Succeeding at Hard Conversations

Unless we have the emotional intelligence gained from tough feedback, we are unlikely to be suitably nuanced in communicating to others.


During this time of teams being physically apart, it is easy for leaders to avoid difficult conversations.

Empathy and compassion matter from leaders at this time, but you will not be serving your team if you use those as an excuse to avoid all criticism or challenging feedback.

For that reason, I am hearing from a number of my clients, who value some help on having more challenging conversations, and am pleased to share another book recommendation. This review covers a book that I have found provides a very useful model.

In her popular book, “Radical Candor,“ Kim Scott shares a model developed during her work at Google and Apple, as well as coaching CEOs in a number of successful startups.

It’s an easy read (though will provide you with plenty of challenge to put the theory into action). In this review, let me walk you through the key concepts and recommended steps (while still recommending that you buy the book).

Radical Candor: the central model of the book

At the heart of this book is the model that Kim presents to help define the term radical candor.

This term and its relevance to having difficult conversations is defined by considering two dimension in a 2×2 matrix. On the horizontal axis, you have the need for challenge directly (rather than avoiding saying anything, or moaning to others, at the other extreme). On the vertical axis, you have the need to care personally (rather than attack verbally just to win, at the other extreme).

The model:

difficult conversations image 1
Radical Candor 4 quadrant model (from Kim Scott)

I hope you can see that this definition of challenging conversations that can help (the radical candor quadrant) is useful in avoiding common mistakes. Kim emphasizes that radical candor is not brutal honesty or obnoxious aggression, as distinguished above.

However, Kim also (rightly in my view) highlights that a more common misstep is to back off a challenge that is needed for fear of hurting someone’s feelings or in response to emotion. That pitfall is defined as ruinous empathy above and is a mistake I’ve made in the past.

Start by learning to take it yourself

Moving on to putting that model into practice, this book recommends first experiencing being the recipient of criticism. In other words, solicit candid feedback.

It sounds easy, doesn’t it? Yet, most bosses will acknowledge that they rarely hear critical feedback from their peers or team that will help them improve. Unless we have the emotional intelligence aid of learning to experience receiving this, we are unlikely to be suitably nuanced in communicating it to others.

This book tackles the challenge head-on, with another model to guide you in requesting criticism. Kim proposes the following steps:

  1. Ask a go-to-question
  2. Embrace the discomfort
  3. Listen with the intent to understand, not respond
  4. Reward the candor

As an executive coach myself, I can see so much coaching wisdom in each of these steps: practicing asking open questions that cannot be answered superficially, getting comfortable with silence, silencing your inner defenses and offering appreciation even if it hurt.

Readers could learn so much from this book, even if they only became skilled at putting this part into action.

Praising can be difficult, too

When hearing the common term, difficult conversations, it is tempting to always think of giving or receiving criticism. But delivering praise can be hard, too.

As Kim highlights, it is easy to remain so high-level in praise that it does not help the hearer and comes across as insincere -- just saying that.

This book has a framework to help you provide more effective praise. It uses the acronym of COR:

  • Context: What is the context for your feedback?
  • Observation: Describe what the person did or said.
  • Result: What is the positive consequence that is most meaningful to you and them?

Such a simple formulation, but following that guidance can make such a difference in communicating praise that people take on board.

See also: Mental Health Even More Critical Now

Mastering criticizing productively

The book does go on to what readers probably expected guidance about: how to challenge someone, or communicate criticism in a way that is helpful. That balance is described in Kim’s initial model, of challenging directly while also caring personally.

Here, too, Kim provides a model/framework/acronym. It is labeled as HIP, but really it’s the slightly more clunky HHIIPP:

  • Humble: realize it is only your perspective
  • Helpful: make sure your goal is to help the person
  • Immediate: provide as close as possible to the event
  • in Person: where possible, meet in person
  • Private: find a private place away from others
  • not about Personality: Be specific and focus on behavior, not motive

Once again a helpful guide in a book packed with practical suggestions and examples from the rough and tumble of office life.

Are you having difficult conversations?

I hope that book review encourages you to both read this book and put this advice into practice.

Do you agree that difficult conversations are being neglected? Have you ever been trained how to do this well? How are you managing to still have these types of conversations when working from home?

I look forward to hearing your experience and advice.

Paul Laughlin

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Paul Laughlin

Paul Laughlin is the founder of Laughlin Consultancy, which helps companies generate sustainable value from their customer insight. This includes growing their bottom line, improving customer retention and demonstrating to regulators that they treat customers fairly.


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