The world needs more successful software.

It can improve our lives individually and it has the potential to create financial growth for our businesses and the wider economy.

And, yet, we as a community can still struggle with building and managing successful software products.

You know the statistics: 9/10 software startups fail, and 85 percent (or more) of internal software projects are either challenged or abandoned completely.

Below are just some of the unique tactics we’ve seen successful leaders employ to steer their companies clear of those damning odds. That’s no small feat.

Stay close to your customers, even the ones you don’t have yet.

“We care about our customers.”

Sound familiar? But be honest: in your last staff meeting, how much time was devoted to talking about your customers? How about your last scrum meeting? What about your last financial report to the board?

The leaders we work with who talk directly to customers deeply understand the problems they’re facing—and more successfully understand how their company can provide an indispensable solution. When you find your customers’ pain, and you will find the problem you need to solve.

Yes, this is fairly common sense, but it’s a surprisingly easy thing to lose track of, especially as your company hits new levels of success. CEOs who carve what time they can to sit in on customer service calls or personally answer customer emails are far more likely to remain lock-step with what their customers want and need.

In an interview with Drift, Toast CEO Chris Comparato says:

… I often start with the customer and work from that dimension when looking at the customer experience including what to sell, what to build or enhance, and the customer’s journey once they are on our platform. Today I still have several meetings and calls a week with customers. Some brand new, some old, some happy, some perhaps not.

Simply put, there is no growth without customers, and leaders with deep customer knowledge and empathy make better decisions for the future.

There is no “perfect” software, there is only “ready to ship” software.

This is one of the trickier, but more important concepts when it comes to working in software–it is never “done” and it will never be “perfect.”

Plenty of smart leaders have pushed off a release, waiting for a software product or feature to be “perfect.” We get it, it feels like the right thing to do. What you may not realize is that that delay inadvertently creates the space for your customers to settle on another solution.

Software is just that, soft, and the most valuable software will change and grow as your business and customers need it to.

CEOs at SaaS companies who are successfully attuned to their customer base have the hard-won confidence to step back and let their product live for a bit. This patience and space allow the customer to guide them to what needs to be tackled next—a key to cost-effective product management and development.

The product going live is just the beginning, not the end.

Hand your developers business goals, not just a spec sheet.

Most of the leaders we work with have come up through the ranks because they know how to sell and grow a business, not because they know how to write code. Lacking a shared vocabulary or common expectations with developers is, therefore, a natural blind spot for a lot of our clients.

It’s also one of the main reasons non-technical CEOs reach out to us, we help leaders bridge the gap of understanding between business vision and production tactics. Software development runs deep in our DNA, and we infuse nearly every phase of our Product Management practice with the driving mantra
that technology should support your goals and provide a good return on investment.

A leader who can help his or her developers understand the larger business context of what’s being built (beyond just a feature list or bug ticket) finds the fastest route to that good ROI.

Developers’ understanding of what the product is trying to accomplish, who will be using it, and why helps ensure true product-market fit with efficiently built, scalable software. After all, developers are often the last line of defense against unnecessary feature creation or poor software architecture decisions.

Leaders who give developers the bigger picture empower them to build the software that meets it.

Help your Sales team walk away from imperfect opportunities.

CEOs and Presidents who have a clear understanding of their target market are able to set realistic sales expectations and ensure their Sales team is spending their energy in the right places.

In other words, keeping Sales away from bad revenue.

It can be tempting for your Sales team to stray, even just a little, from your product’s core offering or service philosophy to close a deal. But smart leaders know that deals that are “close enough” can be miserable and costly, and they make sure their Sales team knows it, too.

The “close enough” customer is often the squeaky wheel that can lead a product astray with ad hoc feature requests. By creating the space to walk away from bad revenue, you avoid the time sunk in these accounts that can extend beyond sales, to your product and development teams. A losing proposition, all around.

Presidents and CEOs who empower their Sales teams to honestly tell “close enough” customers “No” or “Not right now” will better serve everyone in the long run. Those customers will either come back to you when the timing is right or send a referral your way who is a much better fit.

Consider the opportunity costs of pulling your team’s focus.

One of the hardest parts of leadership is balancing the resources you put toward growth with those required to keep the machine running and on-track.

Most leaders live in the future—thinking about staying a few steps ahead of the competition, or what would happen if they pursued the recommendations in that article about building software of tomorrow that blew their mind.

At the same time, the work their product and development teams are doing right now is critical to the organization’s ongoing success.

As a leader, you have to think about moving big pieces, whereas your teams are focused on fulfilling their accountabilities.

Leaders who realize that interruption stresses everyone out (and ultimately makes their job more difficult), often lean on trusted outside resources. As they come across the next great experiment they’d like to try, they’ll call on someone not responsible for next Wednesday’s goals to vet the new idea, thereby avoiding disrupting the internal teams.

