Business guru Peter Drucker gave us five things a manager does: Plan, Organize, Integrate, Measure, and Develop. For 70 years, that list has held. AI is going to break four of them in the next 36 months, and the manager who survives is going to look a lot more like a shoulder-to-shoulder mentor than an ivory tower desk worker.
Drucker’s 1954 book The Practice of Management is widely considered the foundation of modern management as a discipline. Why have his five functions held so long? A broad document like Drucker’s thesis or the United States Constitution, when it’s well written, anticipates future innovation and is flexible enough to serve as an overlay for many years to come. Drucker may or may not have foreseen the arrival of AI, but nevertheless, all things change, and Drucker’s management construct is no different. So, which of these roles will be preserved and enhanced, and which will be eliminated by disintermediation? Let’s explore this metamorphosis of the 1954 manager into a 2026 player-coach. There’s still time to plan proactively rather than deal with change reactively.
Rebooting Drucker’s Five Functions for 2029
Plan (Enhanced) — Any seasoned leader will tell you they want all the information they can get their hands on while planning before executing anything. Over the past 30 years, we’ve seen the rise of search engines, vertical databases like LexisNexis, and assistance tools such as augmented reality enter the market in a highly fragmented state. The ChatGPT moment in late 2022 gave us a glimpse into a new world where an AI planning agent becomes a co-pilot in anything novel. After all the pearl-clutching around hallucinations and bad results subsides, we will be left with a series of highly specialized and incredibly powerful sub-agents. In the hands of people who know how to ask the right questions, these will have 10-100x planning capabilities over today’s tools, giving rise to superhuman management capabilities and immediately rendering anyone exhibiting Luddite tendencies obsolete. AI won’t replace planning. It will make planning faster and more accurate. The human will still own the final call (for now).
Also by Henry Clifford: AI Hack #683: Learn The Tools
Organize (Eliminated) — Drudgery is an easy target for automation. No one likes manually pulling reports, updating spreadsheets, or building project plans. Managed AI agents will be able to automate almost all of this work in short order with a human in the loop for exception handling. Any employee whose role consists of 80% or more of repetitive production work like this will have a stark choice in front of them. They can lean into the 20% that they actually enjoy doing or be forced to consider other opportunities in other parts of the business. The allure of speeding up the flywheel or, as Google DeepMind’s Demis Hassabis calls it, the “sweetness” of invention, will be too irresistible for businesses owners not to leverage. Even if we wanted to slow it down, the second your competitor across town starts to implement a new innovation, you will have no choice. Depending on which side of the optimism/pessimism fence you sit obviously affects your perception over this one. In Dan Sullivan’s book, 10x Is Easier Than 2x, he talks about two types of people: Those who live in the gap and those who live in the gain. He claims most entrepreneurs live in the gap and are destined to be continually unhappy. The gain, on the other hand, invites the business owner to measure what has been accomplished and focus on optimism. The gain may be a more productive lens to view the world through in the face of increasingly uncontrollable elements.
Integrate (Enhanced, Then Transformed) — Think about all of the software tools you use in your business. While some of them have integrations with other software platforms, most integrators report extreme frustration with their technology stack. Platforms like Claude are knitting together software in ways that are extremely easy to implement, with practically no barriers to entry. A few examples include:
- Harvesting actual customer spend and sending out highly personalized “it’s time to upgrade your system” email messages.
- Serving up one previous customer per day to a sales rep, including their purchase history, last time they were contacted by the company, and a sample outreach message to use by text or email.
- Building a direct mail system without the need for an expensive building permit aggregation subscription.
- Automating labor forecasting and utilization reporting, wired in live to project management and payroll data.
- Prospecting for deal activity and sending automated email outreach to prospects in your voice.
While we’ve lamented for years that none of these platforms could deliver these opportunities, they are all happening at warp speed, right now. Audit your software tools and vendors. Who has a solid application programming interface (API), live product data available via comma separated values (CSV), or model context protocol servers (MCP) available for your AI to use? Shift your business to partners exhibiting openness to share and treat with immediate suspicion anyone keeping their systems closed.
