Managing in the Age of Uncertainty
I went looking for the future - and I found it with Blake Wood
I’ve always loved this quote by William Gibson of Neuromancer fame: “The future is already here; it’s just unevenly distributed.”
The arrival of agents as full-fledged members of a team — working side-by-side with humans — will happen in some way for most in 2026.
I write here about the differences between managing as a boomer versus managing as a millennial and gen-z. I focus on the implications to a team when biological and digital people sit at the same table.
All of this change is happening in real-time, it seems to me. But I know from experience that any technology revolution starts with a small set of early adopters — teams that are way ahead of the curve.
So I went looking for an early adopter of agents — and found one with Blake Wood, a childhood friend of my son. Blake’s now a sales leader at Salesforce. I was lucky to interview him last week.
This was clear: Blake is living in the future — what managing will look like for everyone else a year or two from now.
Here’s another thing: his unabashed enthusiasm for the agents felt like generational thinking to me. Like, “this is the way things are supposed to be.”
This blew my mind: I literally laughed out loud when he said the greatest benefit of agents came down to the quality of his sleep.
Seriously.
“I used to have a notebook on my nightstand where I’d wake up at 3 a.m. and jot down notes — I slept horribly,” Blake says. “But with the agents we’re using, I’m sleeping the best I ever have.”
Which is surprising, because his job is nuts when you hear about it. But then again, maybe this is what the power of AI is all about.
WHY: Managing a team today is at least an order of magnitude more complex than it was for boomers.
It’s hard for boomers to understand the pace and complexity of managing a team today. Here are three differences:
Millennial and gen-z managers have twice the number of direct reports as boomer managers.
As flatter structures replace the hierarchical structures of the boomer era, today’s managers spend more than 50 percent of their time collaborating across an organization versus within it.
It’s not unusual for a manager today to spend 80 percent of their day with communication tools like email, Zoom and Slack coordinating with people outside their organization to move projects forward.
The collaboration “tax” is very real.
Blake says that each account executive on his team coordinates sales activities with about 75-100 other sellers inside Salesforce. That’s right: Blake’s organization has to align its work to more than 1,000 other people in the organization — every minute and hour of every day. And as all of us know, sales people live in the moment, not in the future. So that’s a lot of voices to listen and talk to every day.
“There is just no way to track everything that’s going on,” Blake says. “We have to leverage our AI products here internally — to prioritize the work, to prospect, to find new insights, to do deal inspections.”
Think that stat about spending 80 percent of your day communicating in some way is a little off?
It might actually be low.
“People on my team typically have only 6-8 hours a week of non-meeting time,” he tells me.
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WHAT: To agent or not to agent? The people are speaking.
Here’s what hasn’t changed between boomers and the current generation: you need the best people on your team.
The best people know agents are the future — and want to be the ones building and operating them.
Blake is clear some people are resisting agents, especially people with more “tenure.”
“The younger people coming into the business are all over it,” he says. “They are the ones actually creating new ideas of how to use agents.”
Millennials and gen-z know the corporate ladder is dead, and all they control is their story. No doubt agents as productivity or innovation tools will be central to writing a bestselling chapter of a career story.
As a reminder, agents are not chat bots; they are autonomous pieces of software that occupy job roles on a team. “Agents don’t just summarize a situation; they prompt ideas and new ways to think about information, “ Blake points out.
Here are five use cases of the agents working on Blake’s team:
Morning account briefing — Every morning, each AE gets an autonomous overnight summary of everything that happened in the last 24 hours on their key account: support cases, internal Slack messages, meeting notes, CRM data, Google docs — all aggregated and summarized with prompting ideas on how to act on it.
Prioritization and prospecting — Agents help the team figure out where to spend their time across a portfolio of 75-100 co-sellers, surfacing which accounts to prioritize and why.
Deal inspection — Agents pull together deal data to help AEs assess the health and status of opportunities.
Case trend analysis — Agents surface support case history: volume, average resolution time, topic commonalities — to help identify adoption challenges or technical health issues in an account.
Meeting time tracking — An agent that tells Blake how much non-meeting time his people actually have in a given week.
HOW: Avoid the “Wild West”
Agent adoption right now is, in Blake’s words, “a little bit of the wild wild west.” There are no limits on how many agents your team can build — and at Salesforce, anyone can build one often in less than five minutes.
That’s exactly why you need a weekly meeting.
Once a week, Blake sits his team down and asks one question: who found something new? “Almost every week someone’s got something that is helpful,” he says — and that single meeting is what turned his most resistant people into believers.
Here are three questions to put on the agenda every week:
What did you build or try this week — and what did it save you?
Where are you still doing work at night that an agent could do for you?
What agents aren’t working and what can we learn?
The wild west needs a sheriff. For managers, the weekly meeting is it.
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ManagerMentor • All Rights Reserved • The Culture Platform, Inc. • 2026