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Fundamentals. Basic blocking and tackling. Practical habits that work.

Starting Out

Early in any career, there is a lack experience, wisdom and industry knowledge. That’s to be expected. But in its place there should be plenty of something else: energy, work ethic, curiosity and character. The best advice I can share is to use those qualities to their fullest early and often.

Don't overthink things, and don't prepare excessively. Instead, dive in. Make calls, make appointments, make presentations and make mistakes. If you make lots of the first three, you'll make plenty of the last. Which is inevitable. Learning and experience typically accumulate through failure and error; real accomplishments seldom occur without them. Own up to them, learn from them and then move forward.

To their credit, most people are surprisingly quick to forgive mistakes, even sizable ones, if made with good intentions and ethics. Just apologize to the victims with genuine, sincere conviction and keep going. It's actually reassuring to witness how tolerant and even encouraging people tend to be to those who make big, bold, creative errors.

Ideally, you're in a job with a company and a boss that understand the value inherent in trying. If you’re not, maybe it’s time to move on. Because the way to accumulate that experience, wisdom and industry knowledge is to pour yourself into the job, learn as much as you can as quickly as you can, and make a bunch of mistakes along the way.

So, dive in.

After the Interview

So you’ve aced the interview and all that comes after it. Now they are preparing to offer you the job. Let’s take a minute to cover a couple ‘surprises’ that never seem to get any attention but that are as reliable as the next sunrise.

The first of these is the elapsed time between “We like you and we’re going to offer you the job” and actually getting the offer letter itself.

It will seem ridiculously long for someone eager for confirmation and looking to dive in. It could easily be a week and just as likely two or three. Or longer.

Starting Your First Sales Job

And the waiting will be miserable. You’re in limbo. You’ve decided, at least in your head, but it’s not really mutual yet. It’s like that awkward gap after you’ve finally summoned up the courage to say that first, hopeful ‘I love you’ but the only thing that follows is a long, excruciating silence.

Hey, there’s no point in worrying. Most companies (and people) just slow down after they’ve made a big decision. Maybe it’s tiring, or they feel like they’ve enough work for that week. Nobody really knows why.  Just relax. You’ll get the offer. Go celebrate.

Which bring us to something you probably should worry about. What happens once you start.

There’s an excellent chance that the job you interview for won’t be the job you end up doing. It won’t be the territory you were promised, or with the job title, or the sales compensation plan. You may not even end up working for the manager you interviewed with and thought you’d be reporting to.

Anticipating the Pitfalls

I can’t explain why this happens nor can I offer a good solution when it happens, but the chances of it happening to you at some point in your career (and more than once) are really good. Easily better than 50:50. I know because they’ve all happened to me, and I consider myself pretty lucky.

All I can suggest is this: Be prepared. Try to uncover as many of the potential pitfalls during the interview process. Walk through a few ‘theoretical’ scenarios, explain past job surprises that you’d rather not relive, get as much of the job description in writing as possible.

It won’t completely eliminate the possibility of a significant career surprise. But should improve your odds.

Five Things to Anticipate
in a Sales Presentation

  • It will take longer than you thought to sign in at security, and the client’s office will be at the far end of the building.
  • The audio/video process requires them to call in someone ‘from IT.’
  • Because something has ‘come up,’ there’s a hard stop 30 minutes earlier than scheduled.
  • There’s some mystery person in attendance.
  • The client now wants to ‘start things off with a few slides’ (that you haven’t seen.)

Being on Time

Be on time.

Show up on time. Arrive promptly for all meetings, events, conference calls, webinars, every customer interaction. Even better, arrive a few minutes early. Make it a habit. Few efforts telegraph respect and professionalism more quietly and effectively than being on time.

Obvious stuff, but it happens less often than you’d think.

This is basic, stick-to-the-knitting sort of advice. (Skip ahead if you’re already on top of this.) Yet it's one of the many little efforts that create the impression from which customers operate and form their opinions. We may think that purchase decisions are made solely on important product features and functions, but that supposes that human beings are consistently rational and logical.

They aren’t. At least not consistently. Emotional factors play a huge role. And simple, seemingly trivial details can have outsized importance. Things like "She returns calls right away," "He shows up on time," or "She helps me look like I know what I'm doing.”


Being Sales Ready

Being on time becomes an even bigger challenge when you’re herding a crowd, but that only makes it that much more important. The big meeting simply demands more planning: for the time-suck of calling and getting a hold of your sponsor, for signing in, for security inspections, for the mile-long walk from lobby to conference room, for setting up A/V equipment and the inevitable troubleshooting that follows, etc. But make it organized and productive and you’re on your way to establishing real credibility and an even better impression.

If you really want the deal, and the deal that comes after that one, you’ll make the effort. Set an alarm, include a cushion for delays and unforeseen circumstances, or take a course in time management. Do whatever it takes.

Just be there.

Being Late

You will be late. It may even be unavoidable. The birth of a child, a death in the family, a flat tire. These things happen. Life has a way of making things complicated.

As soon as you know and it is practical to do so, let your client know. This is the real reason cell phones and text messaging were invented. An email or phone call twenty minutes before your scheduled time saying you’re running ten minutes late is far better than just showing up late. For both you and your client.

