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 Skiplist.com

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 Skiplist.com

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 Skiplist.com

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 Skiplist.com

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 Skiplist.com

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.

Imagine you are given a product to sell. Where do you start? Maybe marketing has put together a competitive landscape. Your job is not to only to sell but sell the shit out of it. You are left as the salesperson to figure out how to sell the product. Good luck. Anyone see a problem with this?

The problem is as a company you are hoping the sales people know what to do. That’s why you hired them anyway, right? By not taking a deeper look at the nuances of selling, you are leaving money on the table. You are not maximizing the potential. You are leaving yourself vulnerable to being “out sold.” Vulnerable to competitors. That is why a sales strategy is so critical to reaching higher without wasting money.

Frontline Sales Strategy?

I hesitate to call this a sales strategy. A sales strategy means something different to different people. It could mean deciding whether to go with direct sales people or a distribution channel. Or possibly how a specific territory may be split up. Who gets the big anchor accounts? Who goes after a geography? It’s too general.

That is the not the sales strategy I am talking about. The most critical component of any company strategy should be incorporating a well thought out and adaptable frontline sales strategy. Frontline are the sales people in the field. The grinders. The callers. The ballers. The road warriors. The hustlers who get up everyday and hit the pavement looking for the next sale. They are the frontline. What we go through on a day to day basis is rough. Exhausting at times. Yet at the same time hectic. A good hectic. By adding frontline my intention is to emphasize the importance of focusing on the sales people in the field. Not a corporate sales strategy.

All too often the battle being fought in the trenches goes unnoticed. There are too many companies relying on hope. As you know hope is not a strategy.

The Difference

A frontline sales strategy is important and very critical to excelling sales without much added cost. I always ask “What is the difference between your product and the competition?” I strongly believe, ABSOLUTELY NOTHING! People will spew off better specs, faster, easier to use, etc. Those things are important, however the main different is…..YOU. The sales person is the most important factor in the sale.

Another one of my strong beliefs is there is no such thing as B2B. I really don’t like that term. There is no such thing as business to business selling. Intel doesn’t sell to Apple. Slack doesn’t sell to a startup. The deals are negotiated by people. Person to person or P2P is much more appropriate. A sales strategy is far more effective with a micro view rather than a high level macro view. I caution though micro doesn’t mean micro-management. That is the last thing you want to do to your top sales people is kill their freedom.


A simple example is looking that differences between an iPhone and Android. Not really much difference but asking the question of how a person uses the phone leads to a different conversation. On an iPhone you can’t attach an excel file to an email for example. For work, you might find that important.

Frontline Sales Strategy Suggestions

  • Tactics — A method is working better than others. An example could be to bundle products together. Gives customer a complete solution.

  • Tips — Feedback from sales on a particular improvement.

  • Gotchas — How to handle objections? Or how to handle product flaws. Delivery issues.

  • How to convey a confidential roadmap

If you agree P2P is important, then the next question is why isn’t there more emphasis on developing better frontline sales strategies? Most likely people don’t know this problem exists. Maybe. Or because it’s hard to do. It requires continuous attention and refinement. Good collaboration is necessary for it be effective. Management to marketing to engineering to sales need to be on the same page.

This isn’t about tricking customers or manipulating the conversation. This is about understanding the customer requirements and constantly aligning your products and strategy around those requirements. Ultimately improving the sales process and securing more business. Make it rain!

I keep hearing business to business selling or B2B. I have seen this in job postings, articles, everywhere. It is common work jargon. The idea that a business is selling to another business seemed always ridiculous. For example does Slack really sell to NASA? Of course not. However, the B2B phrase permeates a bad mindset. I find people lose sight that there is no such thing as B2B. Only P2P or person to person selling. People forget the human aspect of selling, marketing, and engineering a product or service. Everything is personal. There is no such thing as B2B.

Why is this important? It has everything to do with being successful. More importantly, how do you differentiate yourself from the competition? Here are some tips or strong suggestions you need to incorporate. I reference a customer in this post, but this can be a prospect, user, etc.


There is an art to being a good listener. A big misconception in sales is you have to be a good talker. Garbage. The most important skill you need for a meeting is to spend more time listening. Funny thing happens when you listen more. You get actually get good information. Useful information. That is your time to collect information to build a good proposal and have a better understanding of the opportunity.

People actually appreciate you are listening to them. Mainly because most people do not. This subtle interaction in a meeting can make a huge difference in the outcome. Here is a simple exercise you can try. Ask a question, then stop, then listen.


I guarantee you will find a more productive outcome. A high five at least.


No, not a typo. It is a dramatic emphasis on how important it is to listen.


This one may be the hardest one to conquer. A key part of listening is you really have to care about what is coming back. You have to have a genuine interest in the customer. Their industry and application. What the customer is trying to accomplish. The company culture. Being genuine and actually caring goes a long way. Again, mainly because many people do not care. They are too self interested.


