Episode #004: The Power of a Life Plan [Podcast]

This week, we discuss the power of a life plan. I’m joined by cohost Mike Manion, Area President of Convene’s Mid-Atlantic region and a frequent host on various radio shows and podcasts.

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Why is a life plan important?

A life plan integrates every aspect of your life together We’re not living a zero-sum game, though we often act as though we are With a life plan, my life is more complete and integrated

My life is actually more like the Olympic rings. The more you scale the Olympic rings, the more they overlap. It’s at the intersection points, where the circles touch and overlap, that I learned I need to spend more time and planning.

Figuring out what to focus on is a creative process. First, I had to figure out what my circles are. Then, I had to figure out how they intersected.

My circles are God and my faith life, myself, family (as a husband and as a father and in my extended family), and my work. All of them intersect.

It’s hard to set aside time to think, but I chose to prioritize working on my life versus just being in my life and letting it run me. I was able to find creative ways to let every single circle impact every other circle.

The 2-step process for making your life plan

Figure out what the circles in your life are Spend time thinking about how they intersect and overlap so that they can benefit each other

If you can take the time to identify your priorities and find the ways where they can complement and support each other while driving your forward, you’ll be living an integrated life.

Question: My challenge for your: find the time in the next 14 days to set aside two 6-hour blocks to simply think through your life. What are your priorities? Where do the concentric circles overlap? I’d love to hear from you! You can leave a comment by clicking here.


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The Changing Face of the Modern CTO - David DeWolf

The Changing Face of the Modern CTO

A few days ago I published the job description I wrote for the CTO 3Pillar is looking to hire in the next few months. In that post I mentioned the changing face of the CTO.

In the ‘software is your brand’ world, the role of the Chief Technology Officer is just as much about the product as it is about the technology. Modern CTOs are innovators and strategists. They understand revenue models and work closely with user experience designers to build engaging products.

The pocket-protector wearing CTO that spearheads an R&D organization steeped in algorithm development and academic research has few options. The CTO of the future is being called out of the back office and into the C-Suite.

Modern CTOs must excel at collaborating across the business and providing executive leadership. They must maintain their technical expertise, but, business acumen is just as important.

Three organizational models have begun to emerge among product organizations. Each requires a new breed of CTO.

The CTO as Product Executive

Many organizations have come to expect CTOs to fulfill the product executive responsibilities. They are as much, if not more, Chief Product Officer as they are Chief Technology Officer. This model centralizes product ownership with the CTO possessing ultimate authority and responsibility over the product. The modern CTO defines both the what (product management) and the what (technology, engineering and process) of the product.

In this model, the successful CTO must drive both innovation and results. They not only embrace, but act as the chief evangelist for lean startup methodologies, ensuring that the product is not only built, but, the right product. The successful candidate has come to appreciate customer experience as much as they have software craftsmanship.

This type of product leadership is most common with B2B and B2B2C business models.

The CMO as Product Executive

In most B2C organizations, product ownership resides with the Chief Marketing Officer, who oversees both product marketing and product management functions. This model creates a healthy tension between product ownership (the what) and implementation (the how).

In this organizational model, the successful CTO must collaborate closely with the CMO. The individual provides an innovation engine that can be rapidly recalibrated to build the right product as defined by continuous user feedback. The CTO becomes a chief collaborate with the CMO, two roles that have traditionally combined like oil and water, speaking two totally separate languages. The successful candidate has come to appreciate business language as much as the programming language.

This type of product leadership can also be found in organizations that require a deeper level of technical expertise – such as those with deep algorithmic intellectual property or those relying on embedded software and requiring hardware integration.

The Dedicated Product Executive

Finally, many organizations have a dedicated product executive. This is most common in small organizations, where, the CEO is the product visionary, or, in much larger organizations where the product executive leads a business unit that is supported by shared marketing and technology services organizations.

In this organizational model the successful CTO must be also be politically savvy, learning to collaborate with multiple executives and negotiate different priorities and differences of opinion amongst various stakeholders. In large organization especially, the CTO that operates with dedicated product executives is a versatile executive leader that is able to drive the technical organization while collaborating with multiple business owners.

