The Strategy Maturity Conversation
Most Mid-Market Companies Are at Level Two. Here's What That Means and What to Do About It.
THE MOST COMMON ANSWER
When I ask a CEO where their organization sits on a strategy maturity scale, the most common answer is: ‘Aspirationally a four, but probably a three.’
They’re almost always a two.
This isn’t a criticism. Level Two is where most well-run mid-market organizations land, and it has real strengths. The problem is that Level Two organizations often try to solve Level Four problems and wonder why the solutions don’t stick. Wrong intervention for the actual condition.
Knowing your maturity level matters because the prescription varies by level. What a Level Two organization needs is not what a Level Four organization needs. Think about a Level 3 Leader (Good to Great) deciding to apply Level 5 practices. Applying the wrong tool to the wrong situation is expensive and demoralizing.
Most organizations overestimate their strategy maturity by about one level. That gap explains many failed initiatives. HSS PRIME, SPRINT, BUILD, or SYSTEM services are designed to help move a company and leadership team up the maturity ladder.
WHAT LEVEL TWO ACTUALLY LOOKS LIKE
Since most mid-market readers are here, it’s worth describing Level Two in enough detail to be useful.
The annual plan is real. Real work went into it. Goals set, budget allocated, initiatives named. By February, it’s mostly being executed. By April, the first significant deviations appear. By July, the plan and the reality bear a passing resemblance. By October, everyone is working on next year’s plan while quietly acknowledging year’s didn’t hold.
The leadership team has different versions of the strategy. Ask five executives what the company’s top three strategic priorities are. You’ll get five lists that overlap but don’t match. Each person has filled the ambiguity with their own interpretation, usually the one that serves their function’s interests. Nobody is lying, but also nobody is aligned.
New initiatives keep getting added. Old ones rarely get formally closed. The organization has a list of strategic priorities that has grown by two or three items every year for the past four years. The list has never gotten shorter.
If that pattern sounds familiar, you’re at Level Two. It’s a diagnosis, not a verdict.
WHY LEVEL DOESN’T MEAN GOOD OR BAD
A startup in its first year should be at Level One. Flexibility and speed matter more than governance. A company that reaches $20-30M in revenue with Level Two strategy discipline has accomplished something real. The discipline that got it there, scrappy, responsive, opportunistic, is exactly what was needed.
The question isn’t whether your current level is acceptable. It’s whether your current level matches what your situation requires going forward.
A company about to make a major acquisition needs at least Level Three maturity before the deal closes. An organization facing a significant competitive disruption, losing foundational customers, or feeling the need to match a competitor’s AI power needs something more than an annual plan that won’t be updated until January. The mismatch between strategy maturity and situational demand is where a lot of mid-market firms get into trouble they don’t see coming.
The right level of strategy maturity is the one that matches what the environment is actually asking of you. No more, no less.
FOUR DIAGNOSTIC QUESTIONS
Before you self-assess, four questions are more reliable than the instinct to say ‘probably a three.’
When did your organization last formally update its strategy in response to something that changed in the market? Not a budget revision. Not a new hire. A strategic choice that changed where you compete or how you win. If the honest answer is ‘last year’s annual planning cycle’ or ‘I’m not sure,’ the update mechanism isn’t working.
If you asked your five most senior leaders to describe the strategy in one sentence, how similar would the answers be? Not necessarily identical, but genuinely compatible. If they’d diverge on the substance of the competitive choice, not just the wording, the strategy isn’t shared. It’s understood differently by different people, which means it’s being resourced and executed differently.
How many strategic priorities does your organization currently have? Count them. If the answer is more than five, they’re not priorities. They’re a list. Priorities require tradeoffs. A list doesn’t.
What did you give up or significantly reduce since the last strategy cycle? If you are not making hard tradeoffs in an environment with limited resources, talent, and time, then you are not working a complete strategy.
The pattern in those four answers tells you more about your actual maturity level than any assessment tool.
WHAT THE STRATEGY MATURITY SESSION IS
The HSS Strategy Maturity Session is a 90-minute conversation designed to answer one question: given where your organization actually is, what’s the most useful next step?
It’s not a sales conversation dressed up as a diagnostic. The honest answer might be that you’re not ready for SPRINT yet. Or that you’ve already done the clarity work and what you need is validation. Or that you have both, and what’s missing is the governance rhythm to prevent drift.
The session maps where the organization sits on the five-level model, which inputs are reaching the strategy conversation (from last week’s framework), and where the largest gaps between current maturity and situational demand are. The output is a clear recommendation: here’s what would actually move the needle, and here’s why.
Sometimes that recommendation is to start with PRIME, the one-day diagnostic, before anything else. Sometimes it’s to go straight to Sprint. Sometimes it’s that the organization has done enough diagnostic work and needs Build validation before committing to a major bet.
The maturity level determines the right entry point. That’s the whole point of knowing it.
YOUR MOVE THIS WEEK
Run the four diagnostic questions above with your leadership team. Not in a planning meeting. Informally. Ask each person separately and compare the answers.
Then ask one more: given the competitive environment you’re actually operating in right now, is your current strategy discipline fast enough to keep up?
If the answer is no, or if it produces a pause before anyone answers, you’ve identified the gap the maturity model is designed to address.
Next week: From SPRINT to BUILD. When clarity isn’t enough and validation becomes the necessary next step.
ABOUT THE AUTHOR
Mark Haas is a strategy governance advisor to CEOs and boards of mid-market companies, with more than 30 years of experience across healthcare, defense, finance, social services, and biomedical research. He is the founder of Haas Strategy Solutions, a Certified Management Consultant, former Chair and CEO of the Institute of Management Consultants USA, and recipient of the IMC Lifetime Achievement Award. Mark also served as Ethics Officer for 20 years and holds degrees from Colgate and Harvard Universities.