Remote work. New-age communication tools. The desire for meaningful workplace culture.

Today’s professional environments look nothing like their predecessors. Consider for a moment how the Industrial Revolution shaped workforce habits in the late 1700s and early 1800s. Then, imagine being a railroad or coal-mine worker in the Second Industrial Revolution (also known as the Technological Revolution), clocking in and out, in and out. We forget that it wasn’t long ago when the term “workplace culture” didn’t even exist. We were supposed to adjust to the demands of work—not the other way around.

However, times have changed.

By 2020,  50% of the workforce will be remote. On top of that, the gig economy is booming, and according to CNN, 43% of the US workforce is expected to soon be made up of freelancers. More and more companies are distributed all over the world. People’s expectations for what a “successful” career now includes much more than just a salary and paid vacation days—workers desire mentorship, team cohesion, a larger sense of purpose, even opportunities to invest in their own personal development.

In short, the entire landscape is changing—fast. And the next big shift is going to be from all these new digital tools haphazardly running our lives to smart offices.

Here are the 5 micro trends moving the macro trend of “smart offices” into our everyday lives:

1. Distributed Work

One of the biggest workplace trends today is the rise of remote work.

For context,  the remote workforce has grown 140% since 2005. And interestingly enough, Stanford actually conducted a study showing remote workers took fewer sick days and were actually 13% more productive than their in-office counterparts.

Whether we’re talking about teams in the same state but some working from an office and others working from home, or we’re talking about different time zones in the same country, or if we’re talking about managing teams on opposite ends of the earth, distributed work is no longer up for discussion. It’s effective in allowing employees to have a sense of freedom. It’s efficient in the sense that you can hire anyone from any part of the world. And most of all, it’s allowing for an unseen level of global collaboration.

However, in order to effectively manage such distributed teams (especially hundreds or even thousands of employees), it’s imperative that everyone is on the same page. This is where smart office environments (digital or not), communication tools specifically, will play a big role.

2. Communication Tools

Building on the above, the prevalence of communication tools today is changing the way we, as human beings, interact with one another.

Email, Facebook Messenger, Slack, each of these tools (and more) has redefined what “effective communication” looks like in today’s day and age. A smart office, then, would be the culmination of all these different mediums into a cohesive and understood approach to human interaction within the office environment—internally and externally.

For example, you might have a physical sensor in your office to let people quickly be able to know whether you’re in the office or not—which would better protect your time and availability. Instead of me sending a co-worker a Slack message and then wondering why he or she isn’t responding, artificial intelligence can let me know that based on historical data, this co-worker of mine typically replies 32 minutes after a message is received. Or, right around this time of day, the individual steps out for lunch and isn’t usually active again for another hour.

In a digital world of distributed work, these seemingly tiny details can make a huge difference—in efficiency, yes, but primarily in feeling understood.

3. Smart Assistants

I also believe that smart assistants are going to continue improving the pain-staking moments in our lives where human error thrives.

For example, if I say, “Hey, I need to schedule a meeting with Mark,” the smart assistant will easily be able to “talk” to Mark’s smart assistant, analyze both of our calendars, reference historical data, and then schedule a meeting for both of us. In addition, these smart assistants will know when I work, when I work best, and when I typically don’t work at all.

Where this becomes incredibly effective is when a smart assistant has to choose between two pockets of the day to schedule a meeting—let’s say 10:00 a.m. is available, and 3 p.m. is available. By being “aware” of how I typically construct my days, and when I am most likely to be productive, the smart assistant would then choose to book the meeting for 3:00 p.m. instead of 10:00 a.m. because it knows that I do my best work from 9:00 a.m. to 11:00 a.m. and doesn’t want to be a disruption.

Taking that one step further, a smart office would then learn how to optimize for certain moments. If the smart assistant knows I am most productive in the morning, and knows that I do my best work while standing, then it will raise my standing desk at 9:00 a.m. because it knows I am going to be at the office by 9:00 a.m.

4. Work-Life Balance

Right now, Slack will ping me at midnight because I don’t have Do Not Disturb on.

As we imagine ideal smart office circumstances in the future, it is only a matter of time before software begins to learn whether or not a message is urgent or not. Depending on the time of day, the person sending it, even the contents of the message, all these variables will dictate whether or not it’s worthwhile to wake me up out of my sleep at 1:00 a.m. in order to get my attention.

Combined with the growing trend of distributed culture, these optimizations around work-life balance will become more and more important. Right now, our digital society expects everyone to be online and active 24 hours per day, 7 days per week. If someone doesn’t respond right away, we wonder what they’re doing. If a message isn’t read for an hour or two, we start to get impatient. But it will be smart offices and the adjustments that come with them, that allows people to be more at ease—because they know they’re reaching the other person at that person’s most ideal window of time.

5. IoT & Maximum Productivity

Last, there is a massively untapped opportunity in the physical office space becoming smarter and smarter.

