Most of us struggle to have hard conversations at work. We’re either too nice and don’t get our point across, or too direct and leave people feeling defensive

Do you fall into one of these traps? If so, read on, because kind candour with colleagues is one of the best skills you can develop as an executive.

When you get it right, you’re able to tackle hard topics, maintain relationships and be seen as a true professional.

When I was an exec, our team worked with a woman named Linda who was helping us with our interpersonal relationships as a management team.

This is the first time I really ever saw kind candour in action. You see, my company already had the culture of being direct, so we hashed difficult things out all the time. The problem is that there was a lack of trust, and people’s feelings were often hurt. Grudges were held. Not good.

We were hoping Linda could help.

When I first met Linda, she just seemed like this sweet older woman. But let me tell you, Linda could call you on your shit! And she did it in such a kind way, you’d thank her.

I was so impressed with this skill that I vowed to master it as well. That perfect combination where the person you’re speaking with knows you have their best interest at heart, even when you’re giving them bad news, constructive feedback or debating their great idea.

I realized pretty quickly how unique Linda was. Many people don’t get it right!

And when that happens, the conversation is either ineffective or confrontational. Neither of which results in the end goal.

Don’t get me wrong, I’m NOT saying this is easy. Even after meeting Linda I spent years of my career trying to get this right, and I never really stopped working on it. But I do believe it’s worth the effort.

I’m going to dive into some of the key elements needed to successfully implement kind candour with your colleagues and team.

Start with a foundation of trust

Without trust, doing this well is really hard. Because you’re relying on the person who’s on the receiving end to assume you have good intentions. And when you’re sharing constructive feedback or disagreeing with their great idea, it’s easy for them not to assume this.

So invest in building real relationships with the people you work with. Not just your direct reports, but your counterparts in other departments.

Whenever I’ve started a new leadership role, one of the first things I’ve done is to get to know the org structure and determine who I should be having regular 1:1s with, outside of my immediate team.

As a sales leader, this would often include: Marketing, Customer Success and Product at a minimum.

When someone knows you as a person and trusts your character, you can have very different conversations with them. This will involve a time investment but in my experience, it’s well worth it.

For your direct reports this goes without saying. But the thing I’ll add is, instead of just running down a tactical ‘to do’ list in your weekly 1:1s, ensure you’re having deeper conversations at least monthly. As them about their career aspirations. Get to know the names of the people in their family.

Show you actually care.

Now that you’ve invested in creating world class relationships, let’s get into the conversations themselves. Here are some great rules of thumb when navigating a difficult conversation.

Ensure you’re aligned on the goal

So often the issue is not even what you’re debating about because you haven’t aligned on the goal. I’ve sat in leadership offsites with senior execs who were essentially having 2 different conversations with each other. No wonder it was difficult to come to an agreement!

So even if you think you’re stating the obvious, it can be worthwhile to bring the conversation back to basics. What are we talking about here? What’s the ultimate goal of this project or pivot? Are we aligned?

Seek to understand and lead with curiosity

Habit 5 of The 7 Habits of Highly Effective People is: Seek first to understand, then to be understood. Simple, but powerful shift.

Most of the time we are first and foremost focused on seeking to be understood. The person on the other side of the conversation is doing the exact same thing! And we wonder why we’re getting nowhere.

I’ve witnessed this happening in conversations right in front of me and it’s amazing how not one person involved in the argument picked up on it.

Flip the script. First, seek to understand what your colleague is saying. Be curious here – ask questions and consider the fact that they are likely at least 10% right!

Reflect back to show you’re listening

Reflecting and paraphrasing are 2 great tools for authentic listening. People want to feel heard, and often when they don’t, they just keep repeating the same points over and over.

Have you ever seen 2 people do this? I have and it’s frustrating as hell to watch!

Instead, summarize what you’ve heard and repeat it back to your colleague. Ask them if you’ve got it right, and only once they agree add in your points or another idea.

Keep it objective

Humans are just so messy… my former boss admitted to me once that he would have been much happier if we were all just robots who could keep things 100% objective.

Now, that’s not realistic, but when debating you CAN choose to keep it objective. Never insult the person or their team. Don’t make it about assumed intent. Simply stick to the objective facts. When possible, relate your point back to the bigger goal. It’s MUCH more effective.

If you’re giving feedback to someone on your team, make it about the work or the numbers instead of the person.

Be mindful of language

Again… the feelings. Language really matters, especially when you’re having tough conversations.

Let’s go back to the example of having to talk about performance with someone on your team. If this is the first time you’re broaching the subject, frame it in a way as to ask them what they need in order to get back on track. Or if you’ve noticed their work ethic or attitude has shifted, ask them if they’re okay instead of going right to the performance stuff.

The language we use can either communicate care and respect or the opposite.

If you think someone’s strategy idea sucks, don’t say, “I think this sucks”. Instead try, “My concern with this approach is…”. See what I mean?

Take the time to really think about what language you want to use before you say something. Even have a few phrases that you like prepared to use when needed. So much better than winging it!

The truth is, you’re going to have to have hard conversations at work. And if you’re looking to be an exec, well, get ready for more hard conversations at work.

Finding a way to do it and still maintain great relationships is the key here.

Until next time friends… ✌️💜

Katy