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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.

How to have difficult conversations at work
[Source photo: fizkes/iStock]
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One of the disadvantages of living in a civilized society is that there are great incentives to lie to others, especially at work. Many of us prefer fake compliments and sham agreements to brutally honest feedback and honest disagreement because we value harmony and collegiality. This is why so many employees are surprised when they don’t get promoted, get a smaller bonus than expected, or are even fired without previously registering much negative feedback from their managers. Indeed, 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.

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To make matters worse, a dominant trend in organizations—especially in the U.S.—has been to focus formal performance reviews on positive events, making any discussion about negative or potentially touchy issues taboo. This includes the idea that coaching and development efforts should focus on people’s strengths. 

There is a tendency to refer to weaknesses or flaws as “opportunities” and efforts to dilute the concept of employee engagement to a superficial and narcissistic feel-good aspiration. For example, if you have a best friend at work, or you can bring your dog to the office, then you are the ideal employee (assuming there is an office to visit, and you are not forced to come). The rise of the chief happiness officer is another symptom of this wider positivity zeitgeist (but given the small number of people who enjoy their time at work, a chief misery officer may be more suitable in most places).

A few companies, like Bridgewater and Amazon, have made radical transparency a cultural bastion, so they have put in place formal processes that encourage truth-telling at the expense of political correctness, even if it means hurting people’s feelings. These cultures understand that constructive discord can fuel creativity. They also assume a certain level of maturity in employees so that decency and civility can be maintained, and people are not actually hurt. As Ray Dalio says, this doesn’t mean going as far as telling someone their baby is ugly when they show us a picture of their newborn.

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As always, the ideal level of transparency can be found at the center of a continuum that ranges from no filter cruel honesty/confrontation to totally fake conflict avoidance/ingratiation. 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.

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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.

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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.