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Tricky Conversations: Effective Leadership Communication Strategies

Updated: Jul 19, 2023

Tricky conversations are an inevitable part of our personal and professional lives. These are the conversations we dread having but cannot avoid, such as discussing sensitive issues with team members, addressing performance concerns, or negotiating a fee increase with a client. These conversations can be uncomfortable, emotional, and sometimes confrontational, making them challenging to navigate.

by Stephanie Bickel

Effective Leadership Communication Strategies

Use phrases like these to remove the emotions and get people to collaborate with you.

1. That meeting had some highs and lows. I have some ideas for next time.

2. I have some ideas for how our next client meeting I’d like to discuss.

3. I’d like to talk about _______ with you, but first I’d like to get your point of view.

4. I need your advice on x. Is now a good time to discuss?

5. I received your email. Could we talk about that soon?

6. I think we have different views on _________________. I’d like to understand yours more.

7. Your comments about x were very interesting. We may have different information. When is a good time to discuss?

8. I notice a pattern in our meetings that I wanted to discuss with you, and I wonder if you would be up for an experiment.

Do not avoid these conversations. You can do more damage to your teams and client relationships by not sharing your feedback and concerns. Leaders mature fast when that practice escalating concerns.

Avoiding these conversations can lead to misunderstandings, missed opportunities, and damaged relationships. Having these conversations builds stronger relationships, improves our communication skills, and achieves better business results all around.

BONUS: Make this month all about helping your team be more candid with one another. Schedule a team meeting and show one of these videos below. Then, discuss how this topic and tips are resonating with their current work.

(Mel Robbins) (4:50)

Having a difficult conversation can be nerve-wracking, but it's a crucial skill to master for both personal and professional growth. To have a successful conversation, it's important to prepare thoroughly by defining the issue, understanding your own emotions, and anticipating the other person's reaction.

Observe how the boss asks questions to solve problems with the employee (2:23).

(Kara Ronin) (8:01)

Tough conversations at work can be challenging, but they are essential for addressing issues and moving forward as a team. Whether it's discussing a sensitive topic with a coworker or addressing a performance issue with a subordinate, there are tips to make the conversation more productive and less stressful.


Fast track your career path. Speak by Design University is a one-of-a-kind leadership communication program. It’s the only leadership communication program in the world that gives you access to self-paced learning, group coaching and training and, most importantly, private one-on-one coaching. Learn more and register.


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