At a minimum, your customer won’t be hanging around wondering where the heck you are. They might even consider this free time as a gift and a chance to catch up on something.

Yes, this change in circumstances presents the opportunity for your customer to reschedule, or even cancel. It’s possible. But if a particular incident causes them to blow you off, perhaps they weren’t qualified in the first place. (Or maybe they’re just tired of your consistently inconsiderate inability to show up on time?)

Whatever the case, make the call as soon as you can. If you’re calling the administrative assistant, you might get some help juggling things around, but make the call regardless. Apologize. Offer to reschedule. Have alternative dates and times in mind. Be apologetic for the inconvenience, but you don't need to grovel.

But you better show up next time.

Time is Money

Time has value. We spend time. Of course, we want to be efficient with our own time. Just as important, it makes good sense to be similarly conscientious with our prospect’s time. And that respect for a customer’s time can take shape in any number of ways.

Because email has become so central with our sales efforts, it deserves particular attention. Emails should be brief and limited to just the necessary number of sentences to get the point across without extraneous rambling. Use the Albert Einstein rule when it comes to email – “Everything should be made as simple as possible, but not simpler.”  

Format your messages for easy reading -- and if there’s a response needed, the need is clearly explained and the required response apparent. Use a bulleted list to make a necessarily longer message more digestible and easier for the reader to process.


Simple is Smart Selling

If you’re just sharing something simple, fit it in the subject line with a trailing (EOM), as in End of Message. If you’ve got a lot to cover across multiple topics, it probably makes sense to break it up into multiple messages with a quick explanation that you will cover these details in another email. This approach allows the client to digest and respond in chunks at their convenience and on their schedule.

Phone calls deserve similar attention. If they’re unscheduled (interruptions), make it clear that you’ll be brief and just want to cover A and B. Of course, this obligates you to be brief, so plan accordingly. The definition of ‘brief’ varies by customer, with thirty seconds of pleasantries a lifetime for some clients and five minutes of “How’re the kids?” a completely reasonable time span for others. Yes, you can yak away about last night’s Yankees-Giants game for as long as the client is enthusiastically engaged. But be highly attuned to the subtle signals that it’s time to move on to the real business of the call.

Overall, a brisk and concise treatment of the call’s objective is a good strategy. It conveys seriousness and that you’re busy, too. You can always follow up with an equally concise email summary, if appropriate.


It's About Time

Economy of time is especially important with scheduled calls and meetings. Don’t ask for an hour unless you really need it. You’d be surprised what can be discussed and resolved in thirty minutes, or even less. Plus, you’ll get a lot more access to prospective customers if your request is, “Can we get ten minutes to talk about X?” Who has sixty minutes to burn anymore, especially anyone responsible for significant purchasing decisions? Hour-long meetings and phone calls should be reserved for product demonstrations and events that generate lots of questions.

If you have to ask for an hour, make the request with “and we should be able to get it wrapped up quicker.” And then wrap it up quickly. For busy executives, there are few surprises that are more pleasantly received than getting back twenty minutes of their day.

Customers will quickly recognize you as someone who doesn’t waste time, either theirs or your own. You’re seen as a professional focused on being efficient and considerate. Most customers can free up ten or twenty minutes to discuss something important. As long as it’s important, and as long as it’s less than ten or twenty minutes.

Five Travel Tips for
the Stressed Sales Pro

  • Headphones and ear plugs
  • Keep a file of reading materials (e.g. articles, blog posts) to read on the plane.
  • On long flights, sitting at the back puts you closer to the bathroom. On short flights, sitting towards the front gets you off the plane faster.
  • When checking into a hotel, ask for something (e.g. a good view, extra room, a quiet section, something nice.) It almost always pays off.
  • Carry an auxiliary battery. (Ideally, it can recharge a laptop as well as your phone.)

Be Reliable

One of the most basic rules for a successful sales career is to do what you say you’re going to do. You could also argue it’s the most obvious. (It’s also a rule that translates equally well to most other areas of life.) In two words, be reliable.

Deliver on your commitments. Be on time. Make sure your customer gets the document or other obligation you promised when (or before) you promised it. Failing to deliver on time causes a cascade of potential responses, from irritation to frustration to resignation to disqualification. None of them are good and all of them avoidable. When unplanned delays occur that jeopardize the delivery, advanced warning helps. It’s rare that you don’t know well beforehand that something is not on schedule, so there’s seldom a reason not to give your client the heads-up.

Own your mistakes. Be quick to admit an error. A mistake early in the sales cycle is a harder spot to dig out from than one late in the process when you’d had the chance to establish a reputation for professional follow-thorough. This might cause some hesitation, thinking you can let it slide. It’s better to own it. The customer may be disappointed, and even angry, but is ultimately likely to appreciate the update. More importantly, it’s psychically liberating for you almost from the moment you deliver the news. Try it and you’ll see.

The key ingredient necessary to make this rule easier to follow is to be mindful, even cautious, about what you promise and when you promise it. For example, don’t offer to send them a proposal tomorrow if it means writing it up from scratch, requires complex configuration help from others, and/or depends on management approval before you can share it. (Of course, this is where your Sales Toolkit can help.) Similarly, don’t tell them you’ll be there in thirty minutes when it’s a twenty-minute drive and you’re standing in your bedroom, taking the call in your underwear.