As devices become smarter, and voice recognition becomes better, it’s not unfathomable for work environments to become chambers of ideal scenarios. If the smart office knows that the employee in the back office does his best work starting at 10:00 a.m. and typically crashes around 2:00 p.m., the smart assistant will (as often as possible) block those hours off for deep work. The smart office may also know the employee tends to turn the lights down a bit in order to focus, so it will dim the lights right at 10:00 a.m. to prompt the habit of deep work.

The same goes for the temperature in the room, maybe the sound of light music playing from the speaker in the corner—all things the employee may do from time to time to help herself focus, except now they’ll be done automatically in order to create the ideal work environment.

“Simple can be harder than complex: You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”    -Steve Jobs

As software continues to eat the world, it is also eating our wallets.

 68% of software projects fail. Let’s pause and think about that for a minute. One out of every three projects become what might be considered successful. I would classify successful as within budget, on time, provides value, and delightful client experiences.

The high failure rate translates to an estimated $75b a year in rework and abandoned software projects in the US alone. I know, crazy right?

One primary reason so many projects fail is that we tend to add complexity in all areas. From the early sales calls to gathering requirements, to managing expectations, to delivery, to launch, and everything in between.

From my experiences, I firmly believe simple is the way to go from start to finish.

At Skiplist, we deeply believe in simple over complex. Simplicity enables us to stay lean and continuously deliver value. We call this approach Thoughtful Software™.

My hope is you will find the simplistic approach informative and helpful in breaking down complexities you may encounter.

Ultimately, our goal is to work together to flip the abysmal 68% failure rate statistic on its head and transform the software industry.

This is our challenge. There is nothing revolutionary here; it is just hard to do.

 Life is simple. People make it complicated.

There are no shortages of complicated processes and applications in the software industry. People love complicated. It is human nature to add twists, turns, and drama.

Our brains crave stimulation. It likes to stay busy. We tend to think something can’t be this simple and proceed to believe it is more complicated than it is. Commonly referred to as a complexity bias. Relationships, health, and of course, software all succumb to our preferences. It is within these biases we sidestep the need to understand.


“Complexity bias is our tendency to look at something that is easy to understand or look at it when we are in a state of confusion and view it as having many parts that are difficult to understand.” Farnam Street


The problem is that complexity requires more effort to sustain it. There are more chances for a system to break down with more parts.

Simplicity, on the other hand, requires more effort to achieve it. It takes mental brain power to break down a problem to its simplest components.

Take the iPhone as the quintessential example of a complex system tirelessly broken down to simple user experience. Whether you prefer iOS or Android, the iPhone is super easy to use. Apple took a product as complex as building a smartphone and turned it into a device my mom can use like a pro. Brilliant.

Unfortunately, we don’t take cues from successful companies such as Apple. Our propensity to continuously fill our minds with noise creates a sense of urgency around missing the latest information.

It is this constant flow of information where we blur the line of utopia and reality.


To-Do or Not To-Do

Take our obsession with to-do lists. I did a quick search on the app store and found at least 30 or more task planning apps. Why are there so many of these apps? Utopia is, I’ll be an organized ninja and cut down each task one by one. Reality is, after failing time after time to organize the 100 things I have to do every day; I gave up and came up with a simple system.

Every day, I come up my top three essential tasks I must finish and make sure I get those done before the end of the day. Get to my three and everything else I can adapt. I’ll block out time for my top three, but I keep a fluid schedule otherwise. Too many tasks and apps were too complicated.   

I believed the process of getting things done required an elaborate system of apps intertwined in the cloud. What I needed to get organized came down to a piece of paper, pen, and my three things for the day.

Please don’t feel too bad for yourself or me. Complexity sells. Simple is thought to be boring. It might be, but it is also useful and sustainable.

“Everything should be made as simple as possible, but not simpler.” – Einstein


Complexity is free

In his book “Thank you for being late,” Thomas Friedman discusses how the accelerated advancement of hardware and software over the last 20 years has allowed companies to introduce products into the market at a rapid pace.

What once took two years to develop a prototype, is now reduced to a week. We can leverage three-dimensional software, 3-D printers, cloud technology, and several other advanced tools; essentially, the underlying complexity to build a product is now free.

We don’t have to think about spinning up a server or even managing it. Just build. Money has also become more accessible through crowdfunding and the growth of venture capital.

Although Friedman explains that complexity became “fast, free, easy for you, and invisible,” it also comes at a price. Our ability to build products quickly allows us to throw whatever feature we want in without truly understanding the consequences.

We are in the age of accelerators. Computing, access to information, access to people, everything around us is changing rapidly. Maybe this is the new norm. After all, the software industry is only a few decades old. Perhaps this is the time to, as Mark Zuckerberg says, “move fast and break things.”

However, I argue moving fast does not mean we should be reckless. Moving fast does not mean we should compromise our privacy and security. Moving fast does not mean we should build crappy products. Moving fast does not mean we should add complexity unnecessarily.

We should instead move thoughtfully and break the status quo.

First Principles

First-principles is an effective strategy to break down ideas to their fundamental truths. Mostly think like a scientist to understand what we know about a problem. This type of thinking can open up new ways to attack a problem.

