02-05-2025
New Leadership Playbook For The Age Of AI
Man holding book with a human glowing brain.
getty
As AI transforms the workplace, the leaders who thrive won't be the ones with all the answers. Instead, they'll be asking better questions, faster.
These themes came to life at the recent IIA conference at the MIT Media Lab, convened by entrepreneur and investor John Werner and featuring top leaders and thinker in AI.
'Most people are used to things being relatively stable, and the set of practices they're using are working,' said Jeremy Wertheimer, a serial entrepreneur. 'But right now that's absolutely the wrong way to think about it.'
Employees need to change, and leaders need to help them adapt.
Here's your new leadership playbook:
Where to start
You may feel eager to dive right in and start encouraging your people to use AI. You might feel pressure to do so from top executives in your company.
So, as a leader, you may be asking yourself how you should be using AI right now.
Although it's tempting to start with tools, 'that's the wrong question,' according to Jamie Metzl, author of Superconvergence. 'The first question you should ask is 'who are we, what do we stand for and what are we trying to achieve?' Then you can ask how AI fits into that.
Issue an invitation
AI–nor any new technology–won't be adopted unless your employees feel comfortable experimenting and taking risks.
'When you have an aspiration for what you think the company should look like, and it doesn't yet look like that, that's a gap,' said Amy Edmondson, Professor at Harvard Business School and author of The Fearless Organization
According to Edmondson, there are 2 ways to close the gap. You could require people to do what you tell them to. Or 'you could make it attractive for people to close the gap. To do that, you'd frame it, with a great deal of humility, as a learning opportunity for which we don't yet know the answers and we invite you to play with us. Now, that's a pretty good invitation. That's almost an irresistible conversation for most people.'
Get people excited and they'll be more likely to start working with AI.
Encourage using the technology
Creating the culture is one thing. Setting norms is another.
'Any time we do anything more than 3 times, we encourage people to automate using AI,' said Johnny Ho, cofounder and Chief Strategy Officer of Perplexity.
Give people explicit frameworks about when and how they should use AI in their work and workflows. Let them know how they shouldn't be using AI with clear guidelines.
Many employees are using AI and hiding it because they're afraid of being punished, while others are afraid to use it because they're intimidated, according to research conducted by KPMG and the University of Melbourne.
Take these issues off the table and encourage people to use the technology by giving clear direction.
Lead like a researcher
Once employees start experimenting with AI, they won't get it right the first time—and that's the point. The frontier of AI is not a place for perfection. It's a lab.
One way to encourage your employees to keep going is to frame their experiences as experiments. Assume you're not getting a lot done; rather, you're conducting research.
As Wertheimer said, 'Everyone is doing research when you're at the frontier of the unknown.'
Build an entrepreneurial mindset
The skills needed in a workplace with AI are different from the past. As a leader you have to help your people adapt.
One way to help them is to help them build an 'entrepreneurial mindset.'
According to Wertheimer: 'There are going to be fewer roles for workers just doing things, and more roles at the strategic thinking level. You could call that entrepreneurship. Either way, you have to learn to think strategically and to take initiative.'
In large organizations, employees are often trained to follow process—not to think like founders. That won't work anymore.
Discuss the key skills of taking initiative, thinking strategically, and adapting quickly. Work with your teams to discuss ways they'll develop and measure these skills. For example, you could have a monthly strategy session where one person presents a key topic, or you could ask your team to try one additional step before they come to you with questions.
Curiosity is a superpower
As a leader, you are likely also trying to figure out your role in the new world of AI.
One skill you should cultivate is curiosity.
'Ask better questions,' Edmondson said.
For example, you could ask your employees, 'What's something you tried that didn't work—and what did you learn?' or 'How did you approach this and do we need to change our assumptions?'
Focusing on your own curiosity will help you explore more of the tools available and how they can be useful. It will also help you coach your people when they have troubles.
'Curiosity is one of our core values,' Ho said. 'It's a superpower.'
Meaning matters
AI can feel abstract or threatening to employees. That's why meaning matters more than ever. Leaders must help people connect their everyday tasks to a larger purpose—and show them why their work still matters.
'A leader needs to help people find meaning,' Edmondson said. 'Being able to draw a direct connection to the tasks you do, which can seem small or unimportant to a larger vision or meaning that our organization is pursuing is essential for employees and it's very motivating.'
Leadership in the AI era isn't about having all the answers—it's about guiding your people through uncertainty with clarity, courage, and curiosity. Start building your new playbook now.
