A Recent Coaching Session

I want to be a powerful leader.

What would that look like?

I’d be empathetic, caring AND make BOLD requests.

How are you now?

I hold back with my peers even though I’m powerful with my direct reports.

What gets in your way?

I want them to like and respect me. I care about them and how they feel about me. 

What do you want?

High trust, to solve the ‘hairy’ business challenges none of us can tackle alone.

What’s the impact of NOT being straight with them?

I’m playing small. By attempting to accommodate, I’m holding back. I’m in semi-retirement, in the back seat. I know better and feel shame that I’m not leading.

What’s the story/mindset that keeps you from having the real conversation?

If I say what’s on my mind, I WILL BREAK trust. I hedge because I want to be liked.

What do you want to create?

I want to be empathetic, caring and straight so we can deepen relationships, and I want to increase partnership and solve difficult business challenges.

What’s the new story you’d take on to engage like that?

I need to engage IN ORDER TO develop trust.

What would that look like?

I would care about and understand people’s feelings and their points of view. I would also be cognizant of and prepared to address issues directly by providing non-aggressive, straight feedback. I will focus on clear and precise messaging, read the audience and check to make sure they’re with me.

What would that get you?

Straight conversations from the start will set me free! 

The Vicious Cycle 

This recent conversation was with an influential leader on a leadership team committed to high performance, whose team is facing enormous business challenges. It became a vicious cycle: the expectation of all team members to regularly engage in real, direct conversations (which most leaders feel are hard to have) and when they don’t consistently practice this with everyone, they feel shame or guilt about not creating strong, trusting relationships.

It is common for leaders to feel stuck. They want to be influential and create impact. They are committed to working cross-functionally, building partnerships and solving business challenges, yet they are uncomfortable and unsure about how to have tough conversations and know they must. Leaders can no longer solve issues in silos. They must be willing and able to make BOLD requests, to manage conflict and depersonalize, and to give and receive feedback.

How to Have the Hard Conversation

To make hard conversations easier, there are three areas of focus. You may be able to cover these on your own, or you might need to discuss with a peer or trained coach.  

The three focus areas are the biggest challenges that get in the way of having real conversations, so use these three things as a checklist when determining your starting point about where you need to focus:

1. Mindset. Most leaders ask their coach for tips and skills about how to have hard conversations. However, the first place to start is on Managing Mindset. This means looking at the current story or interpretation around having the tough conversation in the first place, and identifying the new story, as you can see above. This is where the breakthrough lies and once you have the insight, it becomes possible to practice the steps below.

2. Comfort Zone. We are wired as humans to stay safe. The answers my partners and I often hear leaders give as to why they don’t want to step out of their comfort zones are: I want to preserve the relationship; I don’t know how they’ll respond; it’s scary and uncomfortable for me; etc. We will cover stepping out of your comfort zone in future posts, so stay tuned. For now, look for ways you can become 10% more courageous and say what you know needs to be said. 

3. Skills. Do not hold back because you haven’t mastered the skills or gotten the perfect tool to give feedback, make BOLD requests, or be honest. (Don’t worry! We will cover useful skills and simple tips we share in high performance leadership team sessions in future posts.) For now, rather than waiting and hoping things improve on their own (which they won’t), you will make progress if you are:

Authentic and honest about how you are feeling (I’m nervous to have this conversation);

Clear about your intention (I value our relationship and want to build trust); and

Clear about what you want (I want to partner with you on solving this challenge together). 

The client referenced above is a role model leader who used coaching to explore how to be a powerful leader, which ultimately focused on how to have hard conversations. Ninety percent of our coaching time focused on step 1 above of Managing Mindset. We ended the conversation by choosing three key peers to speak to and a timeframe in which to have the conversations. We also discussed a few tips to ensure successful conversations. 

Ask Yourself

  • What is the “story” or mindset I have around having hard conversations? (Hint – What is your inner dialogue or Vicious Voice saying when you think about saying what you are REALLY thinking?)
  • What is the new “story” I’d need to create to engage? (Hint – If you’re not sure, ask yourself what it is costing you, your team, the relationship, and the business by NOT having the hard conversations.)
  • What key stakeholder would I be willing to have a conversation with and say 10% more of what I’m thinking/feeling? (Hint – Think of the person with whom you have the strongest relationship. Start small, get some wins and practice consistently.)

Please feel free to reach out to me and my team if you’d like to connect about how to apply these ideas, to help members on your team navigate these conversations, or to discuss the biggest current challenges you are facing today.

Wishing you good mental, physical, emotional and social health.

Remember to find resources to inspire you here.

Yours in practice,



If you are interested in exploring how to unlock the potential of yourself, your team or the women in your organization, contact us for a complimentary discovery conversation.