As a sales rep, likely what you care about most right now during a tough year, is topping up your income by converting leads more easily into customers. Naturally, winning more deals is one of the highest-impact levers you can pull to accomplish this. This means you need to improve the quality of your sales calls.

But, since the average win rate is a little over 20% (depending on your industry and ACV, according to Hubspot and TOPO), I bet that the first thing you’re going to think when you hear “42% win rate” is…

“Bullshit.” Right?

Or, you might think, “You’re a CEO, I’m an Account Executive. Not a fair comparison.” So, before we get started, to dispel these objections, I’m going to post the screenshots of the relevant Salesforce reports.

Here’s an overview of my sales numbers through our Salesforce account for RevenueZen, my current company where I’m the CEO with a 5-figure average ACV:

110 won deals, out of 213 total. Booyah. Only including New Business opps – no easy renewals allowed in on that. 52% win rate. That’s as of November 23, 2020.

Okay, what about my time as an individual contributor sales rep? Here’s the report summary from my last company:

40% of deals won, out of 460 total. So, to be fair, let’s estimate a 12% boost for being a CEO. But the blended average of these data sets is 43.5%. I’ll even round down: 43% is our number.

Who Is This Article For?

The win rate stats I reference above were relevant to my personal sales experience with Small to Medium size companies, generally those under 1000 people, often with <100 people. Some differences will absolutely apply to deals that are with 1000+ person companies. In general, the length of each step in the sales process will increase, and the whole thing will move slower.

For example, you generally can’t get away with screen-sharing a product demo for a multinational on your first call with their team, but you definitely can pop open a generic screen share demo in the first 10-15 minutes with a 50-person company in growth mode.

That said, much of this advice that I’ll offer still very much applies: such as, get into the right mindset, don’t force your script if you don’t have to, ask calibrated (yet not leading) questions, and absorb their situation non-judgmentally.

Now let’s get started!

First, I’ll talk about the opener of a calm, confident, knowledgeable, and efficient discovery call that will minimize your sales cycle and build trust, helping you win more deals.

Minutes -5 to 0 

Prepare Your Mind, Not Just Your Account Research

Your mindset is the single most important thing that will help you build trust with your prospect and win their business.

Now more than ever in 2020, the economic tailwinds are not exactly at our back. Budgets are tight. Your buyers’ budgets, and your own.

The first thing I need you to do is to act like this:

For the benefit of your buyer, and your mental health, I need you to visit the place in your mind where deals are plenty, you don’t desperately need to win this deal, or any deal for that matter, but you will passionately pursue any opportunity to help your prospect kick more ass at their job, because that is just who you are.

Remember, you will make more money this year by saying “No” to the wrong-fit buyers, and trying to get prospects to un-sell themselves. It’ll create magnetism, rather than resistance.

Do this even if – especially if – you’re below target and your commissions or your company’s MRR growth rate are lower than you would like.

Minutes 0-3 

Rapport Means Building Trust, Not Small Talk

From the moment you speak to your prospect, use your voice to put them at ease. If you sound like a robot or like you’re having a bad day, people will think, “another boring sales call to sit through. I knew it was a long shot that this call would be fun, but this confirms my suspicions.

Instead: speak confidently and warmly, at a moderate pace. I love Chris Voss’ metaphor of using your “late-night FM radio DJ voice”.

Almost always, the question of “how have you been?” or “how was your week(end)?” will come up. Feel free to ask it yourself if they don’t right away. The way they respond to this question will largely determine what type of person you’re dealing with.

This is where you can use what I call “the business zone” to identify their level of aggressiveness, which informs how you can effectively mirror them, thus building trust.

The “business zone” starts with a scale of 1-10, with 1 being “bubbly, happy-go-lucky”. This is a butterfly of a person, or a hummingbird. They will talk your ear off and rarely focus and get down to business. This is your classic “Influence” type on the DISC spectrum.

The other side of the scale, a 10, is someone who is so aggressive they come off like a jerk. Far on the “Dominance” side of the DISC spectrum. They’ll say, “Hi Alex, looks like we’re all here. Okay let’s get into the demo please, thanks.”

Here’s the thing: you can only effectively establish trust when someone is between a 3 and a 7 on the Business Zone. You can’t do business easily in the 1-2 zone, or the 8-10 zone.

