Gary Boyle
Every strategic planning session produces a document that feels like progress. The room is engaged, the whiteboard fills up, and the plan that comes out of it is longer and more ambitious than anything the company has attempted before. Twelve months later that document is a source of quiet embarrassment. The goal at the top was usually fine. What sat underneath it was not. Most plans do not fail on ambition, they fail on volume, and the failure is almost always introduced by the people running the session rather than the owner living with the consequences. We have written before about how organizational strategic planning connects to business performance, and about writing a company goal a team will actually care about. This piece is about the layer between the two, the layer where good plans quietly become undeliverable.
The discipline required here is subtraction, and subtraction is the hardest thing to sell in a room full of people who just got excited about the future. An owner who leaves a planning session with fourteen initiatives has not been given a plan. They have been given a list of everything the business could conceivably do, ranked by nothing, owned by no one, and scheduled against a year that already has a full-time job in it. The judgment that matters is not what belongs on the list. It is what comes off. That judgment requires an honest read of what company performance analysis says about where a business is actually weak, a working definition of what an initiative is, and the willingness to tell a client that most of what they want to write down does not belong in the plan at all.
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The Plan That Was Too Good to Execute
Josh Peterson built a strategic plan for a client and Gary Boyle told him it was overbuilt. Not the goal at the top, which Gary signed off on. The milestones underneath it, and the volume of initiatives stacked below those. Josh pushed back, and the detail worth sitting with is the shape of his objection: it really isn't that big of a deal. That is what overbuilding sounds like from the inside. Every individual item looks small. Nobody adds up the total, because the total is not written down anywhere, and the person who would have to live with it is not the person holding the marker.
This is a consultant failure before it is a client failure, and it starts in a place that looks like good practice. An open planning session with every voice heard is the right way to begin. The excitement it generates is real and useful. But excitement raises the ceiling on what a room believes it can achieve, and a plan captured at the peak of that feeling records an aspiration rather than a commitment. The job is to take what the room produced, digest it, and return something attainable. Skip that step and the session's best quality, its openness, becomes the mechanism that makes the plan undeliverable.
- The strongest signal a plan is overbuilt is that no single item on it seems unreasonable.
- Openness belongs in the session and discipline belongs after it. Collapsing the two produces a wish list with a cover page.
- A plan built at the emotional high point of a session is calibrated to the room's mood, not to the company's capacity.
An Initiative Is a Driver, and Most Plans Do Not Contain One
It took Josh six years to understand what the word initiative actually meant. He is candid about why it took that long: when a consultant first told him he had too many, he did not hear the warning at all. He was flattered that someone had called the assorted work he was doing initiatives, because the word made it sound legitimate. That sounds real business-y, as he put it. The vocabulary of strategy is easy to adopt and expensive to misunderstand, and a term that confers seriousness on whatever you were already doing will be adopted faster than one that constrains you.
The working definition is simple enough to be usable in a room. An initiative is a driver. If the goal is two million in revenue, the initiative is the thing you implement in the company today that gets you there. Everything below it is a sub goal, which exists to track progress toward the driver rather than to be a driver itself. This distinction does most of the work, because it exposes the common failure immediately. Create efficiency is not an initiative. It has no direction and no mechanism. It could mean ticket throughput per technician, or dispatching, or a tool purchase, and a plan that cannot say which one has not made a decision. It has recorded an intention to decide later.
- If an item on the plan cannot be stated as a specific thing the company will implement, it is a topic, not an initiative.
- Sub goals track progress toward a driver. A plan made entirely of sub goals has no driver at all.
- Language that makes existing work sound strategic is the most dangerous vocabulary in planning, because it removes the pressure to change anything.
Efficiency Belongs Under Gross Profit, Not Revenue
Gary draws a line that a surprising number of strategic plans cross without noticing. If we are more efficient, we can do things at a cheaper cost, and that is not a driver for revenue. It is a driver for gross profit, and possibly net profit. The sentence is unremarkable as accounting. It is significant as diagnosis, because efficiency work is the most common thing an MSP owner files underneath a revenue goal, and filing it there guarantees the goal is missed while the team reports genuine progress every month.
The mechanism is worth naming plainly. Cost work is easier to start than revenue work. It is internal, it is under the owner's direct control, it produces visible wins quickly, and it does not require anyone to make a sales call. So when a company commits to a revenue number and then goes looking for initiatives, it drifts toward the cost basis of the business because that is where the tractable problems live. A year later the company is measurably more efficient and no closer to the number it committed to. Nobody was lazy and nobody lied. The plan simply pointed the effort at the wrong line of the profit and loss statement.
- Ask of every initiative which line of the P and L it moves. If the honest answer is gross profit, it does not belong under a revenue goal.
- Cost initiatives crowd out revenue initiatives because they are easier to begin, not because they are more valuable.
- A company can execute its plan flawlessly and still miss its goal if the drivers were filed against the wrong metric.
How Many Strategic Initiatives Should an MSP Run at Once?
Josh asked for a hard rule, and admitted he likes clear rules even when clear rules are almost impossible to write. Gary gave him one, scoped honestly to the companies Bering McKinley actually works with, which are between two and ten million dollars in revenue. Four initiatives across the next six months. Two in the first quarter, two in the second. That is the whole answer, and the reason it can be stated as a number is that the constraint being managed is not strategic. It is capacity.
The horizon matters as much as the count. The long term plan gets set once, five or ten years out. Then attention collapses to the first year, because even mature companies struggle to see past it. Then it collapses again to six months, which is the only window where a commitment is realistic enough to hold people to. And the critical thing about the work inside that window is that it is extra. It is work the company has never done before, aimed at owners who are, in Gary's phrase, slaves to being in the business. Four initiatives is not a modest target for someone with spare capacity. It is an aggressive target for someone who has none, which is the actual condition of nearly every owner engaging a consultant in the first place.
