The Software Tour Guides

Sales Engineers face tons of obstacles on their journey to becoming the best. Figure out where your SEs are at and how to get them to the next level.

Picture yourself on vacation in a new city. You can either explore things on your own, or you can look into a guided tour. Which do you choose? 

This is the exact same decision that your prospects need to make when they’re evaluating your software. Do I use the free trial so that I don’t have to talk to anyone? Or do I talk to the tour guides (sales engineer and/or salesperson)? 

First, let’s explore the five Tour Guide Types that you may have experienced throughout your life: 

  • The Historian - Historians are entry-level tour guides. They possess the knowledge necessary for the role, but their delivery of that knowledge is lacking. They recite facts as if their job is merely to prepare you for an appearance on Jeopardy, rather than create a truly memorable experience for you. 
  • The Storyteller - The Storyteller takes the knowledge of a Historian and blends it with a strong delivery of that knowledge. Storytellers are great because they make it easy for you to remember things about the tour and help you repeat what they said in case anyone asks about your trip. 
  • The Entertainer - The Entertainer is a Storyteller with confidence and charisma. You can feel it. Their jokes may even be scripted, but they’re funny so you don’t care. Not only do they deliver well, but they mix in emotion and you’re engaged throughout the tour. You talk about them and recommend them to friends. 
  • The Tailor - The Tailor makes things personal, in a good way. They strike up side conversations, figure out what you’re interested in, and then point out those things along the way. You give them a fat tip because they made it about YOU. 
  • The Leader - Leaders are so special that they change your behavior after the tour and likely for months to come. They get to know you personally and then they make recommendations and give you a plan for exactly what to do after the tour. When someone asks you, you tell them that you loved the vacation, but really it was the Leader that made you love your vacation. They are truly masters of influence in ways that you don’t even know. 

Rarely are tour guides so bad that you’d rather not have them. The same goes for Sales Engineers or the so-called “Tour Guides” of the software world. “Bad” Sales Engineers are few and far between. However Sales Engineers, like tour guides, come in many different forms. With such a limited supply of Sales Engineers, we are forced to tolerate what is often mediocre Sales Engineering. 

Think about it, would you ever complain about a Sales Engineer that tells stories? Would you tell them that they’re not living up to their true potential? Probably not. The only Sales Engineer that has clearly identifiable weaknesses is The Historian. But just because they don’t have weaknesses doesn’t mean they can’t improve. 

What type of tour guides are your Sales Engineers? Do you have a team of Storytellers? Maybe some new folks that are Historians right now, but on the path to greatness? 

From my experience, most Sales Engineers are in the middle. I started as something in between The Historian and The Storyteller. I often call it The Lecturer. If you don’t know what I’m talking about, just imagine that you’re back in a college lecture hall taking an intro level biology or history class. 

Many of the SEs I’ve coached over the years started as Lecturers just like me. That’s because we hire them out of engineering or consulting. If someone is a Historian for more than a few months, you need to get them help. The good news is, it takes relatively little training or mentoring to move them up the ladder to either a Lecturer or a Storyteller. Most Sales Enablement folks can teach storytelling and most SE managers can mentor their SEs to good storytelling (if they’re not too busy with hiring and other activities). If you don’t have the ability to teach internally, look external. 2Win Global and other companies offer excellent options for training and coaching. I’ve been through 2Win’s programs myself. 

The next jump is from Storyteller to Entertainer. This is the hardest jump to make because it involves taking the first step on what I like to call the “Behavioral Ladder.” Historians, Lecturers and Storytellers can be effective just by using their logical rather than emotional brain. You can send them to training or use sales enablement to teach them. Moving to Entertainer involves activating parts of the brain that may have been dormant for many years however and requires very specialized training. Unfortunately, while there is plenty of behavioral training in the market, there is little that is geared specifically toward the Sales Engineering role. Some companies try (poorly) to train these skills by putting engineers through Improv, which is fun, but not effective because it’s not put into context for the SE’s role. Or they’ll do behavioral training that is geared toward salespeople, which is equally ineffective. 

The good news is, once someone demonstrates that they are capable of taking the first step on the Behavioral Ladder, there is no limit to how many steps they can take. Moving from Storyteller to Entertainer, from Entertainer to Tailor, and from Tailor to Leader involves additional steps on the behavioral ladder as well as additional skill development. 

If you have Entertainers on your team, you should be ecstatic. Once they’ve broken through the behavioral wall, which is impossible for some, every other wall is possible to break through. Unfortunately the walls keep coming and the next one that they’ll hit is what I call the "Feedback Wall." Because Entertainers are rare, everyone just tells them how great they are and they never get the feedback they need in order to improve. They become victims of their own success. 

