Fly’s Friday Five: Can Your Team Sell Their Way to Success?

Written by: Gary Fly
Flys Friday Five

I am going to continue the theme that we started a few weeks ago of talking about how to sell your way through these current macro headwinds.


I believe that there are companies that are not going to survive, and there are companies that are going to thrive. Those that will thrive will be the ones that figure out sooner rather than later how to sell in these current uncertain times. I want to share a number of resources with you today: 

 The reason I mentioned those upfront is, over the last two weeks, I’ve had a series of discussions and have been exposed to these articles and more things that created an “a-ha” for me – I keep hearing about some sales basics not being in place. At a recent client meeting, the one topic that came up time and time again was the idea of prospecting, and that their salespeople really did not know how to prospect. That got me thinking… What does that really mean? Why can’t they do that? What do they need to be able to do differently to be successful at prospecting? These articles and book that I mentioned, all came together in a way that helped me form what I believe are five things that sellers can do in today’s environment to help improve or up their prospecting game.  

Before I get to that, I believe there are a few things that we as sales leaders or company leaders need to ensure are in place to really set the tone for success.


  • Our job is, I believe, to help build confidence with our salespeople or our leadership team. But we need to ensure that our team has the tools and training to do a good job, that they know what a good job is, and they have the basics in place to be confident about going about doing their job.  
  • We need to provide clear direction. I think that helps build confidence. But without clear direction, I believe we’re never going to be successful.  
  • We need to make sure that we are building human connections. These have been strange times coming out of COVID when we were physically distanced from one another. We’re now doing a lot more things virtually. And I believe that it really reinforces the need to remember that we’re humans talking about humans. And we need to have a human connection with each other. 

With the stage set, I believe there are five things that you can do to help your sellers prospect better.


  1. Clearly define your ideal client. Find the target that they’re going after. Be very clear about who you’re trying to sell to, make sure your sellers understand that, and make sure they understand why you’re going after that target. Once they do, help them personalize their messaging around these different targets (remembering the idea that we’re selling to humans).  
  2. Teach sellers to sell on value. Your sellers need to be well grounded on the value that your solution brings to the marketplace. If they don’t understand their value – if they don’t understand why people buy from you, or why they buy from your competitors – I believe they’re going to struggle to develop a really good value statement to the client. And they’re also going to revert to price negotiations, which is not where you want to be.  
  3. Train your team to ask good questions. Again, this will help build that human-to-human connection. It will also uncover your client’s real needs. So, if your sellers are well grounded in questioning skills and listening, I believe that they will start to build trust with the client, which is actually the fourth thing… 
  4. Strive to build trust with your clients. Help your salespeople realize that their goal is to build trust. They want to be a trusted advisor, and they want to be a resource solution for their clients. They can do that by recognizing that the buyer journey for each of their clients is going to be a little bit different. They’re each going to have some different needs or will have some different questions. So, the salesperson needs to understand that their job is really to help their client navigate that buyer journey in a very personalized way that builds trust. 
  5. Provide your team with consistent coaching. There are a few keys to good coaching. We need to make sure that we help our team plan and organize their work. We need to make sure that they understand the objectives. They need to receive consistent coaching, and they need to all be held to consistent standards that are well known.  

Always happy to discuss. Always happy to debate. Always happy to provide additional information. Please feel free to reach out to me at   

Written By

Gary Fly

Written By

Gary Fly

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