Is Your Business Strategy Actually Working? Telltale Signs (And What to Fix)

How do I know if my business strategy is working?
Your strategy is working if it changes decisions, behaviour, and measurable results. Look for a clear quarterly focus, a consistent execution rhythm, improving leading indicators (pipeline, margin, retention), leadership ownership of outcomes, fewer repeat problems, and increased CEO capacity. If it lives in a PowerPoint deck and nothing changes in 30 days, it isn’t working.

The uncomfortable truth: most strategies sound good… and still fail

If your business growth strategy lives in a slide deck, a wall poster, or the CEO’s head… It’s not a strategy. It’s a hope.

I hear about this pattern constantly in mid-market businesses: the leadership team invests real time in “planning”, leaves the room energised, and then three weeks later, nothing has actually changed. Same priorities, same bottlenecks, same firefighting.

That’s because strategy isn’t an event. It’s a system built through cadence, clarity, and accountability. When that rhythm is missing, strategy turns into theatre: performed once, applauded, and forgotten.

So today, I thought, as you think about your planning for the New Year – for 2026 or FY27, let’s get practical.

Here are the telltale signs your business strategy is genuinely working and the red flags that prove it isn’t, so you can stop confusing activity with traction.

What a “Working Strategy” Actually Looks Like

A strategy is working when it consistently does three things:

1. Changes decisions (you say no more often than you say yes)
2. Changes behaviour (leaders and teams act differently, not just talk differently)
3. Changes results (revenue, profit, capacity, culture – measurably)

This matters even more in the mid-market, where the business is big enough to carry complexity, but not big enough to hide from it.

9 Telltale Signs Your Business Strategy IS Working

1) You can name the “one thing” (and your team would agree)

Your business strategy has a singular focus, not fifteen priorities, and not “everything is important”.

A strong leadership team can answer, quickly:

• What’s our #1 addressable challenge this year?
• What’s the 90-day priority that moves it forward right now?

If every leader names a different “one thing”, you don’t have a strategy – you have noise, and strategic success will not eventuate.

2) Your calendar reflects your strategy (not your anxiety)

This is one of the most reliable indicators: what do you consistently meet about?

When strategy is working, there is a visible operating rhythm:

• quarterly planning / strategic sprints
• monthly execution and performance reviews
• weekly accountability check-ins or huddles

When strategy isn’t working, meetings multiply… and clarity shrinks along with any meaningful execution linked to strategy, which essentially determines the future value of the business.

3) The same problems stop repeating (especially delegation and succession)

If you’ve been “working on delegation” for three years – or “starting succession planning” – but it still relies on the same few people to hold everything together, you’re not solving it, you’re gambling with your future bench — and your ability to scale without burnout.

And here’s the real cost: when a leadership team won’t delegate (or doesn’t know how to delegate well), you don’t just lose time – you stall capability, create invisible dependencies, and weaken decision-making depth.”. Succession planning becomes a document, not a discipline.

A healthy succession culture isn’t “we have a plan”. It’s “we’re actively building leaders through real ownership”.

When the strategy is working, recurring issues reduce because you:

• identify root causes
• make clean decisions
• embed new systems
• hold ownership consistently

The business starts to feel calmer — not because it’s easier, but because it’s designed.
That’s Freedom by Design in practice: growth that creates space, not fatigue.

4) Leading indicators are tracked (and you act on them)

Lag indicators tell you what happened. Leading indicators tell you what’s about to happen. If your “strategy dashboard” is only revenue and profit, you’re driving using the rear-view mirror.

Healthy strategy execution tracks things like:

• pipeline health (by stage, not vibes and whispers)
• conversion rates and cycle time
• gross margin by product/service line
• utilisation and delivery capacity
• customer retention/renewal confidence
• talent metrics (performance, engagement, regrettable loss)

Oh, and the key point: you make decisions off them.

5) Profitability is improving for a reason you can explain

Revenue growth without margin discipline is just a faster treadmill.

