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How to Have Tough Conversations at Work [1:1 & In Meetings]

To thrive in work and in life, get comfortable with the uncomfortable

May 11, 2021
How to Have Tough Conversations at Work [1:1 & In Meetings]
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

The toughest conversations at work can be the most valuable and productive: 

  • Asking for a raise
  • Speaking to large groups 
  • Giving constructive criticism
  • Challenging conventional wisdom
  • Telling management that the strategy isn’t working

Sometimes these conversations happen one-on-one meetings, and sometimes they happen in a large group.

Whatever the forum, both the person delivering the communication and the recipient hold responsibility for having the emotional intelligence to handle tough conversations. 

In this article, we’ll go through some general tips for “getting your guts up” when under pressure, and specific tips for specific types of tough meetings or conversations. 

Preparing yourself

When it comes to any type of difficult conversation, it’s best to be prepared when you can be. If you know a tough conversation is coming, such as providing 1:1  feedback or asking for a raise, try these methods.

  • Write down your main points and filter for the main ones.
  • Consider the potential questions or objections the other side might have, and write out or practice your answers to those.
  • Rehearse. Get a friend or colleague to role-play with you both the best and worst scenarios. You can also get a professional coach.
  • Be prepared for rejection or a negative response. Rather than pushing back if there’s disagreement, try getting curious and getting deeper into the other person’s thinking.
  • Determine the outcome that you want from the conversation. Is it enough for the other person to listen, or do you want them to take an action?
  • Schedule a time in the day when you are generally at your best, and bring up the topic right away. Don’t wait until the last five minutes of a meeting to bring up the tough topic; make sure you give it the time it deserves. 

Being unprepared

Sometimes those tough conversations just pop up without warning! Your manager might give you unexpected feedback, you have a brilliant but crazy idea in the middle of a meeting, or you might disagree with a presentation. To be prepared even when you’re unprepared, follow these tips:

  • Check in with yourself and speak up if it helps you to mention that this is an emotional situation. Don’t be overly vulnerable in a professional situation, but it is fine to say “I’m nervous speaking in a large group…” or “I’m a little shocked to get hear that…” 
  • Pause and breathe. You don’t have to respond immediately. Pause for a moment, slow down your breath and unclench any tense muscles to relax your body and your emotions. 
  • Take your time. Sometimes it’s best not to react right away and to come back to a topic if it’s triggering for you. If you know you’re the kind of person who avoids confrontation, however, you might want to say something out loud right away so you don’t avoid it indefinitely. Using a phrase like “Can we pick this up again in the next meeting? I want to give it more thought before we decide,” can ensure that the topic gets on the agenda for the next meeting.

Asking for a raise 

Whether or not your company has a formal procedure for salary review, there can be times when you feel you deserve more. Asking for what you deserve is one of the hardest conversations for people, but consider that you’ll do your best work when you’re satisfied with your job. 

Tips for asking for a raise or promotion:

  • Have clear reasons why you deserve the raise. Cite your data about your performance as well as benchmark salaries in the industry.
  • Be specific about how much of a raise you would like.
  • Be willing to accept alternatives, such as a company car, improved title, additional vacation days, tuition for ongoing education, etc. Sometimes it’s easier for a manager to approve items that aren’t’ considered direct headcount expenses.
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Performance review meetings

As far as meetings go, performance reviews can be tense for both the giver and receiver. If you’re the giver, take time to review these tips on giving effective feedback, as well as the tips below:

  • Try not to be in a situation where the feedback was a surprise. Your team members should get both positive and negative on an ongoing basis, so the performance review should just reinforce what they already know.
  • Set the tone right away—let the person know the overall picture of their performance.
  • Establish that the performance review is primarily for their benefit so they can improve their performance and progress in their career.
  • Approach the conversation as a member of their team who wants them to succeed. Rather than scolding someone or criticizing them, talk about how you’re going to help them level up.
  • Use an agenda for the performance review (or the review document itself) and stick to it. Don’t meander or come up with new critiques on the fly.

Presenting in meetings or large groups

Public speaking can be nerve-wracking because the fear of feeling shame or embarassment in public is hard-coded into human beings.

When it comes to presenting in groups, there’s no substitute for rehearsing. The better you know the material, the more confident you’ll be—and even if you’re nervous, you’ll be able to deliver the message if you’ve rehearsed well. 

Get friends or colleagues to serve as a practice audience. Or just practice saying words out loud. Some people find that practicing public speaking by recording a video of themselves, even if they’ll never share it with anyone, is a great way to overcome nervousness.

Also, don’t be afraid to set ground rules for your presentation. If you want people to wait until the end for questions, let them know at the start of your presentation. Also, check out this blog post on effective presentations in meetings

Speaking up when you disagree

Anything can come up in a meeting—but what do you do when someone provides misinformation or makes a proposal you disagree with? 

You can’t prepare for these situations, but here are some tips for handling disagreement:

  • Acknowledge and repeat the point that the speaker made, and the (positive) intention or evidence behind the point. 
  • Transition to your viewpoint by making it clear that this is your opinion, not an attack on the speaker, by saying something like “My perspective is a bit different…” 
  • State why you think it’s important to consider different perspectives, with the good of the entire team in mind. 
  • Be ready for your opinion to be rejected. Allow space for different perspectives and others will be more open to yours. If you are proven wrong, admit it.
  • If appropriate, defend the opinion or offer alternatives and compromises. Don’t let the disagreement devolve into an argument. Disagreement can lead to creativity if handled maturely. 

Presenting unconventional ideas

While companies often tell you they want people to “think out of the box”, it’s easier said than done. Even during brainstorming sessions, people often have trouble saying out loud their craziest ideas, even when they know their ideas have merit. 

To comfortably bring up unconventional ideas, use some of these catchphrases before blurting out the idea:

  • "This might seem crazy, but I think it brings the conversation forward…"
  • "This idea isn’t fully formed, but it could be a direction to think about…"
  • "OK, this is my latest out-of-the-box idea. How about…"
  • "What if we thought about this from a different perspective? For example…. "

Reporting bad news

Nobody wants to bring bad news to a meeting, but it’s a fact of life that things don’t always go smoothly. 

Whether you’ve made a mistake, the customers are dissatisfied, or the quarterly sales are lagging, it’s better to handle problems as soon as they come up. Being able to deliver bad news is better positioned to repair the problems.

When delivering bad news:

  • Start by providing the facts of what happened rather than an interpretation. For example “Ten customers said the product isn’t performing as promised,” and not “The product is a disaster.”
  • Offer at least one solution, and if possible multiple solutions to the problem.
  • If it’s your fault, admit it, apologize, and, where appropriate, offer to take responsibility and make up for the mistake.
  • Create structures or a retro meeting where people can suggest practices that will prevent this problem from happening again.

Organizational culture: Setting the stage

If you’re in a position of authority in your organization, improving the organization’s company culture and ability to receive feedback is part of your mandate. Take note of any “consequences” when people provide negative feedback in the organization. 

Consequences can range from being shamed or ignored all the way through losing a job in the company. On a personal level, notice your own reactions when you don’t agree with someone’s opinion, and get coaching (even from your employees) on how you could improve your receptiveness to difficult conversations.

10X Culture book cover

Culture can break your team.
It can also unleash it.

"It can be read in an afternoon, but you'll be re-reading it for the rest of your life."
—Eric S. Yuan, CEO of Zoom
Thank you! We've sent 10X Culture to your email.
Oops! Something went wrong while submitting the form.
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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with 18 years experience in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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