The Comprehensive Guide to App Feature Selection : Questions Only

A Simplified Look

This excerpt pulls the actual questions from The Comprehensive Guide to App Feature Selection. All context and supporting descriptions have been removed. If you are a first time founder, I suggest you view the full guide. If you’re looking to work through the questions without pages of educational resources, this should serve you well.

Framing Questions

What’s the current status of the app?

  • Just Dreaming.
  • Actively Planning.
  • Live and Iterating.

What stage software are you building?

  • Prototype.
  • Minimum Viable Product (MVP).
  • Full Product.
  • Enterprise.

Who is your target user?

  • Consumers
  • Businesses

Is it downloadable from an App Store?

If yes to App Store, what platforms does it support?

  • Android
  • Apple iOS

Which mobile devices are supported?

  • Wearable
  • Phone
  • Tablet

Are there offline capabilities?

Are there push notifications?

Is there a web interface?

Which devices are most common among users?

  • Phone
  • Tablet
  • Desktop

Are there desktop notifications?

Do users sign in?

How do they sign in?

  • Username
  • Email
  • Facebook
  • Twitter
  • Instagram
  • Linkedin
  • Google
  • Slack

Are there tiers of users?

Do users have profile pages?

Do users collaborate with one another?

Does the app handle money?

Do you charge users?

How do you charge users?

  • Upfront.
  • Subscription.
  • In-app Purchases.
  • Advertising.

How is money transacted?

  • Card
  • Bank Transfer
  • Digital Wallet

Who is your Payment Processor?

Do users transact with you directly?

Do users transact with each other?

Are refunds handed in the system?

If your handling refunds, are you expecting partial refunds or just full refunds?

Which currency is permitted?

  • USD
  • International
  • Crypto

Does it contain social interactions?

Which social interactions are included?

  • Follow / Unfollow
  • Friend / Unfriend
  • Comments
  • Reactions

Does the system use email?

How does the system use email?

  • It sends emails
  • It receives emails
  • It sends and receives emails

Who is your preferred email service provider?

Does the system use text messages?

How does the system use text messages?

  • It sends texts
  • It receives texts
  • It sends and receives texts

Who is your preferred text message provider?

Does the system use phone calls?

How does the system use phone calls?

  • It sends phone calls.
  • It receives phone calls.
  • It sends and receives phone calls.
  • It facilitates the connection between people or groups.

Who is your preferred text message provider?

Do users rate or review?

Does it use GPS or location services?

Is there messaging or chat?

Is there search functionality?

Is there sorting and filtering?

Are there reports on app data?

Does it uses images?

Is there image uploading?

Is there image capturing?

Is there image editing?

Does it use video?

Is there video uploading?

Is there video editing?

Is there audio recording?

Is there video streaming?

Does it use audio?

Is there audio uploading?

Is there audio editing?

Is there audio recording?

Is there audio streaming?

Is there file sharing?

Is there data importing?

Is there data exporting?

Are changes and edits tracked?

Does it communicate to other hardware, other than the device?

Does it integrate with other services?

How many other services does it integrate with?

  • 1–2
  • 3–5
  • 5+

Is there an activity feed?

Is there a content management system?

Does it use machine learning or data science?

Does it use any virtual or augmented reality?

What level of security is needed?

  • Best Practices are sufficient.
  • Air Tight
  • Fort Knox

Are you handling sensitive personal information?

  • Medical Information
  • Social Security Numbers
  • Bank Account Details
  • Legal Documents

What are your expectations on app performance?

  • Quick enough to be enjoyable
  • Very Fast
  • Blazing Fast

Does your team handle hosting?

Does your team handle maintenance?

Do you have terms and conditions?

Which categories best describe your product?

  • Fundraising Platform
  • Social Media
  • Ecommerce
  • Analytic Tools
  • Calculator
  • Marketplace
  • Smart Home
  • Project Management
  • Automation

Which programming languages are used?

  • No preference / Not sure
  • Ruby on Rails
  • React
  • Angular
  • Python
  • Java
  • Php
  • Javascript
  • Swift
  • Objective-C
  • Other

Which parts of the process do you need help with?

  • Strategy
  • User Experience
  • User Interface Design
  • Software Engineering and Development
  • Launch and Deployment


At New Story, we make time every few months for an exercise we call ‘Moonshots’. The term comes from the Apollo 11 spaceflight, which landed the first human on the moon in 1969*. At the time, the idea was truly audacious.

As a team, we get together and dream big. Usually after dinner and over drinks, we throw out big, wild ideas. They’re unlikely, crazy ideas. While the origin of our 3D Printer experiment came out of one of these sessions, the point is not to be practical. It’s about dreaming, not planning.

Controlled Chaos

Some suggestions get a laugh. Others make use uncomfortable. A few have a way of lingering, but most ideas die on the spot.  The point of moonshot is to spark inspiration. Once an idea is put out into the world, the next person can build on top of it. The ideas evolve.

We want to create a place for that to happen. It’s a safe place where ideas and nonsense can coexist. One idea sparks another. Some build upon their predecessor while others seem to nuke the flow. There are no bad ideas.

