You Can’t Run a 2026 Plan with a 2023 People System

You walk out of your planning cycle in January feeling pretty good.

Revenue targets make sense. Margin goals are aggressive but doable. You have a plan to grow security, push more cloud projects, maybe lean into vCISO or more strategic QBRs.

PSA dashboards say utilization is “healthy.” Sales is optimistic. Service leaders nod along.

By March or April, the story is different.

SLAs start wobbling. Escalations creep up. Key projects are slipping a few weeks at a time. The same three to five “heroes” are tagged on every complex ticket and grumpy client. A couple of senior engineers look exhausted.

When you get to QBRs, the slide deck quietly shifts from “Here’s what we are going to do next” to “Here’s why we are behind.”

You did not suddenly become bad at planning.
You are just trying to run a 2026 plan on top of a people system that is still stuck in 2023.

The tech stack is modern. The way you see and deploy your people is not. That mismatch is what quietly kills execution.

Your “People System” Never Got the 2026 Upgrade

When I say “people system,” I am not talking about HR software. I am talking about how you see and run your team in practice.

For most MSPs in the 5M to 50M range (or those that want to get there), it looks something like this:

• An org chart in Lucidchart, PowerPoint, or Miro that gets updated when someone joins, leaves, or changes title.

• Role descriptions written for hiring, not for how work actually happens today.

• Annual or twice-a-year performance reviews hidden inside your HRIS or a folder of Word docs.

• PSA or RMM data that tells you:

  • Ticket counts by tech.

  • Utilization percentages.

  • Escalation volumes.

• Manager mental models:

  • “She is our Microsoft 365 person.”

  • “He is the firewall guy.”

  • “Those two handle all the gnarly stuff.”

On paper, it does not look terrible. You have tools. You have reports. You have managers who “know their people.”

The problem is that this whole setup was built for a different operating environment than the one you are planning for.

Work has shifted:

• More project-heavy work around cloud, security, and migrations.

• More vendor complexity and integration work.

• Clients expecting strategic guidance at QBRs, not just “tickets closed on time.”

People have shifted:

• Skills built through home labs, side projects, informal mentoring, and real client work, not just formal certs.

• Aspirations change every 6 to 12 months. Today it is security, then client-facing, then leadership, then automation.

But your people system still mostly sees:

• Titles.

• Historic performance.

• PSA utilization.

It does not give you a clean view of:

• Who actually has which skills, at what level.

• Who is at or beyond safe capacity.

• Who is quietly underused.

• Where people want to go next.

And you are trying to bet your 2026 plan on top of that.

Modern Tools, Legacy People Practices

Most leaders feel like they are running a modern operation because the tooling is modern.

You have:

• PSA with decent dashboards.

• RMM is doing its job.

• HRIS that tracks headcount, compensation, and maybe some training.

• An LMS or vendor portals where people do courses and exams.

On the surface, it looks like a “data-driven” company.

But look at how the big decisions actually get made.

How staffing and workload decisions really happen

When you decide who takes what work, it is usually a mix of:

• Service manager’s gut.

• A quick scan of PSA utilization.

• Habit:

  • “She handled that client last time.”

  • “He always fixes these.”

  • “They are the A team for anything high risk.”

If you are honest, you are not pulling up a live view of:

• Real skills across the team.

• Burnout risk.

• Underused capacity.

• Who wants stretch work in a specific area.

You are leaning on instinct plus fragmented data.

How development and promotion decisions really happen

When you decide who to invest in, promote, or move into a new area, it usually lines up with:

• How loudly their manager advocates for them.

• Who you have personally seen step up.

• Notes from annual reviews.

• Whether they have picked up a cert that “sounds” aligned with your strategy.

What is missing is a consistent way to see:

• Who is already doing higher-level work without the title.

• Who is asking for more in a certain domain.

• Who is plateauing and needs a new challenge before they disengage.

Why this pattern sticks

With 10 to 15 people, you can keep a lot of this in your head. But then it gets to be way too much. And at 50 to 150 people, across multiple teams and maybe locations, you cannot. And your managers cannot either, not while putting out fires, handling escalations, and sitting in internal and client meetings.