No one today embodies first principles thinking and breaking the status quo more than Tesla and SpaceX founder Elon Musk.

Elon Musk famously said in an interview:


“I tend to approach things from a physics framework. Physics teaches you to reason from first principles rather than by analogy. So, I said, okay, let’s look at the first principles. What is a rocket made of? Aerospace-grade aluminum alloys, plus some titanium, copper, and carbon fiber. Then I asked, what is the value of those materials on the commodity market? It turned out that the materials cost of a rocket was around two percent of the typical price.”

From Musk’s viewpoint, he believed his vision to reach Mars would not be feasible with the status-quo. Rockets were just too expensive, and if he understood the underlying problem of why rockets are expensive, the next logical move was to build his own.

Thus, SpaceX was born, and a fundamental difference with SpaceX rockets is they are designed to be re-usable. In a traditional space shuttle, the large fuel tanks and side boosters are discarded after every launch. Knowing fuel costs are the most expensive part of a rocket, Musk thought to himself, why not figure out a way to land the rocket safely to be able to reuse the fuel tanks.

I’m ridiculously simplifying what Musk thought here.

Notice, to build and land a re-usable space shuttle is a complex project. However, Musk broke down the high cost of rockets to a simple thought. Re-usable rockets. Going to Mars is about as exciting work as you’ll ever find.

Musk will admit thinking from a first-principles perspective “takes a lot more mental energy.” It is easier to explain than it is to practice.

What Musk is advocating is to break things down to their fundamental truths. In other words, get simple. Therein lies our challenge. Simple is hard to do.

A Simple Foundation 

Lego is a great case study of a company that chose to eliminate complexities in manufacturing and operations. Founded in 1932 and until 1998, Lego turned a profit every year until after a series of self-inflicted mistakes led Lego to nearly collapse in 2014.

Jorgen Knudstorp took over as CEO and a principal mandate for him was to simplify everything at Lego. He started by reducing the number of pieces from 12,900 to 7,000. They implemented smart manufacturing practices to reuse certain parts for different sets to reduce the cost of new molding.

By simplifying how Lego operated, they turned around a nearly bankrupt company into one of the largest toy manufacturers in the world.

Lego’s turnaround illustrates a significant point about a simple mindset. There isn’t anything groundbreaking in what they did. Lego just had to think hard about its business and get creative.

To “move mountains” as Steve Jobs put it, requires us to dig deep and evaluate every aspect of a service and products company.

Thoughtful Software is Born

When we set out a few years ago to start a software company, we knew we wanted to take a different approach. We looked at every aspect of building a services and products company — everything from legal to sales to engineering.

We have never lost sight of the high project failure rate in the software industry and our grand vision: thoughtful people and Thoughtful Software™ can change the world for the better.

Granted we are far from achieving our vision but changing an entire industry takes time. We have had our bumps and bruises, and I am sure we will have plenty more. We have also made tons of mistakes. I am not trying to glorify our failures as many do in Silicon Valley. Mistakes are painful. I prefer to make less of them.

The following is a snapshot of how we broke down various aspects of Skiplist built around removing complexity to achieve our vision. We firmly believe if we continue to maintain a simplistic approach, we not only will create more value for our clients, we can stay lean in the process.


A Simple Culture

Thoughtful Software™ is a process, a movement, a mindset, and an approach we believe the industry desperately needs. First and foremost, put people at the center of everything we do.

We noticed a significant reason projects fail is often we lose sight of the goal by adding complexities. We are improving our lives through usable and enjoyable software. We make decisions to solve people problems, not just write lines of code into a machine.

To manifest a culture around people and delightful client experiences, we knew we had to start with a core set of values. Values guide us through difficult times and around blind corners.

Initially, we had ten values, but when we couldn’t remember them all ourselves, it became apparent we needed a more straightforward set of values. Then there were four.



1. Simple over Complex

2. Team over Individual

3. Innovation over Stagnation

4. Relationships over Money


Rooted in strong values, we can then begin to shape a better client experience. I’ll admit creating a delightful client experience is quite hard and I wholeheartedly agree with Musk, it requires a great deal of mental energy.

Expending the extra mental energy to simplify though, is worth it every time. The alternative is the current environment where complexity sells, especially in the consulting industry with more information, more abstraction, and expert hand waving.


Embrace Complexity

Client experiences matter whether you are selling a product or a service. Clients and users have a myriad of options to choose from today.

We should not ignore complexity but embrace it to make better decisions for our clients and users.

Complex products are challenging to learn and use. The iPhone wasn’t the first smartphone, and Apple made it simple to use. Complex products and systems are difficult to maintain and can be hazardous within specific applications such as medical and transportation.

When we know where the complexity lies, we can build products and systems and   earn our complexity.


Thoughtful Journey

For us at Skiplist, we didn’t set out to revolutionize work or publicize our unique way. We have a standard policy to evaluate and iterate if we can make things better. Be comfortable with changes. Iterate over perfect.

