One of the biggest things to adjust to when approaching sales for the first time is the often counterintuitive shift required to your mindset. This is especially true for founders with a background in non-sales disciplines like engineering, product management, finance, or even marketing.
I like to joke with new members of my team that doing sales changes neural pathways in your brain—but it’s really not a joke. They end up agreeing with me a few months in. A lot of the behaviors required for sales success are a massive departure from the ones you’ve valued in your career to date, even from generally accepted ways of being in society. But while they may feel uncomfortable at first, they’ve led, time and time again, to sales success.
This isn’t to say you need to run out and adopt all of these behaviors immediately, right out of the gate. My goal is simply to lay out a number of the sales mindsets that you will encounter. I want to validate, ahead of time, that when you do run into these, yes, you’re seeing what you think you are, and you shouldn’t be surprised. While a change, these new ways of thinking and interacting should be expected, and welcomed. And yes, if you can start driving yourself toward these attitudes in a proactive way, you will increase your success.
With that said, here are some of the mindset changes that will help you in the transition from founder to sales professional.
Generally speaking, we’re taught that we should conserve resources. We’re told not to waste things. We’re all probably guilty of this—saving those extra MP3s in our iPhone’s music app, or leaving that email in our inbox, telling ourselves that we’re eventually going to get around to it. Don’t throw away that half sandwich; you can keep it in the fridge for later.
Stop that, now. Reject a mindset of scarcity—and, hence, hoarding—and embrace a mindset of plenty. The thinking should be, “Even if this one does not work out, there’s a line of thousands standing behind it that I need to get to.” So if a deal is stalling, if the customer doesn’t have the budget, if it turns out an account is not a perfect fit, and so on, great, fine, close it out. On to the next. You’ll get them the next time around.
The thing that is scarce in sales is time. To quote one of TalentBin’s key early sales staff, Brad Snider, spending “good time with good opportunities” is paramount. And, by extension, that means not spending time on opportunities that aren’t going to pan out. We’ll talk more about this later as it relates to qualifying accounts, and there certainly is an art and science piece to judging whether an account is worth it.
You should be ruthless with respect to truncating unproductive conversations with marginal opportunities, especially at the earliest of stages, when the world is a greenfield of untouched accounts in front of you.
If you do not, those marginal, crappy opportunities will cruft up your pipeline, hiding the golden opportunities on which you should be spending your time. It will be unclear which action you should take next on which account; the good will be hidden by the bad, reducing your ability to act at scale, and generally eroding your efficiency. Even if you do end up closing the marginal opp, a customer who is a bad target will consume more than their fair share of customer success resources, likely not achieve the best ROI, form a bad opinion of your solution, and tell others about it, before churning out themselves.
Spend good time with good opportunities. Let go of the marginal opps, knowing that you can get them later if they become more viable. There’s plenty of opportunity here.
Everyone’s a fan of working smarter, not harder in the modern knowledge-worker economy. Well, sometimes you just have to grind. Sales, like recruiting, is all about activity and leverage. Generally speaking, activity in equals value out. There are certainly ways to ensure that your activity is high quality; you can also leverage it with technology to get more in less time and higher impact out of each unit of activity. We’ll dig into that more later. But to quote Joseph Stalin (likely apocryphally), “Quantity has a quality all its own,” and internalizing that is key.
More time on the phone. More demos. More proposals sent. More emails sent. More dials. More keystrokes. All of the above is activity, and activity is the goal.
This is often in direct contravention to typical notions of quality work: Thinking deeply about the perfect response to that email. Spending five minutes to game out a call before you make it. Reading, and rereading, that email to understand every nuance. Studying up on the materials to make sure that your pitch is perfect.
No more. Just as you need to shift your mindset from scarcity to plenty, the reality is that in order to move opportunities down the pipeline and close deals, activity is job one. Jump first, prepare midair. Template all communication. Drive activity, and output will follow.
This is not to say that your activity should be crap, but simply that your mindset should be one of productivity. Ask yourself, “How can I do more of X [an input to the deal process] in a given time period?” And if you can figure out ways to systematize more quality, fantastic. This is an exercise in recognizing the point at which you reach diminishing returns on a given sales action, catching yourself, and moving on to the next. The thought should be, “Why am I not on the phone?” or, “Why am I not sending emails right now?” Your default should be activity, and lack of activity should be aberrant. This is why sales managers get skeeved out if their sales floors are quiet—a palpable lack of activity is a bad sign.