If you’re an Entertainer, you know what I’m talking about. How many times does your AE just tell you, “great job,” or “that was an amazing demo.” After a while it gets old. I wish my AEs would tell me things like: 

  • "Great job, your explanations were thorough and clear. What do you think about using an analogy to explain it next time though? I think it could cut your explanation from 90 seconds down to about 10.”
  • “You’re one of the best Solution Consultants I’ve ever seen. But you’re getting too good at solutioning. You need to let the prospect wallow in pain for longer. Once they admit to that pain, we can pull them out. We need them to really feel it so that we motivate them to act now and advance the deal faster.”
  • “You were amazing in the demo portion, when we got into Q&A though, you were noticeably less confident. What happened? You said all of the right things but you didn’t say them with conviction and now we have to do the follow-up meeting that they asked for.”

This is the type of feedback that will help SEs to improve and get better over time. 

In order to promote growth in the SE team, companies should mandate that AEs give SEs at least one piece of critical feedback after every client interaction. It must be AEs though and not just SE Management. SE Managers typically haven’t been AEs before and even if they have been, they can’t coach and mentor from an outsider or prospect’s perspective. It is this feedback that will help SEs ascend to further levels and reach their true potential. 

After The Entertainer comes The Tailor. If you’re in a competitive situation, you need to have Tailors because it’s likely your competition has an Entertainer. The first question that a prospect’s leadership is going to ask your champion is, “why should we buy anything?” Your champion can usually answer that. The harder question for them to answer is, “why THIS product and this product ONLY?” If you have an Entertainer, your champion will tell their leadership that all products will technically work, but they like your product the most. If they say that, get ready for a price war. Even if you end up winning the deal, your ACV is going to drop substantially. Only if you have a Tailor can your champion answer both “why THIS product” and “why this product ONLY.” 

All Entertainers can become Tailors with proper training. It involves minor structural changes to their delivery in order to enhance brevity, clarity, discovery, and impact, as well as refining and developing leadership skills and confidence (i.e. moving to level 2 on the Behavioral Ladder). 

The very last level on the SE ladder is The Leader. Unlike other levels that you can ascend to over time just by getting more reps, you can’t get to the Leader level with more experience because the skills you need are outside of the SE role and very few people know how to train them. 

The best way to become a Leader is to be a Tailor, then move into Sales, get punched in the face a few hundred times, find a way to be successful, and then come back to Sales Engineering. Nothing trumps real world experience in teaching you. As you can imagine, this strategy will never work because if an SE can successfully make the jump to AE, they’ll never come back because they’re either making 7 figures as an AE, or they’re destined to be your next CEO or CRO. 

The other way to get to Leader is to be properly mentored and trained. That is easier said than done however. Training Leaders requires Level 3 behavioral skills, as well as sales skills, in the perfect combination, sequence, and delivery. Even if you have the right training curriculum, you have to have the right trainer. Even with the right trainer, the training sequence has to be right or else it won’t work. The trainer needs to have been an AE so that they can teach you the sales and deal advancement skills along with an end-to-end view of the sale. But they also have to be able to put everything into context for your SEs and the only way to do that is to have been an SE as well. These people are rare and may not exist in your Sales Enablement and Sales Engineering Leadership teams. SE Management is typically made up of elite SEs that were promoted to manager before they could even learn the Leader skills themselves. If you’re an SE manager, you know what I’m talking about - you probably itch to get back in the field at times because you know you would be 10x better than you were when you left the individual contributor role.

If you thought training sales reps was hard, think again, SEs are the hardest of all. It’s not easy to build Leaders, but it is worth it. Here’s why…

A Tailor will get you the Technical Win. But a Leader will get you the Technical Win, shorten your sales cycles, elevate your team, and reduce your CAC. Tailors do whatever it takes. Leaders do as little as it takes. Tailors are stretched thin on a few accounts, Leaders can support many. Leaders deliver massive value to the prospect, but they do it in the shortest amount of time possible. People think of them as a jack-of-all-trades, but they’re actually the opposite. They’re minimalists. They do the least amount with the greatest impact. The prospect loves it and so does your sales team. 

Like Tour Guides, SEs come in many different forms. If you’re getting the technical win more often than you’re closing deals, or you’re closing deals but not doing it fast enough, you might want to take a look at presales. Since most prospects don’t think of SEs as salespeople, your SEs possess superpowers that can be unleashed for everyone’s benefit. Unfortunately, these superpowers often lay dormant because everyone is focused on AEs and sales process. Not that those things shouldn’t be addressed too, but have you taught your SEs how to wield their superpowers so that you can sell more?


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