- Four initiatives per six months, split two and two by quarter, for companies in the two to ten million range.
- Plan horizons should shorten as they approach: ten years for direction, one year for the goal, six months for commitments.
- Initiative work is additional work for people who are already fully consumed. Count capacity, not enthusiasm.
The Rule That Disqualifies What Is Already Working
The last rule is the one owners resist hardest, and Gary states it without hedging. Do not put something in the plan that is working. If the company is already adding two clients a month, the sales engine is running and the marketing is doing its job, then that is not the problem and it is not something to drive harder on. Focus on the problems. If you have something working, let that work.
This is counterintuitive because a working system is the most comfortable thing to write down. It is where the team has competence, where progress is likeliest, and where a quarterly review will look good. It is also, for exactly those reasons, the least valuable use of the four slots available. Gary's example makes the cost concrete: a company printing fifteen to twenty percent net profit with eighty percent of revenue in recurring agreements objectively has no problem on the page. But the typical MSP blend says project revenue should be there, and most clients want to buy project work. The gap is invisible in the financials precisely because the company is healthy. Finding it requires dissecting where a business is doing well, where it can improve, and where it is failing, and then spending the plan only on the third category.
- A working system is a reason to leave something out of the plan, not a reason to include it.
- The most expensive gaps do not appear as problems in the financials, because a healthy P and L conceals revenue the company never attempted to earn.
- If an initiative would produce a good quarterly review without changing anything material, it is occupying a slot that a real problem needed.
Frequently Asked Questions
What is a strategic initiative?
An initiative is a driver. It is the specific thing a company implements in order to reach a stated goal. If the goal is two million in revenue, an initiative might be onboarding two new clients per month for the rest of the year. Anything that only tracks progress toward that driver is a sub goal, not an initiative.
How many strategic initiatives should an MSP run at once?
For companies between two and ten million dollars in revenue, four initiatives across a six month window, split two per quarter. The limit is set by capacity rather than strategy, because initiative work is additional work that the company has not done before and the owner is usually already fully committed to daily operations.
Why does a plan with many initiatives fail even when each one is reasonable?
Because no individual item looks unreasonable and the total is never added up. Dilution does the damage. Working on everything is functionally the same as working on nothing, in the same way that making everyone responsible for something makes no one responsible for it.
Is improving efficiency a revenue initiative?
No. Efficiency lets a company deliver at lower cost, which drives gross profit and possibly net profit. It does not drive revenue. Filing efficiency work under a revenue goal is a common error that lets a company report real monthly progress while moving no closer to the number it committed to.
What are the revenue levers available to an MSP?
Recurring revenue from agreements, project revenue, hourly revenue, hardware and software revenue, and resold cloud revenue. Beyond winning new business, a company can also raise pricing with existing clients or increase pull through by selling more work into the base it already serves. Any of these can legitimately be an initiative.
Should a company put a well performing area into its strategic plan?
No. If the sales engine and marketing are already delivering, that is not the problem and it should be left to run. Plan slots are scarce and belong to the areas where the business is weak or absent. The hardest version of this is a company that looks healthy on paper but is missing an entire revenue category its clients would happily buy.
Episode Highlights
- 00:00 - Josh opens by putting a private disagreement on the record, which sets the episode up as a consultant correcting a consultant rather than advice aimed at the listener.
- 01:18 - Excitement in a planning session raises the ceiling on what a room believes it can achieve, and the plan captured at that moment records an aspiration.
- 02:18 - The attainable half of SMART is where most companies miss, and it fails quietly because nothing about it looks like a mistake at the time.
- 03:40 - An initiative is a driver. Everything beneath it is a sub goal that exists to track progress, not to substitute for the driver.
- 07:06 - Efficiency drives gross profit rather than revenue, which means a whole category of popular initiatives is filed against the wrong goal.
- 09:37 - The full inventory of revenue levers, including raising existing client pricing and increasing pull through, not only winning new logos.
- 10:54 - Four initiatives across six months, two per quarter, scoped to companies between two and ten million in revenue.
- 13:02 - Adding a third and fourth driver dilutes the power of the first two. Working on everything is working on nothing.
- 15:42 - Anything already working is disqualified from the plan, because plan slots belong to problems rather than to strengths.
About the Co-Host: Gary Boyle
Gary Boyle is a Partner for Strategy & Business Development at Bering McKinley. With a background spanning network engineering, entrepreneurship, and strategic consulting, Gary brings real-world operator experience to helping MSP owners build stronger, more profitable businesses. On the Vision roundtable he co-hosts with Josh Peterson, working through the planning and financial decisions that determine whether an MSP grows deliberately or by accident.
Connect with Gary on LinkedIn →
About the Host: Josh Peterson
Josh Peterson is the CEO of Bering McKinley and host of The BMK Vision Podcast. Since 2004, Josh has worked with hundreds of MSP owners to build operationally sound, profitable businesses through consulting, peer teams, and direct coaching.
Connect with Josh Peterson on LinkedIn →
Related Resources from Bering McKinley
- Implementing a business performance improvement plan, from strategy to action
- Why MSPs stall at two million, and what the numbers do not show you
Want to Continue the Conversation?
Choosing four initiatives is not a scheduling exercise. It is a judgment about where a business is genuinely weak, which is the work the Vision Operating System is built to make visible and repeatable. This episode is the first in a run working down through the layers of a strategic plan, and the next one takes up the objection every owner raises here, which is what happens to everything left off the list.