Don’t read the entire email communication history with that prospect before you call him. Just call. It’s probably going to go to voicemail anyway, and you just saved yourself five minutes of unnecessary preparation. One proofread is all that email needs. Send it, and move on to the other fifty you have to send to your pipeline today.
Don’t overthink. Just act.
Society often gets along through polite obfuscation. Through indirection. Through politesse, and circuitousness. Not in sales land, friend.
Much of sales is about getting down to brass tacks: Do you have the problem I’m trying to solve? Are you in agreement that it needs a solution? Are you prepared to spend money to solve it?
In the pursuit of efficiently attacking your account, you, as a sales professional, have full license to be direct in asking these sorts of questions. In fact, you can go all the way up to directly stating to your prospect, with full confidence, that your solution and their problem are an excellent fit and that they should buy X amount of your product to help their business. Asking for the sale is not optional, and it will quickly become second nature.
As Alec Baldwin states so entertainingly in that famous ABC scene in Glengarry Glen Ross, “A guy don’t walk on the lot lest he wants to buy.” People go to singles bars with very specific goals in mind. Your prospects would not be on the phone with you, taking your demo, if they didn’t have some buying intent.
It is imperative to respect their time and yours by being direct and getting to the heart of the matter.
For the first-time sales pro, the scale of person-to-person interaction is a massive adjustment. Think about how many distinct people you typically interact with in a given week. If you’re like most professionals, it’s likely a constellation of one or two dozen people with whom you have frequent, ongoing interactions that build over time and with whom you have substantial history.
With sales, it’s the opposite. If you’re doing it right—see comments above about the importance of activity orientation—you’re having dozens of new interactions a week, and maintaining a pipeline of anywhere from a few dozen to north of a hundred ongoing, concurrent conversations.
It’s a substantial change of pace, and it also puts substantial stressors on you to be able to quickly build and maintain rapport with a new contact, while juggling key deal information, over the cycle of the sale. (Why do you think the weather and sports teams are the sales pro’s best friends? Instant conversation topics.) It puts the onus on the sales pro to keep readily accessible details of these individuals, their organizations, and their pains, as well as general rapport notes—which, of course, is not possible for a normal human brain. It can be exhausting, and it can be taxing. That’s why record keeping and CRM excellence (more on this later) are paramount.
This isn’t to say that these relationships are fake or that they’re not valuable or meaningful. They just demand a different way of interacting with other professionals than what you’re likely used to. To make the most of them, and manage them correctly, requires a change of mindset.
Approach your sales conversations with the stance that the prospect will inevitably be a customer. This is more applicable when you’re at the scaling stage, when it is now clear that the solution that you’re presenting has product-market fit. But it can be helpful even at the earlier stages of your go-to-market period.
What do I mean by a mindset of inevitability? If you have indeed qualified an account as a good fit, then the mindset should look something like this: “This is going to happen. It makes sense for you. This solution is the future, and it will make you more successful now and going forward. So we can do it now or we can do it later, but it’s going to happen, either with me or with a competitor of mine.”
A few helpful things come out of this mindset: First, it frames the conversation as when instead of if. This naturally makes the conversation more consultative and focused around business needs—“This solution exists to solve this problem, and we have validated that you have this problem, so clearly this solution makes sense. Let’s figure out when and how it should be implemented.” Second, it provides a confidence boost to the sales professional, related to the necessary expertness and fearlessness that we’ll talk about next. Third, it sets the groundwork for an ongoing relationship with the prospect; even if they don’t close this time through the funnel (and odds are, they won’t), they will be prepped for the next pass. It will also reinforce your own record-keeping processes, since you’ll know that recording these interactions will enable your future self the next time this prospect passes through the funnel.
It may feel odd to take on such a presumptuous mindset, and by no means is this a suggestion to be arrogant or off-putting in your dealings. But approaching each interaction with certainty will drive success in your conversations.
In most of your professional interactions, you probably achieve some semblance of your goal most of the time, largely because you wouldn’t be engaged in the activity in question if you didn’t think you had a reasonable expectation of success.
