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Having Difficult Conversations at Work: 5 tips for Leaders

Having Difficult Conversations at Work: 5 tips for Leaders

One of the most challenging aspects of acting as a team leader is when you have to intervene in a situation and have a difficult conversation with someone. Difficult conversations can take many forms: 

  • Verbal warnings to let one know about specific things that aren’t done in the best way
  • Disciplinary processes in which you need to communicate failures that might put a person’s employment in jeopardy
  • A conflict between two or more people in the workplace
  • Performance evaluations, awkward moments in meetings, and so on. 

The scenarios are vast. As a leader, you have the right and the obligation to address those conversations; you are not allowed to ignore them. Avoiding them is the easiest way to go through it, but it’s not the right thing to do. Why does it matter? Because, as stated by Jeffrey Fredrick and Douglas Squirrel in “Having Difficult Conversations,”  

“Discussing the undiscussable promotes psychological safety and lead to mutual learning and better relationships.”

In this post, I want to share with you five tips and tricks to help you face difficult conversations, which I have learned during my experience as a leader and a manager, reading books, taking courses, and attending talks in the software development industry. Some of these five have helped me personally, but some others, I still have to work to master them.

1. Positive Assumptions

I took this term from the “Coaching Managers & Leaders for Continuous Improvement” by Lawrence M. Miller. This concept means that you should always approach a difficult conversation with a positive attitude and assume that the person didn’t act maliciously with a purpose to hurt a person, a team, or the entire organization. I strongly believe that people always try to do their best at work. If they do something wrong, it might be because of a lack of knowledge or experience, but never assume that it was because they wanted to cause damage. It’s very unlikely that your teammate is Darth Vader or Thanos. Even if you have some negative history with this person or have a long list of pitfalls to share with them, please reach the conversation free of judgment.

Have you ever been in a meeting in which you immediately felt threatened by the circumstances? Well, you are not crazy, it’s just how your brain works. In her book Conversational Intelligence, Judith Glaser explains that our primitive brain evaluates if a person is “a friend or a foe” when we are starting a conversation, and that judgment process takes only 0.07 seconds. If our brain determines that we are facing a foe, we produce higher cortisol levels, which “shuts down the thinking center and activates conflict aversion and protection behavior.”

On the other hand, if our head dictates that this is a friend, we produce oxytocin, “a feel-good hormone that elevates our ability to communicate, collaborate and trust others.” Does this sound familiar? I bet it does! So please always approach a conversation with a friendly attitude, not an unfriendly one.

2. Stick to the Facts

Lawrence Miller calls this “Pinpoint Behavior,” and I found other authors referring to this as “focus on the actions, not the person,” even when sometimes it’s difficult to separate a person from their actions. The idea here is not attacking the person, not generalizing, and not being unclear on what we say.

To deliver the right message in a difficult conversation, we must have an assertive communication: it must be clear, direct, respectful, based on measurable facts; it must be something demonstrable, something that two different people can see and agree with. As in the previous point, it must be free of judgment and don’t make any assumption if you don’t have all the information about it. We must point exactly the non-desired behavior and actions that the person is doing and even go further and tell them the expectation. It can be just a matter of misalignment. Very important: it must be something under the person’s control, something that can be fixed by them.

For example, it is not fair saying: “You don’t care about your work and your team!”. In that statement, we are making a strong judgment about the caring of the person, for which there is no way in the world for us to know it certainly. Additionally, we are not supporting that statement with any facts.

This particular example would be much better if we communicate something like: “Hey, in the last three sprints, you have failed to deliver 5 PBIs on time and according to the acceptance criteria. Also, you missed three stand-ups without notifying the team. I’m concerned because this might impact the team and the project. Is everything ok? Can I do anything to help you?” 

Can you spot the difference?

3. The 4-to-1 Feedback Ratio

In research conducted by Dr. Ogden Lindsley, the father of precision learning, he studied the interactions between teachers and students. They found that the highest learning rates were achieved when the teacher’s behavior was 3.57 positive feedback (approving, praising, etc.) to 1 negative feedback (wrong answer, correcting behavior, etc.). For practical purposes, this is rounded to a 4-to-1 ratio.

In Harvard Business Review’s The Ideal Praise-to-Criticism Ratio post, Jack Zenger and Joseph Folkman analyze research conducted by Heaphy and Losada to find the best proportion of positive and negative feedback in 60 organizations. They concluded this research in a 5.6-to-1 ratio, very similar to the previous one.

The conclusion here is that we, as leaders, shouldn’t be telling only the good or bad. It is always good to communicate positive feedback accompanied by a few areas of improvement. My recommendation is starting with the accomplishments and strengths and ending with what can be improved.

4. What if I am Wrong?

Have you ever been in a conversation in which you find the other party very stubborn? A conversation in which you are sure that you are right, but you can’t believe how the other party is close-minded and not willing to hear the reasons and the facts? You have the experience and the data that supports you, which makes you think, “Oh my gosh! Why doesn’t this person get it? It’s so obvious!”

If you find yourself in a similar situation in the future and you feel stuck in the conversation, I beg you to stop for a moment, take a deep breath, and ask yourself: 

“What if I am wrong? What if I am missing the point? What if today I am on the single-minded side of the table?” 

Or is it that you have never been wrong in your entire life? Let’s face it: people love being right! It’s human nature. Quoting Judith Glaser and her book: “We can get addicted to being right. When we are right (and others are wrong), our brain produces feel-good hormones. Being right also makes us feel powerful, which can elevate testosterone and adrenaline—together, these chemicals ramp up our ability to feel invincible and smarter than others. An addiction to being right causes many corporate cultures to become toxic.”

5. The Power of Silence

One of the most undervalued and underused tools in conversations is silence. The definition of silence is as simple as “complete absence of sound.” It might even sound contradictory to everything I just stated before. “Are you telling me to stay quiet in the conversation? Not saying a thing and fill the moment with silence?”  Well, yes and no. This approach consists of first delivering difficult feedback and then muting yourself. Thirty seconds would be long enough. It will feel awkward, but that’s exactly the idea. That empty moment should invite reflection and contemplation. You will give the person space to think about what you said, digest it, and find the right feelings and words to talk about it.

During this silence, you will feel tempted to jump in. Please don’t. Remain silent. You would be surprised how this powerful exercise can lead to self-realization and even bring ideas on what can be done to overcome this difficult situation. Plans and ideas created by that person will give them a higher sense of ownership and commitment, which will increase the probabilities of success in the communicated problems.

I hope you liked these points and found them valuable and reasonable. As said before, I don’t consider myself an expert on them, but I’ve been trying to put them in practice. Feel free to leave your opinion, and if you happen to practice any of them, let me know how it works for you. Are there any other tools you usually practice in these scenarios?

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