There are plenty of seasoned experts who can help you evaluate your ideas, validating and quantifying a potential shift until it is well worth refocusing your team’s attention.

Your team, your product, and your customers will thank you.

Interested in learning more? Check out our Product Management process and let us know if you have any questions through our Contact Us form, below.

“If I had asked people what they wanted, they would have said faster horses.”

So said Henry Ford (apocryphally, it turns out), and the misquote has been used for years to justify developing products without thorough customer input. As many innovators soon discover, though, software development is not a Field of Dreams, if-you-build-it-they-will-come scenario. If you fail to solve the right problem, no one will come.

Harvard Business School’s Clayton Christensen shed new light on how we think about products and problems. In the classic Harvard Business School paper, one researcher noticed that 40 percent of milkshakes at a fast food restaurant were purchased in the morning. That’s an odd time for milkshakes, so he started investigating the phenomenon.

It turned out that morning commuters bought milkshakes to both satiate them until lunch and to have a snack that would last the whole commute. They weren’t just buying a milkshake. They were hiring it to fill them up and liven up an otherwise boring task.

The problem customers experienced wasn’t a need for sugar or a variety in flavors. The problem they were solving was completely different, and that knowledge changed how the chain innovated that product.

Solving For X

Business owners do this all the time. We think customers are experiencing one thing, but the truth is they are often coming from a completely different angle. Solving for one problem might drive a little business. Identifying the right problem will produce exponential growth.

Identifying that big problem is the key to great innovation. There are three things to think about before you start:

  • Who to ask
  • What to ask
  • What NOT to ask

Step One: Know Who to Ask

First, make a list of 5-10 friends who could talk about the problem you’re considering.

Don’t ask them.

It’s never a good idea to ask friends and family for one simple reason: they love you. They will want to answer questions in the way that makes you happy, and they will encourage and support even your wildest guesses.

Current employees should also be on the “don’t ask” list. Many of them will be experts in your industry, and that’s exactly why they will struggle to understand the mind of the customer. Employees will also be driven by motives that are different from a customer (the need for a raise or recognition, for example).

Instead, ask your list of people for 5 referrals to others who experience the problem you’re investigating. These 25-50 are your true potential first customers. They will be interested in solutions, not just your success, which will help you get to the heart of the problem more efficiently.

What To Ask To Find The Right Problem

Keep these two tenets in mind: ask broad questions, and then focus on the one you can solve.

For example, you want to develop an app that will streamline the payment process at restaurants, and you’re talking to an owner. You might ask, “What are your biggest problems with collecting payments?

You will probably get several answers. Maybe the waitstaff is too lazy or too busy. Maybe the customers keep walking out. Maybe the system keeps breaking.

Depending on your idea, you could be looking to solve any one of these problems. If so, ignore the noise, and focus in on what you want to solve. You can often solve any problem, but rarely can you tackle every problem.

Your next question will be equally important: How do you solve this problem now?

Every problem in the world has some solution already in place. It might be incomplete or inefficient, but if this is a common challenge for business owners, they are mitigating it in some way. That status quo will be your competition, even more than actual competitors.

This question is also valuable because if you can create a solution that mimics the best part of the current status quo (while improving the worst parts), you will be well on your way to a great solution.

Last question: how much do you pay to solve it now?

Some problems are so painful, people and businesses are willing to pay to fix them. Others are just not that painful. If your target customer feels the pain of collecting payment, but the current solution works just fine, you’ll have a hard time convincing them to switch.

The beauty of interviewing people is that you will have an opportunity to note their body language and tone of voice. When interviewees talk about their problems and current solutions, do they roll their eyes or get agitated? Or, do they seem nonchalant and unconcerned? Simple conversation can uncover more (and more valuable) information that prescriptive questions can.

Do NOT Ask This Question

There are some questions you should ask, but there is also one question you should avoid at all costs.

What do you think about…

This question comes in all shapes and sizes. It can sound like,

  • “I think X, what do you think of my thoughts?”
  • “I solved this problem this way. What do you think?”

This question is ineffective because it narrows the scope too soon. It is inherently future-focused, asking someone to predict if and how they would use your solution in the future. Even Steve Jobs didn’t understand how revolutionary the iPhone was, and if Apple had tried to plan, it would have failed.

If you ask someone to comment on your solution, they will, but you will probably miss valuable data–and long term vision–along the way.

Focus on the Problem, Not the Solution

It’s common advice, but when we get excited about a solution, it can be difficult to maintain. Remember that your first responsibility is to identify the job your target customer needs done. For example, they don’t need sugar or calories. They need a snack that will satisfy them and last for the whole commute.
Solving the right problem results in powerful innovation that sells. Also known as the sweet spot.

When Kyle Duke joined PatientFocus, the company was feeling the kind of pain every company wants to feel. It was growing.

