Getting In Over Their Head

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?

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  • Tom Nijhuis

    Hi Ian,

    Hope you’re well. I’m in this exact situation at the moment with one of my existing clients.

    We seem to have reached a stale mate on new work that needs to be done and I just asked my chief executive to go over his head and directly to the director of the company.

    My boss and his are golf buddies whereas I have no relationship with the person I’m dealing with outside work.

    A strong realtionship matters. I think going over someone’s head helps if you (or your boss) have a better relationship with that person.

    Will let you know how it went!



    • S. Anthony Iannarino

      This is never an easy issue to navigate. I’ll be anxious to hear how this turns out. Keep us posted! 


  • Wholesale Suppliers

    There arises a situation when your efforts just don’t seem enough and that’s when is the time to call in the higher authorities. There was once this deal when I put all my efforts but the results were depressing and I made the decision to go over my head and explained the situation. Thus matters eased a bit and I broke ice making the way in. The dream client is never easy to reach there are many obstacles along the path but once you leap over them the results are fruitful. Talking to a senior is not an easy task as it shows you lack to power to reach it. There are many bosses who have different approach to a situation, but sometimes we have to face the horrible experience of stepping in the office.

  • Ron LaVine

    If the rep started politely at the top of an organization and worked their way down to the evaluators, end users and decision makers, they would have probably eliminated this problem. The subordinate has a hard time saying don’t go above me or go below me since the call was referred to them by their superior or their superior’s office. You can also try an approach called “linking”. This is where you ask the superior if it is okay if you report back to them the results of your conversation with their subordinate. If they say, “yes”, then you can let the subordinate know they need to respond to your request for information so you may inform their superior of the results of the conversation. It is not foolproof method and requires practice however the approach can be effective for some. Keep on cold calling! Ron LaVine, MBA, PresidentAcclerated Cold Call Training, Inc.Cold Calling for Success