SALES TEAM DISCUSSION QUESTIONS

Steven Cesare, Ph.D.

An unsettled business owner from Illinois called me the other day to address mounting concerns about the company’s sales employees. Despite impressive and sustained growth as a leading landscape contractor in the region, the business owner has noticed his four-person sales team has become passive, serving more as “order takers” (i.e., simply receiving requests from prospective clients), rather than as “prospectors” (i.e., taking the initiative to actively contact potential clients).

With revenue approaching $7,000,000, the owner conducted a series of individual and collective meetings to address the causes, consequences, and remedies with his increasingly inert staff, hoping to rekindle their historical motivation. The assessment protocol he posed to each sales employee is shown below.

How would you evaluate your overall sales performance since your previous performance review?
What sales achievements or deals from this review period are you most proud of and why?
What challenges have you encountered over the past year or so related to sales targets, clients, or market conditions, and how did you overcome them?
Tell me about the top three setbacks that impacted your sales performance or commission earnings, and how you have attempted to navigate those challenges.
Describe the most recent time you experienced a difficult sale or client situation that you successfully managed, and what strategies helped you close the deal.
How do you think your sales contributions have impacted our company since 2023?
How do you think your sales techniques and strategies have evolved since 2023?
What new sales approach or client interaction have you implemented since 2023; how, and why?
What aspects of sales do you feel most confident in, and what gives you that confidence?
How well do you feel your current role aligns with your sales skills, strengths, and career interests?
What do you find most challenging related to lead generation and closing deals?
Do you feel comfortable with your sales targets and compensation structure?
What feedback have you received from clients or colleagues this year, and how have you applied it?
What do you enjoy most about selling in this role, and what keeps you motivated?
What tools, training, or support would help improve your sales performance and annual earnings?
What inefficiencies in the sales process do you think should be addressed immediately?
In what ways can I make your job more enjoyable or help you stay engaged in your sales role?
Do you feel recognized and rewarded appropriately for your sales achievements?
What three specific activities do you routinely employ to initiate a new sales lead?
Besides “price,” what single issue do you believe is most critical in improving your capture rate?
What specific roadblocks in lead generation, pricing, or client outreach must be improved upon now?
What market trends have you witnessed and how have you adapted to them to achieve sales goals?
Looking ahead, how can management support you in achieving your sales goals for the next quarter?
What aspiration do you have within our company for this year, and how can we help you attain it?
What opportunities, accounts, or markets would you like to explore to expand your sales potential?
What specific sales skills, negotiation techniques, or industry knowledge do you plan to develop?
What changes in your role, responsibilities, or compensation would increase your capture rate?
What three aspects about the sales culture and team environment should we improve upon now?
How would you describe our communication regarding sales expectations, goals, and feedback?
What coaching expectations do you have of your Manager to ensure you achieve your sales goals?

Thorough to say the least.

Successful business owners, usually are.

Preliminary results revealed the sales employees: (1) became functionally lazy during Covid (which was four years ago, but anyway) since they could not go out and meet new prospects, (2) frequently cited the need for improved marketing resources (e.g., entrepreneurial web site, higher quality materials, more company visibility like open houses, social media, and strategically aligned marketing calendar events), and (3) of course, as capitalists, you know they wanted a commission rate above the current 4%.

The owner readily admitted accountability starts with him; but ultimately resides with his sales employees.

If you have any questions or comments about this topic or anything else related to human resources, Sign Up for Steve’s HR Helpdesk!