The Ultimate Guide to Having Difficult Conversations

Being a leader is tough, isn’t it? ESPECIALLY when you don’t even know that you are a leader yet. You see I believe that everyone is born a leader and often, there are people who go on with their lives and act very leaderly, and STILL, don’t consider themselves as leaders because of what other’s think and say about them. There’s a lot of mixed messages when it comes to what being a leader looks like.

For example, as a training specialist/consultant/facilitator and coach for years in corporations I didn’t have the “manager” or “team lead” title, and because of that, I never felt like I could lead people based on my job title. When in FACT, the majority of my roles were in constant need of me leading, influencing and motivating people from different teams and various positions including leadership roles, and making shit happen (probably more so than a manager does because of their day to day work). Make no mistake, being a leader comes with responsibility and you can’t get away with the same things you used to before you step into a leadership role. All eyes on you and people are counting on you. It’s up to YOU to have the courage to have difficult conversations and in the event of doing so, you will earn more respect because you are setting boundaries, being clear, and providing feedback to your people.

A big reason I find humans engage in conflict is that they lack the skills or language to communicate what they need healthily. This FRUSTRATES people. It reduces trust, makes you question their motives, and you lose credibility. We need humanity to learn the skills and be vulnerable, transparent, have difficult conversations, and lead from the heart again. If you want to know how to be confident in your discussions and step up as a leader, take a look at some how-to examples below.

How to Guide:

1.  Awkward Energy: When there is a feeling of awkwardness or uncomfortable energy between you and another person, you most likely need to have a difficult conversation. ESPECIALLY when you’ve made a big decision on your business or career, and you need to let another person know about it and are afraid of their reaction. THEN, you definitely need to have a conversation. Being a leader means articulating what you want and need in a way that comes from a good place. A place where you take responsibility, don’t blame the other person and relay what you need out of the situation.

For example: If you no longer want to work with someone you don’t have a healthy working relationship with: You can say something like:

Hi there,

I enjoyed working with you these past few weeks. I feel like we are moving in the right direction. Unfortunately, there has been a shift in my priorities for the next few months that I need to focus my energy on. I will need to move forward with my new priorities as of, (insert date here). In order for a successful rollout, I’m happy to refer people for XXXX to help should you choose, kindly let me know how I can help. I wish you all the best. Take care.

OR

Hi XXX,

Thank you for your hard work and leadership on this past project. It has been a pleasure working with you. I wanted to let you know that after much consideration, I am moving in a new direction as I feel that we are not the right fit for future collaborations. I am happy to refer you to someone within my network should you wish, kindly let me know. I wish you all the best in your future endeavors and let’s keep in touch.

Please note: It’s OK to end things with people. You don’t owe them anything either. Sometimes the money just isn’t worth the squeeze. Your mental capacity, emotional energy and time are worth it, and you can use that extra space for what’s more important to you.

2. Expressing what isn’t serving you anymore. Sometimes, we are in relationships whether that be friendships or romantic relationships and our needs aren’t being met, or that person did something that really upset you, and they might not even be aware of it. It’s OK to let the other person know because it shows that you care enough about the relationship and respect the person enough to be able to give them the opportunity to understand you. How they respond to you is NOT your fault. Naturally, it’s more about you letting another human being know what’s up. Sometimes the feedback goes nowhere and the person continuously repeats certain behaviours and patterns that are upsetting. Then its time to make a decision and ask yourself, is this serving me? If not, you need to move on.

For example, You’ve gone on a few dates with someone, and you just aren’t feeling it anymore, and they want to see you again. You can say something like this to their texts.

Hi XX,

I really enjoyed getting to know you better and thank you for “enter date here.” Unfortunately, I don’t see anything moving forward with us beyond friends, and I wish you all the best. Take care. END STOP!

Please note: You do NOT owe someone feedback or an explanation as to why you made this decision. You can if you want. You are not in a relationship with this person and don’t owe them anything. You might be thinking, that message is so abrupt and mean. You want to know how I see it? I just let a guy off the hook and stopped wasting his time WITHOUT ghosting. Majority of the time, they take it well.

3. Family. Enough said. I don’t know about your family, however, mine came with a lot of rules and regulations when I was younger. It was too strict, so then I rebelled. Over time I have come to understand them and be more compassionate with my family as they had their own struggles and challenges to face. However, sometimes you need to have the hard conversations with family so that you can be free of their expectations and opinions. Another tip: You do not need to share everything with them. Even though they love you and have good intentions, they might be in a fixed mindset and will not approve of your choices in life.

For example,
“Hey Mom, I know you want what’s best for me. I feel good in my clothes, and this is what I choose to wear because it’s me and I feel confident in them. If I ever need an opinion on my clothes, you’ll be the first to know! Thanks!

4. Passive aggressive behaviours – you know what I’m talking about. The type of behaviours that are so off the charts and you know it’s triggered by you in some way. It’s triggered by you, and you also know that it comes from a fear of some sort by the other person. Fear of trust for example. I hate passive aggressiveness. It’s not classy, and it indeed is a sure way to kill relationships by not expressing your needs in a healthy way. I find people who are passive aggressive often don’t have the skills to be anything but that. They don’t have the language or confidence to tell you what’s up. My suggestion? Nip that shit in the bud. Because if you let it go on and ASSUME things, it will get worse.

For example,

Hi X,

How’s it going? Do you mind if we touch base for a few minutes over coffee and have a chat?  I wanted to check in with you when you have a few. How about 2 PM today?

Proceed to coffee date:

I wanted to check in as I am sensing that you are irritated or frustrated with me in some way and I wanted to make sure that everything is OK. I’m 100% open to hearing your feedback if something’s up. What’s going on with you?

Please note: Do you see how you are speaking to the person and expressing that you are concerned about the relationship between the two of you? There is no blame, no judgment, just open communication.  The other person will be more receptive to giving you an honest answer without attacking you.

Reach out to me at sonia@soniagrossi.com if you are stuck on what to do next with a difficult conversation you NEED to have and don’t know how. I’m all ears 🙂

xoxo, Sonia

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