When Conversations Get Hard

In business, as in all other areas of life, communication is the key to success. 

One of the hardest things about communication is saying those uncomfortable things that have to be said. We’ve all had those days where we needed to handle a large conversation that was big and scary. When we look at this from a professional perspective, it doesn’t get any easier. 

So, what are the benefits of having those hard discussions with your team?Improving Company Culture Employee Retention Experience Workplace Business

  • Building a culture of transparency and trust encourages team members to work together in a healthy, productive way.


  • Giving valuable feedback leads to better job performance.


  • Psychological safety and feelings of trust within an organization create a work culture of community and connectedness.


That sounds wonderful, doesn’t it? But how do you get there? What are some steps to take to lead your company in that direction?

We hold managers accountable for having those hard conversations. We coach employees on how to have these hard conversations, and their managers as well. Trust, after all, is a two-way street. 

One important step is coaching managers on how to receive feedback. It can be hard for managers to give constructive feedback, or have those uncomfortable conversations, but it’s also hard for them to be on the receiving end. I have found that to be especially true when the feedback is from someone that reports to them.

Finding the right balance in these moments creates a feeling of psychological safety.

If we’re building that culture of transparency and trust, and that open feedback loop; then everybody is likely to be much more comfortable (or as they’re willing to be at that moment) to have those conversations. I believe it helps the organization grow into a healthy, well-organized group who respects each other.

Keep in mind that timing is everything.

If you have something that you need to share, and you’re worried about how it’s going to be perceived, ask the individual if they have some time to have an uncomfortable conversation. You also have to be OK with allowing them some prep time if they aren’t ready. Giving someone a little time may help them get into the headspace where they can receive constructive feedback. Because if they’re not ready, then it’s not going to lead anywhere positive. Timing is everything. We also have to meet people where they are. 

Allowing someone to feel like they are mentally prepared to have that conversation will increase the chances of it being productive. Giving them the option, instead of diving right in, builds trust. You have to look at the whole person. There might be outside forces that are impacting what’s going on at work.

We’re working outside of the office, you’ve got family, you’ve got other things going on, it all impacts the whole self that we bring to work. 

While meeting goals and objectives are important, we can still create a safe space for people to bring their whole self to work, and feel respected, even when the conversations get hard. 

How do you handle tough conversations with an employee, team member, or manager? Share in the comments below so we can all learn together. 

Profile photo of Caitlin Lanning, SHRM-CP, CWWSCaitlin Lanning

VP, People & Culture at Momnt

Momnt powers modern lending solutions for businesses to provide low-friction, affordable financing to their customers at the moment of need. Our mission is to make lending as seamless as possible for merchants, consumers, and lenders. Momnt removes the complexities of the consumer lending process through our easy-to-use, mobile-friendly technology that empowers merchants to provide attractive, real-time loan offers at the moment their consumers need them.



Hiring Recruiting Jobs Recruiter Josh McAfee Tech JobsJosh McAfee is the Co-Founder and Managing Partner at Humans Doing. With over 26 years of recruiting and team-building experience, Josh has worked with startups, SMBs, and large companies to determine hiring needs, develop our recruiting strategies and processes, and connect top talent to fuel growth. In 2021, he became a Wall Street Journal and USA Today bestselling author with his book Measure Up: Mastering Your Career Search Like a Boss.

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