Seven Tips for Navigating Hard Conversations (Part 1)

Seven suggestions for how to navigate the tough love conversations.

Interview multiple candidates

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Search for the right experience

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Ask for past work examples & results

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Vet candidates & ask for past references before hiring

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Once you hire them, give them access for all tools & resources for success

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We need to talk.

These four teeny tiny words can strike fear in any human heart. Probably because we know good news rarely follows. 

Like death and taxes, hard conversations are a part of life. 

This is why taking the time to learn how to navigate difficult conversations is such an important task for all leaders. Truth be told, if you don’t learn to have hard conversations now, you’ll inevitably have even harder conversations down the road.

In addition to being one of the biggest leadership hurdles to overcome, mastering the art of hard conversations is key to some of the most beautiful rewards you will reap in a leadership role. 

So. Here are 7 suggestions for how to navigate the tough love conversations.

  1. Tear off the bandaid. (Aka don’t dance around the purpose of the conversation)

    There are two problems with dancing around the subject. First, most of us are really bad at faking normalcy. Second, even if we manage a convincing poker face, we risk creating a false sense of calm that can damage the trust we need to rely on for a positive outcome. Nobody likes a bait and switch especially. It only diminishes your authenticity and harms your existing relationship with that person.

    Instead, lead with a phrase that lets the other person(s) know that what you are about to say will be challenging/awkward/difficult/upsetting. Pause for a minute so they can let that sink in. Then give it to them straight. This approach works for corrective conversations, delivering devastating personal news, and letting people go. I’m convinced that that leading phrase is the most important one. I always rehearse this line to make sure I’m able to say it confidently as soon as the door is closed and the person is seated.

    Often our instinct to pad the conversation is more about our comfort than theirs. Understand that this is not permission to be abrasive or uncaring. Candor and putting all the cards on the table and then being available for the appropriate level of answers and coaching is the best way to care for people in bad situations.
  1. Be honest, but exceedingly kind.

    Honesty does not mean you have permission to abandon tact. In fact, kindness and gentleness will be essential to a conversation that helps others feel safe. When people feel safe, they are more likely to keep their prefrontal cortex engaged which allows them to hear and fully process what you’re saying. When people feel threatened, it activates their fight or flight response and shuts down their ability to engage. Honesty does mean that you do not shy away from the things that are toughest to say. In my years of navigating some doozy conversations, I have found that acknowledging the awkwardness and admitting that it would have been easier to avoid the conversation entirely, but you cared too deeply to shy away from it, are good ways to assist your forward momentum mid-conversation.

  2. Put in the time ahead of time.

    The moment you utter the words “we need to talk” begins the tense journey for the person on the other end of the table. With this in mind, you must be prepared before you enter a conversation. Your preparation is a gift to them. Winging it not only devalues them by subconsciously signaling that they are not worth your time to think things over before opening your mouth, but increases the chances that it goes sideways. Be prepared with the how, why, and to what extent you want to present the topic of conversation. Preparation takes time - but time is precious and time spent on people registers as an act of love. 

    Part of your preparation should include thinking through their personality, preference, communication style. All humans are wired differently. All humans have individual preferences and motivations. We also have varying conflict styles and even unique apology languages. Do not assume people want to hear bad news the way you want to hear bad news. As you spend time preparing the conversation, take some time reflecting on who you will be talking to and what type of approach will set them up for success. Are they direct? Are they passive? Are there cultural factors at play? Are they seasoned in their career? Do you have their trust (aka is there enough “change in the bank” for the withdrawal you’re about to make)?
  1.  When needed, let silence do the heavy lifting. 

    Sometimes, it’s best to just shut up. Often, we find ourselves babbling just to fill the silence and avoid extending the awkwardness. This is rarely necessary and potentially risks causing more damage. The person you are speaking with may need time to let the news marinate or they may need to figure out what they need to do from this point. Remember - you prepared for this conversation but they most likely did not. Allow them to process what’s happening, and when they’re ready to continue, give them the open space to communicate what is going on in their head. From there, you will have a better idea of how to guide them to the next step and navigate the rest of the conversation.
  1. Know your objective ahead of time. 

    The last thing people want is for this experience to be drawn out or needlessly cushioned with small talk. Knowing exactly what you want to say or accomplish during this meeting will be most beneficial for all parties involved. If you simply need to deliver the news (firing, eviction, etc.), then get to the point. Trust me when I say they will not be thinking about what you think about today’s weather when they’ve just received devastating information. If you’re looking for a conversation, be prepared with questions. Have a few ready that will keep their train of thought on track and moving in the right direction. If you’re delivering a challenge, be prepared to answer questions and to provide some first steps and guidance. 
  1. Be yourself (authentic)

    One of the challenges with difficult conversations - particularly in the workplace - is that they are surrounded by an official tone and a need to be mindful of legality and compliance. This layer of complexity presents a challenge for a leader. How do I keep a personal tone while also remaining professional and compliant? There will be times when your tone in a direct conversation must be colder than you would naturally prefer. The key is to remain as authentic as the situation allows. Use words that are natural to you and choose a setting that fits your style. As you seek out the guidance of others (which is extremely wise), they will likely suggest their preferred approach and give you a script that has worked for them. Be careful not to adopt another script to make it easier. Taking a shortcut is not fair to whoever has to receive the hard news. Join them in the difficult portion by bearing the burden upfront and bringing your authentic self to the table. 
  1. Don't measure success in the short term. You’re making an investment and investments take time to mature.

    All good things in life come at a cost. Money. Time. Energy. Sweat. Tears. The tough stuff is often where the best of life originates. The people that care for you most are always the ones most willing to tell you the things you need to hear, even if it risks temporarily upsetting you. The same is true when the situation is reversed. If you truly care about your people, you must be willing to tell them the things they need to hear even if it risks upsetting them for a time. Hard conversations are an investment in their future. As with all opportunities for great reward, there is risk involved. 

    And remember growth takes time. Do not be discouraged when the minutes, days, or weeks following a hard conversation are filled with some coldness or distance. Ideally, people would see right away that it was equally difficult for you to tell them the truth, but that doesn’t always happen. You must remain rooted in your conviction that you are doing your best to do what is best for them. Then let time work its magic. You are not responsible for others’ journeys or willingness to receive guidance. You are responsible to keep the bigger picture in mind. You are responsible to be patient and remember growth is a process. 

Leaders enter into hard conversations because they care. They want what is best for their people and they are not afraid of a little tough love. No one enjoys these hard conversations but it’s part of the job description as a good leader. The seven tips we’ve outlined should help you handle any difficult conversation with grace, authenticity and kindness. If you’re able to invest the time and love into this interaction, it’s bound to end up being a positive experience for both of you in the long run. And remember, these conversations take time to mature so don’t be discouraged if the outcome is not perfect immediately. Measure success over the long term by how your relationships have grown stronger and more resilient as a result of engaging in tough love dialogue. What’s stopping you from refining your leadership game? Get out there and be the best leader for your people by mastering the art of having hard conversations.

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