Running a Software Company: What My Dog Taught Me

Learning lessons of leadership from unusual places

Eight years ago my wife, then my fiance, and I adopted a Mastiff who became the center of our lives.

We raised her from a six-week-old adorable yet demonic puppy. We were shocked at how much we had to learn.

Over the next few years, Tinkerbell taught us many valuable lessons.

Many of these lessons apply at work.

Below are some of the lessons Tinkerbell taught me over the past eight years.


Lesson 1: Run into the danger

Tinkerbell’s first visit to the ocean (Outer Banks). Running into the danger…and then running away.

When I worked at Franklin American Mortgage Company, my manager used to say “Run into the danger.”

Over the past five years I have been lucky to advance my own career, from Project Coordinator to VP.

Taking measured risks is the key to how I have accelerated my own career.

The first female CEO of a TV network, Kay Koplovitz, discussed risks in her own career:

“You really have to put one foot in front of the other and start on your journey. You have to be comfortable that you don’t know exactly how you are going to get to the results that you want to see. There is going to be experimentation along the way. And you have to be comfortable that you can think your way through and actually execute your way through to the desired outcome. I expected to be successful. I wanted to be successful.”

One of the biggest risks I took in my career was accepting a promotion to Manager of DevOps. I didn’t have a background in DevOps; all I had was passion.

It was the most challenging job I ever had, and I wasn’t ready for it. I spent two years studying every free minute I had while seeking any and all mentoring I could get.

Because I took that risk, I was promoted to Director, and eventually VP.

Smart risks advance your career and increase your experience level.


Lesson 2: Don’t take yourself too seriously

Tinkerbell enjoying the beach

One of the biggest culture killers is ego.

A bad habit of many leaders is adding their two cents to every discussion.

Being a leader is about growing others — not showing off how smart you are.

Marshall Goldsmith, author of What Got You Here Won’t Get You There, said:

Imagine an energetic, enthusiastic employee comes into your office with an idea. She excitedly shares the idea with you. You think it’s a great idea. Instead of saying, “Great idea,” you say, “That’s a nice idea. Why don’t you add this to it?” What does this do? It deflates her enthusiasm; it dampers her commitment. While the quality of the idea may go up 5 percent, her commitment to execute it may go down 50 percent. That’s because it’s no longer her idea, it’s now your idea.

One of my first failures was implementing a mentor program at my first job out of college. The intent was to increase employee retention and improve training.

I thought my idea was brilliant, but it was a complete failure.

I asked around for advice on how to fix it. One person gave me a great piece of feedback and said, “This feels like you created it in a hole. Why should I care about it or put my time in it? Even if it is a good idea.”

I spent the next few weeks meeting with every Lead or Manager and had each help me redesign the program.

Almost nothing changed on paper. What did change was people’s enthusiasm about the program. The Leads and Managers now felt like this was their creation as well and embraced it.

What started as a failure turned into a success, all because I took my ego out of the equation.


Lesson 3: Reward performance and behavior

A beef bone from Porter Road Butcher

Ian Hutchinson, CEO of an employee engagement company, said:

“Your number one customers are your people. Look after your employees first and then customers.”

Every leader understands the importance of taking care of clients
Not every leader believes in taking care of employees.

The problem with that is your employees are the ones serving your clients.

How many times have you called a customer service line to hear a listless voice on the other end? Too many.

Studies have shown that rewarding positive behavior motivates employees more than punishments.

Customers want to buy from companies that take care of their employees.


Lesson 4: Training is vital

Tinkerbell at three months old

Imagine a football coach who holds practices only once a month. Or a silent coach on the sidelines.

You can’t grow people without coaching and feedback.

Invest a significant amount of time coaching your employees.

More than 70 percent of high-retention-risk employees say they’ll have to leave their organization to advance their career.

Leaders must develop a coaching culture and become excellent coaches themselves.

Do you believe your employees require constant micromanagement?
If so, that is a reflection your coaching and leading ability.

In 13 Ways Leaders Can Build a Coaching Culture at Work, a member of the Forbes coaching council states:

A coaching culture encourages employees to learn from their experience by exploring the right questions rather than telling them what to do and how to do it. Next time an employee has a challenge ask them open-ended questions that begin with “how” or “what.” For instance, “What would you have done differently? and “How can I support you?” This way you empower employees to come up with meaningful solutions.

Marshall Goldsmith introduces you to the basics of coaching:


Lesson 5: Rest is essential

One of Tinkerbell’s daily naps

I traveled 40% of my time during my first two years as a manager.

I obsessed about doing a good job. My first year of travel, I would leave from Nashville at 5:00 a.m. I would often arrive in Memphis before most of my people arrived at the office — and with a three-hour drive.

Did it show my dedication? Sure.
But I was barely functioning outside of work hours.

During that time I made more mistakes, had less patience, and didn’t manage my team as well as I should have.

Multitudes of studies show the impact that sleep deprivation has on performance.

You can’t take care of your team without taking care of yourself.

