How to Become a "Difficult Conversations" Jedi

Updated: Mar 7





Last week, I spoke about how to find your voice as professionals from underrepresented backgrounds (Women and BIPOC) and gave you tips on how to start asserting yourself and stop feeling invisible.


Today I want to chat with you about another very common question that I get from my clients and it’s: How to handle a difficult conversation.


First, let’s understand what is a difficult conversation and why this is such a valuable skill and must-have tool for any professional from the underrepresented group looking to break through the next level in leadership.


In his book “Crucial Conversations” the authors define difficult conversations as one “where opinions vary, stakes are high, and emotions are running strong.” Personally, I think of a difficult conversation as any conversation that increases the level of discomfort, in all likelihood a “hot-button” topic involving money, values, family, power, behaviors, feelings etc.


There are countless crucial conversations that you may deal with during a typical day. Some common examples that I can think of:

  • Negotiating a raise

  • Handling a difficult employee, peer, or boss

  • Accepting mistakes

  • Giving negative feedback- to peers or direct reports

  • Point out a mistake or flaw in the strategy plan your boss laid out

  • Taling about behaviors such as microaggressions, discriminations, etc

Why is this important?


As part of being a leader in any organization, it is absolutely necessary to have the ability to communicate objections, call out problems, and directly ask people what is needed. In other words, simply say what needs to be said. If you avoid having these uncomfortable conversations, chances are that you will not be recognized as a leader who can add to the conversation, therefore, losing any open seat at the table


For women and BIPOC professionals (or both), the quality of your professional and personal life will depend greatly on how many of these fierce/difficult conversations you are willing to have.

Yet the reality is that for women, and even more so if you are a BIPOC woman professional, we face a double whammy of cultural programming and systemic discrimination that both condition us to avoid having such conversations. But in many cases, we simply do not speak up because we do not know-how. Neither our families nor higher education is helpful about it. So we avoid, tolerate, and stay silent or in other cases snap.


So let me give you my strategy, which I learned from my years as Head of HR and in coach training, so you can adopt them, practice, and become a Jedi master of difficult conversations in no time.


Heads up, the first two steps are for you to have an internal dialogue and act as a “feelings regulation” mechanism.



1. Acknowledge the discomfort.


If you notice someone said something and it’s bothering you instead of sweeping it under the rug and letting it slide, acknowledge it internally. To acknowledge that resistance it’s the first step to harness our emotions and not letting them fester or run the show.


Ask yourself:

  • What is the behavior that is so aggravating?

  • What is happening here?

  • Why I am [ ___insert feeling____]?

  • Am I making an interpretation or am I telling myself a story here?

2. Define what you want and weight-in your risk.


Once you define why you are feeling bothered or angry, then you can really turn that around and ask yourself what is it that do you want or wish to be different instead.


  • What is it that I want really?

  • What is really going on here?

  • If you had a chance to turn back time, how would you handle the situations instead?


Also, it’s extremely important that you assess what is the risk of bringing things up and more importantly if it safe for you to do so. Note, only you can define the definition of safety and weight in your level of risk you are willing to tolerate. Personally, I prefer to let people know when something is not ok even if they are my superiors or someone with power within a company. I find that as long as I provide this feedback in a way that is not accusatory and private is generally well-received and respected. However, you need to make that choice.


Once you do that, then, you can move to the next steps.


3. Get Curious


Once you decide that is safe for you to approach the other person, then you can select the appropriate space, time and make sure you are doing this on a private one-to-one, not in a public space.


Start with these three words: I notice that [____]. And describe the behavior.

  • I notice that you like to interrupt me and other women while we are finishing our thoughts...

  • I notice that you make a comment about my hair when I come into a meeting...

  • I notice that you look at your phone every time I’m presenting my thoughts...

  • I notice that your comment on my accent quite frequently...


Then follow by asking questions such as: why you think is that?


In this step, it’s so important to not get tangled in veiled accusations, interpretations, or comparisons. Make sure it’s coming from a place of neutrality by describing the troubling behavior. Otherwise, the other person on the receiving end will be perceived as a threat, and the person will clam up or pounce.


4. Summarize and paraphrase.


As you let the other person explain themselves or excuse their behavior, it so important that you remain calm, attentive and let him/her finish Then you can summarize and state it back to them:

  • So if I heard you correctly, the reason you comment about my hair is because xyz reason is that right?


  • To clarify what you just said, you interrupt me and others because you are so excited about sharing your input that you do not realize that you interrupt, did I heard that right?


Why does this work? Here is the thing, we humans want to be heard and understood. If you can demonstrate that you can listen and connect with others then it’s easier to positively influence each other. And when you hear “That’s right” you basically heard the doors of the other person’s mind-opening for you to take it home.


Bringing it Home


5. Impact of the behavior.


Ok, I have to admit this step is probably one of the most challenging because it will feel a bit vulnerable. However, as long as you describe the impact in a way that is language-neutral and business-related, it will work wonders. Depending on your level of comfort, you can also bring in feelings but that is again a call that you need to make.


Describe the impact that the behavior on you and on the business for example:


  • When you interrupt me and other women in the meetings, it looks unprofessional and not align with the company and departmental values of respect and fairness. Furthermore, I feel disrespected and as a result, I feel demotivated and disengaged, which I know I’m not alone, and could imperil the department output.


6. State what you want (from point 2)


Now is the time to drive the point further by stating what you want:

  • “I would prefer if you do not interrupt me or other women before we finish speaking, instead please pause until the Q/A section”

  • “I would like if you to stop commenting about accent in front of others and instead if you have anything to say, please tell privately ”


7. Close the agreement


By closing the agreement I mean to get them to verbally commit to the desired new behavior by asking one of the following questions:


  • Do we agree on that?

  • How does that sound?

  • Do we have an understanding?

  • Would you be willing to do that?


Also depending on the situation, you might want to clarify, if there are any obstacles or if there are any other areas of resistance that you need to re-work for buy-in.


Finally, as an extra piece of advice, if you are having a difficult conversation about something that is HR-related by the biggest piece of advice: memorialized such conversation.


Immediately after the conversation, write it in a journal that is yours, not a company swag, with date, times, and a detailed account of the incidents just to cover your bases. Hopefully, you will not need to escalate but it better be safe than sorry.


Do you need someone to coach you through your difficult conversation?


As an executive leadership coach, I help my clients to elevate their voices and break through the next level leadership position with confidence with my exclusive program “Elevate and Own Your Voice ™️”. Where I coach and equip my clients with the mindset and the skills they need to make it to that next level role.


If you are ready to learn more you can contact me here.