Why Selling to the Top Can Leave You At The Bottom

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If you’re in sales, you may have heard that you want to get to the top.  Why bother with people who can’t make decisions?

And then you attend a sales training session where you hear of the latest clever selling tactics.  How to get around the gatekeeper.  How to bypass everyone else and get right to the CEO.

You’ve heard some of it before:

  • Call just before or after business hours in the hopes the assistant isn’t yet on duty and the phone rings in the executive’s office.
  • Sweet-talk the executive assistant.
  • Be vague, misleading or yes, even lie in order to make it to the CEO or the highest executive you can.

I’m filled with empathy for the sales profession.  After all, my first corporate job was in sales.  (I was also a lawyer, so that may have made me the most hated guy around: a lawyer salesman?)

Whenever possible I enjoy answering my own phone, especially if I know it’s a sales call.  I’ve stunned sales people who are stammering on the other end of the line.  One guy was so ready to give his misleading lines to an assistant that he literally hung up when he realized he already had me on the line.

But, this post isn’t about how to sell to the CEO.  This is about when to sell to the CEO and when not to sell to the CEO or C Suite.

Here’s the problem with the “sell to the top” theory that most trainers don’t understand:

It can be a waste of time.

You can spend all kinds of time trying to reach someone in the C-Suite instead of identifying the person most interested in your product or service.  Let’s say I’m the CEO at a large company, and you call me about office supplies.  The fact is that there’s likely someone in charge of this area, and it isn’t the CEO.  Do you think that the CEO is going to listen to your presentation and then command the purchasing department to override all protocols and buy staplers and highlighters from you?

It can hurt your chances.

If you irritate someone in the C Suite, the chances of you closing a deal anywhere in the company drop precipitously.  This is especially true if you mislead or lie.  One phone call or quick email to the purchasing department about a company or salesperson, and you are shut down.  For good.

It can damage your reputation.

Lying and manipulation are never good tactics.  Your reputation is most important.  What if you end up at a different company, selling something else?  You can be successful if you’re known as someone with integrity.  You’ll never make it if you’ve destroyed your reputation.

It can annoy everyone.

When I’ve talked about this in a training session, someone inevitably says, “Skip, wait.  The good thing is that the CEO can tell me exactly who to call.”  Really?  You think the CEO (or anyone in the C-Suite) wants to listen to your pitch just to be a reference service?  You’ve wasted valuable time.  There are other ways to find out whom you should call.  Use them first.

It doesn’t always help.

Maybe controversial, but I believe that there are many people in organizations who will resist pressure from the top.  What do I mean?  I will give two examples.

  1. Let’s say that a CEO recommends a person for a job opening.  The candidate is ecstatic, thinking “hey, I have the IN!  The CEO is in my corner!”  The hiring manager, however, may think this way, “If I hire someone who knows the CEO, I have a spy on my team.  Every little thing I do or say will be reported all the way up.  I don’t need that kind of trouble.”  Think it doesn’t happen?  It does.  You say, “That shows a complete lack of confidence and unhealthy paranoia.”  Well, yes, I do agree.  But, I’ve seen it.  It doesn’t always happen, but be aware of the potential so you can work around it.
  2. Early in my career, I was taught to go directly to a C-Staff member.  A department manager in the firm was in charge of the relationship between our two companies.  She always signed the purchase orders.  After one training program, I worked my way to the lead partner.  Now, I didn’t manipulate; I was positive and honest.  The result?  The manager was so angry that I “bypassed” her that she cut us off.  I had not only lost the potential for increased business.  I also lost what we had.  It took me a year of apologizing to win her and the business back.  It’s a cautionary tale to be sensitive to everyone’s position.


When selling to the top, the first goal should be to develop a relationship. -Skip Prichard

As someone who has worked on all sides of this issue—on the sell side as the sales person, the sales trainer, the Vice President of Sales–and on the buy side as the VP, SVP, COO, CEO, I have an opinion on selling to the top.  And, it’s just my opinion, so feel free to disagree with me in the comments.  Here it is:  When selling to the top, the first goal should be to develop a relationship. Your first goal is usually not to sell.  That’s right.  When someone takes the time to build a relationship, which is longer-term, unexpected doors may open.  Try to manipulate or bully your way, and you may win, but it will be a short-lived win.  (This is not true if the CEO truly is the buyer and the decision-maker, but that is VERY rare.)

