Team

Milestones

Big or small, internal or external, milestones help people identify with progress. They draw lines in the sand. This clarifies goals while supporting short-term accountability and long-term motivation.

Entrepreneurship is a community sport, but creative problem-solvers working to build a business are still competitive. Milestones tap into this competitive spirit by gamifying a performance-based culture. Recognizing milestone achievements can also boost morale and further unite a team. If you’re collaborating with mentors and/or an advisory team, milestones help keep everyone on the same page as well.

As milestones are established, be sensitive to the diversity of your team. Find creative ways to equitably encourage new and more experienced team members. One easy way to do this, is to establish a few tiered categories for different types of milestones. As you diversify milestones, we’re not creating so many that they become pointless. Instead, you’re curating a variety of dynamic signals that can activate different emotions along a connected and sustained timeline.

As milestones are completed, the culture is nourished with celebration, which we’ll sip on next week!

By Ben McDougal, ago

Playforce

The expectation of top talent has evolved. People crave a connection to time that delivers a sense of purpose and belonging. When work feels like play, the lively environment invites people to take on bigger challenges. To support the future of work, today’s students, educational organizations, employees, and employers must adapt together.

When we think about work that feels like play, it’s not just pinball all day. The definition of “fun” is to spend time doing an enjoyable activity and to feel engaged. When a team has fun with satisfying work that matters, the group’s true potential is unlocked, and individuals are more likely to become indispensable. This leads to more generosity, laughter, caring, scientific questions, learning, gift-giving, and mapmakers eager to go beyond what’s expected.

EXTRA SHOT

This contribution was written by Elizabeth Tweedale. Elizabeth is a founder who is passionate about technology education, AI, and preparing children for the future.

In addition to more flexibility and fair compensation, employees want greater autonomy. Employees want the freedom to be creative and to find purpose in the way they spend their time. When this balance is achieved, people are happy, and the sense of satisfaction they feel allows them to do their best work. This culture leads not only to more innovative productivity but also to lasting retention. It’s an oxymoron, but a playforce earns this lasting retention through a shared freedom to believe in the mission, people, target market, service/product potential, and timing.

Too often, attempts to optimize employees’ work-life balance stems from a flawed assumption that we must create boundaries to differentiate our life and our work. The idea of a “work-life balance” is a corporate illusion not suitable for the entrepreneurial lifestyle.

The neon future of work creates an experience where life and work coexist as one. This is possible when labor looks like work to others but feels like play to us. This activates a culture where retention is natural due to a genuine interest in a shared direction. This type of playforce environment welcomes anyone to leave when a quest is no longer the best opportunity for their life. This bizarre freedom is balanced because it’s shared by leaders who assume positive intent but can also make moves when an employee no longer aligns with the time. This mutual admiration transforms a team that shares a creative way of being.

As today’s workforce is transformed into tomorrow’s playforce, let’s consider the difference between work that feels like play, versus work with proverbial playgrounds nearby. When fun activities serve as a distraction, the facade of fun will wear off.

It’s also important to remember that what’s fun for one person could be more of a chore for others. Personality assessments and ongoing coopetition help leaders sense team dynamics. Acting professionally does not mean dimming one’s honest personality. We want people to be themselves.As professional comfort is paired with an eagerness to make things better, people can focus.

If the future of work is play, we must activate children with creativity, involvement, and adaptability. The future is their playground, and no permission is needed to contribute. Education can be about delivering access to culture, skills, tools, and purpose. When children connect, play, and learn with passion, they engage not because they have to but because they’re having fun. This supportive sandbox empowers students to win the game of education and then go beyond it. As students grow, Playforce Principles help them understand superpowers and build beside evolving interests.

This translates into employers and employees who enjoy significant roles that feel tailored for what they’re best at. Together, we can change the equation and make work our lifestyle, setting us free to have fun while making an impactful and lasting difference.

Brewed From Within
#56 📖 Leadership

By Ben McDougal, ago

Slow & Fast

Slow is smooth, and smooth is fast. This sounds like a contranym, but when we slow down, it’s easier to find a rhythm that activates kinematics to add elegant speed.

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Accuracy sparkles within rhythm.

This concept serves founders who are building with a turbulent sense of urgency. For example, startup life in an accelerator is a compressed environment for ideas to flourish. When mentors and investors are dedicated to helping founders succeed, milestones will be achieved, but growing too fast can leave the team feeling hollow.

