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Time charter

* [artificial intelligence](/partner-content/charter/tag/artificial-intelligence/)  
## artificial intelligence  


# How to Lead Amid the Uncertainty of AI

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#### What is TIME's AI newsletter?

In the Loop is TIME's twice-weekly AI newsletter, written by tech reporter Harry Booth. It covers the reporting, scoops and conversations shaping AI and the decisions facing leaders.

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In the Loop is TIME's AI newsletter, built on original reporting and access to the people building and governing AI. It publishes Tuesdays and Fridays and is free at time.com/newsletters.

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by 

[Kevin J. Delaney](https://time.com/author/kevin-delaney/)

Sep 7, 2025 10:30 AM UTC

![](https://static.time.com/v3/assets/bltea6093859af6183b/bltbb7f469824be2791/6998c99347fe51632e55c0aa/charter-heifetz.jpg?branch=production&width=1200&quality=75&auto=webp&crop=3:2)

by 

[Kevin J. Delaney](https://time.com/author/kevin-delaney/)

Sep 7, 2025 10:30 AM UTC

Charter is today releasing a new research playbook titled “[Leading in the age of AI: Practices for the new era](https://www.charterworks.com/ai-leadership-playbook/).” Published in partnership with c-suite advisory firm [Council Advisors](http://counciladvisors.com), it includes research, expert interviews, case studies, and checklists. You can [download it here](https://www.charterworks.com/ai-leadership-playbook/). 

One of the frameworks for leading through change that we cover in the playbook is known as “adaptive leadership” and has deep relevance for the deployment of AI in organizations. Developed by Harvard senior lecturer in public leadership [Ronald Heifetz](https://www.hks.harvard.edu/faculty/ronald-heifetz) with Riley Sinder and former Harvard professor [Marty Linsky](https://www.hks.harvard.edu/about/marty-linsky), it distinguishes between “technical” challenges and “adaptive” challenges. 


With technical problems, the solution is known and the manager needs to just successfully apply it. With adaptive problems, the right approach isn’t actually known yet and managers need to lead teams through the uncertainty that brings, projecting confidence, and also endorsing the experimentation required to find the best solutions. 

AI is a clear adaptive challenge—we don’t yet know how the technology will evolve or how it is best applied to specific roles or organizations. You can read Heifetz’s extended advice for leaders today in [the playbook](https://www.charterworks.com/ai-leadership-playbook/). As a preview, here are select excerpts, edited for space and clarity:

Sign up for Charter's newsletter to get the handbook for the future of work delivered to your inbox.

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You can unsubscribe at any time. By signing up you are agreeing to our [Terms of Service](https://www.charterworks.com/terms-of-service/) and [Privacy Policy](https://www.charterworks.com/privacy-policy/).

**In times of adaptive challenges like with business use of AI, what do the best leaders do?** 

When you're facing an adaptive challenge, you need a lot of micro adaptations to micro environments throughout a large company through its different functions, product lines, service offerings, interfaces with different locations and so forth. To generate all those micro adaptations or local adaptations to local environments, you want to generate a leadership that's generating more leadership and that cascades down through the organization.


What that means culturally is a bit of a shift from a highly efficient machine where direction comes from the top and then cascades down with clarity in terms of direction all the way down to the front line so that everybody knows what they're supposed to be doing and everybody has their weekly meeting judging the metrics and the proxies to control for efficiencies all the way down the line. 

When you're facing an adaptive challenge, you have to shift from that mode of operating to the support of experimentation because to develop the local adaptation to a local environment requires that local person to engage in experimentation. Because it may take moving through lots of iterations before you build what can become a routine process. 

The question then becomes, what's the latest experiment you've run? Tell me what's failed? What's your next iteration going to look like? Which is a different conversation than the control conversation that would be more sensible in a more efficiency-prioritizing control model in which you're asking a person for readouts" 'How can you get your readouts up?'


**Readouts are things like how you're tracking against your targets?**

Exactly. I'm thinking of an IKEA or a Best Buy—two companies that I've worked with—trying to unleash the leadership at the store level so that each store can have its own local variation because it's located in a different neighborhood than a store maybe two miles away or 2,000 miles away. But unleashing that local leadership to generate that local adaptation is a little bit unnatural to the cultural DNA of a highly efficient organization that has in the past made it in the marketplace because of its capacity to create a cookie-cutter model where you have consistency down through the line.

**Are there other common mistakes that you see in adaptive situations like we are with AI?**

I've worked with a lot of authority figures and there's a spectrum. Some people are comfortable speaking with a voice of authority without having answers. They can speak with a voice of authority where they're raising questions and stating uncertainties. They can speak with the voice of authority saying, 'Here's my risk analysis. Here are the uncertainties. Here are the questions we need to answer. And I hope we aim to answer these questions within X amount of months, but I'm going to come back to you because it's a moving target.’


Other people don't feel comfortable speaking with that voice of authority unless they actually have those answers. With different people, I have to work with them to get more comfortable not having the answers without losing their voice of authority. For other people—particularly people who are new to authority positions, which often includes women—it's how to speak with a voice of authority where you're simply stating questions and facts and have to speak with confidence even when you might be really very nervous inside because the uncertainties are so real. 

**Download “**[**Leading in the age of AI: Practices for the new era**](https://www.charterworks.com/ai-leadership-playbook/)**.”** 

---

## Read more from Charter

[READ MORE](https://time.com/partner-content/charter/)

[Open article: The Role of Unions in Training for AI at Scale](https://time.com/partner-content/charter/7301906/the-role-of-unions-in-training-for-ai-at-scale/)

![An illustration featuring a headshot of Roy Bahat.](https://static.time.com/v3/assets/bltea6093859af6183b/blt10956b9885da6773/6998c83c47fe51c94255be4e/charter-bahat2.jpg?branch=production&width=1200&quality=75&auto=webp&crop=3:2)

### The Role of Unions in Training for AI at Scale

[READ MORE](https://time.com/partner-content/charter/7301906/the-role-of-unions-in-training-for-ai-at-scale/)

[Open article: The case for a ‘chief work officer’](https://time.com/partner-content/charter/7290350/chief-work-officer/)

![](https://static.time.com/v3/assets/bltea6093859af6183b/bltfbd5d1c366f97051/6998c717d32e9304d2cd70fd/charter-athena-karp.jpg?branch=production&width=1200&quality=75&auto=webp&crop=3:2)

### The case for a ‘chief work officer’

[READ MORE](https://time.com/partner-content/charter/7290350/chief-work-officer/)

[Open article: LinkedIn Co-founder Reid Hoffman Believes AI Agents Will Be an Essential Part of How We Work](https://time.com/partner-content/charter/7212218/reid-hoffman-ai-superagency-linkedin/)

![Reid Hoffman](https://static.time.com/v3/assets/bltea6093859af6183b/blt565e13c9f8ba7e55/6998b30793610cf30fc2d747/charter-hoffman.jpg?branch=production&width=1200&quality=75&auto=webp&crop=3:2)

### LinkedIn Co-founder Reid Hoffman Believes AI Agents Will Be an Essential Part of How We Work

[READ MORE](https://time.com/partner-content/charter/7212218/reid-hoffman-ai-superagency-linkedin/)

---

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