Time will tell if the expense was worth it, but there was a lot of upside in attending the HumanX conference last week.
- I connected with some âZoomâ colleagues in real life, - I had deep conversations with new people, - I learned of new products I could use to help my clients improve operations, - and loaded up new creative raw material into my noggin. đ§
Iâm proud to say I had the confidence to insert myself into tables of conversation during the meals, and these meals were the most interesting things each day. My principle is âbe interested, and interesting.â I always started by asking questions of everyone else first.
Where are they from? What are their goals for the conference? What are they looking forward to?
If they asked about me, Iâd do my best to share succinctly all the things I was working on.
Typically this would snowball into a lively conversation over the course of 30 to 60 minutes, culminating in LinkedIn connections.
Lest you think it was all roses, I had my share of goofs. For example, someone introduced themselves to me while we were standing behind the âoperationsâ stage before a talk, and my brain come up with this banger: âAre you into ops?â
The guy was like, âUhâŚwhat?â đŹđ¤Ł
Outside of networking, the other benefit I did not anticipate was the experimental cycle of describing what I do, since literally every person I talked to asked me that question.
How did I go about defining my work?
On the flight over I used Ollama and Obsidian to brainstorm category definitions for the various pieces of my work, using my notes from âPlay Biggerâ (both of those are offline tools - in-flight wifi not required!)
The main principles are to âbe different, not better,â and be a little provocative, to get peopleâs attention.
These principles were easy to see (in their absence) when I listened to vendors and attendees pitch themselves. For example, while calling yourself an âAI SDRâ may help people identify your product, you automatically get lumped into the other four AI SDR products they saw that day.
And if you utter a string of business babble (âmaximize valueâ), no one understands...or cares.
If you can be different and provocative, people will ask you questions to know more, and theyâll be more likely to remember you and your business.
I described what I did 50 times over the few days. Each time Iâd watch the reaction. Were they bored? Did they nod in understanding?
Iâd constantly experiment, keeping what seemed to work, jettisoning what didnât.
Like I shared in last weekâs deep dive, every âfailureâ in conversation helped improve the story for the next conversation. Obviously this is a much better strategy than just repeating the same story 50 times without changing it!
By the end of the week I had a lot of new business connections and a more polished story of my business.
I hope YOU had a great week last week!
Kevin
A Quote
â
Work at allowing more things to unfold in your life without forcing them to happen and without rejecting the ones that donât fit your idea of what âshouldâ be happening.
â Jon Kabat-Zinn in "Wherever You Go, There You Are"
1 - đ¤ Digits, an AI General Ledger This product is an automated general ledger. The four main features, all powered by AI, are: bookkeeping, financial insights, invoicing, and bill pay. At $100/month for the automated product, and $350/month if you want some humans in the loop, this is less than you might pay for someone to run your books each month. And if youâre currently doing this yourself, it should be really easy to pay yourself back in time saved.
2 - đ ď¸ Airia, AI Orchestration Airia was the most interesting tool for general business operations that I saw at HumanX (and a palindrome!). It has a no-code AI agent builder interface, so it should be relatively easy to set up (but Iâll note that lots of no-code platforms are wonky). You can plug in different models (e.g. ChatGPT, Claude, other), enrich with different data sources (e.g. connect to file folders and other source systems), and even put in governance rules (e.g. block users from entering credit cards or social security numbers).
3 - đď¸ DecorX, AI Interior Design This team solved a really interesting problem; AI is really good at creating new things, but how do you get it to keep certain elements unchanged? They figured out how to keep a real piece of furniture and a real room, then combine them in stylistic ways (they call it âinpaintingâ). Itâs a really neat way to improve interior design. Try out their Feng Shui analyzer: https://www.decorx.com/fengshuiâ
(enjoy this 8ď¸âŁ minute read)
Deep Dive on Challenger Safety
Weâve reached the pinnacle of Psychological Safety. The fourth stage. The big dog. The seat of all innovation. Challenger Safety.
This is the stage where you break through the status quo. If you want to retain vibrancy, enhance agility, and remain competitive, this is the stage to seek.
To refresh your mind on the different stages and see where Challenger Safety sits: - In inclusion, youâre asking to be included. - In learner, youâre asking to be encouraged. - In contributor, youâre asking for autonomy. - In challenger, youâre challenging the status quo.
