Sometimes you call on a contact that you strongly believe is the decision-maker only to hit a roadblock. Running into the same roadblock time and time again isn’t a great strategy. You can try to nurture the relationship and create enough value to gain entry over time. You can also try to wait them out.

But sometimes you are the right person with the right solution at the right time, and you need to make a decision. Continuing to go up against an obstacle isn’t going to succeed now. Going over their head means you most likely alienate a contact that will later be crucial to your success.

Do you take the chance and risk it? Or do you stand by and do nothing? Here a couple ideas you might consider.

Have Someone Over Your Head Go Over Their Head

Because you have made so many calls, your going over your obstacles head may be bad form and it might make you an enemy. But there may be a high level executive in your organization that can make a call to a higher-level executive or manager in their organization to open the dialogue.

This may be what is necessary when there is a tremendous amount of value to be gained for your dream client and time is of the essence. It is also may be necessary when you have been locked out for years.

There is no doubt that your obstacle may harbor a grudge, and they will surely be smart enough to figure out that you had someone over your head go over their head. But you may get some grace and cover by explaining that you couldn’t stop your boss, who was frustrated at your failed efforts and took matter into her own hands, because their business was just that important.

Have Someone Under Their Head Go Over Their Head

I am not a proponent of starting high and working your way down the org chart. I find it easier to start lower and work my way up, collecting enough dissatisfaction to be able to have a meaningful conversation about the value I create when I do get up a level or two.

The great thing about starting lower is that dissatisfaction normally exists there. The people who are lower on the organizational chart often have the real power and the relationships to get you in and to influence things your way. They can go over your obstacle’s head themselves, and they know the paths of least resistance to making that happen.

They may even be able to make enough of a case to your obstacle to help you gain entry by themselves. Try it.

Find a Killer Reference

I don’t believe the Internet solved all our challenges in sales; far from it. But it certainly has made connecting the dots between contacts we know and contacts we need to know a lot easier.

Your words may not resonate with your obstacle, but you may know someone whose words carry a lot more weight. You can find a killer reference and ask for them to make a call on your behalf, testifying that you are worth doing business with.

You might even be able to have one of your existing clients make a call on your behalf. If you are doing the kind of work that’s worth bragging about.

It’s not really going over their head, but it is worth trying.

Risk It All

Sometimes the right choice is to continue your nurturing efforts, continuing to create value, and try to actively wait them out. But other times you need to risk it all, including going down in a blaze of glory.

If it is clear that there is no way in, then you have to sometimes make a decision that the result is too important and take action.

Going over your obstacle’s head is going to cause some problems. You are going to alienate them. If this is a competitive situation, you have to know that you have transformed your obstacle into a detractor, someone who is going to work to prevent you from winning and who will influence others.

Should you happen to create and win an opportunity, you and your team are going to have to work tirelessly to repair the relationship. It isn’t easy.

I am not suggesting that the nuclear option may not be necessary. But in my experience, most people higher up the organizational chart have enough respect for those that work for them and with them that they respect their decisions. They don’t like to leverage their authority unless they have to and they prefer to build consensus, improving buy-in—and results.

Ask yourself if you have done all should in the way of nurturing and value creation before you decide the obstacle is an obstacle; you and your approach might be the real obstacle and there are lots of things you can do about that that won’t alienate your dream client.


When is necessary to go over an obstacle’s head?

What are the likely repercussions of having done so?

What other options are available to you?

Have you really done all you should have done to deserve an opportunity?

Sales 2011
Post by Anthony Iannarino on June 29, 2011
Anthony Iannarino
Anthony Iannarino is a writer, an author of four books on the modern sales approach, an international speaker, and an entrepreneur. Anthony posts here daily.
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