Sales TipsSmall Business Advice

How To Approach a Big Company Executive with Confidence

By September 9, 2017No Comments

Small businessman trying to be heard.


As an executive or salesperson representing a small company,  learn to approach big company executives with confidence. These are people whom you don’t know, who are very busy, and who are difficult to get in front of. It’s natural for even seasoned professionals to feel awkward in their presence, and I’ve worked with many entrepreneurs and sales reps who haven’t mastered that core capability.

I do understand the feeling of maybe not measuring up. I remember when I first started my company, back in 1994. I felt like I had left all my credentials behind in another place. Like they didn’t matter in the business world. I just knew that business people looked down on academic people and thought we didn’t know anything about the real world. And to top it all off, I went from the university to a nonprofit organization. Yes, I had been a President, but I was a president of a Humanities Council. Ha!  A HUMANITIES Council! What would that be worth in corporate America? Suddenly it seemed like all the confidence I had built up and felt and actually owned in my prior positions had no value in my new role as a small business owner.

I felt very small. I felt like a solopreneur. I felt like “just me.” And I had to learn to get over that feeling if I were ever to be successful in my new world.

The first thing to learn is that it isn’t about you. Get the right attitude.  It is all about how you value a potential customer and how you bring value to them. So here are my three top tips for how to approach a big company executive with confidence:

One. Show up as a peer.

Don’t waste their time; be someone worth their time. The way to do that is first, own your own credentials. There’s a reason you’re in business and a reason you’re in the meeting. Make sure that you are clear about what your valuable credentials are before you go. I don’t mean what degree have you earned or what school did you graduate from; I mean what do you know how to do, what can you make happen, or what have you observed somewhere else that could be important important new information for this executive in her role. Ask intelligent questions about how her responsibilities relate to the corporate strategy or to current news events about the company, which of course means that you’ve taken some time to do your research ahead. Bring some value right away by showing a link between you and your company and the executive and her company and her role, specifically.


Confidence comes from feeling that you fit it, and you need to work at that. I learned that while I was right in general about how business people felt about “academics,” I misjudged the value they placed on my credential of having earned an advanced degree. They tended to admire the work ethic they associated with that accomplishment. I worked hard at “unlearning” academic jargon and learning business speak. An executive buyer whom I interviewed about dealing with small company sellers told me, “If I tell you I have to have an ROI of 15% EBITDA, and you say, ‘What’s EBITDA?’ then we’re not going to have a second meeting.”

 Two. Set the stage.

Create an environment that’s worthy of an executive’s time an attention. That starts with how you set the appointment. Whether you make the call or send the email yourself or have a virtual assistant do that, act professionally by explaining clearly who you are and what you hope to accomplish in this meeting. Be clear about the date, time, location. Show up a few minutes early and conclude your business at least 5 minutes ahead of time. Look the part. Your personal appearance plus your business card and promotional materials need to be impeccable and portray you as “one of us” in that setting. Be very, very well prepared for every aspect of the meeting.

An executive meeting isn’t the time to stand out for anything other than your insights and ideas related to his company’s strategy and his personal set of responsibilities for execution. Even if you are a very flamboyant person with a creative brand and an outrageous solution, stay inside the lines on your first visit until you know the company and the person you’re dealing with. Make it easy for him to become your champion and bring others to the table. Confidence means you can play by other people’s rules until you fully understand when they can be bent or broken.


Three. Build a meeting process.

That is, develop a system for your company that will guarantee that all your meetings with big company executives always go well. This process will develop your confidence over time, and it will be a blueprint for how your employees will handle executive meetings as your company grows. Your process should include your meeting agenda, which I recommend you send to your executive ahead of time for his review and additions or changes. It’s always good to get their buy-in from the start. Next, write down your goals for the meeting as well as what you think the prospect or customer’s goals would be. Then work out a tentative script for the meeting interaction with questions, key points you might want to make, and your desired outcome–what has to happen so you’ll know the meeting is a success. What is the value you will have added to his or her day? What is the next step that you and the executive have agreed upon? Your process must include how you plan to follow-up after the meeting.

Confidence builds with rehearsal and a sense of knowing what comes next.

As you can tell, it all comes down to preparation, but I’ve also learned that just telling someone to “be prepared” isn’t enough. When the Scouts are prepared, it means they’ve spent hundreds of hours earning merit badges to document the specific skills of preparation for all kinds of circumstances. Spend some time to earn your Executive Meeting Confidence badge and you will be prepared any time you need to have an important interaction with a big company executive.

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