Retaining and Engaging Top Performers with Career Management

Published on
January 30, 2017
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It’s 8:30 pm. There’s a list of customers who need to be called back, the new product line is about to ship, and you need to decide to either sign a lease, or let that new office space go. Just then, you learn that a key employee has given notice, and will be leaving at the end of next week. As the business owner, you wonder how to find more time to get everything done. You love talking with customers and regret not getting to their calls earlier. The new products look great, and you forgot to thank the design and production team for their hard work. Leases and legal agreements aren’t your forte, but you have good advisors around you. But the employee who has quit takes your breath away. How could you have caught this earlier? Is it too late? Why didn’t they come talk to you? Why does this keep happening? You care deeply for your staff. Exhausted, you head home. Tomorrow is another day and you have a family waiting for dinner.

Running a small business requires a diverse set of skills: product development, customer management, operations, financial analysis, marketing, etc. In large organizations, there are departments staffed with specialists, but in small- and medium-sized businesses who employ 90.3% of Canada’s private sector workforce, business owners oversee almost every function.

In the course of my research, 88% of business owners indicated that people-related issues kept them up at night. Yet, few small businesses have dedicated HR staff—if they do have HR support, they are focused on issues related to recruitment, compliance and performance management. They are fighting fires and keeping the company on-side of regulations, but they often aren’t fostering an engaging workplace. In a study commissioned by CERIC (Canadian Education and Research Institute in Counselling) in 2014, the research also indicated a troubling gap: 71% of employers said they have responsibilities for employee career management, however, only 29% felt they were doing anything about it. Employers indicated that they lacked the time, knowledge and resources to be able to focus on this critical area.

Last summer, CERIC approached me to create a Playbook that would bridge the gap between awareness and action for busy business owners. I spoke with people across the country, and it became clear that few people are aware of the importance of career development and management in navigating today’s increasingly mobile and flexible workforce.

Career paths were introduced into companies in the 1970s. Since that time, despite being a manager’s mantra, employees have not truly been in control of their own careers. It is a shared responsibility. One that employees have become quite adept at navigating and where managers have lost ground.

In the late 2000s the balance between managers and employees began to shift. Intergenerational workforces, shifting demographics, increasing freelance labor, and other trends became part of every strategic planning discussion. Firms saw staff leave, some voluntary and some by request. Instead of joining competitor firms, there was an increase in the number of people starting or joining small businesses. Employees were taking more control over their own careers.

In small businesses, engaging in career-related conversations is considered risky—what if the employee asks for more money or upward mobility an organization that can’t accommodate that type of reward? Owners of small businesses often believe avoiding the conversation until the business grows is the safest strategy.

However, avoiding career related discussions is not smart. We are shifting from an era where technology was the dominant business disruptor to an era where technology and talent innovation together present new competitive opportunities. Career discussions are no longer a once a year activity. They happen in real-time, everyday either directly or indirectly as networks learn what it is like to work at your company and at others via social media and through friends. Business owners need tools to fit these important and weighty conversations into everyday activities.

Retain and Gain: Career Management for Small Business provides these tools. For any owner or manager worried about retaining a highly engaged workforce, developing a career management strategy is great place to start. It is an ongoing process that requires frequent conversations and reflection—but the investment will pay off.

Returning to work the next day, you review Retain and Gain and build a “career management itinerary” of activities to implement. Each activity provides an outline of steps and resources to use. First, you take ten minutes to reflect on how your involvement with staff has changed over time. In the early days, you had much more direct contact. Now that the business has grown, you’ve stepped back from some of the daily interaction. You realize it’s been months since your last casual check in with many of the staff, and promptly schedule ten minute windows in your calendar to have at least one “no agenda” conversation with each staff member over the next quarter. Next, you sit down with the employee who quit the day before, and learn that they likely would have stayed if they’d known there was opportunity to advance within your business. Armed with the knowledge that employees crave more information about how they fit within the future of the company, you schedule a one hour meeting with the management team to discuss implementing a Career Champion program to share career management and development resources with your team. At the end of the day, you know that there is still a lot of work to do, but you feel more confident knowing that you are back on track, providing your team of exceptional staff avenues to build their own careers while they help you build the business.

Lisa Taylor is the President of Challenge Factory, a talent equity firm focused on the future of work, providing platforms, products and services designed to supercharge the value of the workforce. Retain and Gain: Career Management for Small Business is available as a free .pdf download at or in paperback and e-reader formats via and