Eventually, it happens. This free exchange of thought begins to achieve the decided effect: inspiration. An idea is thrown onto the pile that causes a moment of pause from the group. While still a longshot, it somehow feels achievable though currently unexplored. These nuggets speed up the energy in the room and propel the conversation forward.

The excitement and suggestions finally wane. With our cognitive capacity exhausted, we push for a final round of ideas then break for the night. It can often feel like a chaotic whirlwind. Where observers might see a whimsical waste of time and effort, we see a mental victory. Breaking the shackles of rationality, we took the time to dance with our imagination.

The notion of dreaming bigger spills into our work constantly. Like a pair of dueling racers, team members push each other to challenge what’s possible. Over time, these bouts have a way of shaping a culture and staying with us. None one knows where the next great idea will come from. But it’s unlikely to be discovered by the people who aren’t willing to look for it.


*Alleged moon landing. Recounting the discussions I’ve had on this topic would require more time than any sane human is willing to commit.

New Year Ritual : Change Your Passwords (plus checklist)

In recent years, we’ve seen massive data breaches come across the headlines. Unfortunately, these reports represent a small percentage of the actual infractions. While our data is only as secure as the people entrusted with storing it, passwords are the first line of defense. Taking an hour or so once a year to update your most commonly used accounts (or as many as you can remember) could safeguard your information.

If you’ve been waiting for the right excuse to start using a password manager like 1Password or LastPass, a systematic password refresh would be great option. You could generate large, highly secure passwords and store them in a safe place.

Below is a quick checklist of common passwords you’ll likely want to reset. There are also great tools to help configure more secure passwords.

Personal Accounts

[ ] Banking Institutions

[ ] Credit Cards

[ ] Insurance Provider

[ ] Personal Email

[ ] Personal Website / Blog

[ ] Amazon

[ ] Facebook

[ ] Twitter

[ ] Instagram

[ ] LinkedIn

[ ] Youtube

[ ] Quora

Business Accounts

[ ] Business Email

[ ] Payroll Service

[ ] Invoicing Service (Xero, Quickbooks, Freshbooks, etc.)

[ ] Project Management Tool (Basecamp, Asana, Trello, etc.)

[ ] Communication Tools (Slack, GroupMe, Hipchat, etc.)

[ ] CRM (Salesforce, Hubspot, Campfire, etc)

[ ] Email Marketing (MailChimp, Constant Contact,, etc)

[ ] Marketing Automation (PersistIQ, Mixmax, Salesloft, etc)

[ ] Form Submission (Jotform, Wufoo, FormStack, etc)

If you’re a security minded individual and interested in other tools to tighten up your digital diligence, here is a list of helpful privacy products.

2018 Annual Report

The act of reflection continues to be the most impactful habit I’ve developed over the years. I’m continually amazed by how much growth can be seen in some areas of life while others seem to shrivel. I’ve broken down my Annual Report into the areas that matter most.

Also, pardon my typos. I had a lot of ground to cover and my usually proofreading process was too much mental energy.


Our family has seen a lot of changes in 2018. From our immediate family, to extended family, it’s been marked by births, moves, and big announcements.

Welcome Rowan!

Our little red-headed bundle of smiles was born on May 21, 2018. She LOVES her big sister. Major milestones at the moment include sitting up on her own, eating real food, and a veracious smile.


Despite some early resistance, we made the move to Smyrna. Walkable to specialty coffee, the grocery store, and local restaurants it’s been a welcome change. The ride to and from work has been somewhat grueling, but I’ve hit my annual target for audio books and arriving home is worth it.

School for Avery

Avery started at a school down the road from our house (about a 10 minute walk) two days a week. It’s allowed her to meet a new group of friends, level up her sharing skills, and increase her immunity to communicable diseases. It’s had the added benefit of allowing Megan to meet other local parents.

Marine Deployment

My brother has been serving in the United States Marine Corp for about the last decade. This year, he shipped out of his third overseas deployment. I continue to be proud and inspired by his committed service. So much of the liberties I enjoy as a husband, father, and entrepreneur are a direct result of people serving to preserve our freedom.

Polar Notion

Founded in 2012 with Josh Wood, Polar Notion welcomed new team members, structural changes, and new service offerings.

New Team Members

In late 2018, we welcomed Kevin and Miruna to the Polar Notion team. Kevin is apprenticing within our engineering team while Miruna is rounding out our design team as a design apprentice. Their fresh perspectives and positive attitudes have raised our average and leave us eager to see what 2019 holds.

Transparent Salaries

As our Leadership Team has dove deeper into operational excellence, we were led to reevaluate compensation and how we handle professional growth within the organization. Pushing the limits on human centered business, transparent compensation felt like a natural next step. The goal was that each person could defend their salary and understand exactly what’s expected to move up.

We’ve defined the levels of growth and mapped key behaviors to categories such as Values, Culture, Evangelism & Sales, Leadership, Client Facing Skills, Industry Involvement, and Knowledge. We learned a lot in the process, but have been pleased with the results.