Fifteen years ago, the market wasn’t ready for PatientFocus. At that time, healthcare costs were primarily covered by insurance. Only 10 percent (or less) of a provider’s revenue came from individual patients. Of that 10 percent, only 10 percent was fully collected, but in the grand scheme of write offs, that wasn’t worth the cost of investing in a solution.

Things started changing in 2008. Today, individuals account for 30 percent of a provider’s revenue, but the collection rate has remained at 10 percent. Do the math, and you’ll see what PatientFocus founder David Frederiksen saw. That’s a hit to the bottom line for the big players. It would be devastating for the smaller ones.

PatientFocus serves hospitals and other healthcare providers by managing collections from self-paying patients. But they don’t do it in the same way it’s been done before. The company works on behalf of the providers, but focuses on patient experience. The system makes it easy for patients to ask questions, get clarity, and set up payment plans when necessary. Often patients don’t even realize they’re working with a third party.

Things were going well for PatientFocus. So much so that in 2015, the company realized a huge bump in sales. And then the technology-related problems started.

“In 2015, the dam broke,” Duke says. “We sold 15 new clients, and nobody could keep up. We couldn’t get them on the platform, it took too long to onboard them…so what we saw was this huge growth in revenue and huge growth in expenses because we were having to add as many people as we were clients.”

When Duke joined the company, he was tasked with finding a solution. His approach could be a master class in adapting technology to solve business problems.

Step One: You Are Here.

Before making a single technology decision, Duke and Frederiksen spent three or four months digging into the core of the business. They hired an outside consultant who guided the process, uncovering data and trends with the cold eye of a third party. With potential revenue being lost every day, and dozens of clients and employees to consider, throwing things at the wall to see what stuck was no longer a good option. They needed strategy a strategy to handle the Iron Triangle.

iron triangle


The timeline for building a new custom platform did not line up with the company’s customer and internal demands. Moreover, with the developer team already working nonstop just to handle maintenance, going back to square one would take substantial investment in technology staff. With serious timeline and budget implications at play, it was clear: rebuilding from scratch would not work for PatientFocus.

Instead, Duke and the team looked broadly at everything they needed their system to do in order to find alternative solutions. They looked at process, workflow, documentation, technology, and where the system was breaking down. The goal was to automate the process, making it repeatable and scalable, while also serving individual clients.

It became obvious that a third party solution–with heavy modifications to serve the PatientFocus purpose–would solve their problems faster, cheaper, and provide better service to their employees.

Step Two: X Marks The Spot.

After settling on a solution, it was time to start building. Which meant a hard conversation with the company’s developers.

“Ok, we are not going to rebuild the platform from the ground up,” Duke remembers telling them. “That was day one. By about day 10, all 8 of them {the developers} were gone.”

It may have been a painful time, but that firm stake in the ground served both PatientFocus and their employees. The developers were able to identify that it was time to find jobs that would meet their career goals more fully, and the company was able to funnel expenses to the right resources.

It’s important to realize, though, that the PatientFocus team could not have outlined this same map when the company was founded. They needed to dive in and build their first MVP in order to understand client needs, their own workflows, and what processes are most easily automated. They drew a solid map from their current location, but, like most successful companies, they had to do some learning and course-correcting in order to reach that spot.

Step Three: Take The Team With You.

Sometimes. As we’ve seen, when there are shifts in technology or strategy, there will be some people who will find new opportunities. But for the team members who stay, technology change is people change.

Frederiksen and Duke managed this change by extending their relationship with their consultant. They understood that even though the team was onboard, change is hard. Even good change.

Every week during the transition, leadership mapped where every single employee sat on the change curve. They made a plan for helping the ones who struggled or fell behind. With timeline as a driver (the rebuild was slowing sales), the company could not afford delays. Duke credits that level of employee shepherding with their success.

“For us being able to start building in December and put the first client on in August, that’s the only way that happened,” he says.

Lessons Learned

Decisions like platform and custom vs. third party seem like technology decisions. But these are really business decisions. With the right strategy, technology can affect every part of the income statement – it can increase revenue, reduce variable costs, and reduce overhead (or keep it constant in the face of growth), all of which results in a healthier bottom line.

For PatientFocus, changing their technology more than doubled their daily activity. On the old system, they completed about 500 outbound calls to patients a day. Today, they can manage up to 1200. Employees are now able to focus on high value work (talking to patients) instead of menial tasks like looking up phone numbers and records. That means more revenue, for them and their clients, while also keeping headcount and overhead low.

At a high level, leadership is no longer worried that the system may crash at any moment. Being secure in the knowledge that the core technology would run smoothly equals exponential return on the CEO’s brain space. Now, rather than praying the technology works again today, he – and the sales team – can focus on growing the business.

