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Top Tips of Executive Engagement

How to Truly Connect with Your Target Accounts 

Table of Contents

Preparation is everything.
Here's how to prep for successful executive engagement.

Email an Exec Meet with an Exec Call an Exec Call a Client Your Resources
+ Don't Do This + Getting Started + Call Prep Tips + Getting Started + Resource Center

+ 5 Great Tips

+ Google Searches + Beyond Social + 5 Key Topics + BI as a Resource
+ Great Example + Beyond LinkedIn + Best Intel Sources + Best Intel Sources Download this Resource
  + Bad Signs + Call Prep Checklist    
  + Good Signs      
  + Prep Checklist      

Executive Engagement

Preparation is Everything

  • Defined...

    "A strategy aimed at building trusting relationships with senior executives in organizations in which you want to do business — developing a long-term business relationship while creating value for all parties involved."

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“Just as this working definition suggests, executive engagement is a complex practice that takes intentionality, effort, and patience on the part of your team. Done thoughtfully, you can reap the rewards of a mutually beneficial relationship and see the returns on your investment in the form of relationships, trusted business partners, and — arguably most importantly — sales.

That’s our mission at Boardroom Insiders, to enable your team to leverage executive engagement and ultimately close bigger deals, faster.
Navigate this page to find our tips on how to tactfully execute executive engagement, and how we can help.”

Sharon Gillenwater CEO/Co-Founder, Boardroom Insiders

How to Write an Email to a C-Level Executive

  • You never get a second chance to make a first impression

    There’s a lot of truth in the most overused clichés. When it comes to getting the attention of busy C-Level executives—which is a priority for many sales organizations these days—this old adage applies: “You never get a second chance to make a first impression.” This is especially true if you hope to stand out in a busy executive’s inbox.

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What Not To Do

Craft an Email Lacking a Strategic Focus

Far too often, salespeople will attempt an overly casual approach, and there’s no better way to get on a CXO’s nerves than to be too casual in your approach. If your emails lack strategic focus, relevance and polish, they are ultimately unworthy of a response.

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Guess at Your Recipient’s Needs

Crafting a lengthy email filled with a buzzword description of what the company does without addressing how that might align with your recipient’s needs will not serve you well. Do your homework, and prove why a meeting with you would be worth the CXO’s time.

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Copy and Paste from Previous Emails

Finally, be very careful when cutting and pasting from previous emails to other C-Level targets. It seems to go without saying, but it happens. Your email can be thoughtfully researched and personalized, but if you make the fatal mistake of leaving information from a previous email, your credibility is as good as gone.


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5 Tips to Crafting an "Exec Worthy" Email

1. Do your homework

With all of the digital tools at our disposal, there is NO excuse for not doing your homework. Take a few minutes to learn something about your prospects and their companies. Then, use what you’ve learned to demonstrate that you’re a real person who cares about their specific issues and concerns. This is your single best chance to earn their attention and interest — and a critical part of successful and meaningful executive engagement.

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2. Find a compelling hook

Based on your research, you should know what their most compelling goal — or pain point — is and how you can help them address it. Lead with that. “You have a problem. I can help you solve it."

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3. Be concise and focused — and always leave them wanting more

These are busy people. Offer a nugget of valuable insight (based on your hook above). Then ask if they want to learn more and leave them hungry for more. Your goal should be to leave them wondering what else of value you have to offer.

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4. Follow up in a thoughtful way

Give them a little time to consider what you’ve said, and then follow up with more relevant information, a little at a time. Stay up-to-date on new developments with the company to uncover new hooks that you can add into subsequent emails. Over time, your contacts will begin to trust that you are earnestly focused on how you can help their company succeed — which will make you worthy of a response.

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5. Remember the basics

Finally, make sure you’re writing to the right person with the right title at the right company. Double check that their name and company are spelled correctly, and that your email has no typos. Eliminate trade jargon and platitudes. Write in an active, not passive, voice in sentences easy for a busy person to scan and absorb quickly.


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What a Good Email can Look Like

Here is an example of an email that is worthy of an executive’s attention and response:

Hello Matthew,
I read your recent interview with CIO.com and noticed that you said that there is “room for improvement” when it comes to automating some of your back-office processes.