The role of the CTO has changed. No longer can the Chief Technology Officer limit herself to deep technological expertise. Regardless of the organizational model, the CTO must, at the very least, collaborate in a meaningful way in ongoing product development.

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What Does a Modern CTO Look Like? - David DeWolf

What Does a Modern CTO Look Like?

Recently at 3Pillar, we began searching for a CTO to join our executive team. As I began to soft launch the CTO job description in order to source candidates from my network, I started to get a curious set of responses. I was hearing from all sorts of folks who didn’t necessarily want the job, or know of a candidate. They were just impressed by the job description.

Here’s one such response:

Sorry I don’t have a candidate, but I just wanted to say “what an awesomely worded job description”!

Who writes them for you?

Also, if you end up in a horse race between two strong candidates – let us know who your number two is. We may need a person like this in about 4-6 months.

Another person commented:

I’ve never seen such a good description for a ‘modern’ CTO. You should publish this.

Here’s what I’ve realized. In today’s digital economy, every single business is becoming a software product company and very few executives know where to start when it comes to hiring a CTO. As more an more stodgy industries enter the digital economy, more and more product CTOs will be needed. In fact, the modern CTOs required for the “Software is your Brand” era are a bit different from traditional R&D oriented CTOs.

And so I’ve decided to take my respondent’s advice and publish the description. If you’re an executive that’s looking to hire a CTO, hopefully you will find this job description helpful in beginning to put your req together.


You are ultimately responsible for creating a culture of innovation, embedding the product mindset, and ensuring delivery excellence is a priority throughout our organization. You do this by leading our Product and Technology teams and instilling within them the product mindset. You are passionate about finding ways for software to disrupt industries, and you know and understand the capabilities required to enable that disruption. Your business aptitude, strategic thinking, and creative abilities and relationship capital compliment your deep technology expertise and passion for agile software development.


Provide corporate leadership, along with the CEO, CFO, and EVP of Market and Client Services as a key member of the Senior Executive team, participating in the refinement of the company’s vision, the development of strategies, governance and the continued success of our goal to be an employer of choice Lead the execution of our innovation and delivery strategy, integrating tightly with our go-to-market team in order to ensure that we deliver on our promises, delight our customers, and achieve the vision of becoming the most respected company in the product development services sector. Actively engage with the market, prospects and clients as a thought leader and expert in software innovation and product development. Become the ‘face’ for our “ProdTech” organization and a trusted advisor to our clients. Lead our product strategy, product management, user experience, advanced technology, and engineering teams. Spearhead and continue to shape our core offerings – Innovate, Accelerate and Elevate. Lead 3Pillar’s internal R&D activities, including the development of 3Pillar Navigate, solution accelerators, and our 3Pillar Labs strategy.