There is no single place where:

• Skills are mapped consistently.

• Aspirations are written down and visible beyond a manager’s notebook.

• Overload and underload patterns are surfaced in a way you can actually act on.

So even though your tools are 2026 ready, your people visibility is still 2023. Static, fragmented, and lagging reality.

How 2023 People Systems Quietly Break 2026 Plans

You do not feel this gap in the strategy deck. You feel it in the day-to-day.

Here is how it shows up.

Execution falls off after Q1

Q1 usually looks okay. Projects kick off. Tickets feel reasonably under control. People are still fresh.

By mid year, you start seeing:

• Large projects delayed because the one person with the right skill set is tied up with escalations.

• New services, like MDR, vCISO, or advanced cloud builds, underperforming because the only people who can deliver them are already overloaded.

• Internal initiatives, such as automation, documentation, and process improvements, getting deprioritized because there is “no capacity.”

The story you tell yourselves:
“We scoped this wrong.”
“Clients changed things on us.”
“The talent market is tight.”

There is some truth in all of that. But underneath, a simple pattern is running the show:

You planned without a clear, realistic picture of who could actually sustain the work.

The same heroes burn out while others coast

In most MSPs, a small percentage of people carry a huge percentage of critical work.

You know their names.

They are on every tough escalation, every tricky client, every project that “just cannot fail.”

What you usually do not see:

• Who could do 60 to 70 percent of that work with some structured support.

• Who has the interest and aptitude but is never in the conversation.

• Who is consistently underutilized on lower complexity tickets because they are not seen as “that level” yet.

The result:

• Your heroes drift toward burnout.

• Your middle layer stagnates.

• Your overall capacity is lower than it should be, given the talent you actually have.

Hidden internal capability never gets pulled into the plan

Every MSP has mid level engineers who:

• Are rock solid on fundamentals.

• Quietly handle more complexity than their title suggests.

• Are already doing parts of higher level work informally.

But because you do not have a clean capability map, they never get named inside your strategic plans.

So when you plan a new service line or a big push with a certain vendor, the conversation is:

• “We do not have anyone who can lead this.”

• “We need to hire.”

Meanwhile, you likely have two or three people who could realistically be in that seat within three to six months, if you deliberately pointed work and support at them.

The issue is not the absence of capability. It is the absence of visibility.

Training and certifications do not change deployment

You pay for training. You pay for certs. You send people to vendor courses and conferences.

Then what?

In a lot of MSPs, the pattern is:

• Someone gets a new cert, Azure, security, vendor X.

• Their manager is happy. HR logs it. Maybe they get a small bump or a pat on the back.

• Dispatch and project staffing stay exactly the same.

Training becomes a line item and a feel good story, not a lever that changes how work is assigned.

If getting a new cert does not change:

• Which tickets you see.

• Which projects you are staffed on.

• Which clients you touch.

Then from a business perspective, the value is mostly theoretical.

External hiring becomes the default answer

When your people system is fuzzy, new initiatives tend to trigger the same response:

• “We need to hire a senior security engineer.”

• “We need a cloud architect.”

• “We need a stronger TAM for our top 20 accounts.”

Sometimes you do. But often, you have:

• People who want to move into that space.

• People who are halfway there on skills.

• People who could cover a good chunk of the role with structured support.

Because you cannot see that clearly, your default becomes:

• Higher salary bands.

• Longer ramp times.

• Existing staff watching you bring in outsiders for every interesting opportunity.

That is how you end up with retention problems on top of execution problems.

Workforce Orchestration: The Missing Layer Between Plan and Tools

This is where Workforce Orchestration comes in as a category of operating practice you either have or you do not.

Workforce Orchestration means you run your people system in a way where:

• Skills, current and emerging.

• Aspirations, what people want more of.

• Capacity, who is over or underused.

• Patterns, who gets what work and why.

are visible in one view and actively used to run the business.

You already have two layers:

1. Strategy: Your 2026 goals, service roadmap, revenue and margin targets, client segment plans.

2. Tools: PSA, RMM, HRIS, LMS, spreadsheets, vendor portals.

The missing layer is the one that answers:

“Given the people we have today, and where they want to go, how do we deploy them deliberately against this plan?”