The PatientFocus story reminds us that business and technology are no longer separate. Finding the right technology is worth the effort because it can literally make or break your business.

It’s 2017. MOST businesses today use software in some way or another. We’ve talked aboutcustom and off-the-shelf software before, but regardless of what your business model is, you probably need at least some off-the-shelf software to run it.

Small businesses need to answer a new question: not “Should we incorporate tech into our practices?” But, “WHICH tech is most valuable for us?”

Thoughts on Business Software Tools

Okay, so if you need off-the-shelf software, how do you know what to pick? Each industry has its own unique tools, but a quick survey of our team yielded some great advice for any business owner.

Bootstrap first. What can you do to duct tape a solution together? If you spend some time solving a problem without software, it will give you a better understanding of what you need and why you need it. Example? We’re currently working on a solution to our complex scheduling challenges. With several developers and projects going at once, keeping up with the schedule gets complicated. Post-it notes and a whiteboard will help us see the whole problem. Then, if that low-fi solution doesn’t solve it, we know where to start building.

Pick the right size. One of the worst things you can do is overbuy. You don’t want software to be so high touch it hinders your team rather than helps them. You also don’t want to buy a whole suite of software for one feature. If you’re going to make the investment, take the time to train and implement the solution fully. You also want to make sure the cost doesn’t outweigh the benefit. Huge licensing fees or custom building costs aren’t always necessary.

Stay close to the money. We say this all the time around the office. Don’t ever let the allure of software distract you from your core business. If software costs (in either time or money) pull you away from building your customer base, shut it down!

Business Software We Use And (Mostly) Love

So, what software does a company full of developers recommend? We do use some software specific to developers, but we also use some tools that we think would benefit any business.

  1. Slack. Hands down. Everyone on our team loves and recommends this chat tool. Even when you run a small team, the accessibility is invaluable. You can talk to the team easily, but you can also share and store documents and other files for easy access. Our tip? Set a company policy for when people will be available and when everyone will be on “do not disturb.”
  2. GSuite. At this point, most of the world runs on Google. But, if you’re still not on board, Google Apps was the second most recommended software in our team survey. Gmail, Drive, and Calendar all work together to keep your team on track. Company-wide buy-in is important, though. For example, at Centresource, most of us keep our calendars up to date so it’s easy to schedule meetings without 50 emails (or Slack messages) nailing down a time.
  3. Project Management. We use Trello, but everyone has a favorite. (And our developers have opinions…) Basecamp and Asana also have their merits. Even if you don’t identify as a project-based company, you probably have projects more than one person contributes to. They could be internal or external, but regardless it’s vital to put all of the information in one place. I use a Trello board for this blog’s editorial calendar. It makes it easy for me to remember, but it also gives my teammates access to what I’m working on and opportunities for them to contribute.
  4. CRM. Regardless of size, customer relationship management (CRM) software organizes contacts and streamlines interactions with them. There are a million options out there. We like Contactually for email flows and Pipedrive for sales pipeline data. The Hubspot CRM is also a great tool that can easily integrate with other marketing efforts.

What tools are you using to build and grow your business?

‘Tis the season for 2017 “tech trends” and forecast articles. (We like Forbes, Business Insider, and InfoWorld.) There are lots of great lists, but we were curious about what trends might affect Nashville in the coming months. So, we asked some experts…the Centresource development team.

According to Business Insider, software spending is projected to reach $357 billion in 2017. For Nashville companies looking to stay ahead of the curve, it might be a good year to consider what custom software would streamline business and increase innovation.

There’s a lot happening in technology, but the dev team had a pretty strong consensus on what trends Nashville should pay attention to.

Machine Learning

Conversational UI and machine learning were both popular choices. Machine learning is a broad section of technology that will undoubtedly make inroads into enterprise in the coming years. This isn’t just robots. It’s any program that can learn and adapt to data without being reprogrammed.

One subset of machine learning is conversational UI. Think chatbots as well as Alexa, Siri, and Google Home. This technology allows the user to communicate with a service just like they would a person, via talk or text.

Why does this matter in Nashville? Machine learning has big implications for healthcare–not by replacing human doctors and nurses, but in aiding them with better diagnostics, treatment, and followup.

But, even outside of healthcare, building a chatbot or other conversational UI program will give customers more convenient access to your company. By helping prospective and current clients answer questions quickly, you could shorten a sales cycle or increase retention.

Finally, as Apple, Google, Amazon, and Facebook open their machine learning APIs to third parties, companies wanting to reach and serve users on those platforms will be smart to start development in 2017.

Internet of Things

Another big topic in our dev talk was the Internet of Things (IoT).

The IoT is not a new conversation, of course, but the increase in machine learning may be the tipping point for all those connected devices. As the ecosystem grows, we can expect to see intelligent devices communicating with each other.