Our team recently helped a similarly-sized healthcare system in Florida with this exact challenge. Our CIO, Joe Blow, worked very closely with this customer and is hosting a CIO lunch next month in your city, so I thought it might make sense for you to connect. Shall I forward you the invitation to the event? Or would you like to chat by phone more?
And Easy...
When you know what to say.
How to Write an Effective Email to an Executive


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Successful C-Level engagement is like drip irrigation. You would never dump a huge bucket of water on a plant and then not water it again for a year. To successfully grow your plant, you need to make sure it gets just the right amount of water over time.

Yes, it might be tempting to write a seven-paragraph email that contains absolutely everything about your company that your prospect might want to know. But just as the single bucket of water will certainly result in a dead plant, a verbose and unfocused email will certainly result in a C-Level engagement effort that is dead on arrival.”

How to Prepare for an Executive Meeting

The Right Way!

  • Take the Time

    There’s no worse feeling than being unprepared for a meeting with a C-Level Executive. Their time is valuable and if you blow it, there are no second chances.

    We think your time is valuable, too. We also realize that sometimes life throws curve balls, and you need to be able to hit them out of the park. You don’t need to be scrambling to do your homework before an important meeting. So we want to let you in on some of our trade secrets, which will help you prepare for a meeting with a C-Level executive.

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Getting Started

Where to Start When Meeting With a Public Company Executive

For public companies, start at SeekingAlpha.com SeekingAlpha is hands-down our favorite source of information on public companies. It’s where you will find all of the public companies’ earnings call transcripts, where CEOs and their peers discuss —in great detail — their companies’ strategies, initiatives and challenges. They also get grilled by analysts, who can ask some really tough questions. It’s all excellent insight for knowing what is top of mind with the company’s senior executives. For a deeper dive on how to scan a Seeking Alpha transcript quickly, see our tutorial.

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Do targeted Google searches

Try searching “company name,” “strategy,” and “20XX” to cut through the clutter and get to the gist of what the company is focusing on.

To narrow your search to a particular area of focus — marketing, for example — search “company name” and “marketing strategy.” Hint: To save even more time and easily decipher what is top of mind for an executive or a company, check out the Audience Analysis feature of BI PRO. Better yet, grab a quick, custom demo.

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Go beyond LinkedIn

LinkedIn is essential, but it can be inaccurate, limited and even inconsistent, since the profiles are maintained — or not — by users.

Make sure to check out your target’s LinkedIn profile, if they have one, and seek out their Twitter and Facebook accounts. Go back to Google to search for any articles for which they may have been interviewed. We search “Name,” “Company Name,” and “interview” to narrow the results. And watch any video interviews that come up, as they give you more of a feel for an executive’s personality and mannerisms.

Doing your homework before a meeting with a C-Level executive can be intimidating. Add these tips into your research efforts to find relevant information that resonates with your audience, and you’ll be making the grade.


Signs That you are Having a Business Conversation

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Conversation is Customer-Focused

Your conversation is focused on your customer’s business initiatives — and how you can help drive them.

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Constructive Topics

Depending on the role of your customer, business initiatives might include margin improvement (CFO, COO) or driving collaboration with the mobile customer experience (CMO, CIO, Chief Digital Officer).

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Making a Connection

You can make a clear connection for the customer — at a high level — between your company’s offerings and their business initiatives.

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Relevant Examples

You can provide specific examples of how you have helped other customers with similar business challenges.

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Discussing Solutions

You can credibly address challenges and issues specific to your customer's industry.

Signs That you are on the Wrong Track

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Too Quick to Pitch

You are talking at the product-level.

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Self-Centered Topics

You are talking more about your company than their company.

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Doing Most/All of the Talking

You are talking more than you are listening.

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Not Clear How to Help

You are unable to clearly articulate how you can help drive the customer’s initiatives forward.

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In the Weeds

You get into the weeds on your product, its features and benefits.

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Being Hypothetical

You are talking about hypothetical scenarios as opposed to real-life business issues.

Preparing for an Executive Meeting

Where to Find the Information You Need

  • The company’s most recent annual report
    (normally available on the corporate website)

  • The company’s most recent quarterly earnings conference call transcript
    (available on SeekingAlpha.com)

  • Any interviews with the person with whom you are meeting (or his/her boss) from the last two years
    (search on Google)

Other Information to Consider

  • Consult with your sales leaders and peers on how to best position your offerings given the customer’s business initiatives.

  • Most companies have defined the alignment between their value proposition and different types of customer business initiatives. You might even have business-relevant case studies that you can leverage. If this is not the case, then it may be up to you and your leadership to frame your value in a way that will resonate with each specific customer.