Most of the time, your client’s expectations are less demanding than your own, affording you room to maneuver. Give yourself some cushion. It’s infinitely easier to be reliable, punctual and responsive when you’ve got time to work with. But once you’ve committed, do what you can to stick to your promises.

Over time, this sort of follow-through becomes habit-forming. And as one of the most basic habits you need to be successful in sales, it makes everything else that much easier.

Don't Be Too Reliable

Of course you should follow up, be professional, and have clients feel comfortable that you can be counted on. But that doesn’t mean you can’t occasionally find ways to amuse or (pleasantly) surprise your customers.

Maybe that means sending over pizza or handing out gifts to the crew. I have hot sauce with ‘Pour on the Heat’ and my logo emblazoned on the bottle as atypical swag. When I was selling to AT&T, I would hand out hundreds of pocket protectors made for the engineers at Bell Labs.

Doing the unexpected has a unique and outsized power that is both disarming and fun to be a part of. Make a point of doing the risky, unexpected, crazy thing on occasion. Comfort and predictability are overrated.

It’s great to be reliable. Just find ways to do it without being dull. Look for little ways to set yourself apart. A little unpredictability properly applied is a reliable way to separate yourself from the crowd.

The Other Elevator Pitch

I happened to share an elevator with two sales guys leaving a sales call. (I think they sold disaster recovery software.) On the long descent, these two proceeded to discuss their disappointing sales presentation, going so far as to badmouth a particular engineering manager at that company. With that manager's associate, from the same department, in the elevator. It’s not hard to imagine that getting back to the wrong person.

Similarly, it’s common to overhear salespeople talking about a deal or a client or some organizational change in the cafeteria, hallway or lobby. It never fails to amaze me what you might inadvertently learn in public settings.

Obviously, be selective about what you say when you're on customer premises. Elevators and bathrooms seem to invite confidential disclosures that are better kept to yourself until you're out of the building.

There’s a tremendous urge to do a detailed post-mortem with your peers the very minute you leave the conference room or get wrapped up in a congratulatory celebration complete with high fives and fist bumps as you make your way to the elevator. Hold off.

Complaining, call summaries, impolitic observations, off-color jokes and strategy discussion should wait until you are in the parking lot. Or your car. Or your office.

Definitely not in their elevator.

Find Your Authenticity

It’s time we got a little touchy-feely.

People want to buy from people they like, trust and can identify with. And those same people can pretty much figure out if they like, trust and can identify with you. In a few minutes. And if that’s true, how can one possibly prepare themselves for that immediate assessment?

Be authentic.


What Makes You Tick?

Good salespeople figure out who they are, what makes them tick, how they think and work and act. They then use that fully informed sense of self as the basis for who they are as a salesperson (and as a person.) They’re authentic. And that authenticity is unique and immediately identifiable.

Customers want a genuine experience, and are justifiably repelled from experiences that feel fake or contrived. When people look to make big decisions in either their professional or personal life, the overwhelming and totally natural tendency is to deal with people they view as trustworthy, genuine and real. (It’s actually hardwired into our DNA.) Certainly, there are situations where people decide against their gut or their self-interest, but those are the very same decisions that most readily get unwound or contested later.  


Stop The Salesy

The fake, slimy salesperson is so common that it’s its own cliché. Perhaps the penultimate example is Alec Baldwin’s ‘Coffee is for Closers’ soliloquy (or tirade) in Glengarry Glen Ross, which has a disheartening 3.5 million YouTube views. One can only hope those views are to remind us sales professionals what not to do.

The world is rife with those who sacrifice their identity, succumb to peer pressure against their better judgment, or otherwise can’t muster the effort to be who they want to be. There’s even a decent chance that your customer is struggling with his or her own authenticity issues, so maybe yours will inspire them.

In my own case, I figured out years ago that I can’t be serious 100% of the time. Or 80%. (Truthfully, 50% is a struggle.) Now I just embrace that and take my licks when I run up against a customer who is serious 24x7. They either warm up (or frown and bear it), or they go a different route. Because the minute I can’t yuck it up or laugh off some idiosyncratic aspect of my sales style is the exact minute it becomes drudgery. And who wants that?

Customers don’t. At least not in my experience. They may act like they want someone who’s all business and serious as a grand jury investigation, but don’t bet on it. I’ve sold to customers as serious as CMS (the Medicare/Medicaid folks in the US government) and engineers designing anti-submarine warfare systems, and they like a good laugh and a relaxed, collegial environment as much as the next customer.


You Gotta Do You

Of course, if you’re one of those people that is genuinely all business, always have all your ducks in a row, and aren’t wired to appreciate the absurdity of the human condition, you need to embrace that 100%. Because that’s you. It’s what you’ve been dealt. And until it’s not, it’s the best hand you’ve got. (This is a great time to suggest the cinematic classic Harold and Maude as the antidote to Glengarry Glen Ross, BTW.)

Ultimately, customers find it liberating to deal with someone who is who they say they are. The contracting is easier and more accommodating, the due diligence is inevitably less rigorous, the paperwork and the process more flexible. An unspoken understanding occurs when the client has the opportunity to work with an authentic salesperson. You stand a greater chance of winning simply because you represent yourself accurately. And it sets you apart because it’s so hard for so many of our sales brethren to pull off.