What does this look like? Smart drone deliveries. Driverless cars. Virtual assistants. It all sounds futuristic, and probably won’t take over Nashville in 2017, but the technologies are being put in place to make it reality.

So, this matters to Nashville businesses….why?

One of the biggest hurdles to the Internet of Things is security. Companies that can figure out how to keep data private and secure in the IoT will be well-positioned to grow in the coming years. Even if you don’t make connected devices, incorporating connected devices into your business model will be beneficial–and the sooner you do it, the better.


Security is an issue with the IoT, but that’s not the only place it matters. No one has really solved the security problem in our new society, and it’s a big one to be tackled in the coming years.

As one of our Managing Partners, Brandon Valentine puts it: “Between the IoT botnet that sprang up this year (Mirai), another banner year for credit card hacks, and the concerns around russia tampering with the election, a lot of firms are going to have to get serious about security in ways they aren’t right now.”

From payments to customer data to HIPPA regulations, security is a big problem to tackle in 2017. Every business, in Nashville or anywhere, needs to be aware of and meeting security threats.

Global Tech Trends

And then there are the big things the global tech community is talking about. Virtual and augmented reality. Driverless cars. Blockchain (which is bigger than Bitcoin and might solve a lot of security woes.) Serverless computing.

These things may not affect Nashville…yet. But the ground is being laid for ever more innovation.

It’s official. Software has eaten the world, just like Marc Andreessen predicted. No matter where you turn, you will find software products and solutions. Sometimes they’re amazing and the perfect solution. Sometimes…not so much.

Either way, in 2017 more people will begin to focus on product development and building great products. After all, if you’re in business, software can solve a lot of problems.

But, what does that mean? Is it enough to know how to operate software? Or do you need to go to software school and learn to code?

Thankfully, there’s always a middle ground. We love product at Centresource, and we know that in the next year more business owners will need to grow their understanding of how software works. So, we asked around the office and got some great recommendations for you to learn more about product ownership.

Web Content

What better place to learn about software development than on the web? There are a few great product blogs out there, but we love these two. Even if you don’t want to be a full time product manager, you can pick up a lot of tips from these experts.

This Is Product Management

Mike Fishbein interviews product experts from across the technology spectrum. Recent topics include the Internet of Things, product validation, and venture capital. Sign up for the newsletter so you don’t miss a post.

Mind The Product

Run by the team behind Product Tank, this site is a wealth of great product content. Their manifesto? To further the craft of product management by bringing together product people of all stripes. We love it!

Centresource Posts

And, of course, we’ve also written about product a lot. Here are some of our best posts:

What Are Your Product Cornerstones and Why Do They Matter

What’s The Difference Between UI and UX?

Learning Product Management From…Fruit Salad?


If you’re really ready to dive in, there are plenty of great books on product development, management, and ownership. These are our favorites:

Making It Right: Product Management For A Startup World–Rian van der Merwe

Hooked: How to Build Habit-Forming Products–Nir Eyal

The Innovator’s Solution: Creating and Sustaining Successful Growth–Clayton M. Christenson and Michael E. Raynor

Don’t Make Me Think: A Common Sense Approach to Web Usability–edited by Steve Krug

The Design of Everyday Things–Don Norman

In Person

Okay, reading and listening is great, but sometimes you just want to talk to real people. Nashville has some great product and UX meetups, where people in all stages of interest get together and discuss product topics. Think Homebrew, but in Nashville.

Nashville Product Meetup–Empowers product people to own the things they know. A monthly meetup with presentations, networking and discussions about product development, management and marketing. If you manage an existing product, are a product owner, are developing a product, or are marketing a product… this is for you.

Nashville UX Meetup (NUX)–Supports, promotes, and teaches UX, advocate the value of UX, and foster strong professional networks. User experience includes everything the user touches: including experience strategy, content strategy, information architecture, interaction design, user interface, and usability.

Nashville Agile User Group–If you’re interested in the development process (or already a developer) don’t miss this group. It focuses on promoting the values and practices of Agile development and is a great place to learn and network.

Design Thinking NashvilleHave an interest in design thinking? Looking for support in innovation or improving the culture of work? This group is for you.

Want more product talk? Need to consult about potential product options for your company or startup? Drop us a line and request a free consultation. Our product experts love this stuff!

Business leaders like Richard Branson and Mark Zuckerberg are famous for making quick decisions to launch and grow their companies. “Move fast and break things” has become a Silicon Valley mantra that permeates all of business.

But since not everyone is superhuman like the Bransons and Zuckerbergs of the world, you might struggle to make those decisions. When there are 15 good possibilities, how do you know which is the best one?

There’s an old (hopefully apocryphal) story that perfectly illustrates the analysis paralysis many of us feel on a daily basis. It goes something like this:

A donkey is very hungry and very thirsty. The assumption is that if offered both food and water, each placed in opposite directions, the donkey will go for the closest one first. However, if the hay and the water are placed equidistant apart, the donkey will be unable to decide which way to go and slowly starve to death.

