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    Initiating Difficult Conversations

    March 10, 2022

    Being a leader can be the most rewarding and the hardest part of your day to day activities. There is nothing better than being able to count on someone else and know that they are going to be just as invested in their piece of your company as much as you are. Leadership means more responsibility. When you hire employees, you must be prepared to handle the difficult conversations that come with leading a team.

    Difficult conversations can be especially hard to navigate because they often happen at you. Instead of having time to prepare your responses, you have to be able to react when a conversation seems to come out of thin air.

    Especially in the online space, there’s a false narrative that you have full control of your environment. Online leaders think that by setting proper boundaries, they can decide to address (or not address) an issue and prepare in advance before doing so. However, I know by experience that this isn’t the case. Avoiding an issue usually just gives it more power.

    Holding a High Standard of Accountability

    As leaders, we feel accountable for sooooo many people ALL the time. Just to name a few…

    • Bosses
    • Business partners
    • Revenue partners
    • Employees
    • Contractors
    • Management team
    • Investors
    • CEOs
    • Family/kids

    When we step back and think about all the people we’re accountable for, it can feel liked we’re being yanked in a million different directions at any given moment. So how do we choose what to prioritize during touch conversations?

    The reality of leadership is that we are only accountable for our personal and company values, and our ethics (putting those values into practice). When a conversation is driven by emotion, the most important thing to remember when responding is, “What is the solution that is most in line with my values and my ethics?”

    Using the knowledge you have about company values, personal values, HR policies, and the way you want your business to be run makes these difficult conversations a lot easier.

    Different Types of Difficult Conversations

    Difficult conversations can take many forms. Knowing what types of work situations could give way to a tough conversation puts how you control the situation back into your own hands.

    Difficult Conversations with Employees

    • performance issues
    • behavior investigations
    • shutting down an employee’s ideas
    • terminations
    • discipline
    • client complaints

    Difficult Conversations with Peers

    • declining a partnership
    • expressing disappointment with an agreement
    • addressing feelings or disappointments

    Difficult Conversations with Clients and Vendors

    • smoothing over complaints
    • owning up to mistakes
    • setting boundaries
    • asking for payment
    • advocating for your needs

    Difficult Conversations with Superiors

    • advocating for a team member
    • advocating for a cause
    • asking for a raise
    • reporting misconduct
    • seeking feedback
    • providing feeding

    Best Practices for a Difficult Conversation

    When preparing for a difficult conversation, remember that any argument you’re making should always be backed up by company values and company policies/ethics.

    If you haven’t yet nailed down how you envision what your company culture looks like in action, I suggest filling out this worksheet first.

    1. Establish a Clear Objective

    First, choose 1 or 2 clear objectives for the conversation. Instead of simply listing all the wrongdoings of an employee, think to yourself, “what do I want to gain from this conversation?” Going for a simple route will be the most impactful.

    2. Eliminate Emotions, Except Compassion

    A lot of business books will tell you to “leave your feelings at the door” when approaching a difficult conversation. To an extent, this is true. You should try not to dwell on the feelings of the situation. However, the person on the other side of the conversations will have feelings, which is VALID. Be compassionate to their feelings without justifying them. Lay out the context and facts, but always give your team member a chance to express themselves and their feelings.

    3. Use Concrete Examples

    Avoid words like “never” and “always that imply generalizations. Especially if the employee hasn’t had a chance to explain the context of the issue at hand, you do not want to imply generalizations about the experiences they may have had. You are, however, allowed to make generalizations in order to get to an action item.

    Additionally, remember that different words have different weights to different people (that’s a mouthful). This can create a situation where two people engaged in conversation feel like their speaking two different languages. Emotionally-loaded words should be avoided when possible to ensure everyone is on the same page.

    4. Establish Clear Action Items

    If you care about your team at all, you probably aren’t having a difficult conversation just to be HR compliant. This time is an investment in the team member so make it valuable. Changes in behavior are rarely a result of one conversation. Give your team member specific action steps they can take to improve their behavior or reach their goals.

    Wrapping Up

    Being a leader is so rewarding, but that doesn’t mean it’s easy. When faced with difficult conversations, keep the values and ethics of you and your company in mind to handle the situation with poise. Remember, difficult conversations can lead to positive changes and growth, but only if you respond properly.

    If you are still feeling uneasy about initiating difficult conversations check out my Conversation Log Prep template to prepare for a difficult conversation and my Conversation Log template to document behavior that doesn’t necessarily warrant disciplinary action.

    If you have a team, are in the process of hiring a team, or want to be as prepared as possible to be a leader in your space, the Paradigm Management Foundations program is the way to equip yourself with all the things you don’t know you don’t know about effective management. Click here to join the PMF waitlist for Q2 (May-July)!






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