Today Iâll share the main tradeoff in Challenger Safety, how to create and sustain the conditions for it, and even how to grant safety to yourself!
Summary of Challenger Safetyâ - Challenger Safety empowers innovation by making it safe to challenge norms. - Leaders must protect individuals who risk speaking up. - Innovation is risky but critical. Leaders who create safety see more ideas, more action, and faster growth.
â
The Core Tradeoff: Candor for Cover
Challenging the status quo is quite risky.
Everything in an organization is built to sustain the status quo; itâs safe, predictable, and less likely to fail. Innovation happens only when someone is brave enough to challenge how things are done today.
But innovation requires failure, and failure is risky! If you want the candor that supports innovation, then you have to offer protection. People will speak more openly and take risks if they know they wonât be punished, mocked, or shamed for failures.
â
If the protection isnât there, a rational person wouldnât try.
If I told you thereâs a 90% chance your idea wonât succeed, and thereâs a 100% chance youâll be rebuked, ridiculed, and retaliated against if youâre wrong, would you try?
Probably not.
But what if you knew youâd be protected, supported, and encouraged to learn from failure? Now, challenging the status quo becomes rational, and innovation is possible.
ââŚwith challenger safety, the social exchange has now gone to another level: The team is asking you to challenge the status quo. Thatâs a mighty ask! Thus, the only reasonable condition is that the organization protect you in the process. If the organization wants candor, you need coverâyou need real and sustained air cover to be brave enough to take what is almost always a substantial personal risk.â
As I was researching this topic for todayâs newsletter, I couldnât help but reflect on last weekâs newsletter on failure, and my experience at the HumanX conference. The experience felt qualitatively different (and better!) than the conference I attended in 2023, and I think itâs because Iâm giving better psychological safety to myself.
My ego / self has been like a bad boss in the past. It has definitely ridiculed me for failures!
It makes me less likely to innovate and try something new if Iâm opening myself up to ridiculeâŚfrom myself.
I was listening to a really old Tim Ferriss podcast with Tara Brach this morning and Tim said something like, âYou have to be comfortable being yourself before you can be comfortable changing.â đ¤
âBeing comfortable changingâ is like challenging the status quo, which is the definition of Challenger Safety.
Youâve got to love and accept yourself in order for your Ego to become a good boss. It quiets negative self talk, which grants yourself Challenger Safety, which helps you take the next step in your transformation.
Psychological Safety may typically be related to team dynamics, but donât neglect the relationship you have with yourself.
âAs I started to love myself, things inside me shifted. Fear strengthens the ego. Love softens it. I became more open, vulnerable. It was natural to be gentle with others, even when they werenât loving toward me.â
Asking questions is the beginning of personal risk. Itâs where an individual is faced with a choice. To intervene and risk rejection, or leave things as they are, which stalls innovation.
đĄ "Should I ask this, or will I be rebuked?
How many problems do you think exist in your company that people see, but donât act on? Theyâre filtering their opinions because they donât have Challenger Safety. They deem it more risky to speak up than to remain silent.
If you want to kick start the process of innovation, you need to first start with making it safe to ask questions and explore. Going back to the tradeoff of âCandor for Coverâ from earlier, you need people to ask questions without fear of ridicule.
Ridicule often isnât dramatic. It hides in subtle eye rolls, casual dismissals, or silence after someone takes a risk. These small actions can be enough to stop innovation cold.
Even a subtle reaction, like your boss raising an eyebrow or pausing awkwardly, can signal danger. When your paycheck, promotions, or reputation feel threatened, candor evaporates. People quickly learn itâs safer to stay quiet.
âHave you cultivated a culture of inquiry that is hospitable to tough, uncomfortable questions, and do people really feel that? If you want a surge of ideas, you first need a surge of questions. If you want a surge of questions, you need to nurture the highest level of psychological safety based on the respect and permission that you give people.â
This is such a critical point, and one that I see commonly ignored in discussions of Psychological Safety: Not everyone is granted Challenger Safety.
Just like in earlier stages of Psychological Safety (except inclusion, which everyone gets), this is an earned right. Youâre granted Challenger Safety based on a track record of successful performance in the past.
You canât change industries, walk into a new company on your first day, declare that everything theyâre doing is wrong, and expect to be listened to.
Thatâs an extreme example, but the principle applies inside your existing team: Are you believable? Are you often correct? It doesnât mean everything you do works (innovation requires failure), but your approaches are sound.