Friends and Family

Our design team has launched a monthly design program called Friends & Family. It provides a low cost, low commitment, friendly way to create a better brand experience. This is a major milestone because it allows us to continue serving small businesses while our skills and rates increase.

Imminent Survival

Near the end of 2017, a client defaulted on an invoice costing us over $100,000. It created a grueling start to the year, but through creative problem solving and team buy-in, we’ve made it through the worst of it.

New Story

In the summer of 2018, I eclipsed my second year at New Story at CTO. The most notable changes surround our rapid growth. Ten team members have started at New Story within the last 12 months.

Team Members

I have the fortune of leading the Tech Team alongside Matthew Marshall, but we’ve seen growth in every department.

Shane Ardell
Tim Whitacre
Vi Pham
Sam Ballmer
Gary Carrier
Genna Heidkamp
Annie Brannon
Nathan Bach
Katie Tynes
Ellen Paik

3D Home Printer

This was a HUGE milestone as a company and for the home construction industry in general. You can read more about that moment here, or watch the video.

Atlanta Office

Originally meeting from the Polar Notion office, New Story is now in a space of their own. There is still room, but it’s filling up quickly.

Saas Product (Spoilers)

We haven’t shared a lot publicly, but we’re packaging up our learnings as a housing organization and rolling out a Saas (software as a service) product to allow other organization to experience the same efficiencies that have been driving our organization forward. We’ve set our sights on ending global homelessness and are equipping other organizations and governments to join us.


Apparently there are certain fish that never stop swimming. Asleep or awake, they never stop moving. I’m not sure if that’s true but love the notion. As humans, we have a remarkable ability to collaborate and adapt. This section highlights person changes or milestones this year.

New Roles

Board Chair for Entreprenuers Organization‘s Accelerator Program.

Mentor for Founder CEOs at Atlanta Tech Village

New Habits


Since running cross country in high school, I’ve always defaulted to water over any other beverage. On top regular trips to the water fountain throughout the day, I’ve added more thorough hydration to my morning ritual.

100 Somethin’

To get my blood flowing in the morning (inspired by Own Your Day), I’ve started doing 100 of some type of movement each morning. Squats, trunk twists, overhead press (unweighed), etc.

The whole process takes just a few minutes but immediately gets oxygen pumping to my brain.

Generous Followups

Most business people have a solid followup cadence for meetings and appointments. I took it up a notch by sending a direct message to the person who introed me to the person I met with and intro-ing that person to 1-3 other people. Example: I had a 30 minute coffee with Adam. Later that week: Send followup to Adam. Send thank you to whoever introed me to Adam. Make 1-3 intros to other people in my network Adam should meet.

New Tools

RealtimeBoard (

A virtual whiteboard. I have never fallen so fast for a product. It does exactly what you’d hope and the collaborative nature is excellent. Personally, Polar Notion, and New Story are all using it now.

Notion (

Wow, this tool has taken over my life. Best in class organizational structure for documents. It’s everything I wished was possible with Google Docs but couldn’t wait any longer.

Otter (

A native app for recording thoughts and meetings. I use it while I’m driving to riff on ideas and convert into articles later.

Lyft (

After a year full of Uber scandals, enough was enough. Yeah, it’s more expensive but our dollars are votes.


In no particular order.

  • Las Vegas, NV
  • Tahoe, CA
  • Austin, TX
  • Chicago, IL
  • San Francisco, CA (2x)
  • Seattle, WA
  • Chattanooga, TN


Building a StoryBrand: Clarify Your Message So Customers Will Listen

A great read if you looking to clarity your business’ message and position to customers. Also, the author has a worthwhile podcast that combines anecdotes with actionable insights.

Lost and Founder: A Painfully Honest Field Guide to the Startup World

A must read for founders. Whether you’re on your first business or fifth, it’s dispels common myths and resets expectations around starting a business, especially a tech startup.

The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change

It’s a reminder of timeless truths that continue to yield extraordinary results. There is a lot of complex advise and insights, but Covey boils it down to the fundamentals. Likely worth revisiting each year.

Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets

Great read for marketers and founders about the art and science of creating a ‘Category’. Rather than trying to compete with the noise of a crowded marketing, creating a new Category and becoming it’s king has a proven path to success… if you can do it right.

The Creative Curve: How to Develop the Right Idea, at the Right Time

Creativity isn’t magic. We are all creative creatures and it comes back to a balance of consuming and trying stuff. Great for people who view them selves as ‘non creatives’ or other who think they have some magic ability. The brilliant minds we elevate as a culture we’re too different from us, which is worth remembering and this book breaks that truth down well.

Own the Day, Own Your Life: Optimized Practices for Waking, Working, Learning, Eating, Training, Playing, Sleeping, and Sex

Rather than complicating health, Aubrey Marcus breaks it down into focusing on just one day. Planning the perfect, thoughtful day. A lot of great health and fitness tips, combined with a casual yet scientific perspective. Our life is merely a serious of choices, he simplifies the importance of choosing well.

