The curiosity and fearlessness of children while playing on the playground or by themselves fascinates me. I find the same curiosity and fearlessness in founders. When approaching the problem they are solving, I am captivated by their sheer ingenuity and innovation. And, like children, seeing those moments of discovery is priceless.

Priceless, that is, until you can put a price on them and raise that first round of investment.

Entrepreneurs have a lot to learn from children who are playing in the sandbox. Founders are a particular type of breed because sometimes they forget that they’re not the first ones going through the entrepreneurial process.

I have coined three types of Business to Business / Enterprise grade founding teams. See if you can identify which category you and your team fall under:

Technical /Scientific Founding Teams

Coming from a large Enterprise, they excel at their craft. As engineers, inventors, they have written patents, have worked at the bench for years; and while their secret sauce has now become a business, the skills and competencies in a technical or scientific founding team are insufficient to scale the company to the next stage. They have so much fun in the sandbox that time gets away from them.

Been There and Done it Founding Teams

Founding teams who have been there and done that, may have the skills and competencies acquired at a large enterprise, family-owned business, been part of a startup, or they are bringing to life the idea of a patented product. Time in the sandbox was never an issue because they had access to abundant resources.

 “Adult supervision” recommended Founding Teams

These founders have never worked for a large or medium-sized enterprise with the processes, systems and operations that enable scaling a company. They have never hired or fired before. There are many firsts that once past Product market fit; it’s about execution at scale. Isn’t there an adult around who can take the time to do those things?

Investors will want to “look under the hood,” and that includes what you do with your time. This means that regardless of the founding team type you and your team might fall into, there needs to be strategy when it comes to the business side of the business – where the rubber hits the road.

In all three types, founders face the same problem. Deciding what to do with their time. How you invest your time is crucial for how you grow your company. And when you know how you spend your time, you can invest it more intelligently.

In fact, on my website, one of the intake questions that I request from people wanting to connect for an initial free consultation is “How do you spend the majority of your time as operator/owner of the business?” I also make sure to indicate to be detailed in the answer.

I get a lot of answers, but I never hear them say the following:

●  I feel like I need to spend time on corporate governance

●  I want to spend more time on accounting so that I can maximize R&D credits and use against future profits

●  I want to raise money in a tax efficient way for the founding team and investors  by using  qualified small business regimen

●  I want to spend hours of time writing job descriptions and posting job positions on job marketplaces so that I can spend time and effort interviewing people

●  I have more time than I know what to do with so naturally I’m going to  write that sales agreement or Master Service Agreement

●  Oh and D&O insurance….

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If you’re a founder and you’ve found yourself disillusioned by starting a business and you don’t feel like it’s fun anymore, it’s probably because it’s not fun anymore. And If you’re not having fun while building your business, your business will suffer.

Here are five (5)” playful” ways to “time management”  that do not stifle creativity or innovation, and allow you to continue in the sandbox.These will pay off big time in the medium to long term (kinda of like a graduation). I encourage founders to explore the 5 concepts of the playful non-sandbox kit:

1. When you play you learn (and you retain)

Have fun on the All Hands On Deck or State of the Union or whatever mechanism used to communicate with the organization you lead.

In one of my clients the CEO in the All Hands on Deck monthly meeting instead of going through the drill of the 15 powerpoint slides when going to slide 2 she asked the team members a question. What had been different on the opening slide with respect to last month’s AHOD?  There was silence – technical folks tend to be on the quiet side. Then finally somebody had the gall to say “I think the logo has changed.” Bingo you are the winner of a $25 Amazon gift card. And so, a tradition began.

Benefits are healthy competition, and retention of the information that will follow. When one is playing the retention of the material of the task is much higher.

One of the objectives with an all-hands-on-deck meeting is to bring your organization along on the journey and what better way than playing.

2. Storytelling: Sharing the Purpose of the Company

I’m a mother of two adults.  I read to them as children. Their favorite stories would be told time and time again and often I would change the ending, to see if they would catch me. 😊

Software or knowledge based businesses make “intangible” products. Software engineers code and use agile methodology with sprints, scientists do the work at the bench, etc. etc. These are some powerful settings with which to tell stories.

Storytelling is a powerful communication tool for the organization as it scales. Stories that “paint the picture”  of what we want to look like when we grow up; or retrospective from where we have come.

3. Good Competition is a Good Thing

In fast paced, resource scarce start up environments, the pressure is always on.

It doesn’t have to be that way, there is an escape valve.

I have found healthy competition between a team in one geography vs. another or a project team X vs. a project team Y provides a bit of healthy competition, coveted prizes, and stories in the making.

In fact, competition amongst team mates is more like coopetition as Stripe COO Claire Hughes Johnson shares lessons in scaling the business from 160 employees in 2014 to 1,500 in 2019.  Write down your principles and if making edits, crowd source within the company; know your forever user, process light, optionality and names stick.

“You will be amazed about how many things you need to name!” the selection of the office conference room names was done through crowdsourcing from employees.

I have found a handy tool for naming conference rooms!  Make it a competition.!

4. Cornerstone to Company Culture

The first twenty hires will set the company culture. Do your hiring appropriately. If you are reading this post on the sandbox and making it playful – if your initial team members aren’t fun – then get rid of them or don’t hire them in the first place.

In startups, I believe it is important to be on the founding team. The ups and downs are tremendous and only if the first hires are the right hires, can you thrive.

Do I need to say more? Yes, after 20 employees, the adventure begins. To ensure that the founding members have the time to recruit (remember those job positions and posting?), doing team interviews, have some rules on how many interviewers must give a green light on a candidate,

( I disagree with Reed Hastings on this no rule;  this is an exception at least 3 founding members must interview candidates after the 21st employee )

In Creating a High Trust Organization WholeFoods Co- CEO John Mackey talks about  “walking the talk”

As the co-founder and CEO of Whole Foods Market, I’m the most visible person in the company. One of the most important parts of my job is touring our stores and talking to our team members, customers, and suppliers. I know that in virtually everything that I say and do, our team members are always studying me, trying to determine whether they can trust me and the mission of the company. I’m always on stage. So walking the talk is very important.

5. Tools and Ideals help you play

You got all the way to Idea #5! These ideas you will like, dear Technical founders, they are tools for fun!

For just a second, think about how many project management and messaging apps or platforms you use. I did this the other day, and I counted 8! I use Asana, Trello, Slack, Monday, Office365, Google Drive, Whatsapp, Evernote, VPNs and firewalls. It can seem overwhelming and annoying, but you can use these tools for team work flow and also you can start your own channel for competitions and prizes, loaded with emoticons 😊

Some tools include:  organization of the teams in “pods,” learning circles; mentor/mentee relationships; a robust onboarding process; “cone of silence” topics; ombudsman for whistleblowers (think of Uber); and all of these tools while being agile. Experiment at first up to 50 employees. After that you need to hire a full time VP HR!

Some additional ideas include: team building activities, giving back community services, and crowning employee of the month. It is all about what you want to reward in your company that will be the next Unicorn!

Your job as CEO/Founder/Inventor is to never lose sight of doing the right things in the early stages of the company and this can be achieved while playing in the sandbox.

The high performing leadership team is better positioned to realize the Enterprise Value of the company when adopting a mindset that “it takes a village” to be poised for rapid growth. And yes, you can still play in the sandbox with guardrails.

If you struggle with managing your time while building your business, try playing with one or more these five activities and if you want to learn more, schedule some time on my calendar,

Onward and upward from your startup sandbox,

Brenda A. McCabe

Founder Next Act Advisors