Tough talk: How to balance confidence, candor, and kindness in difficult conversations

Tough talks can be awkward and unpleasant. But they’re inevitable.

Whether you’re dealing with performance issues, workplace conflict, sharing negative feedback, or even discussing personal issues, being able to address sensitive subjects is an essential part of supporting employees.

Having difficult conversations will always remain a challenge for managers and employees alike, but there are a few techniques you can use to make your tough talks easier. The key is to approach them with the right mindset, empathy, and preparation. 

In this session Sana Keshtkaran, Performance, Executive Coach & Leadership Consultant, and Alyssa Conley, Head of Coaching Success at Lingo Live, will discuss how to navigate having difficult conversations at work with actual examples.

We’ll cover a few scenarios where you’ll have to prepare for a difficult conversation at work, such as:

  • Encouraging an employee to improve their performance
  • Dealing with co-workers with toxic behaviors
  • Resolving conflict between team members
  • Asking for a raise or promotion
  • Giving negative feedback

Why Do We Avoid Difficult Conversations?

It’s natural to shy away from workplace conflict. It throws you out of your comfort zone. These conversation require you to manage your emotions and can go awry very quickly. The problem is that you don’t address challenges if you don’t have those conversations though. You might be avoiding a difficult conversation because of:

  • Fear of confrontation
  • Lack of confidence
  • Bad past experiences
  • Fear of rejection
  • Not sure how to approach it
  • Fear of upsetting someone

Whether as a leader in your profession, or in your personal life, avoiding difficult conversations sows seeds of trouble.  The more you hold off on having an important but difficult conversation, the greater the strain you put into that relationship.

Join us to learn how you can navigate difficult conversations, as a manager or as an employee, and create a better workplace environment for everyone.

Having Difficult Conversations


Sana Keshtkaran

Sana Keshtkaran

Performance, Executive Coach & Leadership Consultant

Sana Keshtkaran is an Executive and Leadership Coach. She has 10+ years of experience working with global companies such as Meta, Airbnb, GitHub, GoPro on their human capital initiatives. Sana’s background is in the areas of industrial/organizational psychology and business analytics. She coaches and trains CEOs, leaders, entrepreneurs, teams and high-performers from startups to Fortune 500s.

She supports her clients to level up in leading diverse teams and help them improve their readiness for change and innovation. Sana also coaches entrepreneurs in the Nasdaq Milestone Maker program, helping late-early to mid-stage entrepreneurs take their businesses to the next level.

Sana turns neuroscience and psychology research into accessible, easy-to-understand, practical strategies. Through individual coaching, she helps clients identify their blind spots and vicious cycles, and from thereon help them develop new mindsets and skills. As a result of working with Sana, her clients become better leaders and create high-performing teams

Alyssa Conley Head of Coaching Success

Alyssa Conley

Head of Coaching Success at Lingo Live

Alyssa Conley is a professional coach and learning designer who specializes in the intersection of creativity and cultural competence as a means to strategic leadership transformation both at the individual and organizational level.

Her approaches and insights to leadership are shaped by 15+ years of experience in teaching, coaching and management, and 10+ years spent living, traveling, or working in 18 different countries. She is trained in applied cultural anthropology and sociology and holds certifications as a Professional Leadership Coach, Korn Ferry Leadership Architect, Team-Building Facilitator and TESOL Instructor.

As Head of Coaching Success at Lingo Live, Alyssa manages the day to day operations for a global community of coaches who provide coaching to thousands of business professionals around the world.

Learn how to navigate difficult conversations at work