TSE Blog 031: 16 Veterans Share Their Biggest Sales Lessons
  • You are here:
  • Home »
  • blog »
veteran sellers, sales lesson, The Sales Evangelist

TSE Blog 032: 16 Veteran Sellers Share Their Biggest Sales Lessons

veteran sellers, sales lesson, The Sales Evangelist

Sellers often learn sales lessons the hard way because humans aren’t inclined to learn from other people. We learn by doing, so we often repeat common sales mistakes because we’re determined to go it alone. 

It is possible, though, to learn from other sellers, so we’ve engaged 16 veteran sellers who work in the trenches and know what works when it comes to sales. Each one has at least seven years’ sales experience and we’ve asked them to share their greatest sales lessons here.

Amanda Thomas, Partner, Konstruct Digital

I am an introvert by nature, and sales has always been difficult for me. My closing rate has always been good, but sales calls are difficult from a mental-energy standpoint.

One thing I have found that helps is having a pre-defined list of questions to ask before jumping into a pitch. The questions help me understand pain points and objections so I know which elements of my pitch I need to focus more on.

Questions like:

  • – Have you worked with an agency before? What was your experience like? Why are you looking for a new agency?
  • – What does SEO success look like to you? What metrics are important to you? 

Having a pre-defined list of questions helps me structure the conversation and understand objections before they come up. Addressing objections before the client has an opportunity to raise them builds confidence and shows that you understand their perspective.

Yuri Burchenya, Cofounder, GetFound XL

There’s no one-size-fits-all for sales lessons, as the rules are not the same for deals of different sizes. But if I had to pick just one thing, have a conversation about budget with the leads early on in the sales process. This qualification step saves so much time and filters out a lot of companies you wouldn’t want to work with.

Combine that with a “paid proposal” positioned as a roadmapping service and you have the basis for your agency sales funnel. 

We used to spend too much time on custom proposals for the clients, so now we offer a roadmap for them which is similar in scope to the proposal, and we get paid for spending all that time on it. This involves a relatively small fee, compared to a regular contract, but money changes hands, which makes it easier to convert the lead for a regular contract later on.  

Tom De Spiegelaere, Director, Mango Matter Media

There are so many layers to closing sales, it’s really hard to just pick one. We like to focus on 3 major points: Minimize objections, gather info, and project confidence.

To minimize pre-meeting objections, we learn from our previous clients and put the most common objections on our website, together with our responses, ideally on the page where we ask them to input their info about budget, needs, etc. Then, depending on what type of client it is, we also address more industry-specific objections in the pre-meeting emails. We want to make sure we’ve dealt with most of the objections by the time the meeting takes place. As for info-gathering pre-meeting, we focus on budget and pain points. Budget is easy to get, but for the pain points, we like to access their analytics so we can track traffic and see where the issues are.

When it comes to the meeting itself, know the agenda, appear confident (never look like you’re lost or not knowing which point to hit next), and most importantly, make THEM feel important!

Remember, we mostly buy with emotion, and then use logic to justify the purchase afterward.

Chris Sloane, President, Heaviside Group

Assuming you have a quality product that solves a real problem, one of the most critical sales lessons you can learn is that it’s not about you. Your prospects don’t care about your tech stack, or your SOPs, or your carefully worded email sequence – which they generally don’t read anyway. They care about one thing and one thing only — whether or not you can solve a real problem for them and whether they believe you can deliver. That’s it.

Speaking as a business owner, I ignore dozens of sales emails and phone calls every day. If I see the “just following up” email, I block you permanently. I don’t care that you only want 15 minutes of my time. That’s wasting my time, and I don’t have enough of it as it is. If I notice something customized to my business, about a problem that is real, and it’s clear time was spent crafting it, I’ll listen.

I started my agency after 10 years in outside sales, and I recognize now the things I did wrong in my sales career. Don’t cast a wide net hoping for a 1-2% conversion rate. Develop a much smaller ideal client list, customize your approach, and shoot for 10-20% or more. You’ll see huge improvements in sales.

Curt Storring, Founder, Floor500

One of my most valuable sales lessons was learning that a sales call doesn’t need to involve a bunch of convoluted rules and strategies. Sales doesn’t come naturally to me, so I thought I needed to read a bunch of books and memorize a bunch of “expert sales tactics” in order to close the sale. It just ended up making me anxious and more likely to screw things up.

When I realized that all I needed to do was know my product inside and out and ask questions to truly learn how we could serve the potential customer, calls became much easier. Now I like to learn as much as possible, not only about the company but about the person I’m talking to, in order to relate to them as a human. This lets me lay things out honestly and without having to resort to “ninja hacks” to close a sale. 