So if you feel like you donât have Challenger Safety, itâs worthwhile to inquire into yourself. How is your track record of performance? How did you do with the autonomy granted in Contributor Safety?
â
Why itâs Hard
Challenger Safety is rewarding for all involved, but itâs difficult to achieve. If you donât think itâs hard, how many companies are stuck doing things roughly the same way theyâve done it for years?
I see these main contributors to the difficulty:
Itâs an Unnatural State As we learned in metacognition, our brains are lazy, energy-conserving objects. While brains can adapt, they default to their current state. Teams are the same way; they can change, but itâs significantly easier to keep things the same.
Your People Have Been Hurt Before Iâd be willing to bet that everyone reading this, and all of your employees, have been subject to ridicule for trying something new. That scar tissue exists and causes them to filter themselves in new situations. You may be a baller boss, someone doing all the right things, but anyone whoâs been burned before is going to be cautious.
It Requires High EQ in the Leader Each of your employees is different, so as a leader you canât just have one way of speaking, one way of being, and assume itâll work for everyone. Youâll have to monitor each person and each team for their sensation of safety, and know to incrementally build it up. Youâve got to be a student of people.
Stairs Up, Elevator Down Challenger Safety is built up in increments, brick by brick, but it is lost in an instant. You can do everything right as a leader, but then one day you scoff, or tease, or otherwise remove safety, and youâve set yourself back a year.
You can climb the stairs of building safety, but the elevator may take you back where you started.
Other People are a Factor You donât exist in a vacuum. Companies are made up of many people. And while you might have the largest impact on safety as a leader, other people are a factor as well. If the personâs peers ridicule, or thereâs a mean comment on a public page, those events detract from a personâs sense of Challenger Safety.
Just because Challenger Safety is hard, doesnât mean itâs not worth doing! We just need to focus on what we can control.
â
How Leaders Build Challenger Safety
What can you as a leader do to encourage Challenger Safety on your team?
Embrace Humility If you need to own every idea, scrutinize everyone, then you wonât create Challenger Safety. If youâre spending the majority of meeting time doing all the talking, then you wonât be getting the best of others. You want good ideas to flourish, not your ideas to flourish. Embrace being wrong at times and let your team explore.
âYou must be humble and open, and you must listen, and if you donât, the people around you will eventually have nothing to say.â
Create a Team, not Siloâd Individuals According to âThe 4 Stages of Psychological Safety,â âInnovation is the process of connected people connecting things.â A team is a group of connected people. A group of siloâd individuals are by definition not connected and will therefore not provide the company with innovation.
Assign Dissent One of the strongest things you can do as a leader is encourage dissent. You can do this explicitly by defining it as a role. In a meeting, tell one person their job is to challenge the thinking. You can also assign a âred teamâ or âtiger teamâ to probe for areas of weakness in the company. Youâre creating a culture in which dissent isnât an accidental thing; itâs core to how you operate.
Reduce Ridicule This starts with you. No ridicule allowed. From there, you need to establish that ridicule is not culturally appropriate anywhere on the team. No demeaning jokes or retribution for people. After that, ensure youâre creating an environment of peer accountability so it doesnât require you to be present in every interaction.
Stop Looking for Certainty Innovation doesnât operate on a schedule. Itâs non-linear and messy. The more you push for certainty, the more youâre going to squash the natural process of innovation. Allow for meandering.
âWandering is an essential counterbalance to efficiency. You need to employ both. The outsized discoveriesâthe ânonlinearâ onesâare highly likely to require wandering.â
Challenger Safety is essential to break out of the status quo.
Your action this week is to ask someone on your team: âWhat do you suggest we change to improve things around here?â
Their response will give you clues! Do they say, âUh, no, Boss, everything is great around here! Youâre amazing!â You might be awesome, but thatâs likely a clue that they donât feel safe đ
If, however, they share ideas with ease, thatâs a good sign. Be mindful of your reaction! Be curious. Be supportive. Be interested.
Iâd love to hear what you discover. Hit reply and share your experience!
Kevin
â
PS - If youâre feeling brave, also look inward. Is your ego being a good boss, or is there any personal ridicule or negativity youâre subject to? Give yourself a little love this week You deserve it. â¤ď¸
Are you interested in topics like today's Deep Dive?
â