Your Mid-Year Sales Career Check-up

By Michael J Griffin

6-minute read

Last week, I wrote a blog on a personal development mid-year check-up. This week, let’s review how you did as a salesperson for the first half of 2025. With these questions and your answers, you can then reflect and prepare for an even more successful second half of 2025 and end the year well. As you read and answer, take notes on what you will do differently in the second half have a more meaningful, successful second half.

Sales Managers: Use these questions as a one-on-one discussion and coaching session with your salespeople!

Review Your Sales Achievements & Progress

1. What sales accomplishments are you most proud of from the first half of 2025?

2. Which deals or client relationships brought you the most satisfaction or growth?

3. What new skills, techniques, or habits have you developed so far this year?

Learning from Your Sales Challenges

1. Which of your prospecting activities generated the highest quality leads, and which were time-wasters?

2. What obstacles or setbacks did you face, and how did you respond to them?

3. Which deals didn’t close as planned, and what can you learn from those experiences?

4. What patterns do you notice in your most successful deals versus the ones that didn't close?

5. Are there any recurring challenges or objections you want to get better at overcoming?

6. What constructive feedback have you received from clients or colleagues, and how have you acted on it?

7. How are you doing in building rapport and trust with the different customer personalities you interact with when you sell?

8. What's one area where you know you're still leaving money on the table due to a skill gap?

Your Self-Reflection & Growth

1. How have you grown personally and professionally since the start of the year?

2. What motivates you most in your sales role, and has that changed this year?

3. How have you managed your time, energy, and stress? What could you improve?

4. What habits or routines have helped you consistently perform at your best?

5. How does your personal health, diet, exercise, or sleep nurture and support or hinder your ability to maintain high energy and drive?

Looking Forward in the Second Half: Motivation & Action

1.  What is your biggest goal for the second half of 2025?

2.  What would have to happen in the second half for you to look back on 2025 as your best year ever?

3. Which relationships (prospects, customers, or internal team members) deserve more of your attention in the coming months?

4. Which market segment or customer type should you spend more time pursuing based on your first-half results?

5. What's one process or habit you need to eliminate because it's not serving your success?

6. Do you have a personal learning plan with specific actions or changes will help you achieve even better sales career?

7. How can your sales manager support you to achieve your second-half of sales success? Can you discuss this with him/her?

8. What new sales strategies, tools, or training would you like to sign up for in the coming months?

9. What can you do to maintain your sales motivation, persistence, and resilience through the rest of the year?

10. Do you take off days to recharge? Are you taking your holiday time?

11. What does a truly fulfilling and successful year look like for you, and what’s one bold step you can take now to make it happen?

12. Does your current sales career give you meaning and satisfaction? Or do you need to change jobs?

May these questions, your reflections, and the actions you decide to take from July onwards lead you in 2025 to your most successful year in the honourable career of sales!

Michael J Griffin
CEO & Founder ELAvate
Sales Productivity Consultant
michael.griffin@elavateglobal.com
+65-91194008 (WhatsApp)