Atomic Habits: Tiny Changes, Remarkable Results

In listening, it reminiscent of The Power of Habit (from my 2016 reading list) but the tips and principles are worth repeating. Listening to Atomic Habits around the same time as Own the Day really drilled home the point. They compliment each other well. Also, the author (James Clear) has an active twitter account full of great habit-forming wisdom.

Thirst: A Story of Redemption, Compassion, and a Mission to Bring Clean Water to the World

Our team at New Story has long admired Charity Water. Ironically, Matthew and Brett both applied to joined their team. Fortunately for the earth’s homeless population, they didn’t get the opportunity. 😉 Scott Harrison’s journey and life transformation is inspiring. It provides useful wisdom for nonprofits of all ages. Not a nonprofit leader, if you have a pulse you’ll likely connect with Scott’s inner wrestlings and vulnerability.

This Is Marketing: You Can’t Be Seen Until You Learn to See

Seth Godin continues to rank among my favorite authors and thinkers. He connects dots that others don’t see and continually challenges others to think differently. To think better. Make things better by making better things. I bought the preorder, the special edition, and some other thing associated with the launch.

Dear Seth, take my money.

Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.

A Polar Notion team member helped me climb aboard the Brene Brown bandwagon in 2017 and Dare to Lead prompted me to settle deeper in my seat. Her practical approach to human psychology provides a need voice and her unapologetic pursuit of breaking down the walls between people is motivating. If you lead people, this will challenge commonly held beliefs. If you don’t see yourself as a leader: read this book, change your mind, and get started.

Alie Heenan your confidence and courage led me to give Brene a chance. For that, I’m grateful.

It Doesn’t Have to Be Crazy at Work

Jason Fried and DHH provide an extreme anchor to the hustle-grind-madness that has come to define startup and entrepreneurial ventures. It’s easy to reject their position at face value, but when you hear their passion for a better style of workplace it’s worth the dissonance. It’s unlikely any business can implement everything they mention, but don’t throw the baby out with the bathwater. Their investments in human-centered work are only the beginning of a massive shift we will experience in the next 10-20 years.

Matthew Marshall, thanks for the advance copy. I’m love building a world class company culture with you.

The Great Game of Business, Expanded and Updated: The Only Sensible Way to Run a Company

Rather than keeping team members in the dark, The Great Game of Business showcases what’s possible when you trust people to show up with their whole selves. Exemplifying a transparent business, it’s refreshing to hear how successful their unique recipe of trust and openness has become.

Thanks Adam Walker and Shantel Khleif for the recommendation here.

The Servant: A Simple Story About the True Essence of Leadership

If you can’t make time to read this annually, you should start by reading it daily. It’s a powerful story about leading from a place of submission and servanthood. Tim Dorr turned me back onto it and I continue to be challenged and inspired.

To Sell Is Human: The Surprising Truth about Moving Others

As humans, we’re always selling whether it’s in our job description or not. When my daughter brings me the remotes and says, “watch Muana”… she is selling. Rather than rejecting the notion, To Sell is Human adds new color and clarity to how we bring our ideas into the world.

Never Lose a Customer Again: Turn Any Sale into Lifelong Loyalty in 100 Days

Customer experience is more important than even. If you’re a business owner who thinks sales is the key to growing your business, pause for a moment. Customer retention is the backbone to business growth and this book provides tips, strategies, and a way of thinking about customer advocacy.

Unshakeable: Your Financial Freedom Playbook

Tony Robbins simplifies basic financial strategy. He breaks down wealth creation, retirement planning, personal spending and more. If you’re ‘playing the stockmarket’, this conservative approach to playing the long game might be just what the doctor ordered.

The Thank You Economy

Gary Vaynerchuk has strong opinions shared intensely, but his predictions and understanding of how human connections have and will shape the economy is impressive. What’s most impressive is how well the content has help up so many years after publication. So much is still right on point.

The Art of Significance: Achieving the Level Beyond Success

I’ve been heavily focused since September on developing a personal purpose statement. This book gave some helpful tips and insights. Nothing comes to mind off the top of my head, but was worth nodding along to.

Great by Choice

Jim Collins scientific approach to business analysis is illuminating. A great read for founders and business leaders working to build a lasting business of significance. Spoiler: It rarely happens by accident.

The Road Back to You: An Enneagram Journey to Self-Discovery

The New Story team read through this book together and we’ve engaged in dozens of meaningful conversations. It describes each personality type of the Enneagram. I’m an eight (challenger) with seven (enthusiast) tendencies. This book was the origin of a lot of reflection and self discovery. It also sparked great conversations between me and Meg.

Thanks Annie Brannon, fellow 8, for pushing this forward like only a Challenger would. 🙂

No More Cold Calling: The Breakthrough System That Will Leave Your Competition in the Dust

I’m not the ‘cold call’ kind of salesman. I’ve always found it to lack empathy and pretty inefficient. This book talks about the value of investing in current customers to drive referrals. It lands on the importance of relational business.

If we’re the average of the 5 people we spend the most time with: Kara Brown, you continue to raise my average. Thanks for the suggestion.

Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal

A helpful guide for getting and keeping people’s attention. It’s easy to assume people say ‘no’ because they don’t want something when more often than not it’s because we’ve poorly engaged them.