So how do you pull someone toward the zone, if they’re outside of it?

You can’t take a 9 and make them a 4, and you’ll never turn a 2 into a 6. So don’t try. Instead, focus on turning a 10 into no less than a 7, and turning a 1 into no more than a 3.

Cooling Down Someone In “Jerk-Mode”

In other words, give the person in jerk-mode enough warmth – consistently – that by Minute 5 of the call, they feel awkward staying in jerk-mode. They will loosen up just a bit. They will still come off more aggressive than average, but that’s okay!

The goal is to bring Dr. Jekyll back into being Mr. Hyde.

Respond instantly to this by firming up your tone and inserting a couple notches more assertiveness into your voice. Take the opportunity to find a way to slip in the idea that you, too, think about the world in a similar way – you are also busy, and enjoy when people don’t waste your time.

Here’s an example of something you might say to build trust with the high-D type:

“Awesome. So if we’re ready to get started, I don’t need to walk through a lot of these initial questions but before we get started wanted to confirm some of the info I have on file from my research – can we get some of that on the table before we dive into how this works?”

They’ll respond, tersely: “Sure.”

You might say, “Awesome. And I know we don’t have enough time blocked off for a full demo, but if it’s helpful to reinforce anything we discuss, I’ll show a few things from our platform so you know our conversation is headed in the right direction or whether it’s totally off base from what you’re looking for.”

Telling them that you’re actively skipping some ‘normal steps’, that you have done your research in advance, and overall that you are focused on maximizing the value for both parties in the allotted time, will allow the aggressive person to breathe a sigh of relief. It’ll let them know this call is tailored to them, which will comfort them and set you apart from the generic competition.

They will think, “This person is on the same page as me. I feel comfortable following their process, knowing they are actively trying to avoid wasting either of our time.”

Focusing the Butterfly

Likewise, give the butterfly enough focus – with kindness, always – that they feel good about turning their attention to the task at hand. The butterfly will want to talk about their weekend, the river rafting trip they went on, why they love working remotely in Montana vs where they used to be in NYC, oh and how is everyone else doing today for that matter? That’s okay!

It’s your job now to find an opportunity to tie something in their personal life to the agenda of your call. This takes practice,  but let’s look at an example. They just told you they went on a hike in the hills near their house, and just moved out of NYC a few months ago.

You might say, “That’s awesome you’re getting outside so much more these days. How’s it been being away from your old NYC team, or are you enjoying working remotely more now?”

Let’s say they respond, “Oh it’s wonderful, we’re still working really well together!”

Here’s your chance to bring the small talk back to earth. Try something like, “So glad to hear that! And you’re still finding time to look at new initiatives like sales call intel even when hundreds of miles apart. Good for you.

No doubt, they’ll interpret this as the signal to start talking business, but you didn’t do it in an awkward way and you didn’t throw a wet blanket on their desire to build trust with you by socializing in their own way.

You listened actively. Good job!

Minutes 3-5 

Make Sure the Agenda Is Clear

Many sales experts will tell you that you must set a formal agenda on each and every sales call. My experience has been that this isn’t so cut and dry: setting a formal agenda and gaining acceptance for it can work in highly-structured environments, or when you’re relying on a very clear script that you don’t feel confident you can deviate from.

Instead, think about it this way:

Setting a formal and scripted agenda has the effect of making the call feel more formal and process-driven.

At this point, having built trust and knowing a bit about the person, a sophisticated salesperson should be able to understand whether it’s a good idea to make this crystal clear, or to let the conversation flow forward naturally.

Your goal should be to have the agenda be clear – not to make sure you’ve said a particular block of your script.

When Should You Definitely State a Formal Agenda?

When your prospect seems to be having trouble focusing on the value of the call.

If they came to the call a little unprepared or not seeming to understand the value of talking with you, I tend to “firm up” a bit so they better-understand the value of the meeting they’re in. Setting an agenda helps you accomplish this.

If the prospect seems to naturally start saying something like, “So does it make sense for me to explain what I’m looking for and you can tell me if there’s a fit?” then you don’t need to force your pre-scripted agenda into the mix. Instead, just add a bit onto what they say.

Here’s an example:

You: “Well that’s great to hear, I’m glad things are going better this quarter than last. Sounds like you’ve made some good changes around there.”

