Intrapreneurship

Tenured & Tired

Recognize, connect, and support those who consistently delight those they serve over a prolonged period of time. Rewarding such an initiative makes sense, but at what point does the comfort of a rewarded role devolve into a willingness to sail into the sunset?

When starters run into the aloof, misaligned energy can lead to a standoff. Time is the ultimate release, but what if progress is needed now? Every situation is different because of the complexity of an environment and the people/organizations involved, but here are tactics that seem to work no matter the circumstance.

The first uses social currency. It requires a change maker to set their ego aside, and instead, celebrate all that’s been achieved by the accomplished, yet tired gatekeeper. Use respect, kindness, and appreciation to form a bond. Relationships that feel less transactional often create leniency toward new ideas. When a crack in the wall of inactivity is created, be glue that maintains the integrity of the existing system. For example, “I’m too busy” is a common qualm, so lean into that pain by offering to execute on the idea that has sparked mutual interest. It’s important to be realistic in these moments, because when promises are made, credibility is on the line. As you not only light a path toward progress, but also champion change by evolving ideas into reality, trust is gained and your ability to continue making a ruckus increases. Want to extend your leash further? Take responsibility for failures, but give all the credit away when success is achieved.

If a larger organization is involved, another interesting tactic invites the tenured leader to level up the team by activating a colleague. This provides a new hire the chance to get involved within the entrepreneurial ecosystem, while the organization is seen as engaged within their community. It’s hard for some to understand that time spent in the wild is often more valuable than clocking time in the office, but if the organization allows this person to show up without limitation, everyone wins. The new community member feels the innovative energy and brings more intrapreneurial vibes into the organization, while the community benefits by having another trusted organization in the mix.

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“The way we make things better is by caring enough about those we serve to imagine the story that they need to hear.” -Seth Godin

If you’re reading this, you may be tenured, but it’s unlikely you’re tired. That said, we’ve all found ourselves in a motivational rut or lacking a clear sense of purpose. Along with a few solid sleeps, when I feel the urge to settle, it helps to have fun, build into other areas of your career portfolio, take a few days to rest if necessary, and then get back into the startup community. This creates opportunities to #GiveFirst, ask for help, or get extra curious about the creative work of others. Soon you’ll find new opportunities to collaborate.

New connections that emerge can bring you out of the motivational rut. They can boost your care meter and will add fresh personality to your work. Along with sparking fresh direction(s), you’ll be motivated by others and soon find new ways to be generous with your art. If you’re still thirsty for motivation after tapping into the entrepreneurial ecosystem, I’m here for you as well. Together, we can refuel the idea machine to avoid wasting any more time with being tenured, but tired. Sleep when you’re dead, my friends. Let’s keep building.

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“There will come a time when you believe everything is finished. That will be the beginning.” -Louis L’Amour

By Ben McDougal, ago

Bloop

Imagine yourself as a circle.

It’s tempting to suggest a sphere, but the added dimension is not necessary for this metaphor. Alright, with your circular self, take a tiny portion of the arc and “bloop”… push it beyond the circle’s circumference. Even the smallest nudge gives the entire circle space to expand.

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I had fun making all sorts of sounds as I considered the title for this reflection, but I’d love to hear how you’d describe the sound of such an expansion. Also, since I had to look up the terms to ensure this metaphor was translated correctly, here are the parts of a circle.

There’s plenty of research behind the idea of small improvements adding up. As we hear from inspired speakers and read about in Atomic Habits by James Clear, if you get one percent better each day, you’ll end up thirty-seven times better by the end of a year. It’s hard to define “better” and such steady progress would surely require sacrifice, but most will agree that small choices don’t make much of a difference, until they add up.

While establishing systems that support good habits and compiled improvements are great, this reflection is more about welcoming singular moments of exploration and growth, even when it seems unrelated, weird, or insignificant.

Perhaps it’s trying something new without preconceptions, saying yes when no is status quo, or being the initiator when movement is seen as risk? As we poke the box and invite a bit more bloop in our life, we give ourselves an opportunity to grow as our own circles expand.

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To thank those who have enjoyed brewing on these Roasted Reflections every week for almost two years AND to say hello to some new friends, here’s a free gift just for fun!

By Ben McDougal, ago

Launch

A successful launch rewards hard work.

No matter the audience or how heavy the news, introducing what’s next is your opportunity to spark energy. This milestone will soon be celebrated, but rocket ships do not launch without intention.

The excitement of sharing something you’re proud of can be intoxicating, but we can only be new once. Launching before you’re ready can lead to carnage. Limping into a launch without a connected cadence will also reduce excitement as attention becomes diluted.

Let’s first look at how to avoid launching before you’re ready. There’s value in shipping your art often, as this is the only way anything is set free to evolve toward product-market fit. This, however, does not give us permission to be careless. Research, internal planning, strategic development, thorough testing, and working with true fans is the easiest way to stress test whatever you’re building. When we normalize a nimble, but detailed-oriented approach, you’ll create confidence in what’s being launched while also allowing your art to connect within the market you seek to serve more often.

When the time is right, planning a strategic launch sequence can initiate a boost loud enough to create attention and also long enough to push through the thick atmosphere of endless distraction. Instead of a single celebration, think of your launch as a connected collection of memorable moments.

The most common misfire is overloading your audience too soon. This may be part of the strategy with a short launch sequence, but when a launch lingers, duplicative content will numb an audience before the intended culmination arrives. One tactic for staying patient is mapping the overall launch sequence. This helps sync development with the timing of communication. Such planning also provides internal clarity and connects valuable context to each transmission.