Except it’s not that hard. You just have to be you.

Five Familiar
Conference Call Comments

  • “I didn’t get the invite. Can you send it again?”
  • “I’m sorry but it’s not on my calendar.”
  • “I dialed in but nobody else was on.”
  • “A demo? But I’m driving. I just thought it was a phone call.”
  • “We can’t get this to work. Let’s reschedule?”

Can We Be Honest?

Be blunt, be direct and be honest. Even brutally honest. But don’t feel compelled to act this way because it’s the right thing to do. Do it because it’s effective and expedient. Do it because it’s easier to remember. Do it because it saves time. Do it because it’s disarming and unexpected.

Honesty is a corollary of authenticity. But honesty should be easier to pull off. We’re wired to be honest and have some inherent sensor that tell us when someone is being untruthful. (Authenticity is tougher to pull off because the social pressures to conform are more insidious.)

As salespeople, we’re constantly faced with situations where it would seem that the easy, expedient and lucrative option is to bend (or completely break) the truth. After all, it makes the product sound better, it makes you look better and more accommodating, and because it’s often what (you think) the customer wants to hear.

Except none of that is true. Let’s assume that your career, reputation and legacy are being measured over a span of years rather than that of one deal. In that case, being honest with customers is a better, more lucrative strategy. Customers remember. Word gets around. Plus, you and your fellow employees won’t be burdened with trying to support any unattainable claims or promises.

Most importantly, it’s tough to be genuinely good at something if not staying within the rules. People prefer a fair, well-played contest. And we feel somehow swindled when one player or team gains an unfair advantage by circumventing the rules. Resorting to falsehoods and misrepresentations means you’re no longer selling. Instead, you’re just cheating.

Ultimately, excellence in any endeavor is its own reward. Yes, excellent salespeople arguably sell bigger and better deals. Those successes generally lead to more money, which can be excellent, too. But I’m here to suggest that, as trite and predictable as it may sound, the real reward is in the execution.

You can’t cheat your way to excellence.

Tech Support

I hate waiting. Standing in line for anything is torture. As is being kept on hold. I can do it, and I consider myself relatively patient. (Others may not agree.) But when it comes to computer work, waiting is misery. And money.

If you’re a typical salesperson, you spend a lot of time in front of a computer screen. (Too much, probably.) If you’re anything like me, it’s mostly internet browsing, email, staring at a CRM, crafting PowerPoint presentations, or working on the occasional spreadsheet. Whatever you’re doing, my guess is that you’d probably prefer to get it over with as quickly as possible.


Getting More Sales Time

Give some serious thought to the machine you’re using. Chances are that you deserve something better. Honestly, I’m a recent convert to this perspective and the epiphany was long overdue.

I recently made a significant upgrade. I’m not exaggerating when I say it has changed my life.

Here’s the pitch: Invest in a good computer. The difference between a decent laptop and a really good one may only be a few hundred dollars, but the dividend that additional investment pays out can be enormous.

This is especially true if a big chunk of that investment is in computer memory (Random Access Memory, or RAM). Today’s internet browsers all now have a standard tab feature. I customarily have a couple different browsers open with fifteen (or more) tabs open in each. (Who uses bookmarks anymore?)

The problem is that all these tabs eat up huge chunks of your machine’s memory and, and the overall performance suffers as a result. Which means you’re waiting for pages to load, refresh and even transition among tabs. Having a lot of RAM helps reduce the waiting.

The same is true with large spreadsheets, or video editing, or ponderously fat PowerPoint presentations. They, too, can eat up your machine’s limited memory. A faster processor, solid state hard drive and a dedicated graphics card also help. (More on that in a moment.)


It's Simple Sales Math

The math is simple. Add up the time you spend waiting for your computer to boot up, load pages, complete complex Excel macros, etc. in a given week and then multiply it by how much your time is worth. (BTW, do you know how much your time is worth? That’s a topic for a future blog post.)

Just having the awareness that your machine has you idling is half the exercise. I guarantee you that the cost should have you heading off to Best Buy or scouring the web faster than you can say Kingston PC3-10600R Registered ECC Server RAM.

But before you set off on a shopping spree, let me make a more radical suggestion. Rather than try to upgrade your laptop’s resources or buy a new one, consider assigning it to ‘travel-only’ status and buy yourself a used desktop machine.

Of course, this makes less sense if you’re constantly on the road. But if you work primarily from home or a remote office and spend most of your time at the same place, buying a well-configured but lightly used machine can change your life.


Your Inner Sales Nerd

I know what you’re thinking. “Who buys a ten-year-old computer?” This guy does.

Let me geek out on you for just a moment. It is brain-dead simple to find a machine that has a processor way more powerful and with way more memory than any laptop you can expect to buy, and with a dedicated graphics card and gobs more storage. For less than $400. Yes, the machine will be five to ten years old, but these are workstations and servers that were built for incredibly complex work like CAD/CAM and video editing, and probably cost several thousand dollars new.

The machine I bought for $370, including shipping, has 32GB of RAM, a 2GB graphics card and two hard drives. That same machine originally cost over $8,800 when it was churning through elaborate 3-D rendering or complex statistical models. It can certainly handle my 32-slide presentation and a few dozen browser tabs.

