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Uncomfortable Talking to Executives? How to Do It Like a Pro

Uncomfortable Talking to Executives? How to Do it Like a Pro - Janice Mars

Uncomfortable Talking to Executives? How to Do it Like a Pro - Janice MarsI hear a lot about salespeople feeling uncomfortable talking to executives, especially to those at the C level. It makes sense to me. Sometimes, it’s because of lack of practice and exposure. So much of a sales person’s time is spent working to help C-level executives’ direct reports solve their day-to-day business issues. And, because we are so uncomfortable talking to C-level executives, we tend not to get a good picture of the bigger business problem they are trying to solve over the long term.

The good news is that executives are humans – people, just like you. They just have more people reporting to them and typically make more money. But they put on their pants, as they say, the same way we do – one leg at a time.

Make It Conversational

If you could get into executives’ heads and see through their eyes, wouldn’t that make it easier to talk to them? This takes time and it takes preparation. Lots of it. And the higher up you go in your customer’s organization, the more precise you have to be with your messaging. It’s not easy to do. You cannot do it in a PowerPoint or a proposal. It has to be conversational, which means you have to know your customer equally or better than they do. So, where do you start?

What can make talking to executives a whole lot easier? Understanding their business and the role they play every day.

Understand their Business

To reach executives, you must look through their lens and be able to have a conversation that provokes how they see their business both today and in the future. You don’t have to be 100% right. And, they may have already come up with a similar idea. But, the fact that you are thinking about how to make them and their organization more successful builds tremendous credibility. The ability to talk to them conversationally, with confidence, doesn’t hurt either.

But at a minimum, you must:

  • Understand and validate their business goals at all levels
  • Be familiar with the trends in their business/market(s)
  • Recognize anything disrupting their business/market(s)
  • Know their individual risk tolerances
  • Find out if they are front-runners or laggards when it comes to implementing change

To do this right, it takes time and research. But it ultimately allows you to influence decision makers. The higher up in the organization you go, the more zeros you may add to your proposal – and shorten the sales cycle. Why? Because you are help solving problems that move the major KPIs that executives think about every day.

Understand the Executive’s Role

You have never been in the same or similar role as this executive you’re targeting. And you’re a bit intimidated that you cannot have the appropriate conversation. What can you do? Here are a few simple ideas.

  • Talk to the C-level executives in your own organization to best understand what they care about and what resonates with them
  • Talk to others you may know in similar C-level positions and ask the same
  • Learn about the differences in what C-level people care about the most, since it will vary depending on the role (finance vs. operations vs. manufacturing vs. IT, etc.)

Talking to Executives Takes Preparation

Once you gather all this knowledge, then you have to take the time to prepare. This can be bothersome for many sales people who don’t want to put in the hard work. But, the payoff (remember, the added zeros) could be amazing. Plan to do many dry runs with different people to ensure you are concise and on point. Don’t practice in your head — say the words out loud. It always sounds different, and better, when you practice in your head.

Talking to executives does not need to be uncomfortable. But you only have one chance to get through to an executive – show how you can make a difference to them and their organization. They will appreciate and admire your preparation and tenacity. And the good impression you leave will come back to you down the road. Hopefully, in more zeros.


Janice Mars, Principal and Founder of SalesLatitude, is a sales performance improvement consultant and change agent focused on growing top performers to impact bottom line growth. With more than 30 years of experience as a senior business and sales executive, she helps companies build successful sales teams by maximizing their time and resources, selling from the buyer’s point of view, and strengthening the effectiveness of leadership. View my LinkedIn profile | Twitter


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