Crushing It!: How Great Entrepreneurs Build Their Business and Influence-and How You Can, Too

A firehose of social media insights and marketing expertise. It’s on the other end of the spectrum from It Doesn’t Have to Be Crazy at Work but gives some helpful advise for building a business. Especially in the early years, the lift is often quite heavy.

Peak: Secrets from the New Science of Expertise

Perhaps my favorite book of 2018, Peak talks about the effort required to achieve mastery in almost anything. Unwilling to settle for the idea of ‘natural ability’, he presents compelling evidence that supports the thoughtful, consistent student. As someone who never really excelled at anything growing up, I’ve felt the compound effect of his insights throughout my adult life. The importance of consistent, deliberate practice rings load in this book and it’s value has been felt thoroughly in my own life.

Managing Oneself + The Effective Executive: The Definitive Guide to Getting the Right Things Done

I lumped these together because they’re so similar. Akin to The 7 Habits of Highly Effective People, Peter Druker has a succinct, straight forward way to hitting the essentially for personal growth. Special thanks to the Dave Gerhardt and David Cancel from Drift for recommending.

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs

Intent on finding a better process for tracking goals, we read through Measure What Matters with New Story Leadership this year. Stilling looking for a tool that’s not Excel to track progress but the shared vocabulary and simple framework has proven helpful. We’ve bounced around a little with the best way of breaking annual, quarterly, and monthly OKRS into personal, department, and company items but it’s a work in progress that’s picking up steam.

Smartcuts: How Hackers, Innovators, and Icons Accelerate Success

I’ve always struggle with the idea of social norms or unwritten rules. Smartcuts spotlights entreprenuers and innovators who found broke these cultural constraints to achieve extraordinary results. For myself, I’ve begun referring to the idea as ‘coloring outside the lines’, and this book echos that ethos.

Sarah Lee, I own you one here. The mention of DHH put me over the edge.

Sell or Be Sold: How to Get Your Way in Business and in Life

We’re either selling something (a service, a widget, a preference, an idea) or being sold by someone else. It can create a paradigm shift for most people but seems ideal for founders or sales people.

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

As I mentioned in my personal recap from 2018, we had some major challenges at Polar Notion. This book came at just the right time and served as a reminder that challenges are part of the journey. Rich with stoic principles, it’s a worthwhile read for anyone who has felt the urge to complain about almost anything.

Be Obsessed or Be Average

Grant Cardone is a madman, but a great reminder about the importance of finding something you enjoy and throwing your whole self into it. I have a tendency to obsess things, so left me feeling like I was in good company.

Principles: Life and Work

I enjoyed hearing Ray’s thoughtfilled approach to almost everything. Rather than viewing life as a random series of events, he provides a wealth of knowledge and insight about distilling thoughts into repeatable processes. Instead of relearning, his approach to principled living was impactful and has led me to think more about the ‘why’ behind decisions.

Top Posts

Annual Reflection Framework

Bringing Humanity Back to Email

Unbridled Diversity

Work Life Harmony

Purpose Eats Work for Breakfast

Special Mentions

I attended two funerals this year. Two men whose legacy has had a lasting impact on my life. I’d spent little time with them personally but their children and grandchildren have marked my life beyond compare.

Bob Ardell

I came to know Bob Ardell through his son, Jason Ardell. For years, Jason has been a close friend and early mentor as I began a career in technology. Through stories shared, it was evident that Bob was an avid reader for decades and continually invested in his family.

Read Obituary

Warren Wood

I met Warren for the first time in middle school. He was grandfather to Josh, one of my longest friends and business partner. Warren’s son, Mike, continues to display an advanced work ethic and stoic resolve that seem to have been a direct result of Warren’s leadership and modeling.

Read Obituary

Effective Leadership Teams

Over the last few years, I’ve watched first-hand as two teams transition out of reactive decision making and into more proactive choices. In both cases, defined and organized leadership teams are at the center. Regularly confronting organizational patterns and trends becomes a gateway to improved performance. It also provides increased alignment around company vision, values, and behaviors.

Beyond traditional c-level leadership, interdisciplinary leadership teams can also be highly impactful. Take Business Operations for instance. Operations is one part of the organization’s needs, but a growing company will eventually require more specialization.  Selecting key members within operations will allow for increased buy-in and deeper focus are the vital part of the organization.

In a recent session with our Operations team at Polar Notion, we distilled the form and function into the following concepts.

The Purpose

We should explore current operational pains, in order to produce lasting organizational gains. The discussion time should focus on things that are high impact, high frequency, and high volume.

High Impact items are those which present substantial cost, unsustainable inefficiencies, or significant opportunities. A problem around company culture, for instance, runs the risk of effecting every part of the business.

High Frequency problems are felt on a regular and recurring basis. Assuming all things are equal, a pain felt daily is more important than one felt annually.

High Volume problems impact multiple people. While it’s important to address problems of all sizes, the cost is much great when felt in mass.

Ideally, issues appropriately sized for a leadership team would overlap in these areas. The goal shouldn’t be to tackle them all at once. If appropriately prioritized, the gains and improvements will likely compound.