To map a launch sequence, start by creating intrigue with as little information as possible. Think of this subtle stage like a notice to save the date. Next, create excitement by leaning into the pain. Leak a little on why the audience should be excited for what’s to come. No need for too many details quite yet. Those will land next.

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As the countdown ticks toward zero, fortify the team to determine how you can effectively respond to every type of inquiry during launch. With internal operations ready to rock, release one final burst of hype before delivering the payload on launch day. As thrusters fire and liftoff occurs, you’re now set free to release your art into the universe. Congratulations!

Within the early moments of flight, keep messaging sharp. Deliver on the promise, include singular calls to action, and track analytics to stay strategic.

A thoughtful launch can create a flurry, but attention is hard to earn and it’s gone before you know it. As the loudness of a launch begins to fade, hit the free prize inside button to activate a few more extraordinary insights built to fuel lasting momentum. Once in orbit, maintain a smooth onboarding process for late arrivals and enjoy the view knowing elevation makes us all feel successful.

By Ben McDougal, ago

Online Event Management

Live event management is a handful. Virtual events should also be well thought out. How can we create a memorable experience when everyone is participating online? Let’s teleport into this topic together.

First, consider what must be accomplished. What cannot be achieved without this time together? Determine how long the virtual experience should last. It’s usually less than you think. Next, line up the right technologies to ensure it fits the needs of your virtual experience. As tech is selected, use security tactics to avoid unwanted distractions. With objectives and logistics in place, it’s time to flesh out the experience.

While our connected era has unlocked the next level of efficiency with these virtual interactions, a drawback to online gatherings is the lack of time before and after a meeting. This means there’s less serendipitous interplay. Stay efficient, but it may be wise to weave in random value through manufactured moments that still feel natural for participants.

As attendees arrive, use your opening remarks to set the tone. Generate cohesion with jolts of genuine energy as any rules of engagement are quickly confirmed. If there’s a meeting agenda, run through that and connect it with meeting goals so attendees know what to expect.

After a welcoming attendees with a concise, energizing, and clarifying introduction, have fun unpacking the primary discussion. Stay on task and try to avoid distractions, but leave time for interactive dialogue. With less open dialogue due to the limitations of a virtual experience, this is one way to create space for those manufactured moments of serendipity. These conversational buffers help to avoid having the loudest voice be the only one that’s heard and invites an inclusive environment with deliberate space for everyone to participate.

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The term “hybrid” is hard to define. There’s value in weaving tech into in-person events so that others are able to virtually feel the experience. There’s also value in keeping things simple so the focus remains on your attendee’s engagement. Experiment with what works for you, but one interesting combination is to go all-in with live events, and then add strategic online events into the mix. This avoids fragmented coordination, eliminates the hollowness of virtual content within an in-person experience, and creates ease for organizers who benefit from both types of environments.

As you bring your online events together, you want interactivity so it’s not talking heads with attendees pretending to listen. Do this by including icebreakers, musical moments, pop-up polls, breakout discussions, scavenger hunts, doodling exercises, physical activities, and scheduled breaks. Encourage note taking and grab screenshots as artifacts to share later. Leave time for questions before wrapping things up.

As you bring things to a close, it’s important everyone feels a sense of accomplishment. If ramblings drag on before the meeting abruptly cuts off, people will leave feeling empty. Keep the virtual energy juicy, review key takeaways, and encourage action to tie a bow on the efficiency of all your online events.

By Ben McDougal, ago

Live Event Management

There’s something exhilarating about bringing people together to enjoy an experience you built. Anyone can bring a few friends together. Creating an environment for the public to connect requires more attention.

Controlling the chaos of an event is easier with solid planning beforehand. First-time events are always the hardest, but every event has unknowns. The more thought put in before people arrive, the smoother your attendees’ experience will be.

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I’ve developed and managed countless events throughout North America. More tips and tactics, as well as, insight from my own experience is layered into the Event Management section of YDNTB.

Basic details include the venue, time, and guest list. Who’s the audience? Based on those you want to attend, how can the venue support the right vibe and is it accessible? How will transportation and parking work? Looking at community calendars, will your event compete with other related events?

With basic event details in place, how can you promote this event so people you want to attend notice it? Will a website be needed or is social media enough? Is it free to attend or will there be a cost? If it’s free, how will you cover costs? Speaking of costs, how could sponsorships work? What’s the plan for food and drinks? Is there a registration process? If not, will you still be able to gather attendee data? Is security staff needed?

Think about your own goals for the event and how you want attendees to feel when they leave. Beyond the basics, what’s the agenda look like? Will there be any sort of programming? What about special speakers? As the host, if you plan to say a few words, what are the key points you want to make? Are activities planned or is casual conversation enough to keep everyone engaged? Will you be able to capture enough media while still managing the event? If not, does it make sense to hire someone to capture photos and video to use later? Can you rally attendees by connecting them on social media before, during, and after the event? Could showcasing live social media activity boost awareness for those unable to attend? Where’s a good place to send everyone interested in the after-party?

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Stay tuned! Next week we’ll shift focus to online events.

One common mistake is assuming an event is over when the last guest has left. Detailed planning leads to smooth events. Concerted efforts to commemorate events lead to future opportunities. Finish strong with thank-you notes, tagged photos, video highlights, recap articles, and follow-up conversations.

Event management is challenging and stressful, but super energizing. The more you bring people together, the more effective you’ll become. As the basics become second nature, it’s easier to get more creative. This leads to larger crowds, more memorable experiences, and longer-lasting engagement. Like everything, the more you practice, the better you get.

By Ben McDougal, ago