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7 Tips for Maximizing Time and Deepening Relationships with Executives

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Written by Bob Croston
Vice President, RAIN Group

 "It's impossible to get serious face time with senior executives."

“Even getting 15 minutes with a senior executive can take 15 months.”

I hear things like this all the time from professionals, sellers, and other business leaders who want to get more time with decision makers, but haven’t yet cracked the code.

Let’s start by setting a few things straight:

  1. It’s not impossible to get serious face time with senior executives.
  2. Getting serious face time with senior executives doesn’t need to take forever.
  3. The code is crackable.


How to Build Rapport with the C-Suite

  1. Establish a peer dynamic
  2. Get over personal hang-ups
  3. Resonate on the business side
  4. Resonate personally, emotionally
  5. Lead masterful conversations
  6. Don’t give up
  7. Craft a meticulous personal brand


It’s a common misconception that senior executives don’t have time. Based on extensive research in the area, I’m prepared to reveal a startling fact: Decision makers have 24 hours in each day, and a statistically significant number of them manage these days in bundles of seven called a week.

Shocking! But true: 24 hours a day, seven days a week.

What may actually be interesting is how they spend this time. They don’t meet only with internal colleagues, they don’t meet only in 15-minute blocks, and they don’t disappear into the nights and weekends to spend extended time only with their families.

Many executives pour their time into meetings and relationships. In our research, executives often cite that their relationships with people across companies and industries—colleagues, partners, and “vendors” alike—are essential to their success.

They have long meetings with people outside their organizations. They have breakfast meetings, lunch meetings, and dinner meetings. They ski, fish, take in games, and go to the ballet. They maintain relationships over time. 

They are, indeed, doing all of these things and more. The question is this: Why aren’t they doing them with you?

Through a decade of sales research—including benchmark reports focused on clients, buying, conversations and relationships, a number of books on the subject, and work with tens of thousands of senior executives on the buyer and seller side—we’ve learned that the best relationship developers get extended time with senior executives when they do the following:


1. Establish a peer dynamic

Under no circumstances should you come across as inferior to a senior executive. This doesn’t mean you need to be an arrogant snot.

It does mean you must have confidence in the value you can offer from a business perspective, and confidence in yourself personally that the C-suite is where you should be.

2. Get over personal hang-ups

Tell yourself any of the following, you’re in trouble:

  • Senior executives’ time is more important than mine
  • Senior executives aren’t my peers
  • Senior executives don’t want to be friends with me
  • I don’t want to be friends with senior executives
  • I’m not interesting enough or don’t provide enough value to be worthy of senior executive attention
  • I’ll just be too nervous; I’ll mess up
  • I shouldn’t talk about, or ask about, anything personal
  • I shouldn’t ask them to grab dinner and then go to an event with me
  • I won’t get through so why bother trying

Often the greatest barriers to establishing ongoing, rich relationships with senior executives are personal hang ups. If relationships with top people are what you want, don’t psyche yourself out of your chance.

3. Resonate on the business side

Often people don’t understand what’s going to be important to senior executives.

One time a friend of mine was sure he was going to win an engagement that would save his client $10 million. Then he lost the deal. Like the sharp cookie he is, he asked why. The client said, “I get that I could do this and save $10 million, but I’m working on $50 million problems as a minimum threshold.”

In this case, the ROI wasn’t big enough for the executive to care about it.

And make sure you don’t just focus on problems. The higher up you get, the more you’ll find people who are looking for business growth, innovation, and competitive advantage. Executives seek ideas that will be “the next big thing” for their business and their agenda. Bring these ideas to the table and you’ll be on your way.

4. Resonate personally, emotionally

Never forget that senior executives are people just like you. They have emotions and personal interests. CEOs have kids, like sports, want to be seen as successful, are passionate about politics, and want to retire, drink fruity drinks with umbrellas and read CIA thrillers.

I’ve seen many a business pundit say, “Don’t get too personal in a business setting.”

Survey says…wrong.

Not sure I’d want to have a long dinner with them. Great relationships are complex. People make connections on all sorts of platforms, and emotional connections are among the most powerful.  

Are you going to connect with everyone? Nope. Perhaps you head down a political conversation path and find you have nothing in common. OK. But next thing you know, you both love coaching kids’ soccer and conversation ensues. And then you rib each other about how the other is wrong about politics.

A partner at a major services firm I know met someone on a plane and ended up talking about how they’re both cancer survivors. They’ve been close for 10 years, and ended up doing a lot of business together. Did they plan it this way? No. Was the partner in any way exploiting cancer? No. It was a real connection and led to real, long-term friendship. This happens.

5. Lead masterful conversations

Leading masterful conversation is a big subject to cover, something I won’t attempt to cover it in detail here. (Wall Street Journal bestselling Rainmaking Conversations is a good place to learn more.)

If you do not lead masterful conversations, you lose executives at hello. Ask irrelevant or too general questions. Go on too long. Make the other person educate you on background. Don’t listen. Don’t provide ideas. Don’t know your stuff cold. Rely too much on slide presentations or materials. Seem uncomfortable or stilted when talking to them. Be irrelevant in any way (see previous point on resonate). Any of these conversational failings will bar your entrance to the inner circle.

Use these 50 powerful sales questions to build relationships with executives, uncover needs, deliver on value, and move conversations forward.

6. Don’t give up

Initially, it might take a while to get discussions with senior executives. Don’t give up. Those who make it to the top are dogged about getting there.

Often, executives will only take meetings through trusted connections. Work your way up through lower-level contacts or other trusted relationships.  

While less common, it is possible to get through without a referral. If you don’t have the contacts that can get you in, reach out directly. Do it enough and you’ll get through to some. (You don’t need to get through to all.)

Don’t give up and you’ll get your first audience.  Heed the advice in the rest of this article and you’ll get the second, the third, the fourth, and so on.

7. Craft a meticulous personal brand

Getting quality, extended time with senior executives is all about being invited to the inner circle. Make no mistake, you will be judged as to whether you deserve to be there. Create a reputation as a known expert in your area. Create relationships with other executives and influential people. Make sure anything you put forth is of the highest quality. All of these signal whose “league” you’re in.


Ultimately, if you want time and relationships with executives, you have to make sure they see you as in their league. It’s up to you to do what you can to get there, and stay there.

Download: The 11 Principles of Influence in Sales White Paper
Last Updated April 24, 2024

Topics: Sales Conversations