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

Work and play are often seen as distinct and different, but the expectation of top talent has evolved. People crave a connection to enjoyable activities that deliver a sense of purpose and belonging. When work feels like play, the fun environment invites people to take on bigger challenges. To support the future of work, students, educational organizations, employees, and employers must adapt together.

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Welcome to your first taste of a new community-driven initiative that will feature special guests sharing occasional contributions. Interested in collaborating? Let’s chat!

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. 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.

A recent study identified 16 trends that are shaping the future of work. It found that, in addition to more flexibility and fair wages, 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 allows them to do their best work. Along with more innovative productivity, this culture also leads to lasting retention.

As today’s workforce is transformed into tomorrow’s playforce, it’s important to consider the difference between work that feels like play, compared to work with playgrounds nearby. When fun activities only serve as a distraction, the facade of fun will wear off. It’s also good to remember that what’s fun for one person could be more of a chore for others. Personality assessments and ongoing interactivity will help you understand individuals and the part they play within the system. The better people know each other, the more inclined they’ll be to act themselves. Acting professionally shouldn’t mean dimming one’s personality. The more comfortable people feel at work, the better they’ll be able to focus on what’s important. Too often, attempts to optimize employees’ work-life balance stem from a flawed assumption that we must create boundaries to differentiate life and our work. Perhaps the opportunity and the future of work, is to create an experience where the two coexist as one?

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This caffeinated contribution was written by Elizabeth Tweedale. Elizabeth has (co)authored six books, exited an AI company called GoSpace, and is now the CEO of Cypher Coders, the UK’s leading coding school for children. She’s passionate about family, preparing kids for the future, and can be found in our Roasted Reflections group.

If the future of work is fun, we must guide children away from an outdated “workforce” and toward a “playforce” to activate creativity, productivity, satisfaction, involvement, and purpose. The world is their playground and no permission is needed to contribute. Education can be about delivering access to skills, tools, and community. When children are encouraged to connect, play games, be kind, and learn with passion, they engage not because they have to, but because they’re having fun. This empowers students and as they reach the playforce, they’ll understand the superpowers they’ve nurtured in their own areas of interest. Beyond the classroom, this translates into employees and employers who are more likely to enjoy their work when given the opportunity to do what they’re best at.

As we see/hear in the closing chapter of YDNTB, “life is too short not to enjoy your work.” Together, let’s change the equation to make work a lifestyle, which sets us free to have fun making a difference.

By Ben McDougal, ago

Listen

Listening is louder than it sounds.

Most entrepreneurs like to talk and the more obsessed we are, the more vociferous we seem to get. Idea machines must be willing to share compelling stories, but listening is a key part of any transmission. This may seem obvious, but with precious air time up for grabs and knowing so much about our own interests, listening can devolve into feeling like a required distraction.

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Hearing is passive. Listening is active.

As we guide people through the layers of understanding, active listening forms a bond much faster than forcing yourself to be heard. The fear of not having time to deliver your message will linger, but when we truly tune into what another person is saying, it shows we care. It also helps us better harmonize our thoughts within the moment and counters the common mistake of overloading others with too much numbing details all at once. Knowing each conversation is part of a broader relationship and community-building journey, good listeners are almost always given a chance to make a bigger impact.

Ready for an experiment? The next time you meet someone new, embrace your inner scientist. Set your introverted/extroverted mindset aside and focus your attention on asking as many thoughtful questions as you can. The less you talk, the better. This will feel awkward if you just fire question after question, so be concise with each response, then return to more thoughtful questions for a more natural interaction. Consider expanding this social experiment by purposely doing this throughout an entire networking event. Remember who you talked with and track how the listening-focused conversations evolve. Over time, how do these relationships built on listening, compare to others where you’ve been more outspoken? Here are a few tactics to support your practice.

  • Center your internal attention.
  • Stay engaged with eye contact.
  • Use jarring questions to dodge small talk.
  • Don’t interrupt or jump to conclusions.
  • Occasionally paraphrase what was said.
  • Avoid the urge to make it about you.
  • Ask curious questions to go deeper.
  • Exit gracefully, without a sense of rush.

This type of active listening will extend your ability to hear more, but also make your responses more in-tune with what others are thinking, versus always trying to prove your point. Selflessness may keep a conversation from landing exactly where you want in that moment, but as you move from one topic to the next, you’ll learn how others work. When done well, an unspoken bond forms. This synchronization creates space to explore more directions you’d like to take future conversations, but now with the priceless ingredient of shared enthusiasm.

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Listening within a support network ignites optimism, connection, and motivation. A healthy balance is to also listen to your challenge network, which keeps us intellectually humble and rooted in reality.

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