  • Consult with your colleagues in both sales and marketing to see if your company has any of the following:

    • Case studies or use cases from your company that align with the business issues of your customer

    • Case studies or use cases that focus on your customer’s industry


Get Your Own Meeting Prep Checklist here!

BI Executive Research Checklist


The key takeaway: Before any conversation with a C-level executive, you have to do your homework.

We're happy to help you prepare. That's why we've shared so many great tips and sources. The Cheatsheet is a great tool to leverage.

But what if you could save yourself the time and energy that goes with all this research and preparation?  

Executive research is our specialty. To know what your executive actually wants to talk about, you need to know what issues are top of mind for them. Take a look at one of our sample profiles and imagine how you could drive a powerful conversation with that type of insight. Better yet, schedule a quick, custom demo to see the power of Boardroom Insiders for yourself.


How to Prepare for an Executive Meeting-1

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“It goes without saying, before any conversation with a C-level executive, you have to do your homework. And luckily, research is our specialty. To know what your executive actually wants to talk about, you need to know what issues are top of mind for them. Take a look at one of our sample profiles and imagine how you could drive a powerful conversation with that type of insight. Or better yet, schedule a quick, custom demo to see the power of Boardroom Insiders for yourself.”

How to Prepare for an Executive Call

Preparation is Everything with Executive Engagement

  • C-Level Call Prep: What Google Isn't Telling You

    How do you prepare for a meeting with a C-Level executive? If you are like most people, you look at their LinkedIn profile. Then, you Google them and look at anything else that comes up — an interview, a blog post, a recent speech, etc.

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...And If you’re lucky

...Google leads you to a recent piece of content in which the executive’s strategy and priorities are served up on a digital silver platter — because knowing these things is essential going into a C-Level meeting.

More often than not, however, Google does not lead you to this information.


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Don't rely on LinkedIn & Google Alone

We have written in the past about the dangers of relying on LinkedIn profiles for sales call prep.

When it comes to researching executives, Google and other search engines also have their limitations. The most common pitfall is that there is nothing out there on the executive you're targeting beyond some basic biographical information. So, the search ends there and you go on to your meeting, blissfully unaware of all of the important stuff that you should know, but don’t.

A few minutes into the meeting, it becomes painfully obvious you haven’t done enough homework.


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So, What Do You Need to Know?

In these cases, sales reps need to do more digging — and know where to dig — to unearth essential insights, such as:
  • The executive’s functional responsibilities

  • The company’s overall strategy, initiatives and challenges

  • How the executive supports the company’s strategy and initiatives

  • What the CEO is saying about the executive’s area of focus (e.g., marketing, sales, technology)

  • What analysts and business journalists are reporting about the company

  • How the company and the executive measure success



Want to know our secret? Most of the insights we gather on executives comes from two places:


Search Engines:

When using search engines, try different search terms, beyond the person’s name. We use keywords from the person’s title. For example, if someone is the EVP of Business Transformation for ACME Company, try searching “Acme Company” and “business transformation”. You might find an interview with someone else in the company talking about their business transformation strategy and initiatives, which should give you some relevant talking points for your meeting. Likewise, be sure to search “Acme Company strategy” to see if you can get some basic information about what the company is focused on overall.


Earnings Call Transcripts:

A must for all public companies is to read the latest earnings call transcript, including the analyst Q&A. These transcripts are usually brimming with valuable nuggets of information about where the company is headed and what it is focused on in the near term. Time-saving pro tip: Search the transcript for terms that are relevant to the executive you are targeting. For example, if you are prepping for a meeting with a Chief Marketing Officer, search the transcript for “marketing” “digital” “advertising” “media”, etc. It is also important to use your business acumen to connect the dots between what the CEO is saying and the executive you are targeting. For example, if the CEO says one of the company’s major initiatives is to “drive same-store traffic,” ask yourself if the CMO would play a role in supporting that initiative. (The answer is “yes”).

Relying solely on Google and LinkedIn seldom delivers the level of insight you need for a C-Level meeting. Use the aforementioned tips to dig deeper. If you can uncover and leverage a nugget of information that your competitor is too lazy to find, you’ll gain a valuable edge that could win you the deal.


How to have an Executive Call


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The most intrepid business professionals know how to find this information — even when it's not sourced directly from the company, or even in the words of the executive they are targeting. 

Why chance it or invest all that time and energy and still not be confident that you have ALL the information you need?

Luckily, this happens to be what we do at Boardroom Insiders, and we are always willing to share some of our proven search techniques and resources.