Nick Eubanks, CEO, From The Future

My favorite way to build trust is by demonstrating expertise and value. I prefer to do this with a very low barrier, either free, or ideally, a nominal amount that delivers extreme value.

I call this initial offer a “trust offer,” and for my audience and services, I prefer to deliver this for less than $1,000 (but with something that delivers 10x the value of the cost). This sets up further discussions, and the best trust offers imply more work. They are literally designed to infer up-sells without you even having to be the person who suggests them. 

Jordan Choo, Managing Partner, Kogneta

One of the most effective sales lessons that I’ve learned in my career is to be curious.  

 The entire reason a company is bringing you on board is to fix a problem, and your job is to solve it. In order to understand what you’re trying to fix, you first need to listen and understand that problem because it dictates how you’re going to solve it. Do that by being curious and asking thought-provoking, questions just like Donald recommends.  

 By asking these questions and being curious about the problem, you will be able to diagnose the strategies and tactics that you need to fix the problem. It will also give you insight into how much it is costing the client in terms of revenue, which will help you maximize your own pricing for the project.

Brad Smith, Founder, Codeless

Too much is made of sales tactics and not enough of sales strategy. The best closing scripts can never outperform better positioning and your brand’s unique selling proposition. Yes, those things are important. You need processes and frameworks to scale any sales operations, but they’re just table stakes. You’ll always be competing on fine margins, inevitably forced into price competition, and discounted prices to get prospects over the line.

Brands that take enough time to carve out their own USP place themselves in that fabled ‘category of one’ — where there’s less price sensitivity and fewer direct competitors. So measure twice, cut once. If the products/services you’re selling aren’t truly unique or better for a particular customer type, start there. Once you’ve ironed these things out, you can perfect your sales messaging, and your customers’ benefits will be far better than any other alternatives. As a result, you’ll be the only game in town for them.

Amplify those things to create more than enough demand that lets you pick and choose clients. Sidestep all of the overly-clever tactics that people with subpar products/services in commoditized markets are forced to rely on.

Dan Christensen, President, MorningDove Marketing

There are so many sales lessons, but perhaps the biggest is knowing when NOT to sell. Understanding your ideal client, their wants, hopes, desires, current revenue goals, and even their hobbies, can help you determine whether or not you pursue them. 

Early on, I went after every prospect with the same intensity, and it led my business to a very dark place. I had revenue coming in, but instead of being happy and optimistic about where I was, I had clients who were constantly looking over my shoulder, questioning my every move, and constantly trying to negotiate my prices lower and lower. When I took a hard look at the situation, it occurred to me that it was actually 100% my fault; I was attracting, and even pursuing, bottom-feeders. 

I revamped my business and my mindset, started turning away more of these types of clients, and eventually replaced them with amazing ones who understand the value of the service and are happy to pay the going rate.

Jason Berkowitz, SEO Director, Break the Web

When you start a conversation with a new prospect, you should actually do very little selling. 

Start with a deep-dive discovery process to understand what your prospect’s company does, what they’re hoping to achieve, what their pain points are, the future goals they are pursuing, what they’ve tried in the past, and who their top competitors are. When you take the time to get to know your prospect right from the beginning, you’ll be able to present your services in a way that makes sense for their business goals. Knowing their pain points helps you understand precisely where they want to go and what they need to do next. 

Offer potential clients value through education and be transparent about what your company can and can’t do to help them meet their goals. Providing them with realistic expectations will save you headaches down the road. Consumers want to be treated like human beings, and you aren’t giving them that if you’re simply running scripts. Following this process helps you establish trust and authority, and that’s how you close a sale.

Joe Robinson, Founder, Green Flag Digital

The biggest thing I’ve learned when pitching and selling to prospects is to listen deeply to fully understand what they’re saying without explicitly putting it into words. I prefer the consultative selling approach, where it’s really a discussion to see whether my services are truly a good fit for them in the long run, rather than trying to make the sale today. 

Throughout that process, I balance questioning with offering insight, so that it’s a mutual exchange of value. At the same time, I always aim for the prospect to talk about 60-70% of the time in order to fully understand their needs.  By listening for trigger words and key pain points, I can more fully see what the larger problem is that they’re trying to solve. For example, oftentimes when a prospect is looking for link-building services, the problem they’re actually trying to solve is earning more traffic for their website. I try to ask questions to help understand how big of a problem that is for them, and help them arrive at what the ROI would be from an engagement.