We encourage open communication and lean practices. We are not fans of meetings or busy work and fewer meetings for more focused deep work.

If we do have a meeting, we keep them to 30 minutes or less. I love 15-minute meetings.

In Legal, we have developed a streamlined system to review and sign contracts quickly. I never understood why it takes months to sign an agreement.

In Sales, we are big on conversations over pitch decks. Decks are boring.

We outlined a simple pipeline and sales process. If your sales team is spending more time on data entry than sales, you have a complex process problem, and it costs you productivity.

Excessive data is crippling. We don’t need expensive salespeople, spending a large chunk of their day updating the CRM.

In Product, we bring in product managers early to sales conversations to help map out ideas and build out what we call product/project briefs. The briefs help the entire team and the client eliminate misunderstandings.

In Marketing, we believe in no gimmicks to our approach. Chasing search engine rankings and clicks deviates us from the Thoughtful Software™ mission. We focus on only a few things,  our podcast, newsletter, and blog.

In Engineering, we often debate the best methods for delivering great work and ask lots of questions.  If we break down a project into eight-week blocks with deliverables every two weeks, would we be able to deliver the value we promised? Do clients understand the deliverables? Are two weeks even appropriate? Simplicity can’t be born from a complex engineering process. We aren’t just looking at agile practices as the “future”; we are always asking how we can simplify our process and practices while creating an exceptional experience for our customers.


Choose Simple Over Complex

All this is to say; we value simplicity. There is nothing revolutionary here, just a relentless mindset to stay focused on achieving our Thoughtful Software™ mission.  

The result is our continuous pursuit to choose simple over complex, provide delightful client experiences, and deliver quality work.

Next-generation applications in healthcare, transportation, education, finance, and so on must be simple and effective. We owe it to the betterment of our society to deliver Thought Software™.

If you’d like to learn more about Thoughtful Software™, please contact our team.  

“Simplicity is the ultimate sophistication.” Leonardo Da Vinci

Timing is crucial to sales and the hardest to master. Timing is what sets Sales apart from just about everyone else at the company.

If you don’t think so, look at the history of great ideas introduced at the wrong time. There is a list of companies in the vast internet graveyard. Even big companies miss the boat such as Microsoft giving Android the phone market. One of Bill Gates’ biggest regrets.

In Sales, deals are no different just on a smaller scale. Every deal has a window of opportunity. 

Regardless of how much a slam dunk you think the sale might be, you have a finite amount of time to close.

Juggling multiple deals while deadlines approaching is challenging. Sales aren’t just about fancy dinners and looking like you’re having fun. Everything is dependent on a monthly, quarterly, or yearly timeline: rain or shine.

The art lies in picking up the cues as you navigate the jungle to lead you to the promised land.

I was thinking about a few tips, but there is just one question which helps me understand the dynamics of a deal.

When do you expect to start?

‍A terrible move any salesperson can make is to be too sleazy and pushy. I once asked a client, “So when are we closing this thing”? As you can imagine, it went over well.

However, asking about the start date is a more subtle way of figuring out the timeframe.

There are other ways to ask this same question, but this one is my go-to. 

The significant part of understanding the start date is it allows me to work backward. If I know the start date, then what does it take to get there knowing we are four weeks away? How long does it take to sign agreements? Is there a budget in place? Who else needs to be involved?

These questions and many more can be asked after the first question. It gives you the best sense of whether a deal is in urgent mode and the steps needed to meet the start date.

Understanding timing is also beneficial for the client. It isn’t a one-way street. You don’t want a salesperson breathing down your neck for a project that won’t start for another six months.

What sets the star players apart are they understanding timing better than anyone else. It may look like luck. It is seizing the opportunity.

For some waking up early and working out feels right. For others maybe it is a midday stroll around the neighborhood.  

Everyone has a preference. There is no right or wrong answer. 

The main point is to have a strong  foundation of how your day will be structured.  Build a system that works for you and only you.  

A repeatable system sets you up for a good day. It helps to reduce the number of decisions we need to make in a day.  

For sales, building your own “system” is absolutely critical to be able to manage the daily grind which will take a toll if you don’t get organized. Building a system applies really to any role.  

Here are a few tips I have found to be useful, backed by sales science. The goal is to keep a simple system that allows you to hit it hard everyday.  

Schedule out time blocks  

  • Early Morning: I like to be early as most of our team is 3 hours ahead of me anyway. My first 1-2 hours before the kids are up are dedicated to writing, thinking, a little prep, and some light email/messages. I have found this routine to be quite powerful in getting me ready for the day. I’m not diving into any projects or heavy creative work.  

  • Mornings: Primarily for client and project related work. Following up with clients. Record an episode for the Thoughtful Software Podcast. Make calls. Creative work.  

  • Afternoons: I feel it is best to have meetings in the afternoons. There happens to be quite a bit of research supporting meetings later in the day. I’ll schedule my 1:1’s, company meetings, project updates, all if possible, in the afternoon. Creating proposals is also good afternoon work.

