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Coaching Brilliant Minds with Strong Personalities: Tales from the Trenches


I've had my fair share of coaching leaders who tend to bulldoze over everyone and everything in their path. But full disclosure, I've been there, and I know them because I also was that hot-headed Italian that needed softening up.


Now, I often receive requests to work with leaders with strong personalities. So, let me share what I've learned along the way that you can apply when engaging with them:


  • Engage with empathy: Remember that strong-willed leaders are often that way because they want to get things done and be successful. So, start by understanding their perspective, where they're coming from, and what drives them. This will create a stronger connection, and they'll be more willing to listen to you when you bring up something difficult to face.

  • Be direct: Don't beat around the bush; these leaders are sharp and can see right through it. They'll respect you even more when you speak their language. Don't be harsh in your language, but be upfront, be direct, and call it like it is.

  • Create scenarios: Use hypothetical scenarios to show how others perceive their actions and behaviors. Even better, ask others through a survey or interview. Without fail, my clients could see things from a different perspective and make a change for the better when they receive feedback from their peers.

  • Don't be afraid to push: These leaders are used to getting their way, but that doesn't mean they always know best. They won't respect you if you're a pushover, so be confident, and don't be afraid to push them out of their comfort zone to help them grow.

  • Be bold and vulnerable: When it comes to strong personalities, it's essential to be confident and assertive, but don't forget to be vulnerable too. I'm not afraid of sharing my past mistakes. Showing you understand and relate to their challenges can help build trust and credibility. It also helps them see that vulnerability is a form of courage. If you did it, so can they.

  • Play the role of the "devil's advocate": Ask if you can shadow their meetings and calls as an observant. Sometimes, leaders with strong personalities can be a little set in their ways, so it can be helpful to observe them, challenge their thinking and help them see things from a different perspective. Just be sure to do it with a smile and a healthy dose of humor!


Now, for you with the dominant personality, it's time to practice something different and get you a bit uncomfortable. You have a strong character; you can face the challenge!


  • Practice active listening: Listen to others' perspectives and acknowledge them, even if they differ from your own. Hold back on wanting to be right and see what you can learn.

  • Embrace vulnerability: Ask for feedback and allow others to share honest thoughts about you. Also, share your own experiences, thoughts, and feelings, especially the difficult moments you've had, and ask about other people. We're all humans; it's going to be ok.

  • Record yourself: While in a meeting, turn on the voice recorder on your phone and later listen to at least part of it. Notice how you talk to people, your tone, and how others respond. Observing yourself is very powerful because you can't unsee it once you know.

  • Ask for help: It's ok to reach out to others for support, whether asking for help with a specific task or seeking guidance on a particular issue. That was a tough one for me, but let me tell you, it feels really good.

  • Reflect on your impact: Reflect on how your actions and words affect others, and try to be more mindful of your behavior. Pay attention to people's reactions when you are pushy. You might get things done in the short term, but how many bruises are they not showing you? Silence doesn't mean they are ok with it.

  • Take a step back sometimes: Allow others to take the lead or to share their opinions and ideas. This will help you to become more approachable and to build stronger relationships with others.


Working with strong-willed leaders requires a unique skill set, but with the right approach, it can be a rewarding experience.


By practicing self-reflection, being open to feedback, showing vulnerability, and asking for help, these leaders can soften up their approach and become more approachable to those around them. The result? A more harmonious work environment and improved relationships with colleagues.


So go ahead, let's make those tough cookies a little bit sweeter!













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