Identifying Warning Signs at Work: Understanding Issues and Sharing Difficult Information

Red Flags at Work: Recognizing Problems and Delivering the Bad News

IN MY early managerial days, I would often ask my bosses and peers how they learned the skill of delivering bad news. Almost always, their answer was: “You will learn it over time,” “There is no compression algorithm for experience,” or some variation of needing to put in the time.

Granted, experience is one of the best teachers, but I have discovered there are tactics that can be learned so you don’t have to navigate without help.

Spotting Problems at Work

Detection is about how to spot problematic situations that might require you to intervene and deliver bad news. This might include an employee who is not pulling their weight, runaway projects, and so on. As a manager, you are responsible for making sure you are getting the most out of your team and for delivering a positive return on investment for your company. You are, by default, supporting all the decisions your team is making, and if you keep backing bad decisions, you will be the one held responsible.

So, how do you decide when it’s time to take notice?

Employees and their personal work-related issues are the bane of every manager’s existence. There are two broad categories of people-related issues in which a manager needs to intervene: individual performance issues and personnel conflicts. They can cause a lot of damage if left unchecked. I suggest you create tenets that employees can use to resolve conflicts on their own versus solving it for them.

Project management, encompassing issues that crop up during planning and issues that show up during execution, is another area that may require your overview and handling. The key to spotting problems is to ask the team to break the project down into milestones, and ensure that the distance between each milestone is less than one month. If they are unable to scope the milestone down, then start cutting scope until you get a milestone that is reasonably timed. If your team is absolutely unable to figure this out after a lot of hand-holding, you probably have the wrong people on your team.

Preparing to Deliver the News

The focus of preparation is on tailoring the tone and temperature of your bad news to match the situation. For example, your response to an employee slipping on their commitments for the first time must be softer than it is for the third time.

Pressure, conflict, or disagreement situations all require a different tone of voice compared to peaceful situations. There might be times when you want to get your frustration across with immediacy and clearly to the other person (or group), but other times, you might not want to go there just yet.

In my career, I have always taken the approach of raising the temperature slowly, and I wholeheartedly recommend that approach as you prepare to deliver bad news. Most people are not good at handling disagreements or conflict situations, especially if they end up on the losing side. The stronger and longer the disagreement, the deeper the resentment by the people who are in it, even if the outcome is a compromise that benefits both parties. They will remember the pain and the emotional toll of the conflict rather than the relief of the outcome. They will personalize the conflict. They will remember names and times.

Raising the temperature slowly doesn’t get people’s dander up, and hence they are more open to sharing what they are actually feeling. They will be more open to compromises and less inclined to hate you if they end up losing their argument.

Raising the Temperature Slowly

Raising the temperature slowly means starting off by presenting an alternative hypothesis (after fully understanding the option on the table), instead of downright dismissing the one presented by the other person (or team) and taking care not to elicit a strong emotional reaction.

For example, when I disagree with a design decision my team is making, this is what my low-temperature pushback will sound like:

I am not sure this is the right way to go about it. I have seen evidence from [insert relevant career anecdote] that this won’t work. Have we considered solving this by doing [insert your option]?

The emphasized words are what make this work. You are starting the conversation by not outright shooting down the other person’s idea. This gentle pushback will invite a healthy, thoughtful, and objective debate, as opposed to an unhealthy emotional response.

In general, stay away from absolutist statements. Those will almost always elicit a strong emotional response instead of a robust discussion and debate.

Start with low-temperature pushback and see if you can get your team to see your side of the equation. If it doesn’t work, you may need to increase the temperature.

Here is an example of high-temperature pushback for the same situation I previously discussed:

This is a bad idea, and I disagree with this decision. I have seen evidence from [insert relevant career anecdote] that this won’t work. It will affect our company by [some catastrophic outcome]. We should do [insert your option] instead.

Be aware that just saying the words “I disagree” will elicit a strong emotional reaction from the other person, but such high-temperature messages will get your point across. Note, too, that there is a fine line between a high-temperature message and rudeness. Don’t cross it.

The bottom line: If you want to build trust with your team and create an environment of two-way communication, you have to know how to detect problems and address them using the most suitable communication possible.

Mahesh Guruswamy is a seasoned product development executive who has been in the software development space for over twenty years and has managed teams of varying sizes for over a decade. He is currently the chief product and technology officer at Kickstarter. Before that, he ran product development teams at Mosaic, Kajabi, and Smartsheet. Mahesh caught the writing bug from his favorite author, Stephen King. He started out writing short stories and eventually discovered that long-form writing was a great medium to share information with product development teams, resulting in his book How to Deliver Bad News and Get Away with It: A Manager’s Guide (January 14, 2025). Mahesh is passionate about mentoring others, especially folks who are interested in becoming a people manager and newer managers who are just getting going.

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Posted by Michael McKinney at 07:21 AM

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