Client Meeting Prep:

5 Things to Research Before a Customer Meeting

  • How to get started

    So, you’ve landed a meeting with a long sought-after customer. Chances are you’ve already done some research to get your foot in the door, but are you able to connect the dots between their business objectives and your product or service? Do you even know what their business objectives are?

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Most people — especially senior executives — don’t want to be sold to.

“The companies that do the best with our team are the ones that understand our business, know the competitive landscape, can articulate our strategy and then orient around those solutions that best help us advance our technology strategy and, more importantly, our business strategy,” says CIGNA Corporation CIO Mark Boxer.

Deep knowledge about the customer is your team’s greatest asset — knowledge about the person or people you’re meeting with, about the company’s and/or the business unit’s overall strategy, their goals, and what they’re up against. In other words, you need to do a lot of research.


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5 Areas you should research:

1. Biographical History

How long have your contacts been in their current positions? Where did they work before? What have been their responsibilities? Where are they from and where did they go to school? Are they members of any professional associations? Do they serve on any boards?

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2. Personal Interests and Affinities

Now, you’re digging even deeper to learn what makes them tick and what you may have in common. You’re looking for hobbies, interests and affinities. Maybe they have a unique or compelling background or family story. Perhaps they have a special interest in mentoring women or young people.

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3. Overall Company Strategy

What direction is the company taking and has it changed recently? Are they courting a new customer base? Have there been recent executive changes or other announcements like mergers or acquisitions?

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4. Current Focus

What are your contact’s current business objectives and initiatives? What challenges are keeping them up at night? How do they measure success?

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5. Key Challenges

With economies and technologies ever changing, companies are facing a multitude of challenges. Is your potential customer facing disruption or a new competitor? Are they reorganizing and cutting jobs and facilities? Are they facing legal issues? Have they had to deal with product recalls? Has there been a recent management shakeup?


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So, where do you find this information?


LinkedIn may be your first source, but it should not be your only source. For one thing, not all executives have a LinkedIn profile, and many are not fully completed or updated. Plus, LinkedIn profiles typically don’t contain all the information you need.

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Facebook and Twitter

If you want to get personal information, check if they have accounts on Facebook and Twitter. If they do, and if they update those accounts regularly, you could learn a lot. But you still may have to verify what you find and make sure it’s current.

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Published Interviews

Published interviews are one of the best sources of information — especially since you can source direct quotes.

Some interviews are useful strictly for learning the person’s professional or business focus or about a new product they’ve launched, assuming the interviews are recent (no more than a year old).

Other interviews dive deep into personal territory and can yield helpful insights into who they are, where they come from, and what matters to them. Even older interviews that are more personal can be useful.

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Other Sources

Resources that identify overall company strategy and current focus or challenges can be found in a variety of places.

Check out the company website for announcements of new products, new hires, upcoming partnerships, new vendors, and new initiatives.

Look for current articles on the business, press releases, and quarterly earnings transcripts.

Of course, there’s an art to reading these transcripts. You’re looking for new announcements, trends, and forecasts — much of which can be buried in answers to analysts’ questions after the leadership’s prepared statements.

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So you’ve done your homework.

Now what?

We recommend organizing the information into a one-pager — what we call an Account Anatomy. It’s a briefing document that zeros in on the company strategy and priorities, sales triggers, and the key people your team needs to know so your team doesn’t get overwhelmed.

Download our Account Anatomy template here:

Download Template


Five Things to Research Before a Customer Meeting


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Take the Time

Taking the time — and it is time-consuming — to do this homework gives you an immeasurable advantage over the competition. While your competitors yammer on about product features, imagine how refreshing it would be to your customer when you show a deep understanding of their interests, their focus, and their challenges — and deliver some thoughtful recommendations that address those issues. The goal? To be the vendor who “gets” them and position yourself as the business partner they’ve been seeking.

Research is time-consuming, and assigning a team member to tackle it may not be the best use of their time or your resources. Boardroom Insiders can manage that critical part of your preparation for you, researching and delivering profiles of key executives for your team.



If this Resonates with You...

...You owe it to your team to schedule a 
quick custom demo,
and let us show you how we can help you connect with your prospects and close bigger deals, faster. 

Executive Engagement doesn’t have to be intimidating, especially with the right team behind you.


For more resources to help accelerate your sales and marketing programs, visit our resource center.

To find out more about how Boardroom Insiders can help your team, connect with us, or schedule a quick, custom demo to experience the competitive edge for yourself!

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