This is definitely not the case in sales. You’re going to get shot down most of the time—you will not close the deal on that particular pass through the pipeline. For whatever reason: there won’t be enough budget, the timing will be off, the prospect will be happy with their current tools, a competitor will win the deal, the prospect will just disappear, and so on. It happens. Depending on your industry, and the point at which sales gets a prospect in the funnel, if yours is a new, innovative solution, a 20–30% win rate is solid.
The mindset change required to contend with this is the ability to hold what are essentially two seemingly opposed ideas in your head at once. You need to have and project full confidence that you’re going to win the deal but at the same time be unfazed when you do not. Being unfazed by rejection, and not internalizing it as a negative reflection on you or your offering, is key to maintaining the tempo and confidence required for sales success.
This is not to say that you should not learn from those losses; the reason for the loss should be recorded to benefit product iteration and also for reference the next time you engage with the account. Be intellectually honest about where the loss came from: Was it timing? Did you get beaten by a competitor because you didn’t follow up appropriately? Or because the product had a feature deficit? And make sure that the answer gets shared with others, so they don’t have to learn the same hard lesson you did by eating a loss. But after honestly reviewing and recording the loss cause, put it aside and move on. You should still expect to win the next one.
As an outcome of sales strategies we’ve already covered—the sheer magnitude of professional interactions you’ll have and the importance of high activity—the reality is that you’re going to classify most of your opportunities as closed-lost. For that reason, a mindset of constant record keeping is paramount for success.
Previously, you could perhaps rely on your own memory to recall what it is that you were working on or what your last conversation with a given person had covered. No longer.
Instead, you need to admit to yourself that there’s no way that you can retain all this information, not just day to day and week to week when dealing with your current pipeline, but month to month and quarter to quarter as you revisit and resurrect previously closed opportunities. On my sales teams, we call it “setting future-you up for success.” When you come back to look at this account in a week, month, or quarter, what information will you wish you had? Record that now while it’s available, and make the ephemeral permanent.
And while your CRM will be the primary repository of this information, this mindset shift includes a variety of tactics (CRM excellence being one of them). In my sales teams, every person has a lab notebook to allow them to take notes during a call (especially during the discovery section), including size of opportunity, qualification details, and so on, to later be transferred to the CRM (not wholesale, but the salient points).
Of course, you don’t need to transcribe each and every thing that a prospect says on the phone. However, you do need to adopt a mindset of persistently pursuing and checking off key pieces of information, in an efficient fashion.
Moreover, once you and your team have internalized this mindset, you can start looking for constant opportunities to use technology (email capture, call recording, presentation recording) to make the capture of this information automatic and instantaneous.
Modern sales is not about trying to sell snake oil to a mark.
Rather, sales professionals are the grease of the market. They seek out inefficiencies in the world in the form of qualified prospects who have the business pain that the proposed solution resolves. Then they engage and consult with the prospect, and propose the implementation of the solution, to help fix that business pain.
As such, expertness in the vertical in which you are selling is an absolute requirement. You need to be a student of the game you are playing and, ideally, even more expert than the prospects to whom you are selling. This means absorbing as much information as possible about the field, the business processes that exist within it, the common organizational players, and the other solutions that already help with these business processes or compete with yours.
This expertness will make you fearless in your interactions. It will help with your activity orientation, removing your desire to over-prep for conversations and empowering you to just call, just email, just act. It will help with your ability to be direct, to operate from a position of inevitability, and to quickly establish rapport by demonstrating authority.
But even before you achieve that level of expertness, you can adopt a mindset of fearlessness, confident that you have enough expertise to engage in any conversation. You’ll find this manifesting in your real life, as it becomes easier and easier for you to strike up conversation with any random stranger on the bus or at the grocery store, knowing that you’ll have no problem participating in whatever ensues. As with others of these mindsets, not only will you start seeing this one show up naturally, you can also push in that direction proactively. Compel yourself to talk to grocery store clerks, people in lines, or strangers at parties with no introductory context. You’ll be exercising your fearlessness muscles.
The level of transparency in a well-instrumented sales organization is a massive change for most people. From win and loss notes and closing ratios to leaderboards and error checking, everything is right there, available for everyone to see.
If you’re doing a good job, you will have all customer-facing interaction instrumented and recorded—every single email, every presentation, and every call—either in its entirety in the case of presentations and email, or in some partial capacity when it comes to calls and conversations. You should get comfortable with teammates jumping into those records and asking questions about why a call went this way or that way. Your creation of this transparent data is of paramount importance for the success of the organization, from both a go-to-market and a product-development standpoint.
