3 Ways Leaders Can Make Difficult Conversations Feel Easier

user Mina Muraki
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Leaders are expected to act as the guiding lights and role models for everyone else. And every leader, no matter how good they are, will eventually encounter the same issue: you have to have a difficult conversation. 

It doesn’t matter how good you are at leading through example, providing clear guidelines, assigning roles and duties, delegating, or anything else. At some point, to be the best leader possible, you will have to sit down with someone else and have a conversation that you are not looking forward to. It could be with a co-founder, an executive peer, a board member, an investor, a subordinate, or a mentee, but the time will come. In fact, it likely already has come. 

Think back to the conversations you remember as being “difficult.” Did you approach them with a willingness and a desire to engage, or were you, like so many of us, nervous or afraid?  

There’s a fear of having a difficult one-on-one, and it’s something that could cripple any business. Unfortunately, the faster a business is growing, the more prevalent the need for serious conversation—and the more likely the conversation will be avoided or incomplete. It could be discussions around strategies, responsibilities, or core objectives, but I frequently see that they are not happening.  

Whether it’s a start-up that just received seed funding or a unicorn preparing to go public, failure to have the difficult conversations can be detrimental. Fortunately for leaders, there are ways to make these conversations feel much easier than they do right now.  

1. Difficulty is a fear reaction  

The thing about difficult conversations is that going into them, the difficulty is 100% imagined. It’s not the content of the conversation that makes leaders fear these talks, but the anticipation of the other person’s reaction.  

Often when someone feels a conversation is going to be difficult, they are imaging their own suffering as it relates to a negative response from the other person. There’s fear of anger, disappointment, or making someone upset.  

When this concern over the other person’s reaction shows up in the conversation itself, it makes things harder. It will force leaders to be less direct, or to withhold the clarity that would actually prevent any difficult feelings or resentment from the other side. 

The trick to managing the conversations is to stop focusing on the other person’s reaction, and instead focus on what message you need to convey. Conversations are only difficult if you worry about what’s going to be projected upon you. 

2. Clarity is kindness

Once a leader is in touch with their own fear of having the conversation and how it might affect their relationship, they can then move on to changing things. Step one is having faith in your ability to tell the truth in a kind, respectful way. 

Most leaders can already gracefully and skillfully communicate the truth. That’s how they’ve climbed the executive ladder. But when entering a conversation with a fearful mindset or even dread, those skills are forgotten or blocked off, which leads to adjustments in what we say. Sometimes, we tiptoe around the truth. Sometimes, we speak indirectly. Rather than clarity, things get murkier. 

Clarity alleviates stress, staves off second-guessing, and means that the other party will leave the conversation understanding where they stand with you. When we muddy the waters, it sets the table for mutual disappointment.   

But the desire to hold back is very real. It often stems from a conflict between being nice and being kind. Being nice typically means that a leader wants the other person to like them at the end of the conversation. Being kind means that the leader wants the other person to benefit from the conversation. 

Anytime you enter a conversation with the goal of making the person like you at the end, you’ve lost sight of the real goal. As a result, your integrity and authenticity take a hit. Clarity is the greatest kindness anyone can offer in conversations. 

3. Respect pays off in the long run

I bring up integrity and authenticity not to exaggerate, but to show the true consequences that can come from operating out of fear, and letting that fear compromise clarity.  

High valuation startups often grow at a breakneck pace. So-called difficult conversations spring up more often at these companies because executives are relatively new and are still establishing relationships when they are forced to sit down with a co-worker or employee. Factor in our current COVID crisis and remote working, and the leader may not have even met this person face-to-face. That’s a challenging mix of factors. It’s understandable that people dread these conversations. 

Clarity is kindness because it drives the conversation toward what has to happen, what should change, or what the other person needs to know. It also tells the other person that you respect them and care enough to give the feedback. That should, in turn, earn you their respect as well, and that’s far more valuable than simply being “liked.” 

I’ve been through this, too, and know how hard it is, and I’ve experienced the difference when I’m able to have direct and honest conversations. In one instance, I delayed a feedback conversation with a challenging client for weeks, hoping that the situation would somehow reverse itself. It only got worse. The client’s own team revolted. When I finally had the one-on-one, a weight was immediately lifted. The client was genuinely unaware of the impact his behavior had on our relationship and on his team. He not only thanked me, but we spent additional time strategizing how he could shift his behavior. He still recalls the impact that conversation had on his leadership. And I think about the needless angst and spin I experienced in anticipating a poor reaction from him. 

Leaders need to come to terms with the fact that they create the “difficult” part in a conversation. They need to be liked, needed, or approved of are the primary distorting factors. The best leaders move beyond that to what’s important, which is being clear with their directives and feedback while showing respect, so that they can receive that same respect back. Treat other human beings as adults capable of reacting to the information in a mature and thoughtful way, and suddenly, there’s no such thing as a hard conversation. 

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