The Confidence Problem

If your sales cycles are too long, sales process alone can't solve everything. You need confident reps and confident engineers.

There’s really only one reason for long sales cycles...

The salesperson allows it to happen. 

If you disagree with that statement ask yourself this...

Do you think your buyer wants to spend 9 months evaluating your product? 


Every prospect thinks that they know how to evaluate your software. How many times have you had a prospect tell you that they needed a solution yesterday, so they just need to see a demo?  

Meanwhile, you’re thinking...”demoing isn’t going to solve this problem.” But you can’t say that because the prospect thinks they know what they’re doing. 

If only people would approach me and say, “Hi, as the salesperson, I trust that you’re an expert at helping companies evaluate your software, so can you please show me the easiest way to evaluate whether or not your product is a fit for us?”

As you can imagine, no one has ever told me that. I’m in sales. No one trusts me (at first). But that’s exactly what I have to do. I have to build trust so that I earn the right to be their guide as they navigate the evaluation process. 

Trust is built over time. Trust is lost when expectations are not met. One of the ways I build trust is by providing a clear plan. At the beginning of every engagement, I present a 1-page (or verbal) plan of the steps customers need to take in order to evaluate my software. If it’s an intro meeting without presentation aids I will just say something like…

“For customers who want to be thorough and also not waste time during the evaluation process, these are the steps that they have taken to reach a decision. How is this different from your evaluation process?” 

That is a magical statement right there because it shows authority (we’ve done this before), provides social proof (from customers similar to you), and invites collaboration and partnership. Frequently, prospects don’t even have a formal documented evaluation process, so they thank me for giving it to them. I just provided value, while also taking control

Some would explain what I’ve just described above as simply, ”Sales Process.”

Having a clear sales process will solve tons of sales problems. However it doesn’t solve everything. 

You also need to have a confident sales rep. Sales reps that lack confidence let buyers take control, which leads to all sorts of delays in sales cycles. Obviously, there are all sorts of wonderful concoctions of sales skills that a sales rep must have to be successful, but confidence (the type that comes from knowing what you know and what you don’t know) is the one that’s most important for maintaining control of sales cycles. 

So if you have a good sales process and confident sales reps, all your problems are solved right? 


If you sell a turnkey product, then you’ll be fine. Complex sales are different. Complex sales involve sales engineers. They involve product knowledge and sales activities that a salesperson does not understand. Demos, POCs, Architectural Deep Dives, and other presales activities must be led by an expert in those domains. That expert is the sales engineer. 

The more complex a product, the more important the sales engineer is to the sales cycles. Marketing platforms require some degree of sales engineering, app dev platforms even more, cybersecurity platforms still further. It is not uncommon for buyers to be in the “technical proof” portion of the sales cycle for 50% of their time. This is especially true given that buyers are able to do more discovery up-front, without a sales rep involved. 

This changing phenomenon means that sales engineers are potentially “leading” 50% of the sales cycle. Leading is put in quotes because while the sales rep is responsible for the end-to-end sales cycle, the sales engineer is running their own mini-evaluation almost identical to what sales reps are trained to do. 

And therein lies the problems with long sales cycles. Frequently, companies will focus all of their time on standardizing and getting their sales process right, not realizing that their presales process could be improved as well. Most companies have a presales process but it’s typically reactive rather than prescriptive. They’ll do whatever the client “needs” and it typically involves discovery, discovery demos, custom demos, POCs, architectural discussions, workshops, and technical discussion after technical discussion after technical discussion until the risk-averse buyer is finally convinced that they’ve seen everything they need to. A more prescriptive approach like one that good salespeople employ will save time and improve outcomes. 

Here’s a simple prescriptive strategy that is guaranteed to save you time in the long run but is not employed by every company. 

Early in your sales cycle, have your SE ask the prospect for a “Reverse Demo.” During your discovery meeting it may sound something like this...”Wow, thanks for sharing this. Your process is more unique than I had expected. When this happens, I’ve had customers do a reverse demo to me because it saves us all time in the long run and makes it so that I can show more of the things you actually care about in the demo. It might even save us having to do a bunch of follow-up demos. Do you have someone on your team that would be able to demo to me?”

You’d be amazed how many prospects will say yes to this, for no other reason than the SE is the one that asked for it. It drives AEs mad that they get told “No, we don’t have time,” constantly and yet the SE walks in and gets what they want. It helps everyone because it’s another discovery meeting where the prospect has their guard down and starts telling you about all the pains of their current process. Unless they’re demoing to you, most prospects would prefer to talk about the solution that they want rather than the pains that they have. Reverse demos also help the SE to be more confident in the demo because they can map their solution to the pains that the prospect has discussed. That shows that the SE was listening, builds trust, and increases ACV. 

