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The 5 Most Persuasive Skills for Selling to Executives

4 min readJuly 7, 2020

This column was originally published on Entrepreneur.com on June 16, 2016.

howard-brownAs my company’s founder, I was essentially its first sales rep. But as we’ve grown, I’ve needed to scale sales and hire new reps. One of the most important lessons I’ve learned from growing a sales team is that spending time with newly hired sales reps early on can yield exponential jumps in productivity and revenue. If you let too much time pass, salespeople will inevitably develop bad habits that are difficult — and sometimes impossible — to break.

Entrepreneurs are busy by nature, but coaching sales reps is one of the best time investments you can make. I have found that one of the best ways to identify areas for individual improvement is to listen to live sales calls or call recordings. However, since time is a factor, focus on coaching the skills that are most crucial. In my experience, there are five key sales skills that are absolutely essential when selling to high-level executives.

1. Being helpful.

Top executives don’t have time to waste. The best way for reps to keep busy executives on the phone is by genuinely helping them and offering them value. Say you sell marketing automation software, and a CMO downloaded one of your Buyer’s Guide ebooks outlining the ROI of marketing automation. In this case, this particular content engagement is very specific and clearly indicates a serious buyer. A rep might start a conversation by mentioning they noticed the ebook download. A good question to follow — “Would it help if I told you about some of the ways our customers are using marketing automation to increase revenue?”

2. Assessing needs.

After breaking the ice with a new prospect, reps should focus on problem solving. This requires asking some questions to discover how to best help. If leads fill out forms, what’s the genesis of their inquiry? Are they in need of a new solution immediately? What pain are they having that is inspiring them to seek new solutions? Discovering a prospect’s problems creates a powerful opportunity for reps to discuss how they can help solve those issues, and how they have relieved similar pain for other companies in the past.

3. Deep product and competitor knowledge.

We’re living in a time where customers can — and often do — a lot of homework and comparison shopping prior to making a purchase, no matter how large or small. It’s actually amazing how often customers seem to know more about a sales rep’s competitors than they do. That’s why sales reps should be able to speak intelligently about each feature, use case and integration point of every product they’re selling.

It’s equally important to understand the competitive landscape in order to be able to communicate why customers should choose your offering over a specific competitor’s. Acquiring this knowledge will help reps demonstrate their expertise. After all, high-level executives don’t like talking to novice reps.

4. Personalized messaging.

Executives in specific roles and industries are often looking to achieve similar goals as their peers. As an example, nearly all CMOs may share a desire for insight into which efforts are driving the best leads. However, CEOs are often more concerned with overall revenue figures. That’s why at my company, our sales reps use buyer persona cards that keep them on-message by listing typical challenges and desired outcomes by role.

When selling to executives, it is also critical to help reps understand what has worked well in the past with particular customers. One way to help new reps improve quickly is by using a repository of model sales calls. This can help reps self-educate by listening to which questions and phrases other reps have used in the past to move similar deals forward.

5. Focusing on objectives.

Every journey of a thousand miles begins with a single step. Accordingly, every deal usually requires setting and achieving a lot of mini goals. Sales reps should always have an objective and should be moving every conversation toward meeting that objective. It could be scheduling a meeting, booking a demo, getting an introduction to a key stakeholder or getting a contract reviewed. Make sure reps are always aware of their objective and are steering conversations toward achieving their goal.

Overall, remember that these are not skills that can be acquired overnight. That’s why it’s vital to create a culture in which new techniques and best practices are constantly being shared amongst your team. By consistently setting reps on the path to mastery, you’ll not only help them succeed, but also transform your sales team into a powerful engine that drives your company’s growth.