Selling to the top of an organization can be smart.  It may short-circuit the process.  You may indeed find it beneficial.  There are many times selling to the C-Suite is the right way to go.  There are also many times when you should do more homework.  The power is not always at the top.  And, above all, don’t lose your integrity in the sales process–because no sale is worth damaging your name in the marketplace.

Do you think it's always beneficial to go 'right to the top'? What selling tactics work and don't work? You can leave a comment by clicking here.
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  • http://twitter.com/SSpanTolero Scott Span, MSOD

    Excellent point, thanks.  Per your question, I think
    the answers is “it depends.” I’ve found it depends on the size of the
    organization and the culture of the organization you’re trying to sell to, as
    well as the personalities who make up those you would be dealing with directly.
    As a small business owner, I often get sales calls directly, even though for certain
    products and services those should go through my BD, marketing ops etc. I look
    at these as educational learning lessons for me.  Given my bandwidth at the given time I may or
    may not engage in conversation or  may allow
    it to go to vmail, though sometimes I will pick up the phone. If, within 30 seconds,
    I can get a clear understanding of the product or service and how it can benefit
    my company, and I sense that they have an understanding of my business and are
    being truthful and not manipulative, I’m likely to tell them to connect with
    the appropriate contact or send me some info via email – if not then it’s a
    polite disconnect.  On the flip side,
    when I’m involved in the direct selling process I agree with your point on
    relationships, take some time to build them and get to know the people or
    company you’re selling to first. That said, I don’t think initial contact needs
    to be overly structured and take a long time or be not direct in nature, but
    you do need to do your homework. It’s important to listen and to ask not prescribe.  I sometimes find the initial services I
    thought they would be interested in are not the best fit however others we offer
    may yield more ROI. Once in a client organization, learn the culture and get to
    know the personalities of those you’re doing business with, if unsure of a
    process or a personal way a contact prefers things handled – check in and ask
    them – it beats possibly upsetting them and losing the work and helps to
    strengthen the relationship. 

    • http://www.skipprichard.com/ Skip Prichard

      very wise counsel and interesting perspective. Thank you for adding this, Scott.

  • http://www.weeklyhustle.com/ Ryan Ridgway

    Skip, this is a great post (and that’s coming from a sales exec here). Admittedly, there is some shady tactics that will work the majority of the time, but you can’t properly build a relationship on shady tactics. 

    I sell IT-security software packages that start around $30,000 and go up to $4,000,000+ dependent on users and implementation. If I barge into a conversation without respect for my prospect I’ve immediately lost all credibility!

    Surprisingly enough, the things that people hate about “salespeople” are only being put forth by a shitty salesman.

    A good sales exec knows how to…

    - Respect your time
    - Find an equal playing field of agreement and casually consult you through any misunderstanding.
    - Build a relationship
    - Navigate among an entire enterprise to effectively get all the right people on a conference call, and do it in a way that respects everyone’s schedules
    - many other things as well…

    The key to a proper sell that will result in a customer who is amazed with your quality of service all starts with this phrase – “Slow down to speed up” – When I’m phone prospecting, believe me, I’m dialing until my fingers hurt, but when I actually have someone on the phone I slow way down, express my intent clearly and ensure I’ve reached them at an ok time before I even think about starting a discussion.

    More salespeople need to learn how to shut their damn mouths and they would sell twice as much haha. 

    Cheers – Ridg

  • http://www.thindifference.com/ Jon M

    Agree completely, Skip. Understanding the organization and building the relationship are the foundation. From here, it helps understand their story. In doing this, we can hone our message, determining what will compliment their story as well as raise it up in performance and results. It all takes work, and taking the time to develop the relationships is essential. Thanks! Jon

    • http://www.skipprichard.com/ Skip Prichard

      Thanks, Jon. It’s surprising how many salespeople won’t take the time to master the basics.

  • http://www.lincolnparks.com/ Lincoln Parks

    Excellent! Seeing that my sales force is a voluntary army this is a great read for any sales person or team. I like the part when the guy hung up when he knew it was you, so funny but shows unpreparedness and he expected not to get to you in the first place. 

    I took some great notes from this post and will share them with others. You make an excellent point that just because you are the CEO, you may not be interested in something that you are not entrenched in daily. Thank you for sharing this knowledge with us Skip.

    • http://www.skipprichard.com/ Skip Prichard

      Thanks, Lincoln. A targeted approach always works best! All the best to you this week.