There are always exceptions to the rule, but I have found a simple daily structure of breaking my day up into time blocks is advantageous.  

Breaking up my day is also helpful to tackle the most challenging part of sales: getting prospects to call/email you back.  

It is not mentally possible to stay in prospect mode all day long. Time blocks allow me to switch things up throughout the day.  

Sales Cadence 

Now that I have my daily routine mostly figured out, time to get into the details. Studies show prospects need multiple touch points to decide to do anything. Most salespeople give up after only 1-2 attempts.  

An easy tip to increases sales without spending a dime on any tools is to increase your activity. The challenge is how do you increase activity without losing your mind. 

I fall back to a simple system. Email, email, call, email, email, call… 

A good CRM should help you manage the activity or using an email sequencing tool is helpful.  

Ultimately, stay focused during the morning session and work on prospecting daily.  


The most fun part about sales is working with people.  

Our mission at Skiplist is to not only help people understand hard technology, but to build it. It is gratifying for everyone at Skiplist to help people be better at what they do.  

It is then absolutely critical to make time to meet with clients and partners routinely.  

I had a sales manager back in the day who used to tell the sales team, “If I wanted you in the office, I would hire better-looking people.” Haha.  

But he had a point. Meet people and see what is happening out on the front lines. There is no substitute for meeting face to face. Even video calls can’t compare.  

Use your lunchtime and afternoons for meetings. Coffee meetings are great. Thirty-minute face to face meetings are fantastic. I did have to switch to decaf as I was getting addicted to caffeine.  

Whatever you do meet with people routinely, Use the mornings to spend time setting up those meetings systematically.  

Systems Produce Results 

As James Clear put it in Atomic Habits, “If you’re having trouble changing your habits, the problem isn’t you. The problem is your system.”  

Focusing on implementing a healthy repeatable system rather than specific outcomes leads to a more manageable balance of getting things done and enjoying your work.  

If we are ever to achieve our vision of making the world a better place through “Thoughtful Software” and with thoughtful people, it will be built on a foundation of excellent systems.  

Figure out the way that works for you and enjoy the rest. If you need help, contact us.

This article was originally published on

Sales is a numbers game and a tough game. Most of the time we are getting told no or even worse getting nothing back. 

“Hello? Is it me you’re looking for?” Nope. 

Searching for potential customers is time-consuming. Painful. Heartbreaking. So, when you do get someone interested in having a discussion it is quite natural to be excited. It happens to even the most seasoned professionals. 

The challenge is how do we find out what is real and what isn’t?

Therein lies the art of qualifying a deal. I have to credit my old pal Will Harrison who gave me an easy and straightforward phrase to remember. Find out if a prospect is dying, lying, or buying? DLB for short.

It’s not as harsh as it sounds but an easy reminder it is ridiculously important to understand the overall status of a deal as soon as possible. I like to think about qualifying a deal in simple terms. 

Who is the coach, champion, decision maker, and buyer? Meddic sales methodology is a popular one. All essential questions but when dealing with dozens of deals going in and out of the pipeline, I always come back to DLB. It feels more organic and natural to my style as I am engaging in multiple daily conversations. 

I’ll share a few tips on how I try to understand what is real and what isn’t. By no means are these tips strict rules. Just some guidelines I use to help everyone involved. Including customers. 

The key though is always to be empathicauthentic, and conversational. Never be robotic and go through a list of set questions when qualifying a deal. Don’t be a jerk. 


Dying deals have all kinds of issues. No internal support. No real budget. No timing. Politics. 

Projects come and go for various reasons. Most if not all projects require some management buy-in and support. 

If your champion does not have internal support, your proposal will be dead on arrival. 

  • Who else needs to review the proposal?

  • How do you usually buy these types of services?

Meeting others involved will help understand the realness of a deal. You’ll also learn more about the dynamics with team members. 

  • Do you your homework also. Some industries such as the semiconductor industry are cyclical.

  • Are you catching them on a downturn? Budgets tighten up.

  • Is the specific company you are targeting dying?

  • Are they getting hammered by their competition?

  • Will your product or service move the needle?

Just a few questions to think about as you find an interesting potential deal. 


In my years in sales, the most challenging competitor I have ever faced and continue to meet is the biggest and baddest of them all. 

The dreaded “Do Nothing.” Three things usually happen in a deal. You win, you lose, or nothing happens. The customer decided to stay put and do nothing. 

In the do-nothing scenario, everyone loses. The first person who got out wins. Don’t be the person who after countless emails and meetings finds out the customer is not going to spend any money at all. Crushing. 

Or maybe they are going to push the project out to next year’s budget. Ugh! Those are the hardest ones to swallow and honestly the hardest part about sales. 

When you get knocked out with a gut punch. 

Often doing nothing isn’t anyone’s fault — just the nature of the game. Shit happens. 

Without hesitation, pick yourself up and dust it off. Our ability to shake things off is also why salespeople make the big bucks. However, the mental anguish does take a toll and sales isn’t for everyone. 