What an ass.

To be honest, the incident never happened, and the theory was never a serious one, but maybe you can identify with the donkey anyway.


  • Do I take the job I hate for more money or the job I love with lower pay?
  • Do I live in the city, where my kids can experience urban life? Or the country, where they have room to ride their bikes?
  • Do I hire Candidate A or Candidate B?
  • When my company is ready to grow, do I buy off-the-shelf software or custom software?


American business values the fast moving, quick thinking decision maker more than other type. But even the best of us can wake up one day and find ourselves paralyzed with all the options.

The Danger of Analysis Paralysis in Business

As a business leader, your daily decisions could make or break your company. How do you know which way to go when time and resources are limited? 

Analysis paralysis–or the paradox of choice–never happens when there is a clear cut winner. You won’t ever choose being trapped in a burning building over taking a vacation, but deciding between the beach and the mountains can paralyze you so much you never pack your bags.

Let’s take the analogy one step further. What if escaping from the burning building relied on your choice between the beach and the mountains, but you don’t know which choice will get you out of the flames?

That’s how it can feel in business. There are only limited resources, and many roads might lead to success. But there’s no concrete way to know ahead of time which those are.

We experience this as a company all the time. Should we focus on building websites or more robust apps and products? Should we spend marketing capital on sponsorships or on hosting our own events?

Should we have turkey or fried chicken for Thanksgiving dinner??

(Come on, team. This answer is so obvious.)

Our Secret Solution to Analysis Paralysis

Terrible menu choices aside, what do you do when you can’t decide which way to go? At Centresource, we have our own unique way of moving forward.

Whenever we find ourselves in a loop–and in a holacracy, this happens a lot–someone always pipes up to ask one of two questions:

  • Is it safe enough to try?
  • Will this bring us harm?

Whether it’s an internal initiative or we need a client to make a decision, these two questions focus in on the things we can really answer.

Is it safe enough to try?


The certainty effect is a key component of the prospect theory, developed by Daniel Kahneman and Avery Tversky. Basically, it says that we are more likely to gravitate towards choices with certain outcomes, even if those certain outcomes aren’t as beneficial as the probable outcomes of a different choice.

We’ll choose safety over risk.

But here’s the thing we forget: there are no certainties. (With medical advances and the current tax structure, we can’t even be sure about death and taxes anymore.)

Choosing an option for “certainty” isn’t always the best, and looking for certainty is likely to hinder you from ever moving at all. That’s why we ask ourselves, and our clients, “Is this safe enough to try?”

There are sometimes real reasons that a solution is not safe enough to try. When a product doesn’t meet user’s needs, don’t launch it. That’s not safe.

When the answer is, “no,” it’s time to figure out what’s keeping it from being safe. Then we can address that issue and move us closer to launch.

Internally, we faced this last year when it came time to replace a project manager. We decided that rather than incurring the expense of hiring, we could distribute the responsibilities to two of our strategists. After a lot of thoughtful planning, we decided it was safe enough to try.

It turned out not to be. The strategists quickly became overwhelmed, and we discovered that the skillsets didn’t align. But, in the interim, we also discovered that one of our favorite PM’s from earlier days was willing to come back to the team. If we hadn’t tried the other tactic first, we could’ve missed out on a great rehire.

Louis C.K. talks about “safe enough to try” in his own brilliant way:

“These situations where I can’t make a choice because I’m too busy trying to envision the perfect one—that false perfectionism traps you in this painful ambivalence: If I do this, then that other thing I could have done becomes attractive. But if I go and choose the other one, the same thing happens again. It’s part of our consumer culture. People do this trying to get a DVD player or a service provider, but it also bleeds into big decisions. So my rule is that if you have someone or something that gets 70 percent approval, you just do it. ’Cause here’s what happens. The fact that other options go away immediately brings your choice to 80. Because the pain of deciding is over.

“And,” he continues, “when you get to 80 percent, you work. You apply your knowledge, and that gets you to 85 percent! And the thing itself, especially if it’s a human being, will always reveal itself—100 percent of the time!—to be more than you thought. And that will get you to 90 percent. After that, you’re stuck at 90, but who…do you think you are, a god? You got to 90 percent? It’s incredible!”

“Will this bring us harm?”


Our second question is the other side of the coin. When we get stuck with the “safe enough to try” mentality, we ask, “Will it bring us harm?”

Sometimes you think you know the answer, but you don’t. (See project manager story above.) But often, the very act of asking the question mitigates the risks. If you understand the potential dangers, you can make a plan to meet those challenges when they come.

The Third Secret…

There is one more element to breaking analysis paralysis in business: a great team.

About halfway through writing this article, I stalled. I was suddenly gripped with burning questions.

“Do I take this angle or the other one?”

Do I use the donkey example or do I talk about the Target CEO?”

“Speaking of donkeys, can I say ‘ass’ in a blog post….”

Yup, while writing an article on analysis paralysis, I found myself paralyzed. A couple of quick talks with teammates smoothed it out, though. Without them, I would probably still be clicking through Google articles, with a dose of Facebook when I needed a breather.

The right team around you will keep you honest. If you get into the habit of asking yourselves, “Is it safe enough to try,” and “Will it do us harm,” all the smart brains in the room with find the answers.

 Then all you have to do is jump.

So, you think you need custom software. Everyone’s doing it, and you’re wondering if it’s time to take the plunge.

But you’re also a little afraid this might be a case of “If all your friends jumped off the Brooklyn Bridge, would you jump, too?”

The custom software question is a big one for all growing companies. It’s expensive, but there’s usually a tipping point at which the ROI becomes worth the upfront costs. The question is, how do you know?

While there are a lot of moving parts in making such a big decision, it really comes down to process and commitment. Are you truly familiar with your process, and are you ready to commit to owning software?

Defining Your Software Needs

The first question you need to ask yourself is, “What do I really need this software to do?” Maybe it’s an internal process or a customer-facing app, but either way, you need a clear idea of the features and benefits of any piece of software.

Off-the-shelf (OTS) software is the way to go if you aren’t clear on those. One of the benefits of OTS software is the ability to help define processes. (It’s also one of the cons, but we’ll get to that in a minute.)

If you are still new to the space, or if the particular process you want to automate is not yet fully defined, chances are good you aren’t the first person to have this problem or need this solution. An off-the-shelf solution will help you define the process and develop a workflow that would be too overwhelming to develop from scratch.


Remember how we said that process-defining ability is a pro and a con? OTS solutions are rigid. Good if you need to define process. Bad if you have outgrown the prescribed workflow.

Let’s take Shopify as an example. Shopify is a robust e-commerce solution that equips a lot of e-commerce businesses. It’s a great solution because of easy integrations and lots of features. As an OTS platform, it’s one we highly recommend in the right circumstances.

It’s not perfect, though. One of the biggest issues Shopify customers experience is the inability to set up recurring payments for customers. Bundling products and easy organization of the front-end are also concerns.

Shopify is just one example of an OTS solution that is great in the early days but is likely to be outgrown over time.

Let’s say you’ve been working with just such an OTS solution for awhile now, and you’re beginning to find its limitations. Maybe it doesn’t give you the freedom your team wants, or it doesn’t perform one little function you’ve discovered you really, really need. What now?

At this point, you can reach out to the company providing your solution and request the feature you need. The problem is, if that feature doesn’t meet the needs of most of their clients–or doesn’t make sense for them financially–you won’t ever solve your issue.

You could also cobble together another third party solution to that one issue and incorporate it into your workflow. This might work beautifully, and you’re off to the races.

Until it doesn’t. Third party software doesn’t always play nice, and you could quickly discover that nothing will integrate seamlessly. Even if you make it work, this cobbling together of solutions will eventually become cumbersome and time-consuming.

While an OTS software is a great way to get started in something new or unfamiliar, once you define your own processes, you’ll probably discover that you need something custom. The bellwether question to ask:

Is my team actually using the software?

If you have a great team in place, and they are constantly dragging their feet to use the software at their disposal, chances are really good that it’s no longer working for them.

Making The Commitment to Custom Software

Let’s be very clear about this: custom software is a long term commitment. It’s expensive on the front end, and you have to budget time and money to maintain and iterate it over time.

That said, much like when you find the right life partner, that long term commitment isn’t scary as much as it is exciting.

With a custom software solution, you will exercise full control because it’s literally made for you. That means you define the features you need instead of the software dictating what you can do. With the right development team, you’ll be able to iterate quickly when it’s time to innovate or update.

Custom software will likely save you time and productivity over the long haul, and as your software gets older, you’ll also need to commit to caring for it. There’s regular maintenance required with any product, but there’s also the need to stay on top of user needs.

But, honestly, there’s regular maintenance and licensing fees with OTS solutions as well. The beauty of investing this money in custom software is that you can build it just for you and your team/users. As needs change, you won’t be beholden to the OTS you’ve always used. Instead, you can adapt your own software as your needs adapt.

The upkeep of a custom software solution never ends, but there is a tipping point where even that upkeep is more cost-effective than inefficient cobbled together solutions.

No really…how do I know?

Okay, so there are lots of pros and cons to both OTS and custom software. When you’re at the decision point, how do you know when to pull the trigger?

Here are 10 ways to know you’re a good candidate for custom software:

  • You’ve tried the best off-the-shelf solutions and still need more.
  • Your current custom software has stopped meeting your needs.
  • You know going custom will give you a true competitive advantage.
  • You spend a significant amount of time and budget on adapting an OTS solution.
  • You know building custom software is expensive, but you also know it will eventually save you time and money if you do it right.
  • You’ve got the budget to build at least a portion of what you need. (Stay tuned for a guide to custom software pricing.)
  • You’ve got buy-in from all the necessary stakeholders.
  • You are committed to maintaining the software over the long haul.
  • Your business model demands custom software (i.e. the custom software IS your business.)
  • You’ve exhausted all other options. No, we really mean ALL other options.

Building custom software–whether you hire developers or outsource to a vendor–is an intense, expensive experience. It’s not for the faint of heart, but it is for anyone who is ready to level up their processes, either internally or for your customers.

If you’ve read all of this, and we haven’t scared you off, you might be ready to dive into the deep end of custom software.

This post is the second of a series about the planning, design, and development of The National Museum of African American Music’s digital exhibit: Rivers of Rhythm. In this post, product strategist Tomiko Peirano discusses the concepting and planning of the application, as well as the user testing process. The first post in the series can be found here.

The idea for the Rivers of Rhythm application was grounded in the client’s desire to illustrate the breadth and depth of American music, and how African American artists drove and shaped that history through an engaging digital exhibit. NMAAM wanted to show the on-going genealogy of our nation’s musical heritage prior to the museum’s opening — a powerful and exciting concept to bring to life.

nmaam wireframesWe started with scribbles on the whiteboard — balancing big ideas with user persona needs, and the data we safely assumed we could get access to (keeping in mind what was plausible for the future product build). A user persona was crafted: the music lover. This user was a tech-savvy man or woman in their early 20’s who thrives on nuanced, obscure information, someone who may ask their friends, “Did you know that Aerosmith were actually big fans of Fats Waller…” (please don’t fact check me on that quip.) 

Working with this persona in mind, we determined what we thought this user needed to see and hear in the application in order to “rabbit-hole” the concept, making the app addicting and easy for a user to get lost in. We identified features such as the ability to go on to a favorite artist’s page and see his or her influencers, their influencees, and so on. We also wanted to create interactive experiences throughout the product, and thus identified opportunities to incorporate audio, video, and text in as many views as we felt made sense for the end users, further adding to the “rabbit-hole” nature of the application.

Once the proof of concept Invision prototype was complete, NMAAM was equipped with a powerful marketing tool to begin raising sponsorship funds — and we had what we needed to conduct user testing to validate our concept. We put the prototype in front of unaware users via We collected great objective user feedback, found out what people expected on certain key pages, what surprised them (for good and bad), and how much explanatory content the application needed. For example, did our concept of influencers/influencees land with people? We assumed a learning curve for any new app, but we needed to see how many great decisions and missteps we had made.

Simply put, the prototype was a success. NMAAM secured a sole sponsorship for the application built from Belmont University and we were armed with invaluable information heading into our technical planning and build. With a deep understanding of the business, marketing, and functional requirements, we went into the application build energized to get started.

Here at Centresource, we love building cool stuff. Building software is like building a house – before you start picking out the floor plan, paint colors and appliances you need to pour your foundation. For us and our software, that means clearly defining answers to the following question – “what are we building, for who and why?” The “What” “Who” and “Why” make up the 3 corners of our product cornerstones triangle and drives the rest of the process.

Let’s start with the who (your Ideal Customer Profile). The saying “if you try to be everything for everyone, you won’t be anything to anyone” couldn’t be more true. Do your research and know who your product is serving. This includes demographics, psychographics and technology savviness among other factors. Don’t assume – get out into the market and talk to your potential users. Find out what motivates them and what scares them. You’ll be surprised what they have to say. product-cornerstones

Onto the what (your Product & Services Profile). What kind of service are you offering? Where are the gaps in the market and who are you competing against? You need to know what problem you’re solving – if there’s no problem or you’re making one up, then you’re in trouble.

Lastly you need to find out the why (your Product Positioning). Perhaps the hardest to define, the why boils down to your products unique positioning in the market and why your target users need what you’re selling.

This shouldn’t be an easy exercise. There’s often disagreements among stakeholders. It can take time to get everyone on the same page. But you need to make smart and informed decisions – get it done and don’t say “we’ll figure it out later.” Because it’s difficult to “figure it out later.” Would you tell your contractor to pour half the foundation of your new house and you’ll figure out the other half later? Probably not.

These early decisions are important because the further you get down the development of your product, the harder it becomes to shift your foundation without implications to your scope, timeline and budget. Imagine you built your product thinking tech-savvy millennials would be using it. You’d probably decide to include a lot of social integrations or a lot of high tech bells and whistles. Three months later you realize that it’s actually grandmothers that want to pay for your product. Their technology needs are much different – all of a sudden, not just the who has changed, but also your what and your why.