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.

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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!

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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.

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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.

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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.

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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.