  • http://twitter.com/LetsGrowLeaders Let’s Grow Leaders

    I have sales people pitching to me all the time.  I also have the ones that try to go to the top.  I have much more respect for the folks who have gone to the experts on my team and they send it to me… and say, wow, this is amazing.  I am all ears then.

    • http://www.skipprichard.com/ Skip Prichard

      I fully agree with that perspective. Much more powerful when it comes in through the organization with an endorsement.

  • http://www.jmlalonde.com Joe Lalonde

    Just like everything else in life there’s a time to go to a department and a time to go to the top. The key is discovering when and how to do this. 

    • http://www.skipprichard.com/ Skip Prichard

      Definitely. Thanks Joe

  • http://garymorland.com/ Gary Morland

    Seems like I could make selling about me and what I want from them, BUT if I really wanted to serve them and benefit them, and found the best way to do that, would I end up selling more? 

    • http://www.skipprichard.com/ Skip Prichard

      Yes, Gary. Right on.

  • Steve Pate

    I wish every sales person on the planet would tattoo three of your words on the back of their hands: “Do more homework.”  Not only do many sales people call–and irritate–the wrong person in the company, they often don’t have any clue what business the company is in.  Even when they have a product or service the company might be delighted to pay for, they lose a sale and a possible long-term relationship simply because they failed to do their homework first.

    • http://www.skipprichard.com/ Skip Prichard

      How very true! It is so annoying when someone is calling to sell you something and they expect YOU to tell them what you do!

  • MJGottlieb

    Excellent post. Your point on relationships I think is critical. In my opinion, relationships are the only way to survive in business. If you are truly authentic building a relationship, that relationship will stay with you forever.

    I also agree that jumping over the chain of command can be detrimental. I have witnessed many times where the sales manager moves from sales manager to VP of sales, to VP of Operations, to President, to CEO. It happens all the time. People retire, get relieved, get recruited by other companies and before you know it, the chain of command as you once knew it plays in reverse. I have also seen many sales people suddenly wind up running the show at another company. If I have passed the chain of command, odds are I will not get any business from them. If I did not, and I have built a relationship, odds are I will.

    I have learned to treat the person in the mail room the same as the CEO as we have seen many a time that same person who was once in the mail room sitting behind a mahogany desk a short time later. Again, great post- MJ

    • http://www.skipprichard.com/ Skip Prichard

      I agree with you on this: treat everyone like the CEO and you won’t go wrong. It is absolutely true for many reasons, and mostly just because that’s the decent way to treat people.

  • http://www.facebook.com/MichelleColonJohnson Michelle Colon-Johnson

    Building genuine relationships can only help you build the most valuable thing that one can take with them anywhere–  Your reputation.

    • http://www.skipprichard.com/ Skip Prichard

      That is the one thing you can take. Appreciate that.

  • http://sparkvoice.wordpress.com/ DS

    I’ve never envisioned selling to the top.  I’m not sure if that’s good or bad, but I’ve learned it’s a lot easier to influence others when you have a relationship with them.  Great examples, and a very interesting perspective for me.

    • http://www.skipprichard.com/ Skip Prichard

      It is often taught that this is the way to start–go right to the top. My post is hopefully challenging that thinking. Thanks !

      • http://sparkvoice.wordpress.com/ DS

        I believe I had positive influence by two insurance companies, Northwestern Mutual and New York Life.  Both strongly encouraged relationships within the sales process.

        • http://www.skipprichard.com/ Skip Prichard

          Yes, that type of sale would be very different, wouldn’t it? And relationship – based. I’m sure you learned a ton.

  • http://www.kentlapp.com/ Kent Lapp

    Absolutely love this Skip!  As a CEO myself I totally agree with everything you’ve stated here.  It’s a message that is not heard enough.  When someone by-passes the proper people to get directly at me it decreases the chance of them making the sale drastically.  I view it as a lack of trust in me personally, I put people in their positions, they should trust that they’re competent and deal with them.

    • http://www.skipprichard.com/ Skip Prichard

      Kent, thank you. You added something hugely important when you talk about the people you entrust in the positions. Well said!

    • http://www.jmlalonde.com Joe Lalonde

      Kent, thanks for sharing your insights on selling to the top. Many salespeople never think about the lack of trust they’re showing to the man/woman they’re trying to talk to by avoiding those they put in place.