Of course, even with a strong presales process, Sales Engineers need to be confident sellers. This is the biggest challenge and it occurs for many reasons, some structural and some behavioral. 

On the structural side, SEs are sometimes not empowered to be sellers because all sales decisions need to be made by the AE. As long as the AE has been an SE and understands the SE’s role, then SE empowerment is not a problem. 

However, if AEs don’t understand the technical side of the sale because the product is too complex, then they have to rely on the SE to lead it. This creates a leadership gap. 

Leadership gaps exist when there is no one leading. SEs are typically told to get the technical win. They are not told to be the salesperson because advancing the sale is the AEs job. When they’re told to get the technical win, they do everything necessary to get it and are usually successful because they outwork the competition. They probably even have statistics on how successful they are POCs, demos, etc. As a result, they give more demos. They have more follow-up meetings. They do more POCs. They talk about architecture. It’s more, more, more. 

Hopefully the leadership gap is obvious. One person (the salesperson) is supposed to be leading, but doesn’t know how to. The other person (the SE) is doing their job by being thorough and complete. After all, we don’t compensate SEs for advancing deals faster and for doing less and talking less. Maybe we should.

The leadership gap that exists in complex sales is one of the biggest contributors to long sales cycles and unpredictable forecasting. If you’re a sales leader you’ve probably already realized this and fixed your sales process. Your next move should be to consider structural changes to your presales process and consider if empowering and training your SEs to be better leaders would help your sales team. It doesn’t fit every company’s model, but have you even considered it? It may be worth looking into because these are quick fixes that YOU are in complete control of. Trying to change your product to be easier to sell is in your engineering department’s hands and takes years to do. 

Moving beyond structural issues, there is another reason for long sales cycles and unpredictable forecasting. This time it is behavioral. 

As an SE that came from a technical background, I can say from personal experience that technology was my “comfort zone.” I was an excellent presenter and was always confident explaining the tech, however my confidence slipped when I was pulled off-script or when I had to field ad-hoc questions from enterprise architects and CISOs. 

How many times have you seen the SE who was amazing when they were demoing, but was noticeably less confident in ad-hoc situations? 

Being an expert in something can also be a curse because you want to talk about it. Most SEs are experts in either their product, technology, or both. 

How many times have you seen an SE overexplain concepts and get into the weeds, just because they could? The worst part is that we often don’t even realize that we’re doing it. We’re having such a good time geeking out on the tech, meanwhile the prospect is eating it up and loving it too, so we think we’re doing a great job. Frequently this sort of behavior just invites more questions and more follow-up activities, which further delays sales cycles. SEs can’t spot this though, only AEs that are bored out of their minds can. 

The combination of structural problems and behavioral problems in the SE organization are completely normal and ubiquitous. But it doesn’t mean they shouldn’t be looked at. They just rarely get the attention that they deserve because companies would rather spend money on lead gen and sales process, and for good reason since those things are very important and solve a lot of other problems. 

If your sales enablement team is doing their job, you should have excellent POC win rates and great engagement. The next thing to consider is teaching your SEs to “forget” most of what they’ve learned and do less rather than do more. This is very unnatural for them, but it can be trained. A minimalist approach of doing and saying less, but doing it more clearly and impactfully, can be much more effective in selling. 

It’s mainly sales process and confidence that can shorten sales cycles. But for complex tech sales we need to work on presales process just as much as sales process. We also need to work on building SE confidence just as much or more than AE confidence. Speaking as an AE now, I have found that when my SE was confident, I was confident and we closed deals. When my SE wasn’t confident, I wasn’t confident and we lost. 

We underestimate just how powerful the SE can be. I personally gained an even greater appreciation for the SE role after I left it. They clearly have the ability to greatly impact their AEs mood, even though the opposite is rarely the case (a confident AE does not make an SE confident). SEs also possess a superpower that AEs don’t have. While AEs spend tons of time building credibility, most sales engineer’s walk into the first meeting and everyone trusts them. They are uniquely positioned to take control and lead, however they are often not empowered and trained to do so. It’s a shame as it’s a superpower that can benefit everyone. Your AEs and leadership want to close deals faster and your buyers want to buy. No one wants to spend 12 months in evaluation mode, so do yourself a favor and teach your SEs to be confident and to be leaders. If you don’t know how, just ask.

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The Confidence Problem

If your sales cycles are too long, sales process alone can't solve everything. You need confident reps and confident engineers.