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The Stay Conversation: Talk Before They Walk

By Eileen Dooley

For many organizations, January 2022 marks the long-awaited return to the office. For others, it is probably not too far away in the calendar. Now that some or all are heading back to the office, it is time to have an important, but difficult conversation: the Stay Conversation. 

The Stay Conversation is going to touch on some key points, geared not just at keeping employees on board, but enabling trust and empowerment within your team. The workplace they left in March of 2020 is not (nor should it be!) the same one they will be going back to in 2022, and they will have their say in it. The Stay Conversation is how we achieve this. 

 At a recent Humance webinar, Dr. Laura Hambley tackled the topic of leading in the Great Resignation, and offered some advice on navigating through the fear and uncertainty regarding the return to the office, or the beginning of a hybrid work arrangement. One of the key takeaways was communication: being open, honest, and trustworthy was crucial while leading during this period. Good communication can also make going back at the office easier on some. With the right approach, the Great Resignation may not hit your workplace.  

The Great Resignation is the buzz term right now. You might have heard many different definitions but essentially it refers to employees quitting or switching jobs en masse due to various factors, ranging from ineffective leadership to lack of growth opportunities. People are looking for “healthy” and more fulfilling work, which often includes a flexible work model, but also more fairness, equality and an adequate workload. It is happening across all the industries, not just the blue-collar ones.

Take, for example, the hospitality industry. Most major centres are concerned about a lack of people wanting to work in bars and restaurants. They cite a labour shortage, but the truth is that there is no such thing: there is, however, a shortage of people willing to come back to the same working conditions, pay, and expectations. Bars and restaurants must change the way they operate and compensate employees if they wish to survive the Great Resignation. 

The corporate world is no different. There is not an actual shortage of talent but rather a movement of talented people who are standing up for themselves and demanding their employers do better by them. It is time for leaders to listen—cue the Stay Conversation. 

Contrary to popular belief, the Stay Conversation is not about asking an employee with one foot out the door to reconsider staying by offering them perks and more money. It is about having an annual, purposeful conversation to explore what motivates them, and truly understand why they come to work every day. It is also a chance to understand what could cause them to move on, while establishing trust and an open line of communication.

Stay Conversations are not part of the performance review. They are also not a survey or questionnaire. They are a meaningful conversation between an employee and their leader with honest thoughts and feelings about the work they do and their workplace. They are meant to be a useful engagement strategy, to get an employee to open up—and give valuable feedback on their experience so far. It is also an opportunity for an employer to take stock on what is working and what is not. 

Sample questions that you can include in a Stay Conversation:  

  • What motivates and excites you about the work you do here, and what would make you want to stay long-term? 
  • What do you like and what do you dislike about your work? 
  • What professional development opportunities would you like us to help you with? 
  • What did you have before that you do not anymore, but wish you had again? 
  • What do you think about on your way to work and on your way home afterwards? 

For most of us trust is earned, not assumed. The Stay Conversation is a great way to start earning back the trust that has been waning for almost two years. 

The Stay Conversation can help you avoid, or even bypass, the Great Resignation but only through a culture of mutual trust and respect. Give your employees this solid one-on-one conversation and act on what comes out of it.  

Eileen Dooley

Eileen works with executive and senior leadership teams to assess and identify opportunities for people, culture, and talent improvements, providing her clients with balanced perspectives that help realize opportunity and potential. Certified in Hogan assessments, Eileen also brings additional skills in mediation, negotiation, and communications.

Eileen is a certified coach who connects deeply with people, providing innovative and personalized approaches to talent development, learning, and ongoing professional development that underpins succession planning and team member skills growth. She has had a career-long focus on supporting effective, high-performance organizational cultures and working with leaders and teams to develop and execute integrated plans.

In addition to her work with Humance, Eileen is a monthly national business columnist with the Globe and Mail and a trusted thought leader on people, culture, and career trends. She is also a source for other national and local publications, and television and radio outlets throughout Canada.

Prior to specializing in leadership development and coaching, Eileen spent 15 years as a communications professional, with a portfolio that includes senior management experience and team leadership.


Work EvOHlution™ has been a world leader in remote work success since our launch in 2014. We are a Calgary-based team of Organizational Psychologists committed to enhancing engagement and performance in distributed workplaces. We offer innovative assessment tools for leaders, teams, and employees based on research conducted since 2003, as well as consulting, coaching, and training solutions. Work EvOHlution™ specializes in supporting organizations both locally and internationally.

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