--- title: How to Have Meaningful Conversations with Employees About Their Well-being description: Get practical tips for starting employee well-being conversations that build trust, support mental health and promote a healthier workplace culture. image: https://engage.wsps.ca/hubfs/one-on-one-conversations.png --- [Skip to the main content.](https://engage.wsps.ca/trusted-leader/how-to-have-meaningful-conversations-with-employees-about-their-well-being#main-content) [![ceo-hs-leadership-network-logo](https://engage.wsps.ca/hs-fs/hubfs/The%20Trusted%20Leader%20BLOG/ceo-hs-leadership-network-logo.png?width=387&height=150&name=ceo-hs-leadership-network-logo.png "ceo-hs-leadership-network-logo")](https://www.wsps.ca) [![ceo-hs-leadership-network-logo](https://engage.wsps.ca/hs-fs/hubfs/The%20Trusted%20Leader%20BLOG/ceo-hs-leadership-network-logo.png?width=387&height=150&name=ceo-hs-leadership-network-logo.png "ceo-hs-leadership-network-logo")](https://www.wsps.ca) - [Blog Homepage](https://engage.wsps.ca/trusted-leader) - Meet Our Authors - [Aaron Marks](https://engage.wsps.ca/trusted-leader/meet-aaron-marks) - [Andrew Harkness](https://engage.wsps.ca/trusted-leader/meet-andrew-harkness) - [Anne Cesak](https://engage.wsps.ca/trusted-leader/meet-anne-cesak) - [Bill Howatt](https://engage.wsps.ca/trusted-leader/meet-dr-bill-howatt) - [Fresh Communications](https://engage.wsps.ca/trusted-leader/meet-fresh-communications) - [Jeff Linkenbach](https://engage.wsps.ca/trusted-leader/meet-dr-jeff-linkenbach) - [Louise Bradley](https://engage.wsps.ca/trusted-leader/meet-louise-bradley) - [Melissa Agnes](https://engage.wsps.ca/trusted-leader/meet-melissa-agnes) - [Michael Cooper](https://engage.wsps.ca/trusted-leader/meet-michael-cooper) - [Michel Rodrigue](https://engage.wsps.ca/trusted-leader/meet-michel-rodrigue) - [Milena Braticevic](https://engage.wsps.ca/trusted-leader/meet-milena-braticevic) - [Sheldon Kennedy](https://engage.wsps.ca/trusted-leader/meet-sheldon-kennedy) Toggle Menu Toggle Menu - [Blog Homepage](https://engage.wsps.ca/trusted-leader) - Meet Our Authors - [Aaron Marks](https://engage.wsps.ca/trusted-leader/meet-aaron-marks) - [Andrew Harkness](https://engage.wsps.ca/trusted-leader/meet-andrew-harkness) - [Anne Cesak](https://engage.wsps.ca/trusted-leader/meet-anne-cesak) - [Bill Howatt](https://engage.wsps.ca/trusted-leader/meet-dr-bill-howatt) - [Fresh Communications](https://engage.wsps.ca/trusted-leader/meet-fresh-communications) - [Jeff Linkenbach](https://engage.wsps.ca/trusted-leader/meet-dr-jeff-linkenbach) - [Louise Bradley](https://engage.wsps.ca/trusted-leader/meet-louise-bradley) - [Melissa Agnes](https://engage.wsps.ca/trusted-leader/meet-melissa-agnes) - [Michael Cooper](https://engage.wsps.ca/trusted-leader/meet-michael-cooper) - [Michel Rodrigue](https://engage.wsps.ca/trusted-leader/meet-michel-rodrigue) - [Milena Braticevic](https://engage.wsps.ca/trusted-leader/meet-milena-braticevic) - [Sheldon Kennedy](https://engage.wsps.ca/trusted-leader/meet-sheldon-kennedy) - Example Link - Example Link - Example Link 3 min read # How to Have Meaningful Conversations with Employees About Their Well-being [![Picture of Fresh Communications in collaboration with WSPS](https://engage.wsps.ca/hubfs/The%20Trusted%20Leader%20BLOG/Author%20Pencil.png) Fresh Communications in collaboration with WSPS](https://engage.wsps.ca/trusted-leader/author/fresh-communications-in-collaboration-with-wsps) : November 9, 2026 ![How to Have Meaningful Conversations with Employees About Their Well-being](https://engage.wsps.ca/hubfs/one-on-one-conversations.png) If you have been following the Trusted Leader blog, you know that in most articles, we encourage open dialogue with employees and check-ins to ensure they have an opportunity to discuss how they are feeling, how work is going and whether they are facing any challenges that may be affecting their engagement. We’ve shared prompts and questions that leaders can use as a starting point for these conversations; however, to some, connecting with employees this way may feel uncomfortable. Maybe you want to introduce this activity in your workplace, but you’ve never done it before and you’re not sure how to get started. Or you are a new leader, and this is a new skill that you’re developing, and you need a little extra guidance.  