Duties Executive Leadership You prioritize your participation in the senior executive team as a top priority. You are driven by a desire to be a part of a high performing team and understand that corporate results are driven by collaboration across the entire business. You are a strategic thinker and natural leader. You develop strategies that align to our vision and translate them into action. You motivate and inspire others to achieve more than any individual could on their own. You galvanize and create high-performing product and technology teams. You hold them accountable and ensure that they deliver high quality products to the market while remaining actively engaged and committed to their professional development and career growth at 3Pillar. You have sound judgment and are unencumbered in making both deliberate and rapid decisions. You are not afraid to challenge the status quo, experiment, or, even fail, but, have you the confidence and experience to ensure that all failures are smart failures and to minimize your losses. You actively live our corporate and cultural values. You are seen as adhering to the highest levels of integrity. You build genuine, trusted relationships with team members and other constituents and treat every individual, no matter how junior or senior with the utmost dignity and respect. You are innovative in your approach to solving problems for clients and colleagues alike – having both a deep understanding of technology and a broad understanding of market trends that impact our business. You demonstrate both the strength and flexibility required to be agile and an agent of change so that your innovative ideas are embraced by others. You are flexible and results-oriented. You can adjust quickly to changing priorities while maintaining an acute focus on corporate objectives. You are able to act quickly when required and deliberately when appropriate. You are the embodiment of our commitment to delivery excellence (across both product strategy and product engineering and advanced technology). You represent 3Pillar to and gain the confidence of prospects and clients. Product Strategy You are a creative innovator. You are able to see things that others can not. You collect volumes of information and naturally draw conclusions about disparate data-points. You recognize market trends and are able to apply them to various industries. You are able to articulate these trends in a way that appeals to a variety of personalities and audiences – the media, clients, prospects board members and employees. You have a strong grasp of Lean Startup methodologies and value principles such as minimally viable products, concept validation and rapid experimentation. You have a firm grasp of the product management discipline. You understand how to rapidly build a roadmap and the importance of continually evolving that roadmap. You are able to mentor others and articulate the importance of strong product management. You value the entire product ecosystem and you understand that to craft successful products all areas of the organization from from marketing and finance to engineering and support must be integrated at appropriate levels and intervals to create optimal outcomes. You can gently guide and influence clients in the development of their product and technology strategies. You have a strong ability to forge relationships to gather information and to craft strategies. You provide them clients and teammates sage advice on the full product canvas and collaboratively guide customers on how to bring their products to market in a way that creates a deeply engaging relationship with their customers and generates additional revenue for our clients. Technology You have a passion for and stay abreast of the latest technologies. You explore new trends and form opinions about which will become mainstream and how they will impact industries and market behavior. You actively and continually share these opinions with the Sr. Leadership team. You have ridden the wave of mobile and big data, you are knowledgeable about predictive analytics and wearables and you understand how these movements reach adoptions and impact business. You have deep experience in architecting scalable solutions and are able to find the appropriate trade-offs between architectural purity and pragmatic realities. You have both deep expertise and a wide breadth of experience in the application of various technologies to multiple industries. You have formed technology strategy for multiple products that have proven successful. You are seen as a mentor by seasoned technologists and are able to go toe-to-toe with architects and engineers. While you have learned to manage a vast team in order to scale, you are able to provide relevant architecture and design leadership to any software product team. Engineering You are skilled at building high-performing teams. You understand how to attract and retain strong engineering talent and excel at building teams that collaborate effectively and deliver results. You have experience working in a global organization and are able to bring the strengths of various cultures and environments together to create a successful product organization. You understand how to balance the reality of changing business priorities with the need to provide predictable releases. You create high-performing agile development teams that are able to quickly iterate and respond to customer feedback while simultaneously delivering predictable results. You are considered an expert and evangelist for agile methodologies. You possess vast experience with software design principles and are passionate about software craftsmanship. You have a love for rapidly bringing software to life and can still be found in the code every once in a while, building a rapid prototype, mentoring an engineer, or, helping to find a performance issue. You have experience working in a distributed environment and with global teams. Requirements You have at least 10 years in product technology leadership and 20 years in a product or engineering related role. You have successfully lead the development of multiple products of meaningful visibility and scale. You have participated in the entire product lifecycle, from ideation through end-of-life. You are the embodiment of the product mindset – strong business aptitude and market awareness combined with deep technical expertise. You are an expert in lean startup and agile software development methodologies. You are a phenomenal teammate and prioritize your team over individual accolades. You are a natural leader and charismatic personality. You attract others and have either established yourself as or can be seen as a thought leader. You likely have an advanced computer science, math, or similar degree. You have consistently demonstrated high levels of emotional intelligence and have received 360 degree feedback supporting your leadership in this regard. Learn to live an integrated life with humble confidence. Get it Now Join the Discussion

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How Do You Decide Whom to Hire? - David DeWolf

How Do You Decide Whom to Hire?

When faced with two equally-qualified candidates, how do you determine whom to hire?

When faced with a difficult decision — two equally qualified candidates — how do you decide which one to hire? I’d be remiss if I didn’t answer that the ultimate decision should come back to a values fit. Is there a cultural fit within the organization?

But let’s assume for a moment there is, because if there’s isn’t, you shouldn’t even be having this hard conversation. There’s nothing to weigh. Non-value fits should be thrown out immediately, at the beginning or whenever you discover the person’s not a fit.

So assuming they’re equally qualified and equally great culture fits for the organization, how would I make that decision? Quite simply, for me it comes back to passion. I look for the person who is the most passionate, the most excited, the most aggressive. I look for the person who wants the role, who shows a genuine, innate desire to perform at high levels.

