How to Have Fierce Conversations with Your Boss and Co-Workers

One of the books we recommend most often to Executive Assistants and Chiefs of Staff is Fierce Conversations: Achieving Success at Work & in Life, One Conversation at a Time, by Susan Scott. Truly, it is a book that any leader who wants to achieve results through others should read.

So, what is a fierce conversation?

It’s a conversation where you are present, authentic, and engaging in real dialogue. You get to the heart of the matter, ask questions, listen, are enriching the relationship, and leave the conversation with more clarity or a different perspective. The goal of a fierce conversation is to interrogate reality, provoke learning, tackle tough challenges, and enrich relationships. Sounds like something we all should know more about!

Below are the seven key principles of Fierce Conversations and how they specifically apply to Force Multipliers.

1. Master the courage to interrogate reality.

There are three sides to every story: my version, your version, and the truth. As a Force Multiplier, being able to see a situation from numerous angles and make the best decision for your Principal and your organization is a skill. It may not always be what you want to hear (oftentimes it means looking at yourself and where you may have come up short), but ultimately it means progress. In addition to hearing things that may be hard to hear, you need to be able to say the things that are hard to say. Being a truth-teller to your Executive and leadership team is a key skill to leading up and being an influential leader. What you have always believed to be true may not be the case after all. By bringing these conversations into the light, you can have real conversations and make real progress. It takes courage. It takes the ability to let go of the outcome and know that what you are doing is coming from a place of curiosity and a desire to create a better relationship or company. And it’s worth it!

2. Come out from behind yourself into the conversation and make it real.

Authenticity is the answer in today’s business world (take a moment to consider whether or not authenticity shows up as a value in your organization). You can get a lot more done, faster, and with much more career satisfaction when you are bringing your whole self to work, sharing your ideas, bringing issues to light, and sharing your perspective. Who wants to go to work every day suppressing parts of themselves? It is a disservice to your Principal, your company, and ultimately to you.

It’s impossible to accomplish your goals if you don’t make every conversation as real as possible. Have you ever gone into a meeting with the noble intention of saying what’s on your mind and finally making progress on an issue that has been bugging you for months? Yet, when the meeting ended, you left without getting your point across? Don’t let fear hold you back. Laying the issues out on the table with direct and honest communication will get results. 

3. Be here, prepared to be nowhere else.

As Force Multipliers, two of our most powerful skills are listening and observing. We are often the eyes and ears of the organization and need to be able to succinctly communicate the pulse of the organization back to our Executive. But that’s impossible to do if we’re rushing from one meeting to the next with our heads down, scrolling through emails on our iPhones. Susan Scott said it best, “Our work, our relationships, and our lives succeed or fail one conversation at a time. While no single conversation is guaranteed to transform a company, a relationship, or a life, any single conversation can.” Being present means putting away your phone, moving away from your computer, and even just mentally and emotionally preparing yourself for a conversation. Clear your physical space and clear your mind so that you are 100 percent with that person in that moment. You might just be surprised at what you learn and it could spark new ideas or solutions to problems.

4. Tackle your toughest challenge today.

You know what it is. It’s that project or conversation that you have been avoiding, hoping that it would resolve on its own. It didn’t. More often than not, this is going to be a conversation with your Executive or leadership team. Perhaps it’s time to talk to them about being a control freak? Maybe it’s time to ask for a raise. Regardless of the issue, it never helps to wait. Most problems can be solved faster, with longer-term results, when done in the moment or as soon as possible. By waiting to have the conversation, you are setting a precedent that the behavior or the situation is OK with you. When you finally confront the issue, six months later, it can cause confusion and resentment. Don’t wait. Confront obstacles in your path and accomplish more! 

5. Obey your instincts.

How many times have you gone against your intuition, only to regret it later? Pay attention to your gut and tune into your radar. Your gut reactions are often subconscious responses to your previous experiences. Gather information and know the facts, but obey your instincts. 

There are ways to approach a conversation that allow you to obey your instincts and interrogate reality with professionalism, respect, and curiosity. For example, if I have noticed an issue a few times with my Principal, I might grab them for a one-on-one (when they are not busy or distracted, but also in a timely manner), and say, “I’m prepared to be wrong here, but here is what I am noticing and how it could be perceived. What are your thoughts?” If I were giving feedback to an employee or colleague, I might say, “I noticed XYZ and I think it could be perceived or is making other people feel [fill in the blank]. What are you seeing from your perspective?”

If you know something needs to be addressed or said, say it. But remember, there are always multiple sides to a story. Enter the conversation with curiosity and a desire to understand. You will get a lot further with the individual and you will likely learn something along the way.

6. Take responsibility for your emotional wake.

When entering into a fierce conversation, you have to check your energy and emotions at the door. This doesn’t mean that you’re an emotionless robot, but bringing your own emotional agenda or charge to the conversation is not helpful for anyone. Maintaining a neutral state, staying curious, listening, digging deeper, and helping you and the individual come to some sort of resolution is important.

As a Force Multiplier, you have significant influence over your Executive, your leadership team, and the company at large. You must be hypervigilant about what you say and, more importantly, how you act. For you, there is no trivial comment, just as there isn’t for your Executive. Something you may have said in passing may actually carry a lot of weight to the people in your organization. Choose your words and tone wisely, because while people might not remember exactly what you said, they will remember how you made them feel. 

7. Let silence do the heavy lifting.

Sometimes the most meaningful conversations have the fewest words. If you ask a question, do not rush to fill the silence, but rather allow the space for someone to actually answer your question. If you ask your Executive a pointed question, stop and wait for a response. It is incredibly hard not to dive in and start talking, clarifying, or asking another question. Or sometimes we are just filling the silence with meaningless chatter because the silence is uncomfortable. Slow down the conversation to allow for reflection and thoughtful responses. Allow the silence and the space and listen for what isn’t being said. Are they processing? How is their body language? How long are the pauses? If you can just wait out the silence, what comes out on the other side can be massive aha’s, insights, thought-provoking questions, or incredible ideas or answers that change the trajectory of the relationship, the company or both. Silence is golden.

When was the last time you had a fierce conversation? What conversation have you been avoiding? Who do you really need to have a conversation with right now? Schedule it! Tackle it today and get it on the calendar. Success in work and life happens one conversation at a time. Get talking. Get fierce. Get results.

Learn how to start a fierce conversation here.

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