When strategy is working, you can connect the dots:

• “We improved margin because we stopped discounting and tightened scope control.”
• “We grew profit because we redesigned delivery, not because everyone worked harder.”
• “We protected cash because we changed the rhythm of billing and follow-up.”

In the Two Tides client portfolio, the long-term pattern is clear: measurable growth follows disciplined execution systems – not heroic effort. Across five years, average turnover growth and profit growth significantly lifted alongside margin improvement.

6) Your leadership team owns outcomes (not tasks)

Working strategy shows up in language.

Listen for the difference:

Task language:

• “I’ll get that done.”
• “I’ll follow up.”

Outcome language:

• “We’re accountable for lifting conversion from X to Y.”
• “Our role is to reduce delivery rework by Z%.”

When leaders own outcomes, performance becomes measurable and accountability becomes normal, not personal.

7) Your customers can feel the strategy (and you can prove value)

This is the PROMISE lens: strategy isn’t working if your customer experience doesn’t improve.

A working strategy becomes visible to customers through:

• clearer value propositions
• improved delivery consistency
• stronger onboarding and communication
• more confident renewals and referrals

Crucially: you can prove outcomes, not just promise effort.

8) You’re building capability – not dependency on the founder/CEO

One of the strongest “strategy is working” signals is this: The business becomes less reliant on one person. If every key decision, customer escalation, and delivery solve still funnels back to the CEO, your strategy is not scaling. It’s centralising.

Working strategy builds:

• decision rights
• leadership depth
• repeatable systems
• coaching-led ownership

Which leads to the real prize: a business that can perform without consuming you.

9) You have more freedom, and it doesn’t come with guilt

This one is deeply human. When strategy is working, leaders experience:

• more thinking space
• fewer “Sunday dread” moments
• clearer boundaries
• less reactive urgency
• more calm confidence

Not because the business has no problems, but because the business has structure.

Freedom isn’t what happens when things quieten down. Freedom is what happens when you design the business to support growth.

The Red Flags: Signs Your Strategy IS NOT Working

If you recognise two or more of these, your strategy likely needs a reset:

• You have too many priorities and no clear “this quarter focus”
• Your leadership team is busy, but not aligned
• Meetings create more work, not more traction
• You’re tracking results but not drivers
• The CEO is still in the weeds (and quietly resentful)
• Margins are flat (or shrinking) despite growth
• The same issues show up every quarter
• “Strategy” feels like pressure, not direction

Whilst none of that means you have a bad business, it usually means you’re missing the execution system – the rhythm that turns intention into outcomes.

A Simple Strategy Health Check (score yourself fast)

Rate each 0 – 2 (0 = no, 1 = partly, 2 = yes):

1. We have one clear strategic focus for the next 90 days
2. Everyone can articulate it the same way
3. We track leading indicators weekly/monthly
4. We have a cadence for planning, review, and accountability
5. Owners, timelines, and success measures are explicit
6. Customer outcomes are measured and used in sales/renewal conversations
7. Profit levers are monitored (not just revenue)
8. The CEO’s operational load is reducing over time
9. Decisions are faster because priorities are clearer
10. Strategy is discussed as “how we work”, not “extra work.”

16–20:     Strong strategy rhythm
10–15      Good intent, inconsistent execution
0–9:         Strategy is likely theatre (and your people feel it)

What to Do Next: Build Rhythm!

If your strategy isn’t working, don’t default to another offsite. Do this instead:

• Clarify the one addressable challenge
• Define 3–5 measurable outcomes
• Set a cadence (quarterly/monthly/weekly)
• Create a visible scoreboard
• Coach the leaders to own outcomes, not tasks

That’s where strategy becomes a living system and where momentum becomes inevitable.

Set Your Strategy for Success

At Two Tides, we help businesses grow through clarity and rhythm. Learn how we work with business leaders to design a Business Growth Strategy that fits your business, and what execution should feel like.