That is not an HR question. That is an operating system question.

It is the shift from:

• Static org charts to dynamic maps of who can actually do what.

• Annual performance reviews to lightweight, regular visibility into skills, load, and direction.

• “Who is free?” to “Who is the right person, and how does this choice support our 6 to 12 month plan for them?”

You do not get there by buying one more tool and hoping it magically fixes everything. You get there by changing the questions you ask, the way you surface the answers, and how often you look.

Start Operating Like It Is 2026 in the Next 90 Days

You do not need to roll out a giant transformation project to start closing this gap.

You can do a lot with what you already have if you install a few new habits.

Run a monthly “overused vs underused” review

Once a month, sit down with your service leadership for 60 to 90 minutes.

Bring:

• PSA utilization.

• Escalation patterns.

• Project assignment history for the past 60 to 90 days.

Ask three simple questions:

1. Who are our top 10 to 15 percent most overloaded people right now?

2. Who is consistently under scheduled or stuck on low complexity work?

3. What 10 to 20 percent of high complexity work could we shift, and to whom?

You are not trying to redesign the whole org. You are trying to:

• Take some weight off your heroes.

• Intentionally move a bit more complex work to underused but capable people.

• Make this a regular rhythm, not a once a year crisis meeting.

Add one question to every 1:1

In every regular 1:1, ask:

“If you could be doing more of one type of work here in the next 6 to 12 months, what would it be?”

Capture the answer in something simple:

• A shared spreadsheet.

• A Notion or Confluence page.

• Even a structured document, as long as it is searchable and shared.

Over a month or two, you will see patterns:

• People leaning toward security.

• People wanting more client facing time.

• People hungry for automation, scripting, or cloud architecture.

Use that input when you:

• Staff projects.

• Assign stretch tickets.

• Decide who shadows whom.

Do not overthink it. Just do not let those answers live only in a manager’s head.

Pick three people you are under-leveraging

Identify three engineers who:

• Are reliable.

• Are curious.

• Are already doing bits of higher-level work informally.

For each one, define:

• One area they could own more of, a client, a technology, or a type of project.

• One specific responsibility you will move to them in the next 90 days.

Align with their manager and any senior engineer they will work with.

Make it explicit:

• “You are going to own X for this client.”

• “You are going to take the lead on Y part of this project.”

• “Here is how we will support you, and here is what success looks like.”

You will be surprised how fast your internal bench starts to look different when you do this deliberately.

Redesign staffing for one critical project or marquee client

Pick one high visibility project or client that always goes to the same A team.

Instead of just throwing the usual names at it, design it this way:

• Keep an A player as lead.

• Pair them intentionally with an underused engineer as a named successor.

Make it clear:

• Which pieces the successor owns.

• What decisions they are allowed to make.

• How you will measure whether this moved them forward.

You are not just delivering work. You are deliberately building capacity.

Install a monthly “people vs plan” checkpoint

Once a month, as a leadership team, ask:

• “Given what we know now about skills, load, and aspirations, would we still run our 2026 plan the same way?”

• “Which initiatives currently depend on one or two people?”

• “Where do we have potential successors we are not pulling into the plan?”

Tie that conversation to:

• The aspirations data from your 1:1s.

• The overused or underused review.

• Real project and client outcomes.

This is how Workforce Orchestration starts. Not as a buzzword, but as a recurring conversation backed by better visibility.

Your Plan Is Not the Problem. Your People System Is.

Most MSPs do not miss their 2026 goals because the plan was bad.

They miss because the plan was built and executed on top of a people system that has not caught up with how fast the work and the team are changing.

Modern stack. Legacy people visibility. That is the default.

The good news is that you do not have to blow everything up to change it. You can start by:

• Seeing who is actually overused and underused.

• Getting real about what people want next.

• Naming and growing the internal bench you already have.

• Making “people vs plan” a regular operating question, not a last minute scramble.

If you are looking at your 2026 plan and realizing your people system is still back in 2023, you are not alone. I am always open to compare notes on what you are seeing and share what I am seeing in other MSPs who are starting to close that gap.