How to Get in Touch With Senior Leaders

When senior leaders hold the keys to closing deals

Good Morning and Happy National Letter Writing Day! While we're not suggesting you break out the pen and paper for your follow ups, there's something to be said for a handwritten letter these days. But the cost of first-class stamps will increase from 66 cents to 68 cents in January, so make sure to stock up before the end of the year. ✉️ 

In today’s Follow Up:

  • Connecting with senior leaders 🤔 

  • 101 sales questions to ask on your next sales call 📞 

  • A cold email sales tip ✍️ 

  • Sales on the internet 🗞️ 

  • LinkedIn sightings & a sales meme 😂 

How to Get in Touch With Senior Leaders

In the game of business, senior leaders hold the keys to closing deals.

Along with having the final say, they also:

  • Know the business needs.

  • Understand the company’s ‘big picture’ initiatives.

  • Have pull with other stakeholders and departments.

They’re the popular kids, and everyone wants their attention.

But getting ahold of them can feel like shooting a half-court shot… very hard to do, but not impossible. 🏀

In a recent HBR article, the CEO of a sales training company discussed how sales reps can connect with senior leaders and earn their trust.

Let’s take a look at what you need to know. 👇️ 

1. Detective Work 🔍️ 

Let’s start with the basics. Throw on your detective hat and fire up the ole’ LinkedIn.

Your goal? Find the the senior leaders at the company you’re selling to, who actually have decision making power over the problem your product solves.

This step involves more than just searching for titles. Dive deep into their profiles to find out how long they’ve been there, what departments they oversee, and who reports directly to them. Remember, just because they have VP or Director in their title, doesn’t mean they’re the leader you want to connect with.

This isn't just stalking, it's strategic research.

2. Make Allies 🫶 

If you’ve made a lot of cold calls in your career, I guarantee you’ve run into a gatekeeper.

They’re like the bouncer at a nightclub, deciding who’s worthy of making it in.✋ 

Their actual title is typically executive assistant, receptionist, administrative assistant, or secretary, but to you…. they’re the person standing in the way of talking to a senior leader.

Here's a secret: gatekeepers (assistants and admins) can be your best allies. They have the power to put you in contact with the decision makers or stop you at the door. Instead of brushing them off or asking them to leave a message, talk to them like a stakeholder. Explain why you’re calling and ask for their opinion.

When you’re friends with the bouncer, it’s much easier to get into the club. 🕺 

3. Referrals > Cold Outreach 🤝

Referrals are your fast lane pass to accessing senior leaders.

Just like dating, being introduced by a mutual friend or connection massively increases your odds of success.

But how do you get a referral? Look around. This will take some digging, but there’s a good chance that someone at your company or one of your customers has a connection to the senior leader you’re trying to reach.

Here’s a template to use:

Hey {Name}! {Insert personalized first sentence}. I remember seeing that you worked with {prospect name} at {company name}, and I’ve been trying to get in touch with them about {your product}. Any chance you’d be open to connecting me with them? It would be very much appreciated! 🙂 

Pro tip: Make it as easy as possible for them to make the referral. Write the introduction email for them and provide the correct email address.

4. Persistence is Key 🔑 

Just like this deep dive, the magic is in The Follow Up. *pun intended*

On average, it takes 8 calls to reach a prospect and over 5 follow ups to close the deal. You’re leaving sales on the table when you stop after a few tries.

But there's a fine line between a persistent sales rep and an annoying one. Aim to bring value in every follow up with things like articles, answers to FAQs, or personalized videos.


  • Detective work: Dig deep to find the right senior leaders.

  • Make allies: Gatekeepers can open the door to connect with decision makers.

  • Referrals > cold outreach: Referrals are your cheat code for connecting with senior leaders.

  • Persistence is 🔑: If you’re not following up, you’re leaving sales and connections on the table.

Does your product require senior leadership approval before your customer will buy?

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101 questions to qualify, close, and negotiate

We’ll assume you’ve done the prep work: getting a foot in the door. 

Now, it’s time to reel ‘em in -— and your line of questioning counts buckets. Here are 101 vetted sales questions to help you finesse the most comfortable fit.

Discovery questions to ask your prospects cover:

  • BANT (budget, authority, need, timeline)

  • Personal details and industry experience

  • Closing, upselling, circling back, and more

Add a handful of these to the master list (since you have one of those).

Sales Tip of The Day 💡 

When writing a cold email subject line, keep it under 7 words or 41 characters.

This will ensure the full subject line is visible on mobile phones.

81% of emails are viewed and opened on a mobile phone, so it’s important to optimize for them.

As always, use the Hemingway app to make sure your characters and word counts make the cut.

Sales in the News 🗞️ 

Cool Jobs at Cool Companies 🤑 

Checking in on LinkedIn 👀 

Stress = Peeing your pants..? 🤔 

Sales Meme of the Day

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