With a home workstation setup, you can then easily configure an existing laptop for travel. Just mirror to a shared Dropbox, Google Drive, or whatever your cloud storage preference may be. Then duplicate any critical apps you might need, and you’re off to the races. Plus, you now have a backup machine should you find yourself in the midst of any sort of computer disaster

Take it from someone with direct experience, from one impatient salesperson to another. Make the upgrade and you’ll never go back.

Your Sales Toolkit

Because a salesperson’s income is directly linked to their sales performance, being more productive pays real dividends. An increase in preparedness and productivity typically translates into an increase in sales success, which should then result in greater earnings. (Or it should.) A ten percent increase in your productivity should result in a ten percent increase in your income, right?

In order to see that kind of consistent return, it helps to have certain processes and practices in place. And one of the most fundamental is creating, managing and updating a sales toolkit.

So, what exactly is a sales toolkit?  

Basically, your sales toolkit is whatever you customarily need to address any significant aspect of the sales process. You will want this core set of sales resources immediately available at the various stages of the sales cycle. In a real sense, your sales ability is evident by what’s in your sales toolkit and how well you implement each of these tools. Having the right tools at the ready and using them effectively is critically important to your success. 

Your toolkit is the collection of resources required throughout the sales process, from initial engagement through the post-contract phase. This list includes, but is not limited to:

Your Sales Toolkit

  • Marketing Materials: sales collateral, press releases, case studies, references, event schedules
  • Sales Documents: discovery documents, call planning sheets, NDA, draft proposals, boilerplate contracts, technical specs
  • Implementation Materials: requirements documents, draft Statements of Work, project plans, timelines
  • Communications: thank you letters/emails, follow up emails, meeting agendas
  • Presentations: branded PowerPoint deck, standard slides on your company, testimonials
  • Giveaways: promotional materials like t-shirts, thank you gifts
  • Anything else that you routinely need in your sales process

These are the resources that should be immediately accessible and ready to edit and share, either when the client wants them or when it best complements your selling situation.

Consider this. You’re no different than the doctor performing an important surgical procedure. The physician’s toolkit naturally includes an extensive set of scalpels, rakes, sponges, sutures and an array of even more specialized and esoteric tools laid out and available in anticipation of any possible medical situation. In the same way, you should have your set of prepared resources ready and up-to-date for the inevitable moment when they will be called into duty. (Hey, if you’re not able to respond properly when you need to, your deal could die…)



Ask yourself these questions:

  • What sales materials do I need at each point along the sales process?
  • What communications do I use?
  • What templates can I use to communicate quickly with prospects and clients?
  • What presentations do I use over and over?

Start by first identifying your key resources. Examine your sales process to determine what tools you have and what you may be lacking. Gather the good stuff, create draft versions of the documents you regularly need but don’t have, and then move everything else off to the side where it won’t be a distraction or get in the way.


Being Sales Smart

Once you’ve got your set of tools created and collected, it is time to figure out a usable, reliable organizational structure that works for your sales style.

Do you make everything templates and stored documents inside your CRM (customer relationship management software)? This has the advantage of reliability and a record of what has been sent to whom. Or do you create a logical set of folders in Dropbox or Google Drive? This has the advantage of being accessible, sendable, even editable from your cell phone. Or are you truly old-school, and paper-based? There’s something to be said for having physical copies of things in an age of electronic clutter that slips off the screen and thus out of the client’s attention.

Whatever works for you and whatever your system happens to be, it pays to review it from time to time. During this review, you should add new documents and templates and cull outdated or less effective material to prevent them being a distraction or sent inadvertently.


It's About Being Sales Efficient

Remember that the primary objective in developing and maintaining your toolkit is 1) to make you more responsive to your clients, and 2) to make you more efficient. Whenever you can deliver more quickly on your commitments and create a sense of responsiveness and reliability over the course of the sales cycle, you’re enhancing both your competitive advantage and your productivity. Ultimately, your goal is to compress time and advance the sales cycle (and your position in it) by having the right tools at hand when you need them.

* Visit to download toolkit samples and templates.

10,000 Hours

Malcolm Gladwell's book, Outliers, has one especially famous and often repeated idea. It’s where he illustrates the point that anyone who is any good at anything commits a lot of time to that thing. Basically, Gladwell reports that it takes about 10,000 hours to excel at something. Yes, 10,000 hours. As in about five years of a 40-hour-a-week job.

Now apply this idea to your profession. The goal is to work really hard to hit that 10,000 hour mark as soon as possible. Make calls, read books, study the industry, develop contacts. Each of these efforts, including any mistakes made along the way, add up. Before you know it, you will have eclipsed the 10,000-hour threshold.

In that process, something obvious occurs. Things get a little easier. Presentations flow more smoothly. Fewer questions surprise you, and your responses are more polished and effective. Ultimately, deals become more predictable and more manageable.

Ultimately, the real idea behind dedicating 10,000 hours is a focus on continuous incremental improvement. Any 1% improvement is negligible in and of itself. But pile a bunch of 1% improvements one on top of another, day-in and day-out, and the result is staggering. (James Clear’s book, Atomic Habits, does an excellent job examining this concept.) By taking a 10,000 hour perspective, those daily investments have a chance to compound into an irreplaceable body of expertise and experience.

