Communication

ChatUX

Chatbots have a PR problem.

On one hand, conversational AI combines large language models (“LLMs”), vast data sets, and interesting influence layers to provide insightful ideas and answers to almost any question. Chatbots provide a personalized interaction with education, content creator, language learning support, financial advice, customer assistance, helpful reminders for important tasks, co-founder assistance, and even mental health therapy. These AI companions munch on mediocre and are always available to chat. ChatGPT is the most well-known example, but other content creation methods, bot building platforms, and layered tools, such as BEN BOT and ChatSpot, are being activated in creative ways.

On the other hand, when most humans hear the word “chatbot”, the word serves up a slimy aftertaste. We think of automated help desks that put us in circles, fake followers on social media, the search tool that can never quite find an question, or that lead generation form that only wants to guide you to the next sale. Even with the best intention, a history of hacks fuel mistrust and makes it hard to avoid the spammy connotation.

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Hallucinating is when AI confidently delivers inaccurate responses.

Chatbots may not be able to interpret complex interactions, decode user intent, express empathy, or keep up with the rapid pace of change in the world, but it feels naive to pretend that conversational AI is not efficacious.

As we continue learning how to interact with this innovation, we need a term that is more inviting. A term that evokes trust. One that describes an intelligent counterpart with no agenda. When the user experience is not misguided by motive and AI is truly conversational, “ChatUX” may be the term we seek.

ChatUX describes the interaction between humans and software, unlocked by conversational AI.

Chat is an informal conversation or to talk in a friendly and informal way. UX is short for User Experience, which describes how we interact with a product or service. It includes our perception of value, ease of use, and efficiency. “ChatUX” can help us understand how to interact with emerging technology, while also improving the chatbot’s image.

ChatUX is not spam. ChatUX won’t take your job, sell you something you don’t want, or take over the world. ChatUX requires ingenuity. It is translation technology designed to access endless insight, with an ability to communicate it effectively. It’s software that speaks our language while supporting a timely, interesting, accurate, unbiased, and meaningful experience for anyone curious and generous enough to build beyond the status quo.

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I’m hosting a new podcast! Stay tuned for more caffeinated conversations around technology, entrepreneurship, intrapreneurship, and community building.

By Ben McDougal, ago

Melting Momentum

Once something melts, it’s never quite the same.

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Inspiration is perishable.

From the moment we decide to start building an idea into reality, the force required is geared toward finding and then maintaining momentum.

Meaningful momentum is awakened in endless ways. Early momentum might mean showing up at an event for the first time, researching the competitive landscape, testing an early hypothesis, leaning into customer discovery, recruiting potential co-founders, building product, and eventually activating a launch sequence. Once a project is launched, the need for momentum never fades. If anything, it only becomes more important. There are many more examples, but growing the business, achieving milestones, and celebrating progress are all forms of valuable momentum. Even in later stages of a company, momentum drives activities like succession planning, navigating a successful exit, and considering how your human, financial, cultural, intellectual, and network capital can be recycled back into the entrepreneurial ecosystem.

No matter where you’re at in your own journey, if momentum is maintained long enough, the result can be a flywheel effect that feeds on itself. Anything you want to grow will always require endless work, but with less friction, momentum delivers more time, understandings, and space for different activities emerge.

On the flip side, if momentum is melting, it’s difficult to recapture. These are moments to consider when and what to quit. If there’s enough energy to keep writing the story, it’s neat how there’s always the option to keep building. A few sparks that can help regain momentum come to mind. For instance, (re)connecting with the startup community, learning something new, saying “yes” to unlock adventure, saying “no” to create space, travel, revisiting customer discovery, building a new feature, considering a pivot, onboarding new customers, and adding to the team.

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Need help regaining momentum?

The longer stagnancy lingers, the harder it will be to realign momentum. Tactics to maintain a creative state of kamiwaza, even when momentum is melting, starts with communication. Keeping honest communication consistent adds clarity and is the easiest way to appreciate the realities of slowness. Reducing the weird by exposing the why, also keeps different stakeholders on the same page, even during more lethargic times. By reducing the tension that quietly brews in silence, teams may be able to run at lower speeds. If left unattended, this can devolve into a lack of urgency that brings new challenges, but at a lower speed, perhaps less movement is needed to regain/retain the sense of shared momentum.

When we play long-term games with long-term people, momentum is crucial, but set your own pace by exploring the type of momentum you need at different stages within the work. This awareness helps you quit chasing momentum and sets us free to forge better art, at a sustainable speed. This helps us multiply mass and velocity, which equates to momentum when, where, and how it’s needed to keep building.

By Ben McDougal, ago

Reluctance

There’s an art to keeping the right people engaged, for the right amount of time. When things feel stale, it’s often a signal of disinclination. One way to infuse new energy into a group, is to create space by releasing the reluctant.

Life happens, so it’s natural for interest and commitment levels to change over time. While engagement may expand, anyone’s ability to contribute can just as easily be reduced as a mission evolves and roles transform.

