and boiled it down to these 5 steps… Here you go 👇

YouTube video version below, or paid members keep scrolling for the FULL framework


The full 5 steps method mastering uncomfortable conversations below is behind a paywall as it is incredibly valuable. Paid members keep scrolling to access.
Free members, to access you can subscribe below to get access to the uncomfortable conversations framework, along with the Leadership frameworks and practical strategies I used to scale a business to £2m+ ARR.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 Heather Elkington
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share