Measure (Eliminated) — Anyone still spending Friday afternoons updating a scorecard is doing 2015 work. This may be the biggest opportunity in the next 18-24 months. The need to manually measure anything that’s meaningful to business performance is disappearing as we speak. Now it’s just a race to stand those tools up and operationalize them.
Imagine each of your employees has a custom scorecard based on their own goals and career path with each being able to connect their role to the overall mission. How would they feel about their career with your organization? What if you told your employees, “Hey, you don’t have to fill out a time card ever again. You don’t have to log time on a job site anymore. It will all be inferred based on where you are, when you are, and who you are.”
Don’t get me wrong, there are some creepy sides to this, and I think workers will naturally feel micromanaged if we’re not careful about messaging and addressing employee concerns head on.
We only need to look at the auto industry and their anonymous reporting of our driving habits to insurance companies or Meta’s recent announcement that they’re measuring keystrokes from all its employee devices. Managing the potential for cultural backlash is critical as we seek to eliminate manual measurement and optimize time for our new player-coach roles to spend the maximum amount of time mentoring and training others.
Develop (Enhanced and Elevated) — The real lifeblood of an organization is (and will stay) all about people. A strong player-coach in this new model is freed up to imagine what outcomes they would like to visualize, measure, and then iterate quickly with their teammates. At the same time, they are able to spend more time in one-to-ones, more time in the field, making employees feel seen, heard, and recognized (HR surveys commonly list lack of recognition as the number one reason employees quit).
Thomas Friedman’s book Thank You for Being Late reframes the age of artificial intelligence as artificial assistance. Best-in-class player-coaches will use AI tools behind the scenes to deliver personalized training and mentoring. Enhancing development with AI will accelerate employees along their career paths and make one-to-ones and chance encounters even more meaningful.
Custom installation features a bulk of work that’s hands-on and manual. We operate businesses with a lot of moving parts and technicians in vans manually installing televisions, racks, networks, speakers, and lighting. New technology tools will enable better coaching on the spot and draw into sharp relief the difference between a merely adequate performer and their 10x rock star colleague.
Watch for organizations like CEDIA and training platforms like IntegrateU [full disclosure: I’m a co-founder of IntegrateU] to launch new offerings aimed squarely at Train The Trainer and maximizing development potential inside all CI businesses. The need to standardize and delight our customers in an industry where the net promoter score is incredibly low creates an amazing opportunity over the next 36 months to completely transform what it means to develop and train. We have a once in a lifetime opportunity to change the current broken dynamic of throwing our employees into the deep end, not onboarding and training them properly, while at the same time eliminating drudgery. This is where the player-coach will live; coaching, mentoring, calling out bad work, and praising stellar performance. AI can score and recommend, but it can’t sit side by side with a new tech and challenge them to master a new skill. This function gets bigger, not smaller.
Who’s going to be doing all of this work? If we currently have pure play managers in our organizations, how will these new player-coaches emerge? What does the 2029 organizational chart look like?
Also by Henry Clifford: Do You Have a Co-CEO?
The ideal player-coach is a senior practitioner who still does the work, but spends a meaningful slice of their week developing the bench. Culturally speaking, we already have some of these behaviors anecdotally in our organizations, like seasoned installers or senior salespeople responsible for juniors. What if we could formalize that and promote our best employees into player-coach roles, pay them more, and help them be much more efficient in their day-to-day by eliminating all their drudgery?
Your 2029 Year Org Chart
Full credit for the 2029 AI org chart goes to business coach Aram DiGennaro, who presented his version of this graphic at the Virginia CEOs spring retreat earlier this Spring. I’ve personalized it for CI. Most articles you get to read and decide if you want to implement its recommendations in your business or not. This one isn’t necessarily as much of a choice, but whether you want to do it proactively or reactively.
Just to make it clear, much as the large AI labs are racing hard right now, CI businesses are locked in a parallel sprint, which should feel familiar to any custom installation business that’s been around longer than a decade. What we are all doing today, in many cases, bears little resemblance to what we were doing 10-20 years ago. The only difference now is that the need to climb and avoid disintermediation is now accelerating. What would Peter Drucker have made of all of this? He would’ve loved it.
Anything that stays still is decaying. Everything goes to zero. What are you doing to lead your organization proactively through the next 36 months?
Stay frosty, and see you in the field.