Passion will help you get through the tough times. Passion helps when things get rocky. Passion will help motivate when you need to go the extra mile. Passion, above anything else I’ve seen, is the soft skill that can push somebody to be great and can push somebody to the next level of competence, to the next level in their career, to be an incredibly high performer.

Question: How do you answer this? Faced with two candidates, equally qualified, how do you determine whom you’ll hire? I’d love to hear from you! You can leave a comment by clicking here. Learn to live an integrated life with humble confidence. Get it Now Join the Discussion

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You Need Vision to Make the Right Pivot - David DeWolf

Why You Need Vision to Make the Right Pivot in Your Business

I am continually amazed at how many entrepreneurs lack vision. Many possess a great idea. Some have discovered a new invention. And many more have found a market that is ripe for disruption.

But very few dream. They are unable to see down the road and paint a picture of what they will become. They struggle to paint the picture of the world as they see it – five, ten, or even twenty years down the road.

Michael was no different.

“I stumbled into Starbucks – my hands full of the cards I collected the night before. My mind was racing and my palms sweaty. Seeing that the line was long, I found a corner table where I could unload my things. I opened my laptop and started to thumb through the cards. As I did, I flashed back to the night before at the convention. I could still feel my heart beating as I shook the Senetor’s hand. I could feel my chin drop to the floor as the Committee Chairman handed me his business card.

“In a short 45 minutes I had collected at least a dozen cards, each of which had the personal contact information of a senior government official. For a political activist, this was gold.

“As I came out of my trance, I realized that the coffee line had evaporated. I got up quickly, hoping to beat the next wave of folks ready rushing to get their Sunday morning cup of joe.

“When I returned – my chin hit the floor. This time, for a very different reason. My stack of cards was gone.”

When I first met Michael Barnett, he was passionate about his invention. His story made clear why he had made it his personal mission to digitize the way business cards were collected. After sharing the history, he opened his backpack and produced a small, handheld device that was shaped as though it would fit perfectly within the curve of the human hand. A single button sat conveniently where his thumb rested. “If i push this button, my contact information will automatically transfer to your device.”

Michael, like so many entrepreneurs, began his company by solving a problem. Entrepreneurs see a need firsthand, and they invent a device or build a new system to get rid of their own pain. Many are captivated by their discovery and develop a deep sense of purpose in changing the way the world works. They want to ensure that no one else experiences their pain.

Unfortunately, very few translate this mission into a vision.

A purpose drives culture and a product solves a problem, but it is a vision that creates momentum. It is the magnetic force that pulls an organization forward and it is the guiding light from which strategy is developed.

Over the past several years I have watched as Michael has transformed his company from a device manufacturer into the premier social marketing platform for the events industry – InGo. This evolution has been grounded in the vision he was able to develop as he transitioned from inventor to leader.

He envisioned InGo technology powering the connection of conference attendees throughout the world. He could clearly describe the massive impact this virtual web could create by bringing virtual communities back together into the physical world.

Michael was unconsciously competent. He developed his vision, not as an intentional effort, but as part of an evolutionary process that he naturally followed.

Having spent the past eight years helping entrepreneurial leaders develop innovative products that disrupt industries, I have begun to recognize patterns that exist in those who are able to make the change. They typically go through the following process, much like the one that Michael went through.

They surround themselves with the best and the brightest.

Inventions are often created in a lab. Innovations are made in society. Entrepreneurs that cross the bridge from inventor to leader seek out the best and the brightest minds to collaborate with. They find mentors and teammates with a diverse set of expertise. They surround themselves with talented comrades – often times those that are even more talented then themselves – and they seek to learn as much as they can from them.

They gather information from disparate sources.

As successful entrepreneurs begin to surround themselves with talented individuals, they recognize the value of the insights they are receiving and they begin to seek out more and more. They are naturally curious, ask a lot of questions, begin to read more often, and find more ways to gather intelligence. They collect myriads of information across a wide variety of related fields and sources and many of them provide context regarding how their invention may be used, adapted, or become mainstream.

They value finding the right answer more than being right.

Entrepreneurs are notoriously stubborn, but, successful entrepreneurs are also dedicated to success. While they remain committed to their mission, they begin to develop a hypothesis around what their company might become. They begin to imagine the future, and incubate ideas of how their company might look in the future based upon the data-points that they have collected. They begin to see into the future and paint a picture of how they will succeed.

