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How would you teach leaders to distinguish a strategy problem from an execution problem?

Distinguishing Strategy Problems from Execution Problems

This is one of the most common diagnostic failures in leadership—and it's costly because the two problems demand opposite responses. Here's how I'd teach it:

Start with the Core Distinction

Strategy problem: We're not sure what to do, or the thing we chose to do is wrong.

Execution problem: We know what to do, but we're not doing it well, consistently, or at all.

The danger is that both often look identical from the outside: missed targets, frustrated teams, disappointing results. Leaders default to whichever diagnosis is more comfortable—often blaming execution ("we just need to work harder/better") when it's actually strategy, because that's less threatening to the people who set the strategy.

Teach a Simple Diagnostic Sequence

1. Ask: "If we did this perfectly, would it work?"

If yes → likely an execution problem
If uncertain or no → likely a strategy problem

2. Look at variance across teams/people.

If some teams/individuals are succeeding with the same strategy and others aren't → execution problem (the strategy is sound; something in the how is broken)
If everyone is struggling despite different approaches and genuine effort → strategy problem

3. Check if the goalposts keep moving.

If leadership keeps adjusting tactics but the underlying plan/thesis stays fixed → possible sign nobody wants to admit it's a strategy problem
Constant tactical thrashing is often a symptom of an unexamined strategic flaw

4. Ask what "good execution" would actually produce.

Have leaders forecast the best-case outcome if execution were flawless. If that outcome still doesn't solve the actual problem or meet the actual need, the strategy itself is the issue.

Use Contrasting Case Studies

Walk through paired examples:

A sales team missing quota because reps aren't following the playbook (execution) vs. missing quota because the ICP itself is wrong (strategy)
A product failing because of buggy releases and slow support (execution) vs. failing because it solves a problem nobody has (strategy)

Having leaders sort actual internal examples into these buckets builds pattern recognition faster than abstract theory.

Teach the Emotional Tell

Strategy problems are scarier to diagnose because they implicate the people who made the choice—often the leaders themselves. Execution problems are easier to talk about because they implicate "the team" or "the process."

Coach leaders to notice their own resistance: if you find yourself reaching for execution explanations before rigorously testing the strategy, ask whether you're protecting a decision rather than diagnosing a problem.

Give Them a Test Question

"If I gave this exact strategy to a different team with more resources and more discipline, would the outcome be fundamentally different—or just marginally better?"

Fundamentally different → execution problem, fixable with better people/process/discipline
Marginally better → strategy problem; better execution just gets you to fail more efficiently

The Practical Payoff

Once leaders can make this distinction, it changes what they do next:

Execution problems → invest in training, accountability, process, resourcing
Strategy problems → invest in re-examining assumptions, market position, or the choice itself

Misdiagnosing a strategy problem as an execution problem leads to burnout and demoralized teams working harder on the wrong thing. Misdiagnosing an execution problem as strategy leads to constant pivoting when the actual fix was consistency and discipline.

Want me to build this into a workshop exercise with a scoring rubric leaders could apply to a live problem they're facing?

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Most leaders never get to the actual diagnosis because they ask the wrong first question — "was this a strategy failure or an execution failure?" — as if the two are cleanly separable.

They aren't. Roger Martin makes the case directly: the work inside "strategy" and the work inside "execution" are the same activity — people making choices about what to do and what not to do.

A CEO who tells her manufacturing EVP to "win on fit and finish" hasn't specified a strategy tight enough to execute without further choices;

the EVP still has to decide which levers matter most and in what order [2]. So the first move in teaching leaders to diagnose this isn't a checklist — it's killing the false binary.

Here's how I'd sequence the teaching, as a set of diagnostic moves rather than a single test.

At a glance

Run the choice audit first
Apply the perfect-execution test before judging the strategy at all
Separate the three legs of the execution system

1. Run the choice audit first

Break the initiative into the specific decisions that had to be made, at every level, from the boardroom down to the front line.

For each decision, ask: was this choice specified clearly, or was it left implicit and made downstream without guidance?

If most of the breakdowns trace back to unspecified choices — the EVP guessing at what "fit and finish" meant — that's a strategy-specification problem wearing an execution costume [2].

This costs time; it means disaggregating a messy postmortem into a decision tree instead of a single narrative.

The payoff is that it stops teams from blaming "poor execution" for what was actually an underspecified plan.

2. Apply the perfect-execution test before judging the strategy at all

Meta's early product leadership uses a sharp filter here: don't evaluate a strategy until it has been executed close to flawlessly.

If execution was sloppy, you genuinely don't know whether the strategy failed or the team never gave it a fair test.

The best outcome is a good strategy executed well; the second-best is a bad strategy executed well — because then you actually learn something and can reset [4].

The cost of this approach is that it demands operating discipline most orgs don't have — clean documentation, simple process, one clear owner — before you're allowed to draw conclusions.

It fits leaders who keep re-strategizing every quarter without ever completing one clean cycle; it forces them to finish before they re-litigate.

3. Separate the three legs of the execution system

A useful structural check treats execution as three ingredients: the strategy itself, the organizational design around it, and the quality of day-to-day management.

Failures get misattributed to "poor leadership" or "inadequate talent" as a catch-all when the actual blocker is structural —

incentives that reward the wrong behavior, or reporting lines that separate the people who decide from the people who deliver [3].

This costs more diagnostic overhead — you need separate instruments for strategy quality, org design, and management effectiveness —

but it fits larger, layered organizations where a single narrative ("the launch failed because of execution") is almost always hiding a structural cause.

4. Check whether strategic thinking is actually distributed, or just handed down

The oldest failure mode is architectural: leadership thinks, management does,

and the strategy degrades like a message passed hand to hand until it barely resembles the original intent by the time it reaches the people doing the work.

If middle managers had no seat in shaping the plan, what looks like an "execution problem" is often a translation problem baked into how the org is designed to move strategy downward [1].

This one costs the most culturally — it means bringing execution-layer managers into strategy formation earlier,

which slows the initial planning phase — but it prevents the recurring pattern where every miss gets pinned on the delivery team.

Given how leaders usually come to this question — after a launch or initiative has already visibly missed — I'd start with move 2.

Most organizations skip the perfect-execution test entirely; they re-strategize mid-execution, contaminate the signal, and then argue in the postmortem about which layer failed.

Establishing a clean execution baseline first makes moves 1, 3, and 4 far sharper, because you're diagnosing against a fair test instead of a muddled one.

The piece of information that would sharpen this for you: is this a pattern across multiple initiatives, or one specific launch that missed?

A recurring pattern points toward the structural or distributed-ownership diagnosis (moves 3 and 4); a single miss points toward the choice audit and the execution-quality test (moves 1 and 2).

Which one are you looking at?

Verified sources used in this answer

01Leading with StrategyTimothy TiryakiBook 02CEOs Should Stop Thinking That Execution Is Somebody Else’s Job; It Is TheirsRoger L. MartinArticle 03How to Move from Strategy to ExecutionTomas Chamorro-Premuzic, Darko LovricArticle 04Meta’s Head of Product (and 29th employee) on working with Mark Zuckerberg, early growth tactics, why PMs are like conductors, and moreLenny RachitskyInterview

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