Be conscious of the time. If a prospect set aside 30 minutes to meet with you then stick to the allotted time. I will even remind everyone our time is up. I want my customer to know I’m not going to sneak extra time just for the sake of it. Time is precious and if my customer says it is ok to continue then we continue. It is like a house guest who overstayed their welcome and doesn’t get the idea to get out. You don’t want to be that person. Take the customer’s perspective in mind. They have other shit to do.


Don’t be offended. I mean well. Seriously though, I cannot begin to tell you how frustrating it is to see meetings get derailed because someone decided to be a jerk. Or you’ll see people approach the conversation in battle mode ready to land some punches. See the tips above. Take a step back and realize why you are there. Also remind other colleagues in the meeting why they are there. Keep your cool at all costs.


Hallelujah! This is one my quests in life to get people to realize they are in sales. Everyone. You in marketing. You in engineering. You in management. You in operations. Everyone means everyone. I’ll have more on this key topic later. I’ll point out sales isn’t a bad thing. Do not take it in a negative way. If you are running your business with the mindset laid out above, then everyone is “winning”. People are getting the right solution. Company gets more sales. There are no cons here.

I have laid out some important topics which I will expand upon. My hope is you will take a different view next time you visit a customer or build a product. By the way, this can apply to all aspects of your life as well. Just saying.

The takeaway is if you are in the business of building an app for example. Maybe take a look at how a user may use the app. Not from your perspective. From the user perspective. I wish someone from Concur (the expense app) would contact me. I have so many suggestions for you. Why does it take 10 steps to fill out an expense? Good app but not great yet.

Steve Jobs was well known to be obsessed with the user experience. Take a more human approach and connect on a personal level. You will see a dramatic improvement. You are leaving money on the table by not taking a more person to person approach.

The next challenge is getting everyone in the organization to be on the same page. We will save that for another day.

Let’s see if this sounds familiar. You have just been hired to a new region. You’re job is to increase sales. Currently the territory is drier than a California drought. Let’s make it even worse. The economy is in the dumps. Your company is not the market leader. You don’t have that many products to sell. What do you do? How do you turn it on and make it rain?

Here are some ideas to get you started. Turn yourself into a rainmaker.

Main goal is to keep things simple.

Step 1. Current customers (The most important)

One quick mistake people make is they ignore their current customers. They go right after developing a territory plan focusing on acquiring new customers. This is the hardest thing to do. Focus your first month on mapping out where the business is coming from. Especially where the business has come from in the last 3 years at minimum. Get comfortable with Excel and pivot table the data to death. If you’re lucky enough to have a legit CRM, then create all kinds of reports. Sales reports. Product data.

Once you have that data proceed to step 2.

Step 2. Massage the data

Once you have all the data then you need to figure out what to focus on. Sort out the big dollar sales. This is where you will spend time on first. The customers who have purchased the most in the past should be a priority immediately. Go out and meet every one of them if you can. Update their software. Do whatever to get in front of them. In person is the best.

Step 3. Get email addresses, email addresses and more email addresses. (Legitimately)

Collect all the emails you have in the database. Scour old trade show leads, webinar leads, etc. Don’t go out and buy a bunch of emails unless you know it is a legit service. Clean them up. I usually get rid of personal emails, consultants, and any other bozos. Get skilled at identifying bozos. It’s a technical term for people who will waste your time.

Step 4. Be your own marketing team

Now that you have a clean email database and an understanding of where the bones are buried, develop a schedule to kick some butt.

Import all those email addresses into an email marketing program such as Mailchimp. Send out a newsletter every month or two with relevant material. Link academic information if you don’t have anything internally.

One thing I hate it is when people complain about leads. There are so many free services out there. Establish the mindset you’ll have to do it yourself first. Coordinate with marketing also if you can. More the merrier.

Step 5. Get hustlin’

Once you have sent out your first blast. Wait a few days and then start calling people. You now have a soft opening. You can say, “I sent you an email, I am the new manager in the area….Can we meet to discuss how you are doing with X product? What support do you need?”

Simple right. Email first then follow up with a call.

Don’t be shy now. This is the time step up and develop a good work ethic. Research shows prospects require a minimum 5 follow ups to make decision whether they want to engage with you. Meaning email, call, email, call, meet, call, email, meet, etc, etc.

Just be relentless.

One last thing. ABC. Always Be Closing. How can you forget that? Work on your messaging over and over. Get better at tweaking it.

Some additional tips

  • Research your industry and competitors

  • Network. Go to industry events. Meet people. Don’t sit behind a computer.

  • Make calls. Yes make outbound calls.

  • Be consistent. Over time this will work. Keep at it.

There are so many more tips and paths you can take. Hopefully this provides you some direction on where to start. You’re not lost. I got you.