That’s the real takeaway here. Work on the next hour and the 10,000 hours will manage itself. Nuance, finesse, technique, gut feel, and competence are the byproduct of effort invested. One hour at a time. Amassing 10,000 hours isn’t a bad way to think about that investment.

A better one may be to focus on the hour you find yourself in.

Call to Confirm

A small but important detail, and a (simple) habit worth adopting, is to confirm your appointments the day prior. The message can be as simple as a one-line email mentioning that you’re looking forward to the conversation, or you can shoot over a revised copy of the agenda or some advanced reading material. You can leave a before-hours voicemail, or send a text if that’s appropriate, but you want to be a day ahead. If the person has an administrative assistant, either confirm with that person (or at a minimum copy them in.)

Make it standard operating procedure. Whenever you set up a meeting or conference call, add a reminder in your calendar to check in the day prior to confirm the appointment. If you’re traveling to see them, reach out the day before you leave.

Yes, the prospect gets another opportunity to cancel or reschedule. Something can always come up 24 hours before the meeting. And by confirming the meeting, you are granting them an out. It’s a calculated risk, but it also telegraphs to them that you’re organized and thorough, and that your time is valuable.

If a prospect needs to cancel a meeting, they’re going to do it regardless whether or not you confirm it. There’s little you can do to prevent a cancelation. But you can use this otherwise insignificant moment as another opportunity to qualify the account, reconfirm the meeting purpose, share an agenda, demonstrate your attention to detail and decrease the chance that your time is wasted.

All it takes is one cross-country, two-day trip for a meeting that gets canceled while you’re standing in the customer’s lobby to appreciate the value of a one-minute confirmation call. A cancellation can be informative, a way to advance the sales process, or a chance to show your sales skills. Or it can be an obligation.

The one thing it shouldn’t be is a waste of time.

Getting Touches

Out of sight is out of mind. We live in a hyper-busy, hyper-distracted world (and as hard as it is to imagine, one that is becoming ever more so.) As salespeople, we’re constantly competing for attention. In many instances, deals happen simply as a direct result of being able to stay front of mind with those making the decision.

This is especially true with complex or strategic deals where the sales cycle is protracted, the problem being solved is complicated, where something is already in place and ‘working,’ and/or you’re competing for staff engagement, and/or integration resources and/or…well, you get the picture.

To use a sports analogy, you want to make sure you’re getting meaningful ‘touches’ throughout the game. For example, any parent looking to develop their kid into a soccer prodigy knows that one of the most important factors is how much time they get on the field and with the ball. It’s intuitively obvious, of course, but getting more touches early has huge implications for future success.

In the world of sales, the same rules apply. A complex and lengthy sales cycle may require you to ‘touch’ the customer fifteen or twenty or even fifty times to keep it moving, to maintain awareness and to elevate it to the priority it deserves. You don’t want your project eclipsed by the sudden importance of other initiatives or distractions. And there are always distractions.

In most cases, you’ll need to have touches with multiple people across an organization and throughout the sales process. It’s a rare situation where any sizable deal is only influenced by one person. (And if you think you’re in that situation, that’s probably something you need look into.)

The challenge is in making the touches meaningful and frequent without being an inconvenience or intrusive. What’s the right level of contact? What’s the delicate balance where you’re neither nonexistent nor irritant? How do you stay relevant and engaged, without turning into the stereotypical sales nuisance?

As with most answers to complicated questions, it depends. It varies by individual, with type and frequency of touch, by job title, the value of the touch to the customer and your level of established rapport.

Some of this gets easier with experience and gut feel (after 10,000 hours, for example), but there is as much risk in doing too little as in doing too much. You have a responsibility, after all, to fully represent and promote the value your company/ product/service will deliver to the customer and so you need to make it a priority to them for the good of their enterprise. The trick is in how you do it.

As you look to connect with your customer over the arc of that big deal, there are a few things to keep in mind:

  • Brevity – People appreciate details, but they appreciate even more a thoughtful summary that allows them to skim an important update. Provide the supporting material along with it, but as reference in case they want to drill down or forward it to a colleague.
  • Levity – Not everything is serious. A little humor can take the edge off any interruption.
  • Value – Few things scream desperation more than an empty email or a generic product pitch. Before sending anything, ask yourself if they would genuinely appreciate the interruption. (Remember, it’s an interruption.)
  • On Target – Make it specific. The more unique and targeted you can make that touch, the more effective it will be. Keep in mind that you’re working with individuals with their own interests and idiosyncrasies.

A well-executed campaign of touches can make a huge difference. Sometimes you’re keeping the deal warm. Sometimes you’re slowly identifying need. Sometimes you’re educating them on some recent announcement, or industry news that should interest them, or getting them comfortable with some new idea, or with the company, or with you. In any event, you want to stay engaged.

You want touches.

Cards and Letters

It turns out that vinyl records aren’t dead. In fact, they seem to be making a vigorous comeback. Want to guess what else isn’t going away?

Paper. Paper consumption in the United States for the last twenty years has increased from 92 million tons to 208 million, a growth of 126%. (At the same time, The Washington Post recently reported that reading in the U.S, is at an all-time low, so thank you.)

