CAREER TIPS - How to have difficult conversations at work
If you can’t cultivate the art of socially skilled conflict and disagreement and make others value your honesty, you are not only depriving others of valuable thoughts and ideas but failing to grow your own potential.
One of the hardest things for managers to do is give their direct reports critical, negative feedback. It’s the kind that helps them understand what they are doing wrong, what they could do better, and where there is a gap between their current and expected performance.
In fact, people do appreciate candid feedback, especially if they understand you have told them what they need to (but didn’t want to) hear. And once you have worked with someone for some time, they will develop a pretty accurate model of your reputation, and it is always preferable to be seen as “tough but honest” rather than “nice but fake.” You can still be seen as empathetic even if you are not conflict-averse, and have the courage to have difficult conversations with your colleagues, employees, and boss.
With that, here are some tips to consider:
CREATE, OR AT LEAST FIND THE RIGHT CONTEXT
Humans are emotional creatures, and even for the most phlegmatic and cool-headed person, some moments will be happier than others. If you are going to have a difficult conversation with someone and tell them something they don’t want to hear, you should start by creating the right context. Prepare them in advance, so they are not taken by surprise. Ensure that they are not going through a hard time already. For example, a Friday may be better than a Monday, during a pandemic is probably worse than a non-pandemic period, etc. Being aware of their personal circumstances is key.
CHOOSE A FORMAT THAT WORKS FOR THEM, NOT JUST FOR YOU
Have you ever been dumped via email or text? It is cruel and cold, but very convenient for the person who delivers the message. Most of us prefer impersonal, technologically mediated channels to convey unpleasant news, but they tend to make things worse. First, you will look like a chicken. Second, you will increase the probability of misinterpretations and miscommunication. Third, you will not be able to show or pick up any empathy.
An in-person message, or the closest we can get to these days (video call), may work best, even if it is not your preferred option. That said, if the other person is highly introverted, reserved, and private, they may appreciate a heads-up via email or text, with the option to discuss in-person or via video later. Try to adapt to them, know their style, and make an effort to adjust to it.
REMEMBER THAT YOU COULD BE WRONG
Most disagreements are clarified once a discussion takes place. This is both humbling and encouraging because it provides the biggest incentive for bringing up difficult topics and having challenging conversations with others. If something bothers you about someone, or you think they need to hear something, then bringing it up is the only way to address the issue.
Most importantly, it is a great opportunity to understand the person better and get a sense of whether you may have been wrong. If you disagree, then being aware of your disagreements is quite helpful, especially if you can find a way of living with your differences, and turns these differences into an actual strength. As Churchill said, “If two people agree, one of them is unnecessary.”
Learning how to deal with other people is not just the most challenging and critical issue at work, but also in life. Shying away from disagreements is like living in denial. It can create a false sense of harmony that does little to advance the enormous power of teams and your own personal development.
If you can’t cultivate the art of socially skilled conflict and disagreement and make others value your honesty, you are not only depriving others of valuable thoughts and ideas but failing to grow your own potential. The only way to learn is to question yourself and others—the former requires humility, the latter empathy, and social skills.
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