It can feel awkward as you begin, but it’s worth pushing through. When you and other leaders connect this way with employees, you deepen trust and create the opportunity to capture valuable insights that will help protect and support employees and your organization. Below are some tips to help you get started: Prepare leaders to engage in these conversations This won’t necessarily be a natural activity for all leaders in your organization. Some may require training and coaching to build the necessary skills.  Consider how you are supporting them. Talk about your intent to build this into employee relationships and seek their input on how they feel they need to prepare. If other leaders don’t feel confident having these conversations, they won’t prioritize them, which will lead to inconsistency and undermine your efforts. You may consider professional development to build soft skills, as well as [specialized training](https://www.wsps.ca/search-results#t=Shop&sort=relevancy&f:@shopifycategory=[Violence%20%26%20Harassment,Workplace%20Mental%20Health%20%26%20Employee%20Wellbeing]) to support employees’ mental health. In this article, [The Niagara Institute](https://www.niagarainstitute.com/blog/soft-skills) describes soft skills as “non-technical abilities that influence how you work, communicate and collaborate with others. They include traits like emotional intelligence, adaptability, and problem-solving that shape your professional relationships and workplace effectiveness.” The article highlights that while both hard and soft skills are important, 57% of leaders feel soft skills are most important because of their impact on long-term success. The need to be aware of and equipped to support employees who are experiencing mental health challenges is extremely important. Not only is it critical in building a healthy and safe workplace culture that protects physical and psychological health and safety, but it has also become a quality that employees are seeking in an employer. Managers don’t need to become psychologists. They just need to understand how to identify employees who may be having difficulty due to work conditions or personal events, and let employees know they can provide support, and direct them to the appropriate resources Lay the foundation If you want to start having regular check-ins, don’t spring it on your employees. Let them know that this is something you will be doing. Explain how it will work, including how frequently you’d like to connect, the length of time you’ll spend together and how you would like to approach the conversations, so they know what to expect. As you begin, you might discover that you want to tweak things and to foster deeper engagement. Consider inviting employees to make suggestions to help shape the approach, so they are more comfortable having these conversations. Consistency is key Make this part of your culture by talking openly and frequently about this activity in employee meetings and one-on-one discussions. By weaving it into all stages of the employee relationship beginning with recruitment, employees and new hires will understand that this is a fundamental part of your relationship with them.  Remember, these conversations are designed to deepen trust, so avoid starting and stopping or cancelling for other “more important” meetings. Set a schedule or a cadence for the conversations and then be sure to stick to it. Committing that time and protecting it is a strong demonstration that these conversations are important to you, too. Figure out the best approach for your workplace If you are operating a small business and space is at a premium, look for ways to connect one-on-one with employees where they will feel safe to be open and engage in the conversation without fear of being overheard. And make sure schedule the discussion during working hours. You don’t want employees to feel that they must give up their breaks or lunch for this activity. It should be part of their workday. Be kind to yourself If this is new to your workplace or just a new skill for you, don’t expect to get it right immediately or necessarily every time. What matters is your intent and approach. Give employees the opportunity to shape the approach and conversation and remind yourself that employees aren’t perfect, and neither are you. However, by working together, you can build confidence