Them: “Yeah, thank you. Hoping it continues. On that note, does it make sense for me to explain what I’m looking for and you can tell me if there’s a fit?”

You: “Sure, that sounds good. At some point I’ll want to make sure we discuss [what growth channels you’re currently running, and the who-does-what of your marketing efforts today, but let’s start with some background and then we’ll get into that later].

Replace the bracketed text with something that represents your business.

Just don’t be a robot and force people to fit into your process if you’re already taking the route you want to take with the call.

Minute 5

Starting Discovery

Now we begin the real meat and potatoes of the call! Start off with a question that’s broad enough to capture a lot of meaningful areas of their department, but is narrow enough to focus on just the areas you want to go over.

It’s also critically important that you ask only questions that they trust you enough to discuss the answers with. If they came to you asking about benefits (or you outbound them about that specific topic), don’t ask about their benefits/payroll and IT and finance and… you get it.

My personal sales process for inbound leads nowadays almost always starts off with a brief ‘state of their union’, so that I know what we’re dealing with, before I know what – if anything – to ‘pitch’. I might say something like this:

“I’d love to start by hearing an overview of what you’re currently doing for marketing and demand generation, and how that’s going for the sales team as well – who’s running what, which channels are working the best for you, and what you feel you need the most help with today.”

Different Discovery for Outbound vs. Inbound Leads

If I contact someone proactively via outbound, I’ll word it differently. I won’t assume that outbound leads know what they need help with, so I’ll offer it up as follows:

“I’d love to start by getting an understanding of how your sales and marketing teams are currently approaching LinkedIn – are you using ads, doing outbound, producing content for the executives, anything like that? And if so, where do you feel that your LinkedIn work could use the most improvement?”

Why narrow down the discovery questions more with outbound leads than with inbound conversations? Because – at least with our outbound, when we do it occasionally – we’ll point out one specific thing that we see they could use help with.

Earn Enough Trust to Ask Questions

To put this another way: If I cold-emailed a SaaS company Chief Revenue Officer letting them know some suggestions about how to improve their SEO, and then I started off the call by asking broad-based questions about their demand generation efforts overall, that would be a little weird, right?

The prospect would probably not trust me enough yet to open up about their whole department; rather, they’d want to open up the conversation discussing just the thing they said they wanted to hear more about.

Then, as the conversation progressed and I shared enough knowledge to build value, I would have earned enough trust to bring up new areas of their business beyond just SEO, such as outbound sales and LinkedIn content marketing.

The principle here is this:

Don’t assume people want to give you the keys to their kingdom, right off the bat. They’re afraid you’ll manipulate them if they give you too much information, because salespeople have manipulated them in the past.

Do not hold this against people. Allow them to let their guard down one step at a time. Encourage this to happen by giving value up front before you ask for it.

How Do You “Build Value”, Exactly?

For what it’s worth, my first sales manager would constantly ask me if I was “adding value” to leads, and not just “pissing all over Salesforce”. In the moment, I hated it. I thought he was trying to take credit away from me on my sales.

But now, I realize that they were helping me build a fantastic habit of genuinely helping people, instead of just making a ton of low-value contacts and claiming I was helping the company out once those prospects I’d contacted, signed up.

Still, “offering value” can be a nebulous term, so I’ll define exactly what I mean by that:

  1. Ask thought-provoking questions that help them reframe their thinking
  2. Offer unique insights they didn’t know before, based on their answers

Can you build trust by doing other things, too? Sure you can. You can come via an introduction from the prospect’s peer, you can have invited them to an executive roundtable in the past that they enjoyed. A number of things.

But if you don’t know this person yet and need to build trust and value from scratch, use my two-step framework above.

It’s repeatable.

Minutes 10-30

Begin to Pitch Something

Yes, you do have to actually describe the features and benefits of your product, at some point!

This is not being ‘salesy’, this is just exchanging value as two businesspeople.

I will caveat this advice, because people have vehemently strong and different opinions about this: I always begin to pitch on the first call. Key word: begin. You’re allowed to leave a little, or a lot, for a future call.

