• Strategic thinking is often messy without the right structure—workshops help teams focus.
• Facilitated workshops provide a neutral space for aligning priorities and clarifying direction.
• Effective strategy workshops balance open discussion with outcome-driven design.
• Bringing in an external facilitator can help uncover insights and foster commitment to action.

When it comes to strategy, clarity is everything—but getting there isn’t always easy.

Teams often have the ideas, insights, and ambition to think strategically, but what’s missing is the structure. Strategy workshops, when designed well, create the right conditions for focused, collaborative thinking that turns ideas into action.

In this post, we’ll explore why structured workshops are essential for strategic alignment, how to design them for impact, and why bringing in a facilitator can elevate the process.

Why Strategic Thinking Needs a Clear Framework

Strategy isn’t just about long-term plans or vision statements—it’s about making choices. And to make smart choices, teams need space to step back from day-to-day pressures and think more deliberately.

But too often, strategy sessions become unfocused:

• Conversations drift.
• Dominant voices take over.
• Key issues remain unspoken.

This is where structured facilitation makes a difference. By shaping the flow of discussion and providing the right tools for analysis and prioritisation, a well-run strategy workshop helps teams focus on what matters most.

The Role of Workshops in Strategic Alignment

Workshops offer a unique opportunity to bring teams together in a way that typical meetings can’t. They create a neutral, participatory environment where:

• Everyone has a voice.
• Shared understanding is built.
• Decisions are made with clarity.

By combining preparation, facilitation, and follow-up, workshops can move a team from divergent thinking (exploring possibilities) to convergence (agreeing on priorities).

Typical Outcomes from a Strategic Workshop:

• Clear goals and priorities.
• Shared understanding of current challenges.
• Defined next steps with ownership.

Designing a Strategy Workshop That Works

Not all workshops are created equal. The best ones balance freedom to explore with structure to decide.

Key Elements of a Successful Strategy Workshop:

1. Framing the Purpose
   Why are you here? What decisions need to be made?
2. Diverse Input
   Include different perspectives—but in a way that keeps focus.
3. Clear Facilitation Tools
   Use formats like SWOT, prioritisation grids, or journey mapping—whatever helps make thinking visible.
4. Time for Reflection and Decision
   Space to think deeply, and then commit to action.

Why Bring in an External Facilitator?

It’s hard to think and facilitate at the same time. An external facilitator:

• Keeps the process on track.
• Encourages balanced participation.
• Brings fresh perspectives and tools.

More importantly, they help create the space where your team can do their best thinking—without getting bogged down in logistics or power dynamics.

Final Thoughts: Strategy Is a Team Sport

Strategic thinking doesn’t happen in isolation. It’s a team effort, and like any team, you perform best when you’ve got the right structure, support, and space to work together.

If you’re planning a strategy session or away day and want to make it count, I’d love to help. Let’s create the conditions for your team’s best thinking.

It probably had its origins in the military and wargaming but, in essence, it’s about having people play the role of a competitor to test your systems or plans.

Sort of like a devil’s advocate but a bit more rigorous. A proof-reader on steroids, maybe.

I found the concept interesting in terms of developing strategies and planning in business.

When working with teams on strategy development, it’s always important to probe and test the group’s thinking during the process.

Looking for data and ways to disprove key assumptions in a plan is essential as we can’t help but get caught up in our own world.

In fact, whenever we’ve invested time working on something, both individually or as a team, we’ve always embedded our own assumptions and unconscious biases in the output.

Have you ever worked hard on a project that you then show to someone else and their honest reaction isn’t what you expected?

They just don’t get it. Or maybe they quickly point out the obvious flaws in your thinking.

It’s easy to call this negativity.

Better to call it feedback.

But the reason I like the idea of the Red Team is that it goes beyond just feedback.

The Red Team’s job is to break your work.

They want to take your shiny business plan and deliberately pull it apart.

When you ask people for feedback their natural tendency is to be positive. OK, they may give some critical feedback, but seldom will they go to town.

Unless you ask them to deliberately find all the holes, they won’t do it.

Or, at least, won’t do it thoroughly.

Another important point, to me, is that the Red Team had no part in making it; they just want to break it.

What would happen if you took this approach in your organisation?

Imagine, you’ve just spent a month pulling together a 3-year strategy for growth. Your PowerPoint is polished and Spreadsheets are purring.

Then you purposely give it to someone and say “here, tell me how you would make this not happen?”

Really? Why would anyone do that?

Here’s two important reasons:

Firstly, if there are any big holes in your work – they should find them.

We’re not talking about rounding errors here. If you’ve baked-in something that everything else hangs around, they’ll see it.

Why? Because that’s the easiest way to break it.

So, putting your Red Team to work will force you to confront key assumptions (and risks) in your strategy or business plan.

Secondly, following on from this, uncovering these things will enable you to either fix them or mitigate against them.

Understanding the critical factors that will break your plan means you can choose the right metrics and measurements to ensure they don’t happen.

Or you may even rip it all up.

If what’s been uncovered is too big, too risky (and potentially too costly)… maybe you need to think again and go back to the drawing board.

This is definitely something that I’ll be advocating to my coaching clients and when I’m facilitating workshops on strategy development.

Even though, as a facilitator, my role at times is to be that challenging voice in the process, I still cannot remove myself from the process.

When my client has found a breakthrough in thinking and they’re all excited about having a new direction for the organisation, part of me will undoubtedly not want to burst their bubble.

And, having a Red Team doesn’t need to be an elaborate set-up.

Just find someone who you can say “here, tell me how you can make this all go wrong”.

Many have seen a dramatic cliff-edge drop-off in revenues, whilst others are struggling to keep up with demand.

