You have paid for the licences and told your people that the new tools are there to make their working lives easier. Six months later the usage figures are flat, the old manual processes are still running in the background, and when you ask why, the answers are vague enough that nobody appears to be at fault. Somewhere between the board’s enthusiasm and the front line’s reality, your AI investment has stalled.
Most leaders read that as a skills gap and commission another round of training. My guest on this week’s episode of Impactful Teamwork, Chris Carolan, founder of Value-First Team, offered a far less comfortable diagnosis. If your people are not used to asking for help, he argues, they will not be any good at asking AI for help either, and no amount of prompt training will fix a habit your organisation has spent years building.
The Habit Your Organisation Taught Its Best People
Martin Seligman’s experiments at the University of Pennsylvania in the late 1960s showed that when effort repeatedly makes no difference, we stop trying, even after the circumstances have changed. Chris describes how it plays out at work in very ordinary terms. Someone knows exactly what they need to do their job well, they ask for it, and the answer is no because of an IT rule or a budget rule. After enough of those refusals they stop asking and build a workaround instead, because they still have a job to do.
He shared a story that will be familiar to anyone who has run a function inside a large business. While training a colleague on HubSpot, he couldn’t understand why she was struggling until he walked over to her desk and found a six-year-old laptop that took ten seconds to load each screen. When he asked why she hadn’t replaced it, she told him she had asked once and been turned down. So she had simply carried on, losing minutes every hour, because asking again felt pointless.
Why AI Exposes The Pattern So Quickly
Generative AI is the first workplace technology whose value depends almost entirely on your people’s willingness to describe, in their own words, what they need. That is precisely the capability learned helplessness wears away.
Chris described watching a highly capable colleague who spent hours moving event leads into Salesforce by hand. The plan was to record the process once and let AI take it over. Halfway through, a message appeared saying her organisation hadn’t switched the feature on. Her response was the one her organisation had trained into her. These are the IT blocks we are used to, she said, and she was ready to log a request and join the six-month queue. The obvious alternative, which was to explain the obstacle to the AI tools she did have and ask how else she might get the job done, simply didn’t occur to her.
This is what we mean at Business HorsePower by entrenched leadership dynamics. The control that made perfect sense when you were a business of 200 people becomes a self-reinforcing pattern at 2,000, and the cost only shows up when something new, such as AI, needs your people to behave differently.
What The Elephant Already Knew
There is an old image I return to whenever this subject comes up. A baby elephant is tied to a post with a chain it cannot yet break, and it learns to stop pulling. Years later the grown elephant could snap that chain easily, yet it stands still, because the lesson outlasted the constraint.
Your organisation almost certainly has chains like this. They are the approval processes nobody has revisited since the last restructure, and the requests your best people stopped submitting because the answer was always no. The commercial consequence is that your AI programme is being judged against people who have quietly learned that initiative is a waste of breath.
Tribal Knowledge Is Expertise You Have Never Asked About
The second half of our conversation turned to something every leadership team discusses and almost none resolves. Chris has been watching organisations name key person risk as a problem since 2010, and then watching it go unaddressed while each new hire spends six months shadowing the one person who really knows how things work. His reframe is to treat tribal knowledge as human domain expertise rather than as a risk to be managed.
In the episode he explains why your experts may actively undermine the AI you build from their knowledge, and why he believes no process should be designed to run without a human in it. I also share the moment my own boss at Arthur Andersen almost stopped me taking a sabbatical because nobody else understood the business I had built, and Chris tells a story about a trade show conversation that shows exactly why your sales and marketing systems are slowing your best people down.
Questions Worth Asking This Week
Start by asking your team what they have stopped asking for. Then borrow Chris’s question for every task on your own desk: is the thing I am about to do going to create value for anybody, and if the answer is no, am I allowed not to do it?
So, as Chris and I asked at the close of the episode, where does the tribal knowledge sit in your organisation, and have you ever asked the people who hold it what they need?
Listen, Then Look At Your Own Leadership Team
Listen to the full conversation with Chris Carolan on Impactful Teamwork. Take the Entrenched Leadership Dynamics Diagnostic and see whether your leadership team’s three levers are moving in step. Or join us at our next executive forum, where we work through exactly this question with leaders of scaling businesses and pressure-test what human leadership needs to look like alongside the technology. Register your place here
Show Notes
- 00:00 — Welcome to Impactful Teamwork
- 00:45 — Opening insight: learning to ask AI for help
- 00:50 — Meet Chris Carolan
- 02:32 — Putting value creation before tools and activity
- 06:04 — When systems no longer serve the people using them
- 10:55 — Simple language, complex organisations
- 14:12 — Learned helplessness and AI adoption
- 20:11 — The everyday barriers leaders can overlook
- 23:29 — Tribal knowledge as human domain expertise
- 25:46 — Where does the human contribution belong?
- 27:12 — Expertise, trust and resistance to AI
- 29:05 — Looking beyond problems to new opportunities
- 31:56 — Connect with Chris
- 33:11 — Your leadership challenge for the week
You can connect with Chris at: https://www.linkedin.com/in/chris-carolan/
