Tips for Tough Conversations

Kevin Namaky
5 min readJul 26, 2023

The first time you get a direct report, it can be both exciting and scary. It’s a sign you’ve been trusted with management responsibility. But what if you’re assigned an under-performer?

Most new managers are tempted to “play nice”. They want to be liked by their direct reports, especially if 360-degree feedback is practiced at the company. You might even find that your new direct report is a “friend” of yours — someone you hung out with a lot as fellow ABMs or brand managers.

Having a tough conversation with an underperforming employee is not fun. It’s especially daunting for new managers but can stump even the most seasoned managers. Managers often struggle with what to do or say. And even if you prepare what to say, it may not go as planned.

From having my fair share of tough conversations, I’ve collected a few critical tips for handling these situations. Here are four important things to keep in mind when having a tough conversation.

1) BE DIRECT

Sugar-coating the situation does not help. If you know they are underperforming, one of the worst things you can do is send mixed messages in an effort to spare feelings.

In the moment it may feel like you are helping them by being nice, but you will actually confuse them.

There’s often a gap between the manager’s perception and the underperforming employee’s perception of performance. And when you aren’t clear and direct, the underperforming employee will likely take away that they are doing just fine.

They will not have the clarity or urgency needed when your meeting with them ends. In many cases you will have to have the same meeting all over again later. So be as clear and direct as possible.

2) FOCUS ON THE WORK

Do not criticize them personally. Your coaching should solely focus on work deliverables and how they’re not meeting expectations.

Too many managers make the mistake of judging or commenting on the person. Here are examples of things I’ve heard managers say that are unfair, unprofessional, or just plain mean:

  • I just don’t think you are working hard enough.
  • What makes you think this is OK?
  • I’m disappointed in you.
  • You don’t seem to pick things up as quickly as [insert another employee’s name].

Never attack or judge a person or their character.

Instead, here are examples of fair comments regarding the work. Notice that they aren’t sugar-coated, but they are clear and nonjudgemental (even if they might be hard for someone to hear):

  • The presentation you worked on last week was turned in two days after the deadline we agreed upon.
  • The presentation you gave to senior management was ineffective because it was missing two of the critical pieces we discussed including.
  • The pricing and margin analysis you delivered had a number of errors in it.
  • Cross-functional feedback from the team indicates that you tend to interrupt others and miss important information as a result.
  • This position requires that you take initiative and lead the project process with the team, but the team doesn’t have a timeline to follow or understand their next steps.

The other thing to keep in mind here is that you should be ready to cite specific examples. And if you don’t provide them, it’s fair and highly likely that you will get asked for them.

3) ASK IF THERE’S ANYTHING SPECIFIC HOLDING THEM BACK

You want to know what’s going on with them because there might be something you can help address. Is there something preventing them from achieving expectations?

This can be tricky because, in some cases, the employee might start to play the blame game. But I think it’s a risk you should take because there could be something going on that you, as the manager, should act on.

They might mention a valid personal issue that you would provide some accommodation for. Or they may be having a conflict with a department or cross-functional team member that isn’t resolvable on their own.

However, in these instances you should make it clear that, even with your help, the responsibility for improving their performance lies with them.

4) SHOW SOME EMPATHY

Unless you’ve already decided to let the person go, it’s good to communicate that your goal is to work together with them so they are successful.

I’ve always found that a “we’re in this together” mindset is better than finger-pointing and making them feel like they’re on their own. After all, their success is your success as a manager.

Everyone makes mistakes, especially early in their career. It’s an important way that we all learn. So, recognize that not everyone performs at 110% all the time and try to be helpful.

And if you have already decided to let the person go, don’t waste time beating around the bush. Just tell them and provide a fair severance. Don’t string them along and surprise them later, or tell them they have a few months of lame duck status that’s embarrassing for both them and the company.

People and Performance Both Matter

If you do it right, the tough conversation should be taken as a helpful one. Yes, you are bringing a performance deficit to their attention, but you’re also there to help and you’re rooting for them.

The bottom line here is to treat people fairly and with respect, while also being clear on expectations. Balancing people priorities and company priorities is the art of managing, and if you do it right they will usually align. It’s difficult at first but definitely gets easier with practice.

This post originally appeared on the Gurulocity Marketing Blog.

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ABOUT THE AUTHOR

Hi, I’m Kevin! I’m the founder and CEO of the Gurulocity Brand Management Institute, a consumer marketing education company that trains and consults for notable brand teams including Kimberly-Clark, Scotts Miracle-Gro, Bolthouse Farms, Ancestry.com, Johnson & Johnson, Sephora and Gorilla Brands.

I’m also a featured instructor for the American Marketing Association, lecture at the IU Kelley School of Business, and have been featured in Ad Age, Forbes, Fast Company, Business Insider and the CMO Council. I previously worked for 20 years in the corporate and agency world growing notable consumer brands.

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Kevin Namaky

Marketing strategist and educator, Founder of @Gurulocity Brand Management Institute. Super-dad by night. http://gurulocity.com