Consistent agenda’s are crucial of standing meetings. Here is a simple example we’ve tried for the operations team.

  1. Everyone brings 1-2 problems and proposed solutions.
  2. Each person shares problems.
  3. Nominate a ‘winner’ based on highest value to organization.
  4. Chosen problem is unpacked in more details along with proposed solutions*.
  5. Remainder of time is identifying and discussing solutions.

*Solution should include:

  • Classification of problem (people problem, strategy problem, cash problem, execution problem).
  • Proposed action?
  • Who is needed?
  • What does success look like?


Continuous, forward movement is crucial for an organization of any size. A healthy cadence of tackling the biggest problems can lead to organizational maturity, growth, and a more enjoyable work experience for all.

Big Meetings and Better Choices

There are few things more costly than large, group meetings. Whether we realize it or not, they are the greatest expense of a business. More than salaries, benefits, or a physical building.

More than utilities, inventory, benefits, or a physical building. They may be needed, but it’s a tall order to make sure they are worth it.

They disrupt the day, occupy limited time, and become bottlenecks to productivity. If Deep Work is where we experience a state of flow and professional achievement, large meetings usually impede that progress.

Here are some strategies to build better meetings.

Choose smaller blocks.

There are plenty of cases where large meetings are needed. Whose says they have to be long? Many businesses default to one hour block. Unfortunately, stuff expands to the space you give it. How different might a meeting flow if everyone knew there was only 30 minutes? 15 minutes? There is nothing magical about an hour, though it seems to be a common interval. For an average work day, 1 hour meeting consumes over 10% of your time.

Review priorities regularly.

As I mentioned in weekly rituals, priorities are constantly evolving. Coincidentally, some meetings are scheduled weeks or months in advance. Before blindly attending, evaluate it’s relevance and have the courage to cancel if it’s no longer necessary. Not only does this free up precious time, but it also respects the time of other attendees as well.

Keep them small.

Other than a demo, I’m skeptical that a meeting with more than 6 people is useful for everyone. Meetings should block as little time as necessary and involve as few people as possible.

Come prepared.

Meetings should have an agenda ahead of time and all parties should come prepare with their contribution. Nothing is more useless than a directionless meeting or one in which everyone isn’t prepared to contribute.

Opt out.

‘Do you need me in this meeting’ is a fair question. Imagine if you don’t understand why you were present you would have permission to leave. More people would welcome this than you might expect. Excusing yourself is more noble and respectable than merely staying because you were invited.

Protect your schedule.

I’ve found meetings work best when they bookend larger chunks of heads-down time. Rather than slicing a 3 hour block in half with a meeting, you’ll have more uninterrupted time if you schedule the meeting at the beginning or the end of that time.

Introduce a Reschedule Limit.

If a meeting gets rescheduled more than twice, perhaps it wasn’t that much of a priority in the first place. When considering how many people are impacted, the act of finding an opening on everyone’s calendar is an even greater drain.

Batch productive time.

Allowing mental space to do great work is important. Identify key days that can be free from meetings. These prolonged strengths of work can often become an oasis from otherwise cluttered schedules. At Polar Notion, we start sprints on Wednesdays and end on Tuesdays. This makes Tuesday and Thursday crucial days in making progress. These days should be as clear as possible.

Shoulder to shoulder

Mentorship and learning is one exception. Meetings that fuel a deeper understanding, rich decision making, and professional development are crucial. We’ll try to invite team members into meetings where they could learn something new or practice a skill they are developing. If you see a particular meeting as a learning opportunity, speak up, make sure you’re in the room, and make sure it was worth it.

Saturday Mornings

The world is quiet on Saturday morning. My phone doesn’t ring. New emails are not piling into my inbox. The time is all mine.

While somewhat overstated, I seem to do 2-3 days worth of work within a few hours. The day is optimized for heads down, distraction free output. I’m afforded hours of deep work.

Why am I working on a Saturday? These days, my schedule is splintered by messages, meetings, and management. I share my time with two business. This allows our family to maintain our standard of living, my wife to stay at home each day with our girls, and my mind to fully leverage it’s passions and interests. The diverse contexts allows me to compress decades of experience into just a few years. I realize it won’t last forever, but I find the work invigorating and impactful.

Balancing Polar Notion and New Story, its likely someone is waiting on me for something. Saturday is my chance to catchup on everything. I crush outstanding tasks, send followups, and finish documenting any lingering thoughts. Anything that builds up during the week, it’s nothing a well managed Saturday can’t address.

I love leading teams and investing in the lives of others, but a block of time to myself helps me stay balanced. I’d likely trade a year of Thursday afternoons for a month’s worth of Saturday mornings.