Speaking with clients and contacts through my network, we’re all seeing this unfold at lightning speed, with critical decisions being made against a fast-moving picture and backdrop of uncertainty.

Broadly, there 3 tactical decisions that businesses are inevitably making – Pause, Pivot or Persist

You could think of these as the business equivalent of the Fight-Flight-Freeze responses we all have when faced with a perceived threat.

Pause – this is a tactic that many self-employed and small businesses are taking, often not by choice. If your revenue stream disappears over night and your market is frozen, then this may be the only option available to you.

For example, we’re aware of a number of small businesses (think freelancers, consultants, etc) where all their work has been cancelled over-night. If you are in this situation, where market conditions are extremely volatile, then investing in new client acquisition activities may simply end up burning through cash that you need to ride out the storm.

So, pausing may be a sensible tactic, although we’d advocate keeping the flame alight for when we’re all out the other side.

Pivot – this is where a business changes tack and either re-designs their existing offer, or pursues new opportunities that open up in the market.

Some of our clients are following this option, as the world of work switches to WFH.

In addition, there are some great examples out there where businesses are reacting to new market demands, such as distilleries producing hand-sanitiser, manufacturers creating parts for ventilators, etc.

Seeing many closed pubs and restaurants switching to take-outs is another perfect example, and one that we should all try to support.

Unlike a planned pivot strategy, this is very much a tactical response to immediate market challenges and opportunities.

Persist – the last tactic we’re observing in businesses is carrying on, as much as possible, with “business as usual”.

Obviously, BAU is an overstatement, but essentially, companies are carrying on with staff working from home, reduced capacity, etc.

For clients that are in this situation, whilst there may be some shift in their revenue streams (more online orders, for example) the core business is still operational.

Each of these tactics will require a different approach to risk management.

Pausing involves dramatically cutting costs, where possible, and conserving resources for when the economy re-boots.

A tactic to Pivot an existing offering will involve some uncertainty, unless you are responding to the draw of huge market demand. Taking a lean start-up approach to managing risk and testing before committing significant resources would be advisable.

This is where recognition of our own Fight-Flight-Freeze responses is essential.

What may seem like a potential way out of a crisis could be a diversion that sucks up precious resources needed for later.

Decisions made under stress can be unreliable, so sense-check this tactic and then test your assumptions rigorously before investing heavily in time and resources.

For those Persisting, many of the usual rules around a down-turn are pertinent. These may be unprecedented times but, remember, cash-flow is still king and ignoring it is like expecting the law of gravity to be suspended temporarily.

Of course, all this is simplified and the situation is always more nuanced, as many businesses have diversified offerings and revenue streams.

Some may pause one aspect of their business and focus on another.

The UK government’s support package which enables companies to furlough workers during this period is effectively a Pause tactic for the nation.

There is no doubt that the COVID-19 pandemic will pass and that, just as economic activity has rapidly shut down it will be re-booted in the coming months.

Once more, this will create opportunities and challenges as the UK economy rebuilds itself and businesses adapt to what will inevitably be a changed economic landscape.

Some of us will un-Pause, some will find that a tactical Pivot becomes a permanent revenue stream, and those that have managed to Persist through all of this will be more readily able to take advantage of the upturn.

Whatever the tactic(s) you pursue, we will get through this together.

Stay safe people.

“What’s your winning aspiration?”

Why is this phrase so powerful? And why should every business owner start with it when developing the strategy for their business?

Let’s break it down:

Firstly, the phrase forces you to think about exactly what winning would mean to you and your business. Some people find this a difficult question since they haven’t really thought about “winning”.

In the book, which is written by the former Chairman of P&G and the Dean of Rotman School of Management, “winning” refers to market position, usually in highly competitive consumer markets.

But the phrase “winning” can be equally applied to smaller businesses.

Now, winning doesn’t have to mean being No. 1, or the largest, or the most profitable. They may all be great goals but the point is that it’s about what does winning mean to you.

Anita Roddick DBE, Founder of The Body Shop, once said:

“Don’t think big, because that’s the obsession with this bloody [business] culture, it’s always got to be the biggest. Why don’t you just be the best or the most creative or the funniest or something?”

When I work with leadership teams of SMEs, and we have this conversation about their ambitions and aspirations, it’s never about size or market share; these are terms that smaller businesses just don’t relate to.

Winning could be building a legacy, being a great place to work or delivering a great customer experience.

In a recent report, when small businesses were asked about their goals for the future, ambition was not just about growth and profit, but also things such as well-being and happiness.

The key message is that it doesn’t matter how you define winning, you just need to be thinking about what winning means to you.

The second element of the phrase “What’s your winning aspiration?” is the word “aspiration”.

Your aspiration is your ambition to achieve something. And for it to be an aspiration it needs to be something that pulls you towards it.

Also, I believe that an aspiration is something that should feel like it’s just beyond what you can achieve.

It should be bold, possibly scary and it definitely wants to be exciting.

And, you should always feel energised when you think about it.

In fact, even the word aspiration stems from the latin word spiro, which means “to breathe life into”.

When facilitating strategy workshops with SMEs, I have found it’s always best to start with the future aspiration and work backwards into an actionable plan, rather than vice versa.

Why?

The problem when you start from where you are now, and project outwards, is that you play it a little too safe.

You think “well I’m here now so an extra X% growth over the next 3 years (or whatever your definition of “winning” is) is realistic.”

Realistic is great for short-term goal setting but it doesn’t energise your or your team to up their game and reach new levels of performance.

So, get yourself a winning aspiration.

Find something that really grabs you and will sustain you through the inevitable ups and downs of business.

Contact us if you want to explore how we can help your business create a winning aspiration.