With decisions at every turn, relationships still take time. Early hires are delicate. Financial modeling is complicated. Sometimes the product isn’t even fully baked. This is when slowness adds a healthy thickness. Patience leads to deeper understanding, which bonds to the urgency. Momentum is not only then accelerated; it’s also geared to scale.

By Ben McDougal, ago

Lone Wolves

A common misconception is that you must have a team to be successful. There is a limit to your own capacity, but it is possible to build rewarding endeavors all by yourself. Solving complex problems may require co-founders and a larger team, but your passionate dedication is all you need to get started.

Lasting energy is required to forge this path, but without the need to answer to anyone, you can stay nimble and be more efficient by eliminating internal delays. To avoid burnout, you must stay mindful of your personal bandwidth. Self-awareness will help you avoid market disconnects, The Headline Trap, and relationship problems as well.

To coordinate new initiatives into your career portfolio, consider how the project connects to your current work. Clear overlaps can be good, but can also cause unwanted tension. A project less related to your existing work actually makes everything easier to shuffle. Even when projects affect different industries, it’s still you making things happen. The option to build into what motivates you in different ways will energize your work on all fronts. Action on one project will provide fresh momentum for others. Learn when to say yes and no, then wisely activate your time on each front.

As a lone wolf, it’s easy to go hard toward your own dream, but know when you need help. The freedom of working alone is within reach, but execution still requires collaboration. The world is full of friends, community allies, and contractors eager to help. Outside assistance may slow you down, but it won’t dilute equity, and it may be the key to a new reality.

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Need someone to bounce ideas off of? Let’s have coffee.

If you venture out alone, prepare for intoxicating highs and crushing loneliness. The consuming nature of building by yourself will incite grit, but don’t let it blind you. It’s easy to build too far into the wrong direction without a team. This is why community and customer discovery are even more important for lone wolves.

By Ben McDougal, ago

Co-Founders

The freedom to build as a lone wolf is exhilarating, but collaboration is how to go beyond your own limitations.

It takes more time to collaborate with others, but finding a co-founder can be life changing. Generosity, transparency, and candidness will bring the right people on board faster. Even if it’s one other person who wants to build in an aligned direction, co-founders pave a smoother path toward success.

Good people eager to collaborate can fall in your lap, but finding co-founders usually requires a concerted effort. If you hunt for the right co-founder in the beginning, it will take more time to make early progress. The trade-off is more creative and cultural alignment when things come together. This makes it easier to evolve ideas when a team finds its groove early on.

If you’ve been building as a lone wolf too long, you may have a harder time working with a co-founder. This is because it’s difficult for others to jump on a bus you’ve been driving the whole time. It’s still possible, but a thoughtful willingness to adapt is required. If you’re merging energy with another lone wolf, take your time. Moving a bit slower will uncover the why behind what was built before the partnership. As trust grows within the team, everyone will have more freedom to make the impact they want.

No matter how you decide to join forces with co-founders, choose wisely. It’s easy to work with someone like you, but don’t clone yourself. As a fun analogy, we also don’t put linebackers at wide receiver, right? Identify what you’re good at and know where you fall short. This allows you to pinpoint people who have complementary skill sets. It will also keep you focused on finding those who can push you further. With indelible honesty, who might be fun to build with?

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Perhaps you are looking for a co-founder? Show up to where the people you may want to work with are congregating. For instance, I met two of my co-founders at 1 Million Cups. We were working on different things, but over time, our shared interests led to a business idea we decided to pursue together.

Like anything new, as a team forms, early excitement will provide a surge of enthusiasm. This will soon fade and at some point, the story of this venture will end. It’s easier to plan ahead than it is to react to problems after they arise. Talk openly about roles and how everyone wants to be involved to avoid future tension. Discussing everyone’s immediate and future commitments reduces the stress of unknowns. With professional transparency a team can also work with more sustained stability. This leads to less drama and more consistent success.

As you solidify complementary co-founders, the goal is to have everyone equally enthusiastic. Think deeply about what a fair equity and role distribution means now and how it can also support future growth. No matter how cap tables look, co-founders expand capabilities and add valuable accountability. Working with others to achieve a shared goal is also more fun than working alone. Collaborate with remarkable co-founders and you’ll enjoy the ride together.

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Want more? Check out the Team chapter in You Don’t Need This Book!

By Ben McDougal, ago