Data is Feedback

The value of data will vary depending on stage of the business. Regardless of ones season of business, the numbers matter. They will likely be different, but tracking key information is no less important. Most often, it’s a few numbers that impact an organization’s performance.
For young businesses, it’s hard to know what matters since change is constant. There is a bent to focus on things that are easy tracked, such as Google Analytics, revenue, or expenses. However, there is more pointed information that can have a greater impact on the business.
At a high level, the data of the business fits into four buckets:
  • Sales
  • Operations
  • Financial
  • Product/Service Data


Sales is the front door of the business and focuses on prospects and new business. A few numbers can determine the health of ones sales pipeline. Also, the right numbers can provide insight into the future business success.
Common metrics include:
  • conversion rate
  • close rate
  • new customers


PersistIQ. An outreach automation tool, PersistIQ simplifies followup emails. It can be time consumng to stay in touch with unresponsive individuals. Persist helps followup at various intervals without pulling attention from more eager prospects.


These are the basics of any business, regardless of size. Common metrics include:
  • Revenue
  • Expenses
  • Profit
  • Gross Margins
An important note, expenses within some businesses are much more important than others. At Polar Notion, we spent some time in early 2018 looking at cutting expenses. As a lean service company, we realized our time wasn’t well spent. Without inventory sitting on a shelf or high overhead costs, we stood to gain pennies. Time spent increasing efficiency however, yielded significant returns.
In ‘Simple Numbers, Straight Talk, Big Profits!’, author Greg Crabtree discusses key financial numbers. His has identified ‘Return on Invested Capital’ as any businesses greatest success metric.


Xero. We’ve used this for years as cloud accounting software. It provides simple reporting and access to our information wherever we need it.


Operational data and metrics speak to the work of the business. This isn’t the data that’s part of the core service, rather it’s information about performance around the product or service.
  • customer satisfaction
  • customers services
  • churn
  • customer retention
Net Promoter Score is a example of Operational Data. ‘How likely are you to recommend to a friend’. It illuminates how well the business is delivering on what the customer is buying. A simple 5 star rating can also go a long way in understanding what matters most to consumers. At New Story, an international housing nonprofit, we track funds received. Atop this common financial metric, we also track how fast we can deploy those funds received. At Sharpp, a SAAS product for franchise management, we look at daily active users.


Promoter. A tool for tracking your Net Promoter Score, Promoter makes analysis straight forward. The net promoter score is a little more complicated than most realize. This tool handles the collection and calculations, which saves time and energy.
Google Reviews. Their simple 5-star systems keeps the barrier for feedback quite low. Assuming the reviews are positive, it can also bolster a brands online presence. If people are searching for your business, chances are they’re using google. Why not show market validation when they find you.

Product/Service Data

Data that pertains to the product or service has become popularized in recent years. Artificial intelligence, machine learning, and data science depend on this type of data.
  • Bounce Rate
  • Pages per Visit
  • Session Duration
  • Popular Search Terms
  • Most engagement content
  • Usage times
Google relies on information like number of times ‘fluffy cat video’ is searched. This drives the quality and price of their advertising service.
Lyft and their ability to match drivers and riders comes from service records. The more they know, the better they anticipate and provide value to customers.
Facebook is best example (though likely the worst if tracking benefit to humanity). Their ability to collect and take action on user data has led them to a half-trillion dollar company. Customer satisfaction is plummeting, but their knowledge of our behaviors is unaffected.


Google analytics, Full Story, and are great tools for tracking user activity. Armed with this knowledge, you can make more informed decisions.

In closing

In the end, everyones key metrics will be different. What matters most is consistency and simplicity. Three numbers tracked daily will prevail over dozens of numbers rarely engaged. Start by identifying 1-2 numbers before group. Online how often you’ll track them and where you get that information. When possible, include others in the process. Consider making those numbers more visible within the organization.
That which gets measured, gets improved.

Making Big Decisions

The discipline of big decision making

As we’re presented with important decisions, it’s easy to procrastinate or become immobilized. Over time, the stakes get higher and our decisions affect more people. To withstand the pressure of major decisions and keep moving forward, I’ve outlined habits I revert back to when big decisions arise.


Before leaving corporate life to raise our kids, my wife was wrestling with a decision for months. At the time, she was not sleeping well. The workload was causing her to neglect her health too. Recognizing the need for a change though feeling too overwhelmed to decide, we scheduled a day or so away at the spa. No work, agenda, or responsibilities she was free to rest up, relax, and recover. Before returning home less than 48 hours later, she knew what she had to do.

Don’t make big decisions when you’re off your game. Being clear headed and calm is invaluable. Sleep, food, and exercise all play a part in our mental capacity. Their presence or absence continually impact our lives.


Think back on past experience. While our victories can be enlightening, our failures are often more useful instructors. Those unwilling to learn from their mistakes are doomed to repeat them. For me, writing is part of my reflection process. I’m constantly evaluating past situations based on my current understanding.

Over the years, I’ve found it enlightening to revisit the same experiences regularly. As we learn and grow, it’s likely our own history will reveal new insights. There are a few anchor moments that serve as a baseline time and time again. Those this can be somewhat painful at times, our past experiences continue to shape us.

Weigh Tradeoffs

Imagine you’re juggling 6 balls. Some are rubber, some are steel, and others glass. Rubber will bounce back quickly if dropped. Steel won’t bounce, but it likely won’t be damaged. Glass, unfortunately, won’t take a hit. You can’t choose how fragile the balls are but if you’re deliberate, you can let the right ones fall.