Stay in close communication. Silence is death for a deal.

  • Confirm start dates. When would you like to start the project?

  • Has anything changed?

  • Get to know more people if possible

  • Build rapport. Relationships are critical.


“What is your budget”? 

One of my very first sales calls in what seems like ages ago, I decided to make asking about the budget the first thing that came out of my mouth. 

To the horror of my sales manager,  like a pro he laughed it off and kicked me under the table. I didn’t say a word afterward.

Although understanding the budget is essential, there is an art to navigating the money question.

I learned a valuable lesson. 

Usually, if the deal is active, you can feel it. There is activity. People are communicating. A solid timeline is understood. We have a budget. We have buy-in. We have a problem to solve. 

We can get into closing a deal. It helps to have a good sales process at this point and be able to walk a potential customer through the process. 

I admit I am not the best at following processes. I prefer a more freestyle approach. I prefer a more freestyle approach but I do have a process I tend to follow in my head. My advice is don’t do freestyle often.

Be disciplined in navigating a lead to close. At any point, buying can turn into lying or dying faster than you can say “Skiplist is awesome.”

There are many variables to consider when qualifying a deal. By being in the right mindset and disciplined you’ll find the early discussions more fruitful and more predictable. 

Make it rain!

This article was originally published on

In 1998, according to the Associated Press, our average attention span was around 12 minutes. A decade later, attention spans dropped by 50% to 5-6 minutes. I’ll bet they are about five seconds today. 

There are many factors for the dramatic drop in these statistics. Social media is a huge culprit that has rewired our brains to make it more difficult to pay attention for long periods. 

If you have ever been part of a long sales presentation and wanted to fall asleep, please raise your hand. I’ll confess, in the past, I’ve wanted to fall asleep in long presentations my colleagues were giving. I also have done hour-long presentations and felt they were about 55 minutes too long. 

So many salespeople still want to set up that one-hour time slot to make a standard pitch using a standard deck. It is not only quite inefficient, but it’s also quite rude. 

The third sales principle is all about empathy. I was going to say “Be Empathic.” However, empathy seems too official of a word. It doesn’t hit on the point hard of don’t be a jerk. 

Align Priorities 

Our customers have many other things to do besides sit in hour-long presentations. They most likely have a difficult job filled with a busy array of tasks, projects, and meetings throughout the day. 

Our goal as salespeople and product builders are to help our customers be better at what they do. First, we must understand the challenges our customers face and position everything to accomplish our goal. 

Anything else is a waste of time. 

Aligning priorities is more about aligning our mindset. That email you just sent to a new prospect, is it all about your company and products or did you take a minute to learn more about the person you’re emailing?

The deck you just prepared is it just the standard pitch or did you thoughtfully prepare to touch on key points relevant to the client. 

The challenge salespeople have they are in a natural conflicted position. Earning the big commission check drives hyperactivity. To achieve the hyperactivity salespeople will rely on a cookie cutter system to contact as many clients as possible. 

It is a challenge I have faced throughout my career. Doing anything custom or personalized slows down my ability to reach as many prospects as possible. 

The reality I came to understand as I spent more time in the field is the standard approach to sales is pure laziness. 

Personalizing our interactions does require more work. However, the long terms gain to spend a few extra minutes in preparation greatly outweigh any short quick mass emails. 

There are a time and place for mass emails such as event notices and updates which isn’t in the scope of this discussion. 

Thoughtful Software Process

At Skiplist, we firmly believe in what we call “Thoughtful Software.” It is more than just building software a certain way, although we do that well, it is an empathic approach to every touch point we have with clients and our partners.

From idea to handoff. 

For example, we rarely if ever will stand up in a conference room and pitch what we do. We prefer and emphasize conversations above all. We don’t even have a presentation anyone at Skiplist can present for more than 15 minutes. Our focus is on the problem we are all trying to solve and not us. 

We make it a point to streamline the legal process to smoothly and quickly start projects. Has anyone figured out why it takes six months to sign a services agreement? 

New technologies such as machine learning and blockchain can lead you down a complicated path when sometimes a more straightforward solution may be available. It doesn’t always make sense to push new technology when it may actually overcomplicate matters.

We value simpler thoughtful interactions to help everyone involved achieve the bigger vision and solve problems efficiently. 

A few final thoughts: 

  • Have an open mindset

  • Adapt

  • It’s not all about the commission. See sales principles 1 and 2.

  • Keep your meetings shorts. 15 minutes or 30 minutes max

  • Focus on conversations

  • Be mindful of your client’s schedule

  • Listen, listen, listen.

You’ll find people will want to work with you more, and your interactions will be more fruitful.   It is a compounding effect that leads to consistent success. 

Oh ya, and don’t be an a$$hole either.

This article was originally published on

When you first set your mindset to help your customers as I discussed in Sales Principle #1, then you are on a journey to immense success. To make the journey more enjoyable and sales less of a grind, I firmly believe being authentic and genuine are essential. 

If you are a complete bozo, I’m not sure what to tell you. Hopefully, this article can help. 

