The Fine Line of Being Bold In Sales

I’ve been in sales long enough to know or witness most of the tricks of the trade. Just when I thought I had seen it all, something took me by surprise: someone I didn’t know or had any previous contact with randomly scheduled time on my calendar (compliments of Calendly, a tool I really like by the way)—with ZERO context or communication prior to the booked time.


To me, this move felt “icky” coming across as intrusive and disrespectful, but I wanted to know what others thought about it to see if my reaction was reasonable. After digesting the details compliments of my LinkedIn network, I learned that the majority felt the exact same way I did. So I began thinking about what said offender could have done differently to secure that time on my calendar without the bold move that turned me off and led to an immediate cancellation with a kind note explaining why. I know firsthand how difficult it is to secure a meeting and how that translates to meaningful results. Begging the question, how should salespeople go about scheduling time with their coveted buyers and customers?


It’s ALL About the Approach


Whether you work in sales or not, there’s no question that experts in your field emphasize the importance of the first impression. This is a cardinal rule in business and absolutely translates to those of us in sales.


Contradictory to this, business experts also express the importance of avoiding snap judgments. In an ideal business world, no one would be judged for their characteristics or previous actions.


In my opinion, people that think it’s OK to schedule time on a stranger’s calendar adhere more to the principle of avoiding snap judgements. One of two things is happening here.  They likely believe that their product is valuable, and therefore worth a prospect’s time or they’re under such pressure internally that they’ll do anything to secure a meeting to satisfy their targets … Even if that means hijacking someone’s time—or trying to—without their consent.


After 20 years in the sales trenches, I adhere more to the principle of the first impression along with the “Golden Rule”. What salespeople often neglect to remember is it’s all about the buyer journey and their prospects’ time is valuable; in fact, it’s one of their biggest assets. As such, it’s obscene for someone to assume that they can attempt to capture some of their prospect’s time without context or illustrating any value whatsoever.


For me, it boils down to this: before you schedule time with anyone, provide context for your request and respect the fact that they have the right to say no or not respond. Make your approach count to outline exactly why you’d like to connect with them, and—more importantly—tell them what your time together will do for them.  Less YOU more THEM. Their time is valuable and you’re not the only person knocking on their door. It’s critical to clearly illustrate the “whys”.


Schedule for Them—NOT Yourself 


After the recipient of your request understands the value you provide, you have one more task: scheduling a follow-up. Unfortunately, this is where many salespeople make a mistake: they TELL their prospect when they will follow-up instead of asking the recipient when their schedule will allow a follow-up. Although some view this as a salesperson taking initiative, they still need to be on the customer’s terms, at this point. I’m afraid to break the news, but it’s not all about you and your sales goals.


Instead of telling your prospect when they can expect to hear from you next, understand what’s happening in their world and find out what works well for them. Once you know this important information, it’s okay to provide options; would they like to talk on the phone, do they want a demo, would an in-person meeting work better for them, etc.? Depending on their preferences, set the stage to make the most of your time together (in my opinion, the first conversation should be no more than 30 minutes).


After your stage has been properly set, technology is here to help.  Tools like Calendly,, and the list goes on are real time-savers, eliminating the back and forth of ever-changing schedules, making it a heck of a lot easier to engage.


Understanding & Learning from Rejection


Rejection is the reality of life in sales and something I tackle daily. Although it’s way easier to be liked and accepted, the importance of rejection shouldn’t be ignored. It’s OK and quite healthy to be rejected; in fact, rejection provides a tremendous opportunity to learn and grow – even though it stings a bit.


Look at it this way, rejection is a direct form of feedback that you can embrace to step up your sales game. Let’s think about the instance I referenced earlier about a stranger scheduling time on my calendar. Out of the 33 comments received, 25 of them mentioned that this approach was off-putting and something they wouldn’t react positively to. In other words, this salesperson would have at least a 75% rate of nonresponse or negative response to their technique.


Taking the time to analyze said rejection to leverage this intel provides a wealth of knowledge to influence strategy. Turning people off 75%+ of the time has rejection written all over it, it also presents a major opportunity to improve. With the right attitude and EQ, the salesperson can uncover the missteps in their approach to use this rejection to shape a revised way to engage with their buyers to increase results.


Disclaimer, it’s important to know that even a well-thought-out, effective approach can receive a resounding “No.” When this happens, it doesn’t necessarily mean that there’s something wrong with what you’re offering—maybe it’s just not the right time with competing priorities.


In this case, it’s best to stay close and keep in touch without being a stalker. Keep up with what’s happening in their world, follow them socially, keep a close eye on their business updates and potential challenges that you can help solve, and remain accessible to them—without being overly creepy or involved.  In tandem, identify other influencers and stakeholders that you can engage with (check out #21).


All In All


In my career, I’ve experienced so many things. And just when I think I’ve seen it all, something new comes flying through the woodwork to take me by surprise (good and bad). Many will be successful enough to become industry standards, but many will crash and burn at the same time—and for good reason.


Everything shared above is what I’ve gathered along the way from my time in sales, but I realize that my thoughts might be completely different than yours; so, let me know what you think! I welcome different perspective and appreciate the opportunity to learn and grow. What is your philosophy on scheduling time with prospects and customers? What is your “Cardinal Rule”?  Where have you stumbled and how did you recover?


As always, thanks for reading!


-Amy Volas