Here are some rules of thumb:

  1. It doesn’t have to be a full product demo. In fact, it definitely shouldn’t be ultra-detailed, unless your solution costs less than $5,000 per year, in which case you do have to move quickly.
  2. It doesn’t need to be a full pitch with an exact quote. In most cases, you won’t have enough information at the end of a 30-minute introductory call to produce a full and exact quote. (However, if you can do this intelligently, power to you! Personally, I’ve always tried to build systems that allow me to quote exact rates for complex product sales in 30 mins. It takes work and careful planning in advance of your pricing model, but it’s possible.)
  3. Your goal should be to have shown enough of a possible fit that the prospect now understands it’s worth their time – or their team’s time – to have a second call with you. That’s it!

If you shoot an entire payload of features and benefits up front and you have a complex product, there’s an extremely high chance your pitch won’t be as personalized and tailored as it should have been. You’ll find yourself backtracking, later – painfully.

On the other hand, if you pitch nothing at all on the first call, your prospect will likely become annoyed or somewhat disinterested by the end of the call, and less excited about the second one.

The right balance is often something in the middle. Pitch the high level, and a few details, but not a complete solution. Make it clear that, through a combination of discovery over email and on the second (or third!) call, or whatever your process requires, you’ll be able to describe a full and accurate solution later on.

Make it clear by which call they’ll have access to the full solution you’re pitching, and what information needs to be exchanged in order to do that.

Close On Next Steps

I cannot stress enough how – just like setting the agenda of the call – the close should not be scripted, and should not force specific steps.

Rather, you’re making sure that the required elements of your Mutual Action Plan get followed, in whatever way you’ve learned that the buyer will most likely adhere to.

For example, if your sales process dictates that the Director or VP of IT absolutely must get involved on a second call, and that person is on vacation for 2 more weeks, and the main decision-maker wants to meet in 1 week, do the best you can to illustrate how the new buying process needs to work.

But please do not irritate the living hell out of your buyer by making them conform to your sales process that was created from a blended average of all of your deals. Every process will have intricacies and nuances, and you have to accommodate these while being firm on your core boundaries, AND educating people as to what it exactly means when they don’t follow your process.

Let Your Sales Process Bend Like Water

Let’s say that they say, “I’m happy to get Lisa from IT involved, but she’s out until the 28th. Let’s meet again, just you and I and with Tom from Marketing, on the 21st, to finish putting a quote together.”

Maybe you’re now thinking to yourself, But how can I put a quote together without IT?

Here’s how to respond to your buyer:

“I’d love to meet on the 21st. My later afternoon is relatively open. In terms of finalizing a quote, I won’t be able to officially confirm it until we chat with Lisa from IT, because it sounds like Lisa is the only person who knows [ZZZ Important IT Metric]. Could anyone else from her team provide that information? If not, we can do our best to firm things up but since [ZZZ] is a core part of our pricing, it won’t be completely possible. Wish I could do more. Given this, what do you think is the best next step?”

What did we just accomplish?

  1. The buyer now knows more about how pricing works. We’ve educated them.
  2. They understand the reasoning behind why someone else needs to get involved. They can now more effectively ‘sell’ the value of meeting with you, to the other stakeholder.
  3. They now have no logical way to try to strong-arm you into giving them a price quote, because they understand the mechanism.
  4. You haven’t alienated them or told them they “aren’t the real decision maker”, because it’s not about their rank per se, it’s about a piece of information or a technical approval process. It’s not personal, and you’re not telling them something like their “rank isn’t high enough”.

The Do’s & Don’ts of Setting Next Steps

DO: Help people understand how smart decisions should be made, and the key milestones involved.

DO: Suggest a course of action based on what is typical and reasonable, but ultimately try to defer to them as to what the best next step should be, in light of all the facts and circumstances.

DON’T: Force a rigid set of required calls, in a particular order, unless there’s absolutely no other way.

DON’T: Make your prospect feel like they’re unimportant or not influential.

Your prospects don’t know your solution as well as you do, but they know their team and their company a lot better than you know it.

Respect them, and respect yourself. Neither let yourself be taken advantage of by agreeing to unproductive meetings, nor make people feel trapped by your fixed and unmoving sales process that you’re unwilling to bend.

A Story of What to Avoid When Closing on Next Steps

Several months ago, I was in the market for a new (five-figure, approximately) solution to help my company set up recurring revenue billing more efficiently.

