How to Get Comfortable with Uncomfortable Conversations: A step-by-step guide

Who likes being uncomfortable and having difficult conversations? I know I don't! But the reality is, as long as you are breathing, at some point they are likely to happen.

During 2020 in the height of the pandemic and the Black Lives Matters movement I worked on a corporate workshop called 'Getting Comfortable With Being Uncomfortable'. It received mixed reviews...which I guess is to be expected with a workshop with that title! I definitely had to put some of the recommendations from the course into practice to receive the not so positive feedback.

One of the outputs of the session that people did find useful was a 'cheat sheet' that Lisa Bent and I developed to provide a step by step guide to helping people navigate difficult conversations at work.

If you have some difficult conversations planned, hopefully this guide will reduce your anxiety (a little) and take the sting out of receiving or delivering the message.

Remember, its often not what you say...but how you say it...and when you say it.

Good luck!


Mastering these techniques will help you build more empathetic team working relationships and help you to become more comfortable with uncomfortable conversations

Are you aware of your preferred people management style and how that is experienced by others?

It is often said people do not leave companies; they leave managers. The more senior you are, the greater your position of power and the likelihood that people are adapting to your style of working.

Flexibility in your approach is a necessary requirement if you have diverse teams and want to empower them to achieve their potential…and help you to achieve your organisational goals.

1. The New Normal

Self-awareness is the ability to objectively evaluate yourself, manage your emotions and align your behaviour with your values. A manager that understands themselves is in a better position to understand their team members, build good working relationships and identify how to lead their team in any situation that may arise. Managing a situation that is unfamiliar and not in alignment with our current values and beliefs needs ‘emotional intelligence’.

“Emotional intelligence (EI) is the practical ability to use emotions to inform the actions you take to achieve the best outcome for each situation”. Prof. Peter Salovey, Prof. John Mayer, David Caruso PhD

Emotional intelligence acknowledges the importance of being aware of our own emotions, understanding how they can impact people negatively and positively whilst learning how to manage them. The World Economic Forum, ‘Future of Jobs report 2018’ cite emotional intelligence (EI) as one of the top 5 skills that will be required by 2022; therefore, like coaching and mentoring, EI is no longer seen as a desirable requirement but a critical skill in times of transformational change and transition.

Being comfortable in discomfort is an art and one which begins with self-awareness. The ability to objectively evaluate yourself, manage your emotions and align your behaviour with your values can create better outcomes at work. When you understand what is going on for you, you are in a better position to self-care and listen to others.

Based on your answers is your Management style, Directive, Democratic, Hands-off, Transactional or Transformative/Coaching-led?

Additional question

  1. What are your values?

  2. How do they relate to the values of your organisation?

  3. Who is your favourite boss? (past or present)

  4. What is their management style? And what qualities do they possess?

  5. Where do you see the gaps in your skill and way of being as a manager?

2. VALUES & FRAMES OF REFERENCE: Improving self-awareness

When you understand what is going on for you, you are in a better position to understand and listen to others.


  • Think about and acknowledge your frames of reference and how your emotions and moods can be impacted when they are challenged. How does this impact your interactions with your team?

  • Identify your strengths & weaknesses and try to improve key areas using the GROW model.

  • Try to manage and control your emotions before addressing situations and making decisions that are based on assumptions.

Continually reflect on the outcomes of situations, and how they might be better approached next time.

3. CULTURAL INTELLIGENCE: Improving social awareness

Cultural Intelligence (CQ) is the ability to cross boundaries and thrive in multiple cultures. The world is shrinking and leaders from different cultures are finding that they need to understand the cultural nuances of geography, faith, gender, sexual orientation, generation, to work together better.

  • Listen carefully to what team members say and seek to understand and empathise with their emotions, needs and concerns.

  • Pay attention to how they are showing up (unusually quiet, emotional, making mistakes in work) and check in to see if they need any support.

  • Identify how best to communicate with each team member to ensure they feel understood, heard, and supported.

  • Continually reflect on how you manage your team in situations that arise, the outcomes, and how such circumstances might be better approached next time.

4. BUILDING EI TEAMS: Giving feedback

Focusing on a specific task, regular feedback helps individuals know what they have done well and what can be improved (developmental feedback). As feedback is sometimes perceived as criticism, it is always good to end with positive feedback.

When done sensitively and skillfully, feedback can help team members:

  • remain focused and motivated.

  • improve their performance gaps and build on their strengths.

  • develop their skills and handle more responsibilities.

Having difficult conversations

Managing staff and engaging in teamwork can be the most rewarding aspect of a job but may also be the most challenging at times based on a variety of social, environmental, business, political and human issues.

5. CREATING A-HA MOMENTS: Self-Reflection

Acknowledging your reaction to certain situations, provides the opportunity to change your behaviour to increase better outcomes. How do you show up in challenging situations? (i.e. do you become silent, defensive, try to flee or freeze?)

  1. What emotions surface when you experience uncomfortable situations?

  2. What is the impact to you and others?

  3. Where has your fear come from?

  4. How can you be more confident?

Learning to get comfortable with having uncomfortable conversations is key to avoiding the following outcomes:

  • No improvement in an activity that needs to change.

  • Gives the impression that nothing needs to change when it does need to change.

  • Gives the impression that you have not noticed or do not care.

  • Patterns of avoidance continue

Receiving feedback

Understanding who you are and how you behave as a manager or colleague, is central in understanding how individuals and teams achieve their potential.

Feedback is a two-way process, necessary for self-development. Feedback from your team not only gives further insight into who you are and how you behave from the perspective of those you manage or interact with, it also tells your team that you are also willing to receive what you give.

Feeling vulnerable is normal however, if you adopt the coaching style to people management, your team will mirror your style. Feedback does not need to be scary. Thank, Absorb and Reflect.

Individuals who feel supported, heard, trusted, and acknowledged become high performing individuals. Leading and building a good working relationship with clear communication, collaboration and a coaching style approach are the stepping-stones.

Conclusion

Who we are is central to everything, and self-awareness, self-reflection, social-awareness and enquiry are key components to becoming a more emotionally intelligent leader/manager or colleague.

Developing these skills can help you to more effectively build high performing diverse teams who can create ‘magical a-ha moments’ through being open and learning to help teams and colleagues navigate uncomfortable conversations and situations.

(c) 2020 Written by Zena (Tuitt) Collins and Lisa Bent

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