Selling is hard. As a sales person, you are pitching your story to clients that you think will fit your solution. If you are a sales professional tasked with selling to the C-suite, here are 13 tips from a C-level guy that gets pitched all the time:

1. Don’t Think That An Hour Is a Small Investment: I get dozens of requests for “just an hour”…hours are precious. If you are selling, don’t make the initial request for a meeting. Get me interested in your value proposition first. If you ask for a meeting to explain your value, you won’t get it. Think of the meeting as your first trial close…I have to be sold on your value before I will spend my time. For many C-executives, their currency is time and attention. Before they will invest their currency, they have to be sure that there will be some return.

2. Your Solution Is Not a Magic Bullet: Regardless of how incredible your solution is, it doesn’t put out all the fires in the C-suite. While you should be authoritative about your solution and the impact, never assume that yours is the solution to the biggest fire in your prospect’s day. The C-prospect has a million issues to deal with, from internal and external constituencies, that all demand resolution. Try to contextualize your solution so that your prospect can see where it fits into their list of things that are on fire. Ask questions, probe and help your prospect see why yours is the answer. It may not be self evident to the prospect. But remember, every vendor is trying to promote their product or service as the thing that needs to be acted upon now. Distinguish yourself by asking great questions, by confirming some intuition you have about the client’s business, by helping your prospect understand that you understand. Hard to do with a quota hanging over your head, I know, but understanding how your solution fits into their world will distinguish you.

3. Don’t Pester: It never helps. If the C-level person doesn’t respond to your VM or e-mail, it means a couple of things – either your value proposition wasn’t clear and compelling enough, or they are just busy! In the space of four days, from one intrepid sales weasel, I got an e-mail, 2 voice mails, and an exasperated e-mail with the subject line of “????!!!!”. That e-mail essentially berated me because I didn’t respond quickly enough. From my perspective, I didn’t know this person, their company, or frankly, what they did. There was no compelling reason to call them.

4.Don’t Sell Against Someone Else: You have competitors. Other people do what you do. Don’t sell me on what they do that isn’t good. Sell me on why you are the best. Sell your strengths. If you bash the competition, you are simply creating an environment where you have me wondering about your holes. Customers buy strengths, not because they wish to avoid your competition’s weaknesses.

5. I Don’t Have a Budget: if you ask me for my budget, it is very, very likely that either I don’t have one for you, OR I am not prepared to tell you what it is. If I tell you that I have a budget of $25K, I can be certain that your product or service will cost very close to that. If I don’t tell you the budget, we can negotiate in my favor. That’s what the C-level gets paid to do…

6. Don’t Ask Me to Link In If We’ve Never Met: I get about a dozen requests a week from people I’ve never heard of on LinkedIn. They are often sales people. If you ask me to become part of your network before I know if you have any value, you have asked me to engage with you without providing value. That is the inverse approach. Provide value, then engage.

7. It Isn’t Always About Price: This is hard. Companies make purchase decisions around a lot of metrics, and price is certainly one of them. But it isn’t the only one. Companies buy because of trust, because of past successes, because of insight…telling me that your solution will cost less than the competitor or whatever will not make the sale.

8. Make It About Me, Not You: The most successful sales efforts come from the point where the vendor has gone out of their way to show me how their solution benefits ME. Rather than focusing on what you do, position this so that I easily understand how your solutions fit inside my experience. Use publicly available data to make guesses, spend some time thinking like your customer, make the effort to make the connections for me. Even if you are wrong, the good C will be able to understand your thinking, and more importantly, make the connections themselves.

9. Listen Carefully: Any executive will tell you what their pain is, if you listen. It may be sales, it may be costs, it may be processes, but when we start talking, the C-suite will always tell you what they need. Why do we tell you? Because we are in the problem solving business. We talk about our problems so that we hope someone will help us fix them. Listen to what we are saying, and you will know how to contextualize what you sell.

10. We Don’t Fix What Isn’t Broken: If we have solution that is working, we aren’t likely to change providers. Even if you are better or faster or stronger, the C- suite is always fixing points of pain. And while we may be change agents, we don’t change for changes’ sake. If we tell you that we have a solution that works, think of that as an opportunity to have an extended dialogue. We’ve just taken you off of the fast-track, but that means that we have the opportunity to explore the fit over time. Seed us with information and content. Fill our head with case studies. Make us want you. Seduce us. Slowly.

11. Make Us Trust You: As a C-level prospect, I have probably been around the block a bunch of times. I know a lot of people. Use my network to influence me. As your customers who they know. Ask if they will make introductions. A referral from a friend or other industry contact will make me listen. If you are selling to the C, you should know the folks that the C knows…other C’s, investors, etc.

12. Know Something About My Business: You should have some idea what my company does. You should know how big I am. You should know if I am a high-margin or low-margin business. You should know why I think my company is special. You should know the value that I provide to my customers. Do some research. Prepare. Don’t wing it. It won’t work. (And show me that you did this research, get me to confirm all of the stuff that you know…)

13. DON’T WASTE MY TIME: This is the most important point of all. Never come to a meeting without a goal. Never make a call without a point to it. We are all looking for incremental steps towards improvement. If you don’t have a purpose, don’t make contact. Don’t be afraid to decide that there isn’t an opportunity. Be decisive, be on point, and don’t be afraid to cut your losses. I will be more receptive the next time you call if we made progress the last time. And if there isn’t a fit, and you pull the plug, the next time you reach out, I will respond because I will have assumed that you’ve discovered a fit. Make every communication high value.

There are thousands of complexities when it comes to C-level sales. These are just 13 quick thoughts. We want the vendor vetting process to be simple, seamless and successful. How can you help?

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Good one Tim. Amazing how many times I can just tell that I’m just another person on the e-mail list to get out todya…

Reminds me of one I’ve done before, but yours is a lot more thorough:
http://rickwatsonsblog.com/post/13776337226/fishing-expeditions-and-sales-fails

October 2, 2012 1:32 pm

Great article, Tim. From the perspective of a sales guy, one challenge we all face in sales, and one thing you have always been really good about, is if the answer is “no” just let us know. This is a huge benefit to a salesperson…no one wants to spin their wheels if there’s no opportunity, on either side of the sale. And saying “no” gives a salesperson the opportunity to demonstrate how they value a relationship. In a way in moves them forward, because the next time they call on you (in six months to a year) they know what you weren’t interested in, and that they need to bring something different, or better, to the table. And of course it gives the salesperson the immediate benefit of being able to focus on clients that are a better fit.

October 2, 2012 2:09 pm

Very insightful Tim- thanks. Would you mind also providing one last tip in terms of phone and email preference. i.e. Do you listen to your voicemail and have you ever called a vendor back? Do you prefer a combination of both email and phone? Or, one of the other?

October 2, 2012 6:54 pm

Chris – this wasn’t a primer in selling to me, but to my way of thjnking, voicemail is a wasted time activity. It takes much longer to listen to a voicemail than it does to read an e-mail.

October 2, 2012 10:54 pm


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