Leveraging The Prospecting Winds
It all comes down to your mindset. Prospecting sucks. But, with determination, perseverance, and the prospecting winds at their backs, they are able to leverage and overcome challenges to close more deals.
Prospecting Is A Necessity and A Challenge
Prospecting can really stink. It’s often uncomfortable and for some people, it can be very frightening. But here’s the reality: If you are in sales, it’s an absolute necessity. The ultra-high performers we encounter have a cool mental trick that they deploy when it comes to prospecting. I call it leveraging the prospecting winds.
Riding Against The Wind
The other day I was riding my bike. As soon as I turned onto a three-mile stretch, a 20 mph headwind hit me. I didn’t want to keep going. It wasn’t at all the relaxed bike ride I hoped it would be. Riding into that wind was physically demanding and mentally tough.
Recently, my son went for a run. He’s a rather talented runner who usually has a very quick pace. The first five miles of this ten-mile run were against the wind. Running into the wind slowed him down. He got tired and discouraged. It took the enjoyable part out of his run.
Last weekend, I played golf. The routing of the course was such that the outward holes were all into the wind. On this particular spring day, the wind was howling. Golf was tough. Hitting balls into a strong wind was challenging, and frankly miserable.
When The Wind Is At Your Back
However, my bike ride was incredible because as soon as I made the turn at the end of the three miles, I had the wind at my back. It was fun, it was productive, and I was cruising.
As soon as my son made the turn at the five-mile mark, his pace picked up substantially. He made great time and found new energy once the wind was at his back, pushing him towards the finish.
Once we made the turn at number nine, our golf balls were sailing much further. We weren’t struggling as much, we were hitting greens every time, and we posted excellent scores.
Prospecting Is Like The Wind
Prospecting is like the wind. At first, it feels like everything you do is against the wind. But the more you persevere and gut it out, the easier it becomes. At some point, the wind will be at your back. You will make more connections. You will book more appointments. You will create opportunities, build relationships, and hit your number.
Ultra-high performers understand this. They know that they must go through the trials of prospecting in order to find success in prospecting. They know that by going against the wind, they’ll eventually have the wind with them as long as they persevere.
They mentally prepare themselves and plan their days accordingly. They front-load their day with the headwinds so that they’re downwind the for rest of their day. When the prospecting wind is at your back, you’ll win.
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![6 High-Probability Moments to Send LinkedIn Connection Requests Prior to an Event Events create natural relevance. Conferences, trade shows, user groups, and local meetups give you a reason to connect that does not feel forced. The mistake sellers make is waiting until the event starts or turning the request into a pitch. A better move is connecting days or weeks ahead with a simple acknowledgment of the shared event. Example: Hi Sarah, saw you’re attending the Midwest Manufacturing Summit next month. I’ll also be there and am super excited! I’d love to catch up in person at the event. In the meantime, let’s connect here on LinkedIn. You are aligning with something already on their calendar. When you see them at the event or reach out afterward, your name is no longer unfamiliar. Following an Event After an event, connection requests work best when they reference a real interaction, even a small one. A short conversation, a question during a session, or a brief introduction creates enough context. The request should reflect that moment, not attempt to convert it into a follow-up. Example: Tim, I enjoyed meeting you at the conference last week. Your take on [subject/trend/idea] was intriguing. I look forward to staying connected and to our next conversation. This reinforces continuity and professionalism without pushing the relationship forward prematurely. After a Sales Call Sending a connection request after a sales call is one of the most underused opportunities in prospecting. If the call was answered and productive, the request reinforces credibility and continuity. Example: Thanks again for the conversation today. I appreciated your perspective on how your team is thinking about next quarter. I look forward to our next meeting and sharing some ideas I have with you and your team. If the prospect did not answer, a connection request can still make sense as a light reinforcement, especially early in the relationship. It keeps your name present without escalating pressure. Either way, the request works because the call establishes legitimacy first. After a Meaningful Interaction Not all interactions happen in formal selling environments. Thoughtful exchanges in comment threads, group discussions, or brief conversations in passing all create natural moments to connect. That might mean running into each other at a non-work event, crossing paths at an airport, or chatting briefly in a line somewhere unexpected. Example: Haley, it was a pleasure meeting you on our flight to Atlanta. Thank you for your restaurant recommendations! I look forward to staying connected, What makes this work is that the interaction was real. The request simply continues it. Mutual Connections Shared connections reduce perceived risk when handled with restraint. They signal that you operate in similar professional circles, not that you have permission to pitch. The mistake is overexplaining or implying endorsement. Example: Hi Mark, I noticed that you are connected to my good friend, James, and since you are also [interested in, working in, located in] I thought it might make sense for us to be connected also. A simple acknowledgment is enough. Familiarity does the work. Profile Views Profile views signal awareness, not intent. When someone views your profile after a call, email, or content interaction, a connection request can make sense as a low-pressure acknowledgment. Example: Wendy, thank you for visiting my profile. I had a chance to look at yours, and based on your interests, I thought it might make sense for us to connect. The discipline is resisting the urge to read more into it than is there. Want the exact framework for integrating LinkedIn into a disciplined outreach sequence without pitching, spamming, or wasting time? Buy The LinkedIn Edge by Jeb Blount and Brynne Tillman today. Sales Gravy is the number one sales training organization](https://salesgravy.com/wp-content/uploads/2025/12/6-Moments-LinkedIn-Connection-Requests-Actually-Work-in-Prospecting-Sales-Gravy-Blog-Featured-Image-768x401.jpg)
