VIENNA, Va. – Dec. 23, 2020  —Our friends at Maestro Group wanted to collect and share the most valuable lessons and sales tips learned this year. Maestro Group, like IES, is focused on actionable best practices and tools. Their sales trainings provide attendees with practical instruction that can be immediately put to use. Their year-end sales survey asked one critical question—what is the best lesson or tip you learned in 2020?

This year has been anything but typical, but that doesn’t mean we haven’t learned valuable lessons to apply in the (hopefully less volatile) future. In fact, the events of 2020 may have forced us as sales professionals to home in on some of the most essential tools and strategies. We wanted to find out from our community the best lessons learned this year and share them with other selling professionals. Here is what we heard.

Risky Business

Nobody likes to think of every little thing that could possibly go wrong, but as a sales professional, it’s part of the job. As one respondent said, “Always be ready to mitigate risk at each connection. Things can always go sideways—be prepared to tackle that risk, and be prepared for it before it happens.”

One of our two pillars at Maestro Group is “mitigate risk.” By preparing for each possibility, sales professionals can turn risk into opportunity. Objections from prospects are often seen as a negative, but if you’ve prepared properly, they can instead provide insight into what your prospect values. Matt Butler, Director of Global Sales at Katabat, said, “There’s no better way to deal with an objection than to anticipate it and have a plan for it going in.” If you’ve prepared ahead for what you’ll do when confronted with a risky situation like an objection, you’ve essentially taken the risk out of it.

Purposeful and Prepared Questions

Account Executive at Matt Nash reported that his best lesson this year was on preparing “question trees.” Creating a question tree is a great way to not only plan your own line of questioning, but also to anticipate answers. It’s an iterative exercise that is a great risk mitigator because it forces you to plan for nearly all possibilities.

Just as important as your line of questioning is how you plan on asking each question. One of our respondents shared that her biggest tip learned this year was to “ask, ‘What part of your question have I left unanswered?’ instead of, ‘Does that answer your question?’” The latter question can only get you a yes or a no, neither of which provide much in the way of information. Open-ended questions like the former both prompt the prospect to think a little more about their response and provide you with a clearer idea of what your prospect is thinking.

Keep It Moving

“Be consistent in the process of moving the sale…along, and you will train the prospect as to what to expect and what next steps are needed,” was the best lesson of one respondent. Several survey participants indicated that their most impactful sales lesson this year was about keeping deals moving smoothly. Sales is bound by the laws of physics: a deal in motion stays in motion. That’s why it’s critical to keep things moving and avoid stops and starts—once a deal stops, getting it restarted can take a good bit of energy.

Another individual replied that his best tip of the year was to suggest three times when asking for a call or meeting as it “easily saves a back and forth step or two.” Finding a time to talk to you for 20 minutes sometime in the future feels complicated, so prospects may put it aside to deal with later (and never come back to it). By providing three specific time slots when asking for a time to speak, your message is harder to ignore and leaves less planning and decision making (friction) for your prospect. See, it’s all about the physics.

At Maestro we firmly believe that if you’re a true sales professional, you can always learn more and continually hone your craft. We would love to hear more of the best sales lessons and tips you learned in 2020. Our survey is still open. Please share your knowledge and strategies here! If you’re interested in learning more about Maestro’s training, contact us at