The Real Deal: Preparation is Everything

June 8, 2023

The Real Deal is a monthly series where sales professionals can get expert advice on literally anything related to their jobs—from asking for brutally honest feedback on an outreach email draft, to seeking specific advice on a path to your next promotion, or finding out if your compensation package is legit. We got you covered.

In this edition of The Real Deal, veteran sales expert David Graswick answers four questions that show how a focus on preparation and efficiency can make a significant difference in driving sales success, particularly amidst today’s economic obstacles.

  • David is the VP of Global Sales at Databook, responsible for leading Databook’s sales team. David brings over 20 years of experience in sales and sales leadership. He joined Databook in 2020, growing accounts in his territory into the company’s largest clients and leading a team of Client Partners. Prior to working with Databook, David held sales and sales leadership roles at Yext, Sprinklr, Jive Software, Oracle, Confluence, and more. Throughout his career, he's built strategic relationships with clients across the CPG, retail, financial services, pharmaceutical, and software industries. David holds a BS in Business Administration from West Virginia University. He currently lives in Pittsburgh with his wife and three kids.

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Q: What's the weirdest place you've bumped into a prospect? And once you realize who you’re next to, how do you start a conversation?

TL;DR: Random encounters with prospects do happen, so be prepared to make the most of unexpected opportunities.

One time, a guy sitting next to me on a flight turned out to be a key decision-maker in one of my target organizations. I was also recently at my golf club's pool bar and ran into the Chief Digital Transformation Officer of a global firm on our prospect list. Totally crazy coincidences, but both encounters led to fascinating business discussions.

There are two reasons I was able to turn these potentially awkward situations into positive opportunities:

  • First, I was already well-versed in these prospect companies and their strategic priorities.
  • And second, I maintained a genuine curiosity in what the other person had to say.

Fortunately, most salespeople are pretty social people. We’re comfortable introducing ourselves to strangers in various settings like airports, bars, or restaurants. Just remember that authenticity is critical to establishing rapport and building meaningful relationships. So if you regularly do your homework, and you really understand your prospect’s business, you’ll automatically find ways to engage in any unexpected interaction. If all else fails, fall back on discovery as a way to show your interest.

Q: In the current macroeconomic climate, what’s the secret to ensuring your prospect is actually able to buy?

TL;DR: Thoroughly assessing a company’s ability to make a purchase requires persistent inquiry and confirmation across the organization.

Qualifying prospects is incredibly important in this economy. You don’t want to waste anyone’s time—including your own. You’ve got to repeatedly put out inquiries to various individuals within the organization. And if you get different answers from different people, that should raise red flags.

But here’s the thing: Before you can earn the right to ask qualifying questions of real decision-makers, you have to establish credibility. Do extensive research, so you understand the prospect's financial metrics and can identify areas of underperformance. Put together a compelling hypothesis that demonstrates how your offering aligns with the company’s specific financial and performance objectives. And whatever you do, come prepared to meetings.

Finally, remember that you’re sent to who you sound like. Executives expect you to speak their language and deliver something of value. Do this, and you earn the right to engage in continued, differentiated conversations at a higher level. Fail to do so, however, and you'll get pushed towards smaller issues—which hinders your chances of securing larger deals that require approval from the C-suite.

Q: After weeks of regular communication, my client has gone dark. What can I do to get them to re-engage?

TL;DR: Engagement (and re-engagement) is all about having the right champion. Keeping this relationship nurtured and strong will lead to retention, renewal, and expansion conversations.

In my experience, when clients go dark, it's usually because you haven't built a strong enough relationship with your champion. If you had, you’d know about shifting priorities or any changes in funding. Why? Because champions have a vested interest in your success. There’s a personal win in it for them, too. A strong champion will not only advocate for you when you're not present but also provide valuable insights that they may not share with your competition. That’s why it’s essential to start establishing your credibility at the very beginning of the sales process, and then continuously test and question your champion throughout the sales cycle to ensure their ongoing engagement and support.

"’s essential to start establishing your credibility at the very beginning of the sales process, and then continuously test and question your champion throughout the sales cycle to ensure their ongoing engagement and support."

Remember: Champions are not the same as influencers, sponsors or coaches. While influencers and sponsors are valuable in promoting your brand internally and providing testimonials, champions navigate the organization and connect you with key decision-makers. Coaches provide guidance and help you identify the necessary contacts, but champions actively work with you.

So if you think you’ve got the right person and the foundation of a good relationship, get back in there with questions. Even if you’re not sure, keep asking questions. Building a strong champion and nurturing these kinds of relationships is absolutely necessary for retention, renewal, and expansion conversations—especially now, when economic woes can stall funding with little notice.

Q: I have so many meetings on my calendar, and they’re draining my energy. Any tips to avoid burnout and stay on my game?

TL;DR: By consciously managing your time, prioritizing important tasks, and investing in thorough preparation, you can combat meeting fatigue and make your client-facing activities truly impactful in driving revenue.

Meeting fatigue is a real struggle since the pandemic. It’s easy to get stuck in a whirlwind of virtual calls—many of them internal team or administrative meetings. But that kind of schedule just isn’t sustainable or beneficial. As a sales professional, your main responsibility is to drive revenue. So start your day by taking a good look at your calendar. Ask yourself which internal meetings are truly necessary, and then clear out the rest. Give yourself the space and time to prepare for the client-facing activities that directly impact your sales. Those are the meetings you really need to nail.

When it comes to meeting prep, I like the “measure twice, cut once" approach.

  • Be rigorous. However long your meeting is, spend at least that amount of time getting ready.
  • Craft a well-defined agenda to share 24 hours in advance, to make sure everyone is on the same page. I call that preconditioning the meeting.
  • Additionally, prepare all necessary materials beforehand. Even if you don't cover everything in the meeting, sharing those materials ahead of time shows that you're on top of things and boosts your credibility. (But remember, you don't want to drown people in PowerPoint slides. Instead, aim for a meaningful conversation and dialogue.)
  • Finally, be mindful of every meeting's duration, and allocate enough time at the end to discuss action commitments. Never leave a positive meeting without scheduling the next one or exploring possibilities for introductions to other key individuals.

Selectively pruning your calendar and leaving space for preparation like this will help prevent burnout and free you to focus on the activities that really count.

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