and boost individual and organizational performance. Additional resources If you are not an owner or CEO, and you think having these types of conversations would bring value to your workplace, you might want to check out these articles about creating a Great Place to Work® to help you build a business case for getting started. [9 High-Trust Leadership Behaviors Everyone Should Model](https://www.greatplacetowork.com/resources/blog/9high-trust-leadership-behaviors-everyone-should-model) [The Positive Impact of Safety on the Employee Experience](https://engage.wsps.ca/trusted-leader/the-positive-impact-of-safety-on-the-employee-experience) Get to know the authors – [Fresh Communications](https://engage.wsps.ca/trusted-leader/meet-fresh-communications) - [Tweet](https://twitter.com/share) [![Identify And Prevent Workplace Psychological Hazards In Five Easy Steps](https://engage.wsps.ca/hubfs/phs-program.png)](https://engage.wsps.ca/trusted-leader/identify-and-prevent-workplace-psychological-hazards-in-five-easy-steps) #### [Identify And Prevent Workplace Psychological Hazards In Five Easy Steps](https://engage.wsps.ca/trusted-leader/identify-and-prevent-workplace-psychological-hazards-in-five-easy-steps) ![Picture of Dr. Bill Howatt](https://engage.wsps.ca/hs-fs/hubfs/The%20Trusted%20Leader%20BLOG/Author%20Pencil.png?width=30&name=Author%20Pencil.png) [Dr. Bill Howatt](https://engage.wsps.ca/trusted-leader/author/dr-bill-howatt) : December 4, 2025 Psychological Health and Safety (PHS) programs are more than policies. They are the foundation for creating workplaces where every employee feels... [Health & Safety Culture](https://engage.wsps.ca/trusted-leader/tag/health-safety-culture) [Read More](https://engage.wsps.ca/trusted-leader/identify-and-prevent-workplace-psychological-hazards-in-five-easy-steps) [![If you’re not investing in workplace mental health you are putting people at risk and leaving money on the table](https://engage.wsps.ca/hubfs/investing-in-workplace-mental-health.jpg)](https://engage.wsps.ca/trusted-leader/investing-in-workplace-mental-health) 3 min read #### [If you’re not investing in workplace mental health you are putting people at risk and leaving money on the table](https://engage.wsps.ca/trusted-leader/investing-in-workplace-mental-health) ![Picture of Dr. Bill Howatt and Michel Rodrigue](https://engage.wsps.ca/hs-fs/hubfs/The%20Trusted%20Leader%20BLOG/Author%20Pencil.png?width=30&name=Author%20Pencil.png) [Dr. Bill Howatt and Michel Rodrigue](https://engage.wsps.ca/trusted-leader/author/dr-bill-howatt-and-michel-rodrigue) : December 2, 2021 The workplace is not immune to the lasting impacts of the pandemic on employee’s mental health. With the fourth wave of the pandemic underway... [Psychological Safety & Wellness](https://engage.wsps.ca/trusted-leader/tag/psychological-safety-wellness) [Read More](https://engage.wsps.ca/trusted-leader/investing-in-workplace-mental-health) [![Building a Strong Business Case for Workplace Mental Health](https://engage.wsps.ca/hubfs/Trusted%20Lead%20Images.png)](https://engage.wsps.ca/trusted-leader/building-a-strong-business-case-for-workplace-mental-health) #### [Building a Strong Business Case for Workplace Mental Health](https://engage.wsps.ca/trusted-leader/building-a-strong-business-case-for-workplace-mental-health) ![Picture of Dr. Bill Howatt](https://engage.wsps.ca/hs-fs/hubfs/The%20Trusted%20Leader%20BLOG/Author%20Pencil.png?width=30&name=Author%20Pencil.png) [Dr. Bill Howatt](https://engage.wsps.ca/trusted-leader/author/dr-bill-howatt) : March 13, 2025 Addressing mental health in the workplace has never been more critical as businesses navigate an increasingly complex landscape. Unfortunately, many... [Psychological Safety & Wellness](https://engage.wsps.ca/trusted-leader/tag/psychological-safety-wellness) [Read More](https://engage.wsps.ca/trusted-leader/building-a-strong-business-case-for-workplace-mental-health) ## Subscribe Here! [![WSPS White Logo](https://engage.wsps.ca/hs-fs/hubfs/Branding/WSPS_LogoNoTag%20R_REV.png?width=200&height=67&name=WSPS_LogoNoTag%20R_REV.png)](https://www.wsps.ca) - [Privacy Policy](https://www.wsps.ca/about-us/policies/wsps-website-privacy-policy) - [Terms of Use](https://www.wsps.ca/about-us/policies/website-terms-of-use) © 2026 Workplace Safety & Prevention Services. All Rights Reserved.