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Sometimes you run into a decision-influencer that is an obstacle or roadblock to a deal. Worse, sometimes it’s a decision-maker that, for some unknown reason, prevents you from advancing your opportunity.

You can try to go around them. You can try to go over their heads. Sometimes these approaches may even work. More often, you should take a more direct approach.

Confronting Without Being Confrontational

When there are obstacles that prevent you from a moving your deal through their organization, it is easy to assume their intentions aren’t good.

You might believe that they just don’t like you, and so they are going to block your deal. You might be right, but it’s more likely that they don’t know you and spend no time at all thinking about you.

You may believe that they have their own horse in the race. Maybe they are blocking you because they have a relationship with your competitor? It’s possible. It may even be likely. Or it could be that they don’t know you or your competitor.

You could believe that the person blocking you is protecting their turf, protecting the status quo. Maybe this is the one area where they get to exercise their power, power that gives only to the authority to tell you no. But maybe they don’t really want to protect the status quo at all, and maybe they don’t have any real reason to exercise the power they have.

Before you decide that their intentions are bad, before you decide to go over their head, and before you decide to go around them, go and ask them directly what you need to do to move your opportunity.

It can be difficult to confront your obstacle directly, but it can be the best and most effective method for moving your opportunity. Instead of assuming their intentions are bad, start with the assumption that their intentions are at least neutral. Start with the assumption that they have real and serious concerns and that it is your job to help resolve their concerns.

The right mindset allows you to confront them without being confrontational.

Try: “I understand that you have some real and serious concerns. I’d like to try to address those in a way that would resolve them for you. I want to make sure you so that you are 100% confident in moving forward with us. Can you share your concerns with me?”

As a follow up, ask: “What would you need to see from me in order to be confident in supporting our initiative? What would you need to see to no longer be concerned?”

You can’t resolve concerns that you aren’t aware of. Resolving their concerns may make you an ally. Going over or going around can create a powerful enemy that derails your solution and your results. Ask directly, but then . . .

If There Intentions Are Bad, Take Your Shot

Sometimes you are dealing with an obstacle that has no intention of ever moving. They intend to prevent you from winning an opportunity, even though you have a solution that will benefit them and their company. Could be that they have a horse in the race. Could be they are protecting their turf and throwing their weight around. Could be they just plain don’t like you or your company. Maybe there is no reason at all.

If you have gone through the process with your dream client power sponsors and run up against an obdurate obstacle after determining that you really create value, you may have to take your shot.

Sometimes you need to take your shot even though you are going to be making an enemy that will work to undermine your efforts. Sometimes, when the opportunity is fleeting and isn’t likely to reappear anytime soon, you have to go the mat and do your best to force the deal through. Winning may require that you go over or around your obstacle.

And it’s not just about what you need. If you are really going to create breath-taking, earth-shattering, jaw-dropping, mind-melting value that helps your client increase their revenue, increase their profit, or decrease their costs, you have to go for it.

This isn’t ideal. Fortunately, it isn’t often that you can’t find a way to resolve their concerns or at least find political allies to help move them. Before you exercise the nuclear option, you are better to go and ask directly.

Note: In large complex deals, some people on a buying committee vote against you. You still have to work with them to get your client the outcome they need from you. You may have more opposition than you know, more often than you know it.


What are the assumptions that you make about obstacles within your dream client?

What if your assumptions are incorrect?

Do you owe it to your dream client to resolve the real concerns of those who have them–even if you could force the deal through without them?

When is it right or necessary to go over or around an obstacle and force a deal that they oppose?

How do you deal with the obstacle in the aftermath of having won against their opposition?

Sales 2011
Post by Anthony Iannarino on September 1, 2011

Written and edited by human brains and human hands.

Anthony Iannarino
Anthony Iannarino is a writer, an international speaker, and an entrepreneur. He is the author of four books on the modern sales approach, one book on sales leadership, and his latest book called The Negativity Fast releases on 10.31.23. Anthony posts daily content here at TheSalesBlog.com.
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