I contacted the company’s chat sales rep, who asked me a few basic questions, which I was happy to answer. They set an appointment between me and someone who I thought was an account executive.

Instead, it was a different SDR, who asked me several questions, most of which were the same ones asked over chat. They provided no meaningful detail on their solution. At this point, I was mildly annoyed: I’ve invested 30 minutes in total, and received nothing I couldn’t have gotten from the website.

Worse, I’d invited my COO to the call, thus I wasted his time too. So I made sure to confirm that the next call was going to include an AE or a subject matter expert. The SDR did not recognize my irritation but confirmed that I was correct.

You can imagine how my team and I arrived at the Discovery Call.

To remain professional, I put aside my annoyed attitude, and had a discovery call with the AE. We got into deeper questions about our situation, which sounded good. But to my dismay: the AE shared no additional meaningful information about the solution, and rejected my request to see any of the product.

I was slightly more annoyed, but still interested. After all, I had a problem to solve, and I wasn’t going to let a poor sales process get in the way.

Fortunately, by the end of the call, the AE did share what information was needed to compile a full quote, and said they would email me to gather that. They did, and I responded.

At this point, the AE replies, saying the quote is ready. I ask for the proposal. The AE says, I need to review the proposed quote live, on a call. It couldn’t be shared over email.

I remember my response, clear as day:

“Ok. If you insist.”

At this point, I’ve become more than a little irritated. Yet – again, because I have a burning problem I want to solve – I continue and book the call.

On the call, the AE finally recognizes my irritation. The answer I’m given is, “I know you seemed a little annoyed. Sorry. This is just the way I have to run the process. Hope you can understand.”

I didn’t understand. What was the point of requiring the proposal review call – to try to make sure I don’t have time to think through it clearly in advance?

It didn’t matter much. The proposal was extremely different from the company’s list prices: it included what seemed like an enormous, yet required professional services component to implement it. It was higher than the price listed on the company’s website, for our usage level. There was a lot wrong with it, that I could have explained over email.

Instead, here I am at the end of a proposal review call sharing the same feedback that could have been shared over email, before meeting live.

What’s the Moral of This Story?

First things first: I didn’t buy from them. I went with a competitor that didn’t put me through that agonizingly rigid, irritating sales process.

To focus purely on what could have been improved about this discovery call and not the SDR/Chat process… here’s the lesson: whenever the buyer (me) tried to deviate from their sales process, the AE should have taken a moment to educate me on what the impact would be of my attempt to do so.

Here’s an example of what the AE might have said instead:

“I understand that it might seem easier to review the proposal over email – however, I’m worried that it won’t be very clear unless we can review it live.

Since I can tell you really prefer to review it in advance, I’m attaching it to this email. I’d just advise that you save questions for when we can walk through it together. But if I’ve missed anything important or left something out, please let me know. Then I can make any corrections, and we can review details together. Sound fair?”

Even if the AE has to deal with me having sticker shock over email, they have at least braced me in advance, and I’m ready for it. I’m less surprised than if I hadn’t been briefed. I trust the AE more, because I was educated throughout the process.

So, the lesson is:

Don’t pull buyers through your hoops on a leash. Let them sniff around a bit as they go. You’ll earn much more trust.

Key Takeaways

If you walk away from this article with anything, let it be these principles:

  1. Approach every call as if you don’t need anyone’s business in particular. Your sales are abundant. You care only about aligning buyers with relevant solutions. May the best product win, even if it’s at the expense of your personal commission check.
  2. Rapport means building trust. It doesn’t necessarily mean making small talk. Instead, try to bring people a little closer to a ‘moderate’ energy level, if they’re at an extreme, and make sure that in some way, everyone knows the purpose of the meeting.
  3. Ask only the questions that you’ve earned enough trust to ask. This often means approaching outbound and inbound leads differently.
  4. Build more trust over the call by sharing insights that are tailored to the answers your prospect has already given you,
  5. Share enough of the features/benefits of your solution that the prospect actually wants to attend the next call.
  6. Don’t annoy people by forcing them through your sales process. Instead, educate them on why your process is the way it is. If you must bend it at their request, help them understand the impact of having bent it for them, so they aren’t surprised.

Most of all: good luck out there.

Stay calm.

And do your best.