Brandyn Morelli, CEO, Tilt Metrics

One of the sales lessons I’ve learned during the sales process is to focus on providing value upfront. I see a lot of competitors who talk to prospects, throw out a blanket proposal, and hound them for a decision. They are hesitant to spend any time that they feel is wasted since it’s pre-engagement, but a few hours of work can help separate you from the pack. If you take time to look at the project from the client’s side and understand the root problem they’re facing, you have a huge advantage. 

Clients aren’t looking to buy services, they’re looking to solve a problem. It sounds basic, but it’s surprising how many agencies are looking to pitch their services, without digging in to see that they’re proposing the right solution for what’s keeping the customer up at night. So on your next call with a client, focus on asking deeper questions, and spend less time on highlighting your agency and accolades.

Kevin Hilton, Director, Multi-Layer Media

The biggest sales lesson I have learned is that not everyone is MY client. This one can be a hard lesson to learn and can take a lot of time. When you first start out you want to take on as many clients as possible, but as your business grows and progresses, you realize that you only want to work with the right clients. You need to define for yourself what makes a client “right” for you and your business, whether that is having a complete understanding of what you do, paying on time all the time, or having respect for your time and your work. Ideally, your clients should do all of those things anyway.

Remember that if a client causes you headaches and you don’t enjoy working with them, it makes it much harder for you to deliver the best possible service. So when taking on new clients, learn how to decide whether they are the right fit for your business. Be prepared to fire a client if they turn out to not be a good fit. Once you weed out the clients who aren’t ideal for you, you can spend more time on getting clients that are ideal.

Paul Leary, Founder, Are You On Page 1

I‘ve had a few sales mentors throughout my short career that all taught me the same three fundamental things.

1. Put yourself in your client’s space

Business owners get inundated every day from providers with product offerings ranging from the tile on the office floor to the commercials you’ve seen on TV. They’re tired of hearing about how great you are and that you’re number one.

As sales specialists, we can make the mistake of steering the discussion toward why WE are great vs. prioritizing the business needs. 

 2. Accurate information on your value should be presented to the client and how it will drive the best ROI for their company.

Research is key. Will your product/service make something cost-efficient or faster? Will the buyer be able to capitalize on a missed stream of revenue?

If yes, what impact will it have on their bottom line? Concrete projection numbers, references, and case studies should cement why they should invest in your services.

3. Follow-up is key

Not following up with previous sales before taking on new ones is a terrible mistake most sales professionals make. We get so busy that we forget about what we’ve got brewing in the previous pipeline.

Michael Costin, Founder, Local Digital

When I started my agency I didn’t come from a background of sales. Rather, I had been an SEO nerd working on client campaigns for years. I very quickly learned that no matter how good you might be “on the tools,” it’s the ability to prospect for new customers and then sell to them that matters more than anything.

First of all, you need to constantly self educate. Read as many sales books as possible. Start with Fanatical Prospecting by Jeb Blount, Predictable Revenue by Aaron Ross, and Spin Selling by Neil Rackham. Second, use tools to make your life easier. A good sales-focused CRM that shows your full sales funnel and what stage each prospect is at is vital, especially as you start to track more deals at the same time. I use Pipedrive for this, but there are numerous options out there. 

If you’re doing outbound email prospecting, tools like Mailshake or Hunter can help you track down contact details.

But the biggest tip is that when selling, make it all about the prospect, not about you. Speak to them, qualify them, identify their pain points, and uncover what is truly motivating them to speak to you. Then, tailor your service to their circumstances and show how you are the solution. Craft a story in the sales process that shows prospects that you hear them and understand where they’re coming from and where they want to go. Clearly articulate how your service is the must-have element that will make that all happen.

Stephen Sumner, Founder, Optimise Agency

I have learned, perhaps the hard way, that the first thing you need to do in sales is to listen and understand the client and their challenges. Once you actually understand the client and their challenges, you can devise a solution, instead of the other way around. If you oversell or lay down false expectations, it will creep back up on you and bite you on the bum.

Being an agency that offers SEO services, we have set a minimum price we will work for. In the early days, we took anything we could get, but this ended in failure. We were not able to provide the solution the clients wanted for the price we had sold on. As a result, we no longer take projects that don’t have a solid financial foundation as they are destined to fail.

Bio: Ted Lowe is the content marketing manager at Empirepromos.com. He loves to breakdance when no one is around.

About the Author The Sales Evangelist

Donald is the host of the popular sales podcast,"The Sales Evangelist". He is the founder of The Sales Evangelist Consulting Firm where he helps small companies develop killer sales process to scale their business and increase growth.Donald is also an award-winning speaker, sales trainer, and coach. He's a big fan of traveling, South Florida staycations and high-quality family time. Donald has a belief that “anyone” can sell if they have the desire and receives the proper training.

follow me on: