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You aren’t everyone’s cup of tea. There are some people with whom you just won’t click. And there are some people that are very difficult to work with.

Some of the people with whom you won’t easily develop a relationship are contacts within your dream client’s company. They may be contacts that you need to win an opportunity, and they may be contacts you need later to succeed for your client. They may have their own horse in the race, and you may become public enemy number one by coming in and threatening to displace their existing relationships.

When you have the sponsors in place to win without the difficult contact, it’s easy to avoid them completely (and there are some occasions when that may be the right choice). But much of the time, avoidance is a poor strategy.

It looks like fear

Avoiding the difficult contacts within your client accounts can look like fear. Your fear to engage with that individual can be perceived a number of different ways, and you don’t get to choose the interpretation. It might be interpreted that you fear engaging with the contact because you know that your solution is inferior, at least as far as it concerns its affect on this contact. It might also look like you fear having to deal with difficult people, even when it is going to be required.

And, it doesn’t only appear like fear to your difficult contact. Other contacts are judging your performance with their challenging peer.

It looks like neglect

Sometimes the most difficult stakeholder is important to an opportunity or important to your ability to succeed for your client. Avoiding this person can look like neglect, and they can very easily make that case when asked.

You know they have needs. You know that they are important to a deal. You also know that they can be unpleasant. By avoiding them—and their needs—you allow the trying contact to make the case that you are neglecting them and their needs. This can undo your sure thing deal.

It looks like disrespect

Ignoring people is disrespectful. Avoidance can give the appearance of disrespect, even when that is not your intention.

It can appear to the difficult contact that you don’t care about their needs. It can look to others like you have your sponsors within their company, and you are going to work for those sponsors and avoid anyone who might be difficult to serve—even if they have real needs.

This make avoidance a difficult choice. Much of the time, you will have to choose a strategy of engagement.

Three ways to deal with difficult contacts

First, it’s better to be transparent and engage than it is to avoid the difficult contact. It shows that you aren’t afraid to engage with them, that you aren’t going to neglect their needs, and that you respect them. Sometimes just engaging, making sure that your difficult contact knows you respect them, can make an enormous difference in your relationship. The power of just listening is truly underestimated here.

Second, decide whether to meet directly with difficult contacts alone or with one of your sponsors. Sometimes, you may want to meet with a difficult contact alone. This can help prove that you are going to engage with them and that you don’t fear working with them. With really adversarial contacts it is sometimes necessary to have one of your sponsors join the meeting with you to run interference.

Finally, sometimes you need a real charm offensive. You might need to bring someone from higher up in your organization to meet with your obstacle to acknowledge their importance and their power. You might also need to make some exception that serves them as a gesture of goodwill.

Like much about what we talk about here, none of this is easy. Sometimes you have to win over a difficult personality, and other times you have to win over their opposition.


How do deal with difficult contacts?

How do you deal with obstacles to your obtaining or winning an opportunity?

What messages might you be sending by avoiding a difficult contact?

Who might being making some judgment about how you are dealing with an obstacle?

When it is right to win over the objections of an obstacle?


Sales 2011
Post by Anthony Iannarino on December 29, 2011

Written and edited by human brains and human hands.

Anthony Iannarino

Anthony Iannarino is an American writer. He has published daily at thesalesblog.com for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success.

Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. You can reach Anthony at thesalesblog.com or email Beth@b2bsalescoach.com.

Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at iannarino@gmail.com

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