At any time there are dozens are competing priorities. Time, cost, quality, and satisfaction are just the tip of the iceberg and they rarely work in unison. It’s important to spell out what’s most important and be willing to compromise on the rest. We’ll never be perfect, but we can choose where to double our efforts and what we should let slide.

It’s also helpful to assess the consequences. Some choices have limited consequences while others may be painful to recover from. Decisions with a large upside and limited downside are usually a great place to start.

As leaders, common tradeoffs include:

• Timelines

• Budget

• Morale

• Quality

• Speed

• Value

Due to so many tradeoffs, there is rarely a ‘right choice’. Optimize for the most important factors and let the rubber bounce.

Gain Perspective

In 2017, our team at Polar Notion was pulled into a law suit. The experience shared by fellow business owners and entreprenuers proved priceless. Not only did their perspective help reframe my expectations, we went into the situation more informed and level headed.

Ask others who have made similar decisions and whose insight you trust. Leveraging their expertise and insight, filter your situation through their perspective. Beyond settling for ‘what would you do’, inquire about a time when they were in a similar position. ‘What did you do’ will lead away from speculation and toward real world experience. You path will be different but the exercise can reveal new insight.


In 2014, separate from our existing business, we tried to launch a software company. The market seemed solid and the technology worked well… the issue was our commitment to the idea. Allowing ourselves to be distracted by other projects, the failure can be attributed to our level of commitment.

The final and most important step is taking dedicated action. More often than not, failure can be traced back to weak commitment, not the quality of our decision. When you take action, commit fully. A mediocre decision, fully execute beats a great decision with half-hearted effort.

If you have take the time to rest, reflect, weigh tradeoffs, and gain perspective you should trust your conclusion enough to move forward confidently.

Weekly Rituals

Over the years, I’ve developed a series of daily, weekly, and monthly rituals designed to keep me focused and moving forward. Rather than allowing each day to dictate my priorities, these rituals provide a cadence of thoughtful progress.

In recent conversations with entreprenuers and business leaders, some of my weekly rituals have been of particular interest.


Before the momentum of a week, the following actions help things stay within my control.


Priorities are constantly evolving. Coincidentally, some meetings are scheduled weeks and months in advance. Before blindly attending, evaluate it’s relevance and have the courage to cancel if it’s no longer necessary. Not only does this free up precious time, but it also respects the time of other attendees as well.

A business meetings without written agendas should be prime candidates.

“Time is our most valuable asset, yet we tend to waste it, kill it, and spend it rather than invest it.”  – Jim Rohn


If you have a full schedule, doing a bit of restructuring can free up whitespace. For example, meetings across the city can be grouped to reduce travel time. Our office is on the west side of town, so I want to make the most of an eastbound trip.

It also helps to look another week out. Meetings late one week can often be pushed into the next, especially when it adds focus and attentiveness.


Nothing will waste more time than arriving at an appointment without your details in order. Even if just a few bullet points can help keep the conversation on track.

As I’ve become more intentional about adding value to others, I’ll look over their social profiles and see what they’ve been up to. This can frame a social interaction and illuminate where I can be more helpful.

“If You Fail to Plan, You Plan to Fail.” -Benjamin Franklin


If we are not careful, one week will easily bleed into the next. A post-week ritual can reduce the mental load heading into the weekend. Knowing you’ve closed a week well can be the catalyst for great rest and relaxation.


Before following up with people I met with throughout the week, I take time to reflect on who introduced me to the other people involved. Whether personal or professional, I’ll reach out to the person who made the introduction, express gratitude and when appropriate, share about the meeting I had as a result of their generosity.

This includes recent and age-old relationships. Even after catching up with an old friend, I’ll send a quick note to the person who introduced us long ago. In a recent interaction, the friendship was over 10 years old.

“How do you know if someone needs encouragement? If they are breathing.” -Truett Cathy


Once I’ve expressed gratitude, I’ll followup with the actual attendees from each meeting. Whether we exchanged a quick call or a monolithic meeting, I touch base. Obviously touching on any commitments made in the meeting and passing along any addition words.

When appropriate, I suggest next steps with clearly defined options so they don’t have too struggle through a similar response. Yes, by end of week some people have waited a 3-4 days for a followup. I’ve actually found this delay helpful to actually process our conversation. Also, it sets healthy and sustainable expectations for the future.


After the followup, I’ll push myself to make introductions on the attendees behalf. Rather than asking for something, I end the ritual with a deliberate attempt to add value.

If the meeting was with a code school student, I’ll intro them to fellow graduates in the community or potential employers.

If it’s a potential client, I’ll connect them to other professionals within their industry or people who they would like appreciate getting to know.

This habit creates a great sense of accountability during our time together. As they talk, I’m actively listen for ways to amplify their interests.

“If you help enough people get what they want, you will get what you want.” – Zig Ziglar

If you haven’t noticed, each of these habits pertain to time. At the beginning of the week I set out to protect it. After the week is over, I want to make sure it was as valuable as possible. Time is our most valuable asset. Our behaviors should reflect that.