Similarly, activity levels, or lack thereof, should be clearly documented and inescapable. If a rep spaced out today for some reason, the lack of calls and emails will be fully observable. And if your CRM is really well done, it will be observable down to the granularity of which hours of the day that rep was lagging.
So too with error checking. If your CRM is well executed, you will have reporting that shows exactly which opportunities and accounts have been missing activity for a certain period of time and are in danger. The only question that will remain is why you haven’t hopped on top of that! In fact, your CRM reporting should yield valuable insights all the way down to every single closed-won and closed-lost opportunity. For every win, you can see the strategy that sold five seats instead of two. For every lost opportunity, you’ll see what went wrong: budget, competition, a prospect not yet convinced of your solution’s value, and so on. But you lose this insight without transparency.
And while this may sound frightening, it’s actually extremely beneficial, both for the individual and, in aggregate, for the organization. It creates an environment of accountability and shared learning that drives a positive, self-reinforcing feedback loop. Your staff focuses because there’s no way not to. There’s no excuse to not work on high-priority items, because the errors are documented and visible. Flubs and failures are socialized so other staff won’t crash on the same rocks, but also so they’ll realize that failure is part of the game and not to be feared. And that foments a culture of action orientation rather than loss aversion, because fear of failure is one of the biggest blockers of action. If you remove that fear, you remove that brake on activity. And when you transparently share wins alongside losses, your staff know that they’re real, and not puffed up, and thus can take them as helpful guideposts for how they should execute.
Document all of your team’s activity, and everyone can simply put forth their maximal effort without worrying what will be available to whom—because the answer is everything, to everyone.
When people think about what is needed for sales success, they jump to a lot of what people consider to be right brain activities. Storytelling, persuasion, rapport building, and such. Socialization, drinking, and dinner. Shooting from the hip and making it up as you go. They often don’t consider, or at least not as much, that sales is something that involves lots of metrics, math, and reporting. Guess what? You can’t escape math in sales either—especially if you want to have success at any amount of scale greater than a single rep.
All that instrumentation and recording that we talked about needs monitoring and analysis. Want to know how many emails to how many prospects are generally needed to get a demo on the board? You’re going to need the relevant Salesforce reports for that. Or want to know how many opportunities are required to close a deal, and what each of those opportunities is worth? Better have your win rates instrumented and reported on. Did you want to understand if you can afford to hire a sales development rep to feed your calendar? You’re going to need to know your average contract value. Did you want to know which of your sales reps are most efficient at converting opportunities into wins? You’ll need to split those win rates by rep, and probably add a revenue component to your calculation too. The sales leader who struggles with Salesforce reporting and Excel pivot tables is going to have a rough time in a high-velocity, high-scale sales environment.
Sales in the movies may be about dinners, suits, and booze, and there’s certainly still an expense-account-dinner component to it. But all of that activity is underpinned by a healthy helping of metrical excellence. You won’t be able to avoid it, so you might as well start getting cozy with it.
These certainly aren’t the only mindset changes that you’ll notice starting to take hold. However, they are the ones that are initially the most crucial for your transition from founder to sales professional. Moreover, as you may have seen as you read, these first mindset shifts have a complementary, multiplicative impact on each other. Success begets success.
If you record everything, you can be direct and non-scarcity-minded, quickly identifying opportunities to spend your time on now. You’ll be free to move on from imperfect opportunities, knowing that you can come back later to get them because you did a great job of recording the customer interaction and creating backstops for future engagement—all of which will raise your activity levels and efficiency.
Or if you expect to win, are unfazed by loss, and have adopted the mindset of expertise, it’s easier to adopt a stance of inevitability. That, in turn, will help you be fearless and authoritative in your interactions, and more consultative, which will lead to higher close rates.
Or if you expect that you will have high volumes of shallow relationships, you will be prepared to be more direct and efficient in surfacing relevant business details. That will focus you on the importance of efficient record keeping, which will better empower your future self to pick these conversations back up if they do not close this time through the funnel.
And the permutations go on and on.
importantWhile you may encounter some of these mindset shifts before others, and while some may be easier for you to adopt than others, the important thing to internalize is that the universe of enterprise sales has its own “physics”—and you’re subject to those rules now. Proactively identifying, embracing, and driving toward them will foreshorten your learning curve and make you more successful in your efforts, faster.