Sales Strategy

Keep Your Team Engaged With This Midyear Assessment

Working in sales is a grind. Ask your team these questions to boost morale and keep employees engaged...

June 21, 2021

Assess Where The Team Stands Midyear

It's halfway through the year. We certainly know where our team stands against the quota and KPIs, but what about outside the numbers? Do we know about the engagement and mental wellbeing of our reps? Are they still committed to the mission and the team or biding their time until that job offer comes along?

Use Positive Framing

There's no "silver bullet" to recharging our team's batteries, but reps need a mental break. Using positive framing with our inquiries in one-on-ones and team huddles can help. Try asking these questions in July to improve our chances at keeping our best people and finishing the second half strong.

If the team conducts skip-level meetings, this might be the perfect time of the year to do another round. Experiment with the "skip level" if you haven't yet.

  1. What's your favorite part about this company?
  2. What's your favorite part about being on this team?
  3. What's your favorite part about this job?
  4. What's been our top achievement as a team so far this year?
  5. What's been your top achievement so far this year?
  6. Why are we winning deals today?
  7. What are the top 3 collective strengths of the team today?
  8. What are your top 3 strengths?
  9. Where do you currently feel the most supported?
  10. Tell me about your favorite sales moment so far this year.
  11. How can I help you? Or, what can I do to make you more successful?
  12. How can we help you from a mental health and wellbeing perspective?
  13. What fun trip or vacation are you looking forward to later this year?

Bonus Questions, Tread Lightly

Other questions to consider asking during one-on-ones if we want to veer into problem-solving mode:

  1. Which sales task would you automate if possible?
  2. Which part of our sales process is your confidence the highest?
  3. What's working with our lead gen efforts right now?
  4. What's our top differentiator when it comes to our product or service?
  5. How confident are you about your current pipeline?
  6. Are you learning and growing here?
  7. Are you happy with the money you're making here?  


Post-Assessment Actions

If you choose to ask a few of these questions, be prepared to take action. A solid first step would be to share a summary with the team and a plan to double down on what's working well.

Another action item could be asking your CEO or senior sales leader to join your huddle or mini kickoff for an all-team rally. Team building, if possible, could also be an effective option to boost team morale.

The goal should be to get the team excited and pumped for a successful last six months to 2021!

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