My suggestion is that you embrace paper in at least one respect: Cards and letters. It’s retro (which makes it very fashionable,) but it’s also effective. For gifts, meeting follow up, passing along interesting articles or business cards from restaurants you think someone might like.  

This is my system. I have cards and envelopes printed with my name and address. (It’s super classy.) They sit in a folder in my briefcase, complete with a book of stamps. If I see something of interest in a magazine, I’ll tear it out and stuff it into an envelope with a quick note. “Saw this. Thought it interesting relative to your XYZ initiative.” No product pitch, nothing remotely salesy.

Or right after a meeting, I’ll scratch out a quick “I’m at a layover here at O’Hare Airport and wanted to quickly thank you for your time today…etc., etc.”

Nobody does this anymore. And the disposable, ephemeral nature of email and texting make this sort of gesture stand out that much more. The physical arrival of a handwritten note in the mail is a genuine rarity. And another touch.

Q & A

Selling is just another form of problem-solving. The problem may be real, and it may be serious, like having software security exposure issues or needing more top-line revenue. Or perhaps the problem is trivial or imaginary, such as some slave to fashion needing that 20th pair of shoes. (I’m likely to get schooled by someone for describing shoes as trivial.) Whatever the reason, our job as salespeople is to solve problems.

To do that effectively, we first need to know what that problem is. But we need to know more. Things like:

  • Does the customer recognize the problem?
  • Are there other problems that need to be addressed?
  • Is it a big enough problem that they want to overcome it?
  • Do they define the problem the way that you do?
  • Is the problem solvable? From whose vantage point?
  • Who benefits from the solution? And who doesn’t?

That’s a lot to uncover, and in order to help solve this problem and make a successful sale we’re going to need answers to questions like these. Some of this information can be gathered through background research and your own knowledge of the specific situation, but it all needs to be confirmed and substantiated with the customer. After all, the prospect may very well be contending with a serious security risk or desperately need to add customers and revenue, but unless they recognize that reality it’s essentially impossible to solve the problem and complete the sale.

And to do that, we’ll need to be able to ask questions and get meaningful answers.

The ability to effectively ask questions delivers several obvious benefits:

  • It provides the chance to learn more about the customer – Both specifically about the issue(s) at hand, and more broadly.
  • It conveys genuine curiosity and interest – It’s natural to want someone to take an interest in us, right?
  • It gives the customer the opportunity to contribute to and be engaged in the conversation – People generally appreciate an active, collaborative dialogue.
  • It communicates your experience and understanding of the customer’s business requirements – Done right, it’s an opportunity to demonstrate expertise.

To do all this, we need an effective discovery strategy, one that relies on the ability to ask good questions and get revealing, useful information. This doesn’t eliminate the need to construct and articulate an attractive solution, but every sales success begins by understanding the problem and making certain that the customer is seeing the same problem.

The challenge, of course, is getting answers to everything you need to know in a civilized, socially-acceptable way. It would be so much easier to simply hand the prospect a twenty-page questionnaire and wait for the results to come back, but that isn’t happening.

A good discovery process requires strategy, tact and finesse. And time. Subject your client to a ham-fisted interrogation and they predictably shut down, become alienated, or worse.

What is your current discovery process? Examine it from every perspective. Consider the information you need to understand the problem, the client objectives, and the decision-making process. Budget, timing, key players, etc. are all obvious data points, but so are more esoteric (but equally important) details like “What happens to Bob Smith in Materials Sourcing when costs decline by 15%?” Or “How does the decision impact the folks in outside sales?” The goal here is to get a broader, more expansive perspective on the purchase impact, both positively and otherwise.

The process needs to be conversational. Nothing is as uniquely off-putting as a salesperson conducting a clichéd staccato-style, one-sided interrogation. You should be able to learn volumes about the company, customer, market and the big issues and do it in a relaxed, natural conversation.

Have a strategy - Part of the appeal of sales can be its unpredictability. It is by nature dynamic and complicated, usually with several major players and plenty of opportunity for mistakes, surprises and setbacks, so a tightly choreographed sales plan can only take you so far. Regardless, it pays off to identify what you don’t yet know but should, the key data elements you’ll need to gather and the general order in which you might approach collecting that information.

Have a list - You can download an editable Discovery Worksheet at That document has a core set of questions, and space to add questions specific to your circumstances, like ‘Who is involved in the decision-making process?’ And ‘How does implementing this solution impact other departments?’

Again, it’s a conversation and not a formal inquiry. Open questions that encourage dialogue are (usually) better. Who knows what you may learn if you simply allow your customer to ramble? There are times where simple yes/no questions are applicable, but they don’t encourage the information-rich exchange that will help you find out what it is you don’t know that you don’t know.

Craft your questions – They should fit seamlessly into the dialogue. “What’s your budget?” is essentially the same as “Given the economic conditions and the potential impact of the stimulus dollars that may come into play, what’s your thinking around investment costs and expectation of returns?” Except that it’s not. The first is abrupt and confrontational, while the second is thoughtful, informed, conveys interest in the prospect’s thoughts and opinion, and is specific to the customer’s requirements and circumstances. Plus, it’s consultative.

Be curious - Not every question has to move you obviously forward. Genuine curiosity is disarming, and even flattering. 