This is more about building real lasting relationships. None of that fake stuff. Keepin’ it real. 

At Skiplist, one of our core values is “Relationships over Money.” Easy to say but very hard to practice. 

Everyone at Skiplist profoundly believes in our core values. This is our differentiator and what makes working at Skiplist a blast. 

The Long Game

Salespeople are pulled in all kinds of directions. Hitting your yearly, monthly, or even weekly quota is difficult enough. How do you focus on relationships when your manager is breathing down on you to sell, sell, sell? Not easy. 

The top salespeople and great companies understand deals don’t happen overnight. They take time. Our job is to guide deals through the process which on average can take six months or more.

Don’t get me wrong, even though deals take a long time that doesn’t mean you sit around. I’ll talk about pipeline management in another principle. 

Throughout the length of a deal, you’ll want to be on constant communication. 

Good solid communication is not going to happen if you don’t have a good relationship with your customer and you won’t have a good relationship if you are not really authentic throughout the process. Customers can snuff out fake. They will be less forthcoming with crucial information. 

If you are not always focused on short term results and you genuinely care about your customer’s success. Everyone can feel it, and the oddest thing happens. Deals close smoother and become more predictable. 

A salespersons’ dream. 

Scaling Values

When Andrew and I were in New York recently, we spoke to Gary Vaynerchuck about scaling values in an organization. It was a fascinating discussion around how he leads by example. We could see and feel it with everyone we met in his office. 

Imagine how VaynerMedia then treats its customers. I’m sure it is an excellent experience from the salesperson all the way to Gary. 

There is no such thing as B2B really. It is all P2P or person to person. Authentic relationships matter. 

Fortunately, there is a ton of opportunity as most salespeople focus only on the transaction. 

As a final thought, I recommend never go through robotic scripts, don’t be transactional, be a giver not a taker, build a close network of people who love to help, and please never go through the motions. 

Instead, be present, be thoughtful, be authentic, be genuine, and always hustle.

This article was originally published on

Check out my original post on why I decided to start writing about “Sales Principles.”

I’ve heard many definitions of what is sales, but Mark Cuban put it best, “Selling is not convincing. Selling is helping.”

It is unfortunate that “sales” is often associated negatively. I’ll admit sales rightfully gets a bad rap, and there are many bad salespeople out there. We have all experienced a tricky or pushy salesperson. You feel horrible and used. 

Have you seen Broiler Room, Glengarry Glen Ross, Wolf of Wall Street and so on? Slick hair, thousand-dollar suit. Excuse me while I clutch my wallet.

These experiences lead people to be cautious when buying products. Understandable. 

Well, sales isn’t a bad word, and the great salespeople know how to help customers not convince them. 

Evolution of Sales

Sales have changed quite a bit in the last thirty years. Consumer consumption and demands have also dramatically become more complex.

It first started with feature selling. Present the customer with how fast your widget can do something. Remember the computer processor wars? 1.5GHz vs. 1.7GHz! I’m going with the faster processor. I need my browser to open a few milliseconds faster. 

Don’t get me wrong it is essential to discuss the specs. However, your product is more than just bits and bytes.

Feature selling is a losing strategy. The rapid pace of changing technology and the rush of new entrants will put you on constant shaky ground. 

Then came solution selling where the salesperson focuses on the customer problem and matches it to a product or solution. 

Theoretically, solution selling seems like a home run. However, in reality, the complexity of each situation does not allow for things to work out that easy. 

“Everyone has a game plan until they get hit in the mouth.” – Mike Tyson 

Rarely in my career have I ever walked into a sales pitch where the stars aligned and I walked out with a signed deal. The one to one match of a problem to a solution doesn’t exist, especially in custom software development services. 

The other challenge is solution selling doesn’t take into account the personal human aspect of buying and selling. You’ll need to get the customer to offer up what problems they are facing. What if they don’t want to tell you about their problems or don’t know exactly themselves? 

Also, buyers are coming in well prepared and better educated. Open-ended questions to learn more are hard to get answered. You can’t just fit your solution in nicely to a specific problem. 

Buyers are dealing with more complex problems than ever before. 

Then why do so many salespeople beat this to death? I don’t know. Laziness, ignorance, greed…?

Today, there is a shift to focus more on insight selling. This type of selling focuses on helping customers work through challenging problems together. 

Insightful salespeople:

•    Actively listen

•    Ask the right questions

•    Bring ideas

•    Collaborate

•    Roll up their sleeves to help come up with answers 

We are in the idea economy. Bring ideas. Be a helper, not a seller, and your customers will come back to you again and again. 

One Size Does Not Fit All

Features, solutions, and insights. What is a salesperson to do now? 

The answer is all of the above.  

It is imperative salespeople today possess the ability to navigate deals with every possible tool to help customers achieve their goals. 

This complexity makes selling extremely hard. Rapid changing technology means you always have to stay up to date. Continuous learning is a vital part of sales. 

Not to mention salespeople today must possess a high emotional intelligence (EQ). 

