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5 Guidelines for Tough Conversations

with David Wood



with guest David Wood #MakingBank S4E35

Strong relationships are built on communication, but even the best communicators can tend to avoid the tough conversations. When we hit problems in our relationships – both personal and professional – it is more important than ever to have open, honest dialogues that bring everyone back together and restore relationships. 

But these conversations can be extremely uncomfortable, causing many of us to veer away out of fear that we will somehow make the situation worse. In fact, if we don’t make sure to communicate in a respectful, polite manner, sensitive subjects can indeed wind up turning into arguments, shouting matches, and broken down relationships. 

Nonetheless, avoiding tough conversations will only cause problems to fester until a similar blow up occurs. Letting the problem linger simply doesn’t work. We need to find a way to have tough conversations in order to have strong, trust based relationships, and the way we conduct ourselves in these moments can actually go a long way towards building mutual respect and commitment. 

While there’s no exact science on tough talks, and every person may have to be dealt with differently, you can rely on a few basic guidelines to help keep your convos respectful, professional, and moving in the right direction. 


  1. Take time to think about what you want to say 


The first rule of thumb that needs to be applied to any tough conversation is to not rush into it, especially if the need for the convo was sparked by a particular incident that upset you. If you rush in, you will be much more susceptible to letting your emotions get the better of you, which can lead to the conversation going off the rails quickly. 

Take some time. The bigger the convo or the more strongly you feel about it, the more time you should take. Run through what points you want to make and why. Practice your talk with someone or record yourself with an app and play it back to see how it sounds. 

You can even ask a friend or coworker if what you’re saying is respectful. An objective, independent 3rd party can help see your emotions seeping through where you may not. 

Once you have your thoughts together you can head into the conversation calmly, confidently and respectfully, which will result in a better outcome 100% of the time. 


2. Build a connection 


There’s a reason this person is in your life. Whether it’s someone in you know personally, an employee or even a coworker, you have a relationship with them and your goal should be to make that relationship as strong as possible. With that in mind, there’s little to gain by admonishing them or talking down to them. 

In order to get your message across, the recipient first needs to understand that you respect and like them. If it’s at your job, let them know you value them as a team member and that you enjoy working with them, but that in one specific area you felt you were let down. Maybe they are consistently late and you feel your time isn’t being respected. Maybe they’ve let personal issues creep into their work and it’s noticeable. Whatever it is, remembering they’re a person first and not a number will have you off to a good start. 


3. Try not to take things too seriously 


When times get tough, it’s the people who are able to stay loose that ultimately wind up faring the best. One of the greatest moments in sports history came late in the 4th quarter of Super Bowl XXIII, when Joe Montana nonchalantly asked his teammates if one of the spectators in the stands was actor John Candy. In a moment when everyone else was tight, tense and laser focused on the task at hand, Montana was able to step back and seem as if he didn’t have a care in the world. 

The 49ers won Super Bowl XXIII and Montana went down as one of the greatest QBs to ever play the game, thanks in large part to his ability to remain calm under pressure. 

Your office probably doesn’t bring quite the same level of tension – at least hopefully not – so you should be able to manage this as well. Don’t be afraid to take people off campus, have a beer, or lighten the mood first by talking about subjects unrelated to work. You will convey the message that what you’re talking about isn’t the end of the world, and everything can be smoothed over. 


4. Ask yourself where you’re coming from 


How are you feeling going into this conversation? In some way you feel you have been disrespected or let down, but are you still mad about it? If so, refer to step 1. 

Is your goal to complain and nag and get back at the person for having commit some wrong? Or is your goal to improve both of your situations and establish a better relationship moving forward? 

If you have too many lingering negative sentiments, they’re bound to leak into your conversation even if you believe that you’re following these guidelines. Try to remind yourself how that will affect the outcome of the conversation, and what you truly want to achieve. Once you feel like you are coming from a place that is genuinely positive you will be in a much better frame of mind to approach the conversation. 


5. Ask them how they feel 


Now for the most important part. You’ve had the convo, you’ve aired your grievances, and you managed to do so respectfully! You feel heard and are happy with yourself for remaining professional. 

If you truly want this conversation to end well, you need to ask them how they feel. They also need to feel heard, and that their perspective matters to you. Do they have an alternative view or a way to solve the problem you hadn’t considered? Maybe there was a legitimate reason for their actions that you didn’t know about. 

Mastering this type of communication doesn’t happen overnight, but by following these steps and wrapping a tough conversation up like this everyone can walk away feeling respected and heard, and you will have established the lines of communication to strengthen your relationship. When you do that, everyone wins.