Take notes - You’re uncovering a lot of important details, information that will require follow up and thought. Write it down. The client will likely appreciate the attention to detail and may even add to it as they see you taking note of something important. Especially any action items that you, or they, have committed to deliver on.

A critically important and powerful step at the close of any sales call is to summarize any follow up and action items that resulted from the conversation. The combined act of restating and writing it down reassures the client that you’re committed to delivering on whatever promises were made during the conversation. Plus, it gives you a plausible reason to circle back and confirm what was understood.

It can be a smart strategy to ask a question to which you already know the answer in order to confirm an assumption, establish agreement, or challenge a position. There’s no crime in being confused or needing more explanation. But be careful not to appear as though you haven’t been listening. Like a baseball pitch, it’s all in the delivery.

Being skilled and creative in sales discovery is among the most important qualities a salesperson can develop, and one that is critical throughout the sales process. It’s instrumental early in the sales cycle to understand customer needs and problems, but equally valuable later on to confirm assumptions and uncover changes in the selling situation. Whole sales books have been written on just developing the skills necessary to conduct an effective sales discovery process, and a thorough investment in this topic is worth every minute spent. Study up, practice, figure out what works and what doesn’t, and hone this aspect of your craft.

Any questions?

Will You Just Listen?

Okay. You’ve asked the question. Now what?

Shut up and listen.

The stereotypical talking salesperson isn’t a stereotype by accident. It’s reality. Most salespeople simply talk too much.

Here’s a better reality. Talk less. Listen more. Fight the urge to comment on everything or respond to every customer objection with some vivid, artfully crafted description of a product feature. We understand that it’s not easy to fight off the urge to sell, but choosing to pick your battles and simply listen has advantages.

Here’s why. Once the customer feels they can talk, and can really explain something without interruption to a genuinely interested listener, the entire sales dynamic begins to change. You no longer have a customer across the table who feels they are competing to get a word in. Instead, they can take their time, relax, compose their thoughts, and speak at will. And given the opportunity, they invariably will.

Conversely, it’s completely normal for a customer to shut down or provide terse, clipped answers to even complicated questions if they suspect you’re not listening and are simply waiting for a pause in the conversation to counter with a product benefit or a knock on the competition.

Let them talk. Listen to what’s being said and what isn’t. What’s important? What’s bothering them? Where’s the pressure coming from? Are things getting better, or worse? If you’re doing it right, what you learn can be breathtaking.

Acknowledge without speaking. Nod. Smile. Show surprise. Or “Hmmm.” Or “Really?” Then, when they’ve finished their point, wait. Take a second or two to see if they’re actually done. The pause tells them that the floor is still theirs. You’re interested. Go on.

Who knows where this may take you or what you might learn. They may go on to explain what the latest reorg means or who has a new project getting started. All you need to do is sit there and listen. Intently.

Yes, it might be about their maddening kids or last weekend’s pool party. (They can’t all be earth-shattering discoveries.) Whatever may be said, it doesn’t get said if you’re busy talking.

Be aware of your body language. Are you leaning forward, or slouched? Where are you looking? Do you look interested? And when you do respond, pay attention to the tone of your voice and your delivery.

Be actively engaged, but relaxed. Don’t interrupt. Let the customer completely finish her remark. Again, pause. It’s brief, but apparent. It lets the customer know they can speak without interruption and at their pace. That you’re listening. Often, they’ll take right up again, sharing more and likely telling you, however indirectly, how to sell to them. If you’re listening.

Listen for hard data and for softer emotional insights. Both are obviously important, and either might be good reason for further clarification and conversation. Who else in the organization is affected by whatever problem your solution will solve? Ask how they feel about the problem to further draw out the emotional significance.

Try not to dispute issues or argue every position. Let the client speak freely and at length. You can handle objections later. Often, simply being able to speak and be actively heard is enough to cause them to want to move forward. At a minimum, you’ve gained some goodwill.

If your competition is discussed during your meeting, it’s best to avoid jumping in and disparaging them. It’s inevitably safer to take the high road and focus on why your company or solution is the best choice.   Or ask them to explain what it is that the competition is doing, what they like about them, or how they differentiate the various alternatives.

All of this is easier in a one-on-one setting. Add a third person and the sales call takes on a whole new dynamic. Bringing along a second salesperson adds even more complexity and is one reason why I prefer having more individual sales calls. (See Smaller Calls.)

With larger meetings, you’ll need to be more rigorous with your ‘listening strategy.’ The internal prep call will mean discussing objectives and roles with your peer(s) before the call, potentially directing certain questions specifically to one or another and divvying up the conversation so that everyone feels they’ve had a chance to speak.

Done properly and with sales egos in check, a group sales call can take on a relaxed, conversational pace and be informative and effective. (Just don’t expect the sorts of revelations that you can get speaking with someone one-on-one.)

Active, engaged listening takes effort, energy, skill and experience. And in my experience, the idea of active listening may be the most important lesson you can take from these pages. Once you get the hang of it and make it a habit, you can expect your client conversations to elevate to a completely different, more effective and professional level.

Become an expert at asking good, incisive questions. And then become an expert at listening intently and patiently. When you do, your customers will tell you how to sell to them, tell you how to beat the competition and tell you exactly how to win.

Just listen.

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