The spiral of someone’s reluctance will soon create stress between others who are still devoted. The longer this misalignment lingers, the more tension it creates. Even so, people hold on too long and the group fears confrontation. This extends the pain for everyone. The reluctant feel guilty for not contributing, while the zealous begin to resent the perceived lack of integrity. Along with internal toxicity, those being served experience less dependably, which devolves into reduced trust, enthusiasm, and engagement.

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“Winners quit all the time. They just quit the right stuff at the right time.” -Seth Godin

Keeping an eye on our personal bandwidth adds clarity for what and when to quit. This self awareness helps us stay centered and motivated by the way we spend our time. It also helps maintain good relationships by avoiding the unnecessary roughness of dramatic encounters, even when it’s time to explore a new direction. When bridges don’t get burned, we can make a ruckus, move on, and actually expand our impact while still staying connected.

For leaders dealing with lingering reluctance, let’s finish with a few friendly tactics to keep the group vibrant, while maintaining lasting loyalty from the departed.

An easy way to start, is by respectfully inviting individuals who have written their story, to graduate gracefully. Sometimes, good people simply don’t want to quit on the people/program they care about. When given a polite opportunity to exit with elegance, appreciation leads to a smooth transition. Another approach is to invite everyone to do more. Inviting initiative often provokes less committed members to bail. Lastly, know the end will always come. Be clear with expectations, transparent as things evolve, and keep succession apart of ongoing planning. Compliment the internal clarity with external celebration. Make a habit of recognizing individuals who made a difference in the past and praising those who are being generous now. This nurtures an environment where people are inspired to do their best when they’re involved, without feeling a sense of loss when it’s time to let go.

By Ben McDougal, ago

Breakout Valuation

Breakout valuations are achieved when a business is valued based on how it makes people feel and its future potential, not just what it’s done in the past.

The nine components of a breakout valuation are confidence, vision, curiosity, people, communications, cash management, financial forecasting, capital strategy, and business design. Whether or not you sell your company, business owners who optimize in these areas, position themselves to capture a breakout valuation.

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This caffeinated contribution is a special adaptation from Breakout Valuation, which is the #1 New Release in Venture Capital and was written by my good friend, Patrick E. Donohue. Patrick is an entrepreneur, mentor, advisor, investor, valuation expert, and community builder who offers unique insights into the dynamics of money and business.

While you’re running a company, breakout valuations make everything easier. It attracts talented employees and quality customers. This expands your market position, makes financial capital less expensive, and invites vendors to extend better terms based on your surging trajectory.

Knowing what your ownership of the business is worth helps you make important financial decisions and becomes increasingly important as a business matures. If a business grows to the point where it becomes valuable to acquire, academic and finance professionals attempt to make valuation objective, but the complexity of each transaction makes valuation subjective in the end. Along with all the objective data, valuation is highly influenced by the environment, relationship, and personal views of the participants in a transaction. Knowing how investors and lenders use objective valuation tactics is crucial, but understanding the potential value of the business, articulating it to potential partners, and having them buy into the vision will arm you with an advantage to get what you want—a breakout valuation.

Breakout valuations are not aspirational. They emerge from what you are doing right now. It’s all about being clear with your mission and vision. It’s knowing your numbers and how everything comes together through a shared mindset, communication, and workflow. The pursuit toward a breakout valuation compounds, requiring attention today, and every day moving forward. This aggregates understanding and builds confidence. When the day comes to part with some or all of your business, the confidence from a breakout valuation will maximize the payout or deliver assurance in walking away from the deal.

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What are we doing today to support our goals for tomorrow?

By Ben McDougal, ago

Follow Up

As you continue to show up and stand out, it’s important to wrap a bow on your interactions by following up. Why? When creating connections, a single encounter is rarely enough. Whether it’s an email, phone call, social media connection, or handwritten note, follow up.

These tiny touch points can root a relationship. Even if there’s no obvious ways to collaborate right away, take a moment to say you enjoyed meeting that new contact. If possible, include something memorable from your encounter to personalize the message. This is also another chance to ask if there’s anything you can do to help, then close by sharing how you look forward to staying in touch. Whether they respond or not, this follow-up will increase the chance you’ll be remembered.

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The moment you meet is an effective time to connect on social media.

As you meet more people, it can become hard to maintain this habit without support. Don’t be afraid to use relationship management tools to keep conversations organized. Hubspot, Airtable, and other free CRM tools may be a good place to start. These platforms can automate your communication efforts, but play it cool. This is not the time to sell or bombard someone’s inbox. Instead of a pre-determined cadence, make a simple note to follow up. Use this reminder to comment on a social media post, share a quick idea, suggest a meaningful introduction, or invite your new contact to an upcoming event. While these follow ups are unscripted, it doesn’t hurt to internally track how many times you’ve touched base.

This balanced, friendly, and ongoing effort to stay connected will separate you from the pack and keep you on that person’s radar. Business may not spawn from these touch points, but there will be fresh context the next time you see each other. If opportunities to collaborate emerge, you’ll have a channel of communication already in place. Either way, showing up, standing out, and following up makes it easier to explore engaging ideas with your evolving network.

By Ben McDougal, ago