They develop the 3 sights of vision.

As this initial painting is incubated within the entrepreneur’s head the 3 sights of vision begin to emerge. The first is “foresight”. This is the ability to see how the world is evolving and predict where it’s going to be. Second is “insight” – the ability to identify the unique assets available to the entrepreneur that can be used to participate in and push forward the changes that will the entrepreneur believes will occur. And finally, is crossight. This is a hypothesis about how the company will interact with others within the space and integrate with the ecosystem that either already exists or will ultimately emerge.

They continually paint, refine, and expand the vision.

It is at this point, once the 3 sights emerge, that the entrepreneur has found a robust vision. Successful entrepreneurs begin to share their vision by painting a clear picture to everyone who will listen. In doing so, they gather more and more feedback, refine their hypothesis and expand their vision. This continual cycle builds momentum and creates a self-fulfilling prophecy.

Many in the lean startup world would correctly recognize InGo’s transformation as a series of “pivots.” What these same folks would likely miss is that these pivots would have proven fruitless without a vision. A pivot requires that one foot is firmly grounded while the other moves. Without that foundation, you are simply spinning your wheels.

InGo is a great example. It’s mission has not changed, but, the vision has undoubtedly evolved and the strategy pivoted around it in order to ensure success.

Entrepreneurs must learn how to create a compelling vision. A clear vision is the basis for successfully navigating a market.  Surround yourself with exceptional talent, collect information, value finding the right answer, develop the 3 sights of vision, and continually paint your vision for others, and then rinse and repeat. It’s not easy, but it’s simple.

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Beyond Hiring Biases to Build Great Teams - David DeWolf

Challenging the Typical Hiring Biases and Building Great Teams

A recent article in Forbes challenged entrepreneurs to limit their hiring to senior developers, a practice that runs counter to the conventional wisdom of so many organizations.

While good intentioned and directionally correct, the piece falls short on logic.

The foundation for the argument seems to be based upon “the method that he implemented five years ago when he launched Smartling with cofounder Jack Welde: ‘find the right people and keep them motivated’.”

There’s no doubt that getting the right people on the bus is essential to any business. I agree wholeheartedly. But when did “the right people” translate into “senior developers”? I see two flaws in this thinking.

Seniority (years of experience) plays a role in one’s capabilities, but it does not tell the whole story.

My first management job was two years out of school. I took over the leadership of a small, high performing team of “senior” developers. One teammate, in particular, had 20 years of experience, a PhD and a resume that boasted of her “seniority.” I learned the hard way that this seniority didn’t translate into her ability to produce. Within six weeks it was obvious that there was one team member not pulling her weight and I was forced to let her go from the team.

On the flip side, several years ago, near the beginning of the 3Pillar run, I hired a junior developer who was one year out of school. This individual may have been one of the most talented, productive and innovative team members I’ve ever seen in action. He literally pulled the weight of multiple developers. He was inexperienced but had wisdom beyond his years.

Seniority is not the only measure of talent.

A group of “senior developers” doesn’t translate into a high performing team.

You don’t field a baseball team with nine shortstops. All nine shortstops may be the best athletes, but they won’t win the ballgame. You don’t field a basketball team with a bunch of veterans. You need to mix in some youth to make sure you have the legs left to get through the season.

The same goes for building software products. The right mix of talent, experience, creativity, passion, and, yes, even wild-ass, crazy naive ideas is important.

I have seen teams struggle to innovate because everyone wanted to lend experience and nobody wanted to think outside the box. I have seen teams struggle because everyone wanted to make design decisions and nobody wanted to implement new configurations. The right mix of folks is essential.

So, what is the right mix?

There is no cookie cutter answer, but it’s likely not an entire team of “senior developers,” nor is it the traditional “leveraged triangle.”

In my experience, the most innovative product engineering teams require a well led with deep experience, a small handful of senior developers to collaborate, lend their experience and challenge assumptions, a sprinkling of productive developers to fuel throughput, and a sharp, passionate all-star that’s a little wet behind the ears.

Question: What does your experience tell you? How do you create high performing teams? I’d love to hear from you! You can leave a comment by clicking here. Learn to live an integrated life with humble confidence. Get it Now Join the Discussion

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