At Skiplist, we don’t look to push machine learning for example, on a project just because we do those projects well. 

We look for areas where we can provide the most value as it relates to the bigger picture. 

Do we need an ideation session first to flush out the goals of a project? Maybe we can stand-up a basic architecture quickly to start testing our assumptions before moving to the next phase. Is there something off the shelf that can help us during this one phase? 

Our Innovators Toolkit is often helpful to think about those early questions. 

I recommend rather than getting lost in a specific sales methodology or try to do everything at once. 

Focus on one thing.

How can you help your customers be better at what they do?  

Help don’t convince.

This article was originally published on

My journey at Skiplist has been nothing but exciting. Over the last year, we have grown tremendously with each person bringing a diverse background to the table. Never a dull moment at Skiplist that is for sure. 

From starting our podcast to meeting Gary Vaynerchuk, the opportunity to work with some of the brightest minds is genuinely humbling. 

Our clients and partners are the best and believe as we do, thoughtful software and thoughtful people can change the world for the better. 

Our mission has and will always be to transform the software industry with incredible and thoughtful software. 

For me, leading our sales, marketing, and product efforts, I keep pondering one question.

“What do we want people to remember about us?”  

To formulate the strategy of Skiplist and our various teams, it is critical we root our decisions with strong values and principles. 

There is already enough nonsense out there. We don’t need more.

I’m a huge fan of Ray Dalio and his book “Principles.” A truly transformative read. 

Inspired by Mr. Dalio, I figure there is no time better than now to share over the next few weeks my thoughts and principles on sales, marketing, and product. 

My primary goal is to share how we think about customer experiences and what we want people to remember about working with the great folks at Skiplist.  

I’ll start with my ten “Sales Principles.” I probably have a hundred but ten seems like a good start.

We are visual creatures. Society places a tremendous amount of importance on what we see. The way we dress, our shape, and our color. It is so powerful in fact, billion dollar companies such as Instagram are all about visuals.

It is this urge to appeal to our visual senses where our reality gets distorted. We are able to filter the output and filter the input. Or that is what we are led to believe.

Tuesday afternoon around 2:15pm. Cranking away on a report due in a few hours. Ding. A notification pops up on your phone. A post from a former colleague from two jobs ago. Someone you have not spoken to since you stepped out of those office doors.

A picture from their family vacation. Cool.

Posting a picture of a fabulous vacation in the Bahamas sends a lasting ripple through our mental networks, causing more harm than good.

This is a shallow activity yet perceived to be important.

What we see fires off our neurons in our brain to feel the joy of the Bahamas. Often it turns into jealousy and anger.

“Why am I here working on this report when I could be in the Bahamas?”

Instead of focusing on the report, our mind is distracted. The attention economy is in full effect. You’re plugged in now. Get ready.

You’ll end up wasting a considerable amount of time on the Bahamas now. Also, trying to convince your wife the trip is a good idea.

I bring up this small scenario as recently I read “Deep Work” by Cal Newport. This is one of those books where when I was done, it changed my reality. I had been living in the matrix all along.

Seemingly, innocent notifications drain our mental capacity and set a chain reaction of shallow events. All to appease our urges.

The question then is does being connected all the time in real-time be a fruitful way to live? Newport argues it isn’t. I agree.

There are extreme measures some take by completing cutting themselves off. Digital detox I think its called. Abstain from technology for a period of time.

I’m not buying it. It is just like any diet. If you’re back to your original weight then what was the point?

This require a lifestyle change.

Deep Work is about increasing our mental capacity to reach new heights in getting important things done.

Setting aside hours a day of uninterrupted work sessions. Scheduling out your work day. Being diligent about what to focus on.

I have noticed this has offered me more rewards than before.

More time with family. More productivity in the best way. Less busyness, higher quality output.

Newport offers several tactics to support how we can incorporate “Deep Work” into our daily schedule. 

Some are interesting. However, I fear many won’t take them seriously. So I offer two simple suggestions to be more productive and reach new heights.

  1. Use “Do Not Disturb” feature on your phone and laptop religiously. When you are working on important work. Turn it on and focus your attention on your work. No notifications.

  2. Turn off all notifications. I mean all of them all the time. You choose who to give your attention to and when.

After some experimentation, I tend to prefer the second option. I get so much more done. It’s ridiculous. Almost like a super power or what dunking on someone might feel like.

This by no means is easy to do. I still struggle with this as an entrepreneur and being a part of a growing startup my time is often fragmented. That’s ok. Just keep doing the best you can and try to block out a few hours of uninterrupted a day. 

In a deep working session, focusing on the task at hand is critical. An innocent email popping up can derail everything.

I’m not against social media and as Newport says it isn’t a “moral” issue for him. Not for me either. It is all about getting things done. Important things.

Be focused about where your attention goes and to whom.

This isn’t easy but I can promise you one thing. You’ll find life more rewarding.

It turns out we don’t need to be connected all the time. We just need to go deep.

This is the “Deep Life.”