Sales Skills Boot Camp: The Recap

Backgroundsales skills boot camp

A few months ago, I was chosen to participate in an advance sales skills boot camp with HubSpot.

For those of you who don’t know, HubSpot is a leading marketing software company that combines all marketing functions and tasks into one platform. Because my firm, Hey Now! Media, is an Agency Partner with HubSpot, one of the perks of the partnership is continuing education and professional development for our staff.

When I was approached to be a part of this select sales training group, I wasn’t sure I really needed the class and if I even had the time.  Reluctantly, I decided to join and give it a try. After taking the course, I’m glad I didn’t pass up the opportunity.

The sales skills boot camp was led by David Weinhaus, Manager of Partner Sales Enablement at HubSpot. David is a sales rock star who has been with HubSpot for over seven years. His sales philosophy is that selling is all about finding good fit prospects and solving business problems, and after taking his course and looking at our current clients and projects, I wholeheartedly agree!


1. Keep asking why

One of my biggest struggles in sales is that I am extremely quick on my feet and can envision how a company can grow just a few minutes into a meeting. Because of this, it has always been very hard for me to stick to the line of questioning to un-cover the prospects goals, challenges, plans and ultimately the solution that will best help them achieve these goals and grow.

While it’s good to excite the prospect in the sales process, the point of the first meeting is to keep asking questions to determine what path will be best for them. Exciting the prospect should be kept to 10% of the meeting.

After the sales boot camp I realized that I spent around 80% of meetings exciting the prospect and talking about this grand vision I have for their company, brand and marketing. Instead, I should stick to asking strategic questions so that my solution can include the clients buy-in too.

One amazing trick I learned, when you are having trouble with this is to just ask “why?” 


Prospect: “We’re down 30 percent from last year.” 

Me before the course: “Oh, wow, I am so sorry to hear that… you should switch from newspaper ads to Facebook retargeting!”

Prospect: “I don’t know what you’re talking about but it sounds great and I’m thrilled because your tone of voice is prompting me to respond with excitement. However, I remain confused.”


Prospect: “We’re down 30 percent from last year.” 

Me after the course: “Why?”

Prospect: “Great question. We think it’s because our audience no longer finds the copy or value proposition of our ads to be compelling. We have been looking for a solution for this pain point.”

2. Curiosity

Asking why helps lead the client through the discovery process effectively. Plus, asking questions can help lead you to the solution you think would be best without you explicitly telling them the best course of action.

Sales is all about curiosity. It’s not about coming in with a solution in mind and trying to sell the prospect on it –it’s about really getting curious and asking questions to uncover the challenges and pain issues they face. 

Making a sale isn’t simply telling the client what they need and that you can do it well – it’s about asking questions that get the client to say out loud what they need and have them realize the solution with you. Collaboratively.

Arriving at a solution together is a great way to improve your sales pitch and makes the prospect more likely to convert. If you can get the prospect to say out loud and realize your strong case for change, then you no longer need to sell them on a solution.

3. Pre-emptively Surface Objections

That’s right, sometimes playing devil’s advocate with yourself can help your sales pitch.

Unless you have an amazing, no-issues pitch (in which case, congratulations!), your prospects will have at least one objection to your solution. However, if your solution is best for them, it will still hold up under the weight of any objection.

Some objections will be common, like time and money. Some prospects will timidly or subtly raise these objections while others will present them outright. At the first sign of objections, have a solid, practiced answer ready for the prospect.

Your prospects can poke all the holes they want in your solution, but if it’s best for them, you should be able to surface these objections and immediately quash them. Subtly leading the prospect through their objections before they become a huge obstacle will ultimately make the case for working with your business stronger than ever.

Do you have sales tips? If so, please share them in the comments below!  We would love to hear from you.

We also learned how to generate tons of leads through inbound marketing in our HubSpot training and we’re passing the knowledge on to you! Click below to download your free lead generation eBook.


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