A quick overview of the impact of sleep deprivation:


Lesson 6: Engage your team

Tinkerbell enjoying a Puppucino from Starbucks

Engaged employees are the holy grail for managers.

Having engaged employees lowers turnover, increases work quality, and increases customer happiness.

Yet, businesses are terrible at engaging employees.

Only 33% of employees in the US are considered engaged at work.

In the world’s best organizations, 70% of employees are considered engaged.

One of my favorite examples comes from Jack Welch’s book, Winning. He describes a time a factory worker spoke up at a town hall meeting. The employee felt that managers didn’t care to hear ideas from their team.

“For twenty-five years, you paid for my hands when you could have had my brain as well — for nothing.”

Four steps to improving employee engagement:

  1. Measure current engagement — An engagement tool can assist and automate engagement measurement. I would personally recommend Insight or CultureAmp. These tools are simple to use and good for medium to large companies.
  2. Leaders set the tone — Align performance expectations with engagement. Empower managers to make a difference in their environment and teams.
  3. Managers need to care — The key decider for engaged employees is their direct manager. Managers must take a direct role in ensuring employee engagement.
  4. Communicate what engagement is — Abstract definitions of “engaged employees” create confusion with expectations. Define and discuss engagement with your team. Use simple and realistic examples from their day-to-day work. Create a common understanding of what engagement means.

Want to see want an engagement tool looks like? See the video below.

To measure engagement, check out tools like Insight.

Lesson 7: Be radically transparent

Tinkerbell taking a nap under our bed

Zenefits defines radical transparency as “…the belief that all corporate entities should be honest, open, and straightforward.”

Radical transparency can be a powerful tool. It can cut through poor communication, empower employees, and help create a meritocracy.

Ray Dalio is the founder of the biggest hedge fund in the world and manages over $160 billion. He is a key thought leader of radical transparency. One of his favorite stories is an email he received from an employee after a meeting.

“Ray — you deserve a “D-” for your performance today in the meeting … you did not prepare at all because there is no way you could have and been that disorganized. In the future, I/we would ask you to take some time and prepare and maybe even I should come up and start talking to you to get you warmed up or something but we can’t let this happen again. If you in any way think my view is wrong, please ask the others or we can talk about it.”

Radical candor helps authenticity and increases employee engagement.

Even if your company doesn’t embrace radical transparency, it can help you as a manager.


Lesson 8: Help your team enjoy work

One of Tink’s favorite toys

Your team cannot be engaged without enjoying what they do.

In The Happiness Dividend, Shawn Achor says,

A decade of research proves that happiness raises nearly every business and educational outcome: raising sales by 37%, productivity by 31%, and accuracy on tasks by 19%, as well as a myriad of health and quality of life improvements.

The Corporate Leadership Council conducted an employee engagement study. The CLC surveyed over 50,000 employees across 59 companies. In the study, they found:

Those employees who are most committed perform 20% better and are 87% less likely to leave the organization — indicating the significance of engagement to organizational performance.

Want to build a great company? Then you want happy employees.


Lesson 9: Embrace the pack

Tinkerbell and Bill enjoying a car ride

Embrace the pack = break down silos.

Team members often focus on the individual team they are a part of instead of the larger company.

Investopedia defines silos as:

“An attitude that is found in some organizations; it occurs when several departments or groups within an organization do not want to share information or knowledge with other individuals in the same organization.”

Company size has little to do with silos. They exist everywhere, even in small teams. Beneficial silos are rare. The job of a leader is to find and help remove unnecessary silos.

Eash Sundaram, CIO of JetBlue, discussed silos in an interview. He stated:

“The most important thing we are doing here is collapsing the silos. When we think about a program, we don’t think about IT and finance and commercial operations. We think about how the program improves our customer or employee experience.”

A lack of trust, accountability, and poor leadership create silos.

Patrick Lencioni, author of Silos, Politics, and Turf Wars, suggests:

The key to eliminating silos is simply to provide a compelling context for colleagues to understand that they should be rowing in the same direction. While leaders have been focusing on punishing negative behaviors that lead to internal conflict, they have often failed to give people a clear understanding of what they have in common, and why serving the common good is better for them than looking out for number one.

Lesson 10: Encourage positive conflict

Tinkerbell wrestling with her brother Bill

Positive conflict can increase organizational health.

It acts as a check on ideas, decisions, hires, and everything in between. Conflict grows teams through feedback, challenges, and defending ideas.

Fear of conflict is a challenge in almost every organization.

Patrick Lencioni writes about the fear of conflict in his book The Five Dysfunctions of a Team. Below is a video discussing parts of it.

Help your employees understand what positive conflict looks like and what behavior is unacceptable.

Encourage and reward positive conflict. When employees speak up and say difficult things, thank them and encourage others. Discuss it in reviews and in one on ones.

Am I missing any lessons here? Feel free to add in your own in the comments.


There is a lot of content out there.

I appreciate you reading mine.

I write about software development, and how to run software companies. 
Feel free to reach out to discuss either. I’d be glad to talk.
Connect with me on LinkedIn or visit my website.