How to Win Over Gatekeepers and Close More Deals

Navigating gatekeepers is an inevitable part of sales. Here’s how to start working with them rather than against them to close more deals. 

Written by Michael Hinkle
Published on Apr. 16, 2024
How to Win Over Gatekeepers and Close More Deals
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Every salesperson has run into a gatekeeper who wouldn’t let them speak with their boss. It’s an inevitability. That is their job. 

But when you’re trying to hit quota, it can be easy to start blaming them for blocking you from doing your job. The reality is, they’re not the problem, and with the right approach, they could even become an ally. 

If you have a gatekeeper between you and the decision-maker at your client’s place of business, your approach needs to be very professional and with a defined purpose.  The job of a gatekeeper is to prevent their boss from wasting time with people who don’t benefit the company. And guess what? An unknown salesperson is almost always considered a disruption in one’s day.

6 Keys to Win Over a Gatekeeper

  1. Always be professional with them.
  2. Always be truthful with them.
  3. Always be transparent with them. 
  4. Ask for their help in achieving your goal of seeing their boss.
  5. Treat them in the same way that you would treat their boss.
  6. Don’t overlook them.

You need to realize that the gatekeeper is the key to your success with this client. They’re a critical part of the process to gain a new client.  

In fact, this approach with gatekeepers can be applied to every aspect of your career. Whether you’re interviewing for a new position or just seeking input about your effectiveness with your own boss, how you deal with the gatekeeper never changes. They have control and influence over your ability to reach those whom you are seeking to meet with. That role for them never changes. So, if you choose not to treat them with respect, you do so at your own peril.

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5 Questions to Ask a Gatekeeper

It’s important to remember that the gatekeeper is your ally. Even if you believe that they’re not, they are. Their job is very important, and their boss often seeks out their opinion to determine if you’re worthy of their time.

You may feel like there is no connection with the gatekeeper, and you see no way of befriending them. But do not make the mistake that they are someone you need to get past and that they are in the way of a successful sales call. They aren’t, and if you step over them and make them look bad to their boss, they will remember it. And then you will always have a person in the organization who will be working against your success.

I find that the toughest gatekeepers are the most loyal advocates within any organization. That means when you win them over, they will be a fan of yours and valuable intel will always flow to you through them.

Your approach to difficult gatekeepers needs to be the same as to one that is extremely helpful to you. You can’t be afraid to ask them for help in getting through the door.  After all, since they are the guard, they already know what it will take for you to do that. 

Some of the questions I like to use when working with a gatekeeper, especially one who is protective of their boss’ time, include:

  1. What is the best way to approach the boss — email, phone or to schedule a face-to-face meeting?
  2. Is there someone else I should speak with who will be a part of the decision-making process?
  3. Do you know who you presently use for the service or product you are showing to them?
  4. Does your boss like to meet new providers over lunch or coffee appointments outside of the office?
  5. Most importantly, what is your beverage of choice — latte, mocha and so on? 

Each of these questions allow you to build a relationship with them while also giving you valuable information that will allow you to work with the gatekeeper, rather than against them. 

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How to Build a Relationship With Gatekeepers

In addition to asking, maintain a high level of professionalism every time you are dealing with them. Anything other than fully respecting their position and the authority they have will result in you earning a very poor reputation with them and their boss.

Don’t bad-mouth the competition. Perhaps the present provider has done a great job of winning the gatekeeper over, and they’re not only protecting the boss from you, but they are also protecting someone else who they consider worthy of their protection. When that is the case, you need to be extremely careful in how you speak about the competition. Also, look for ways that your product or service is better. But don’t point out the weakness of your competition. 

Just like with difficult clients, the key to success with gatekeepers is a very simple formula:

  1. Always be professional with them.
  2. Always be truthful with them.
  3. Always be transparent with them; they know why you are there, so do not pretend it is about something else.
  4. Ask for their help in achieving your goal of seeing their boss.
  5. Treat them in the same way that you would treat their boss.
  6. Don’t overlook them.

That last one is critical. In my years in sales, I have had more than one gatekeeper compliment me on the professionalism and positive way in which I have always interacted with them. Having a supporter in any organization who is such a trusted individual is priceless. That relationship helps you in so many ways toward your goal of establishing a long-term relationship with this client.

Gatekeepers are everywhere you go. Learn to master the skill of working effectively with those who are in between you and your goal. 

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