It’s easy to treat Shadow AI as a compliance risk. And it can be – particularly when sensitive data is shared with public tools. But it’s also a signal: of unmet needs, bottlenecks in innovation, and a workforce eager to improve how they work.

What Shadow AI Tells Us

Rather than viewing it as something to clamp down on, Shadow AI is worth understanding. It tells us:

• People are hungry for better ways to do their work.
• Employees are already building the skills and confidence to experiment.
• Traditional processes may not be keeping up with demand for innovation.

In many ways, Shadow AI is a vote of confidence in the potential of new technology – people want to try it. The challenge is to make sure they do so safely, responsibly, and in alignment with organisational goals.

The Risk of Clamping Down

Some organisations have responded with outright bans. But bans rarely work long-term. They can drive experimentation underground, limit learning and create a culture of fear rather than curiosity. Worse, they may push your most proactive employees – the ones who could help you lead AI adoption – into the shadows.

What’s needed isn’t control, but conversation. Not restriction, but responsible exploration.

A Better Path: Explore AI Together

That’s where our programme, Explore AI Together, comes in. It’s designed to help organisations bring Shadow AI into the light and channel it into something productive, safe and strategic.

Through a series of structured phases, we:

• Assess what’s already happening, uncovering both risks and opportunities.
• Assemble a diverse team – including early adopters, sceptics, and leaders.
• Align around shared principles, setting the tone for responsible innovation.
• Build skills and understanding across teams.
• Explore real use cases and test them safely.
• Reflect on learning and shape next steps.

The goal isn’t to slow people down – it’s to create the space, structure and support to move forward with clarity and confidence.

From Shadow to Strategy

In the end, Shadow AI is less about policy and more about potential. It’s not something to be feared, but something to be understood and harnessed.

Your employees are already experimenting. The question is: will you meet them there?

If you’re seeing signs of Shadow AI – or simply want to take a proactive approach – let’s explore what responsible AI adoption could look like in your organisation.

Get in touch to find out more about our Explore AI Together programme.

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”.

It’s said that it’s sometimes lonely being the boss, and CEO/MDs will often confide in me that they don’t have anyone to talk with about challenges in their business.

You’d think that this isn’t a problem when there are Co-Founders or Directors working together, but it is.

Here are some real examples I’ve encountered over the years:

• Co-Directors not being aware of each other’s plan to retire, leading to significant succession issues.
• A Founder unable to speak openly with his investors about challenges for fear of not looking in control.
• Family members not communicating with each other about the future direction of the business.
• Decisions made solely by an entrepreneur which have resulted in costly problems to clear up.

The final example is something I’ve seen many times over.

When I’ve asked the entrepreneur why they made the decision and what advice they sought it becomes clear that they just decided on their own, often on a whim.

They were in a “silo of one”.

This is one of the reasons I enjoy facilitating peer-network sessions; sharing a challenge with others in a similar position can unlock new ways of thinking about a long-standing issue.

It’s also why having the support of an external advisor or coach can be so valuable.

Sometimes, the process of working through a specific challenge with a professional is all you need.

Or you may want a regular sounding-board; someone who you can bounce your thoughts off and talk through a challenge before acting.

Whether it’s a working with a trusted paid-for professional or a more informal peer-level relationship, getting outside our own “silo of one” is important for all of us.

The concept is an environment in which an individual only encounters beliefs or opinions that coincide with their own, so that existing views are reinforced, and alternative ideas are not considered.

And it’s also something that occurs regularly in all organisations.

Good governance processes should always be in place to prevent groupthink, but the reality is that when I work with many enterprises, there can often be a real lack of diverse thinking in senior teams.

It’s only natural.

In many smaller organisations, where the founding team and/or a small group of leaders are steering the ship (often without the structure of a formal board) this is more likely to occur.

It’s not uncommon for there to be little or no change in the senior team within small entrepreneurial and family-run businesses over a period of decades.

Next time you are sat with your leadership team – look around.

How long has everyone been in their role? How diverse is the age/gender/ethnicity, etc of your senior team?

I’m not saying here that you must appoint different people; it’s just a reality check.

It’s somewhat inevitable that in many small organisations there will be less diversity in backgrounds as it’s a reflection of things like the founding team, family, local talent pool, etc.

But that shouldn’t mean less diverse thinking.

Bob Garratt, in his book The Fish Rots From The Head, writes about the need for Directors to be continuously scanning the “changing external political, trade and social environments, through travel, consulting, personal coaching and mentoring of top people”.

Increasing the diversity of your thinking when it comes to strategic planning and key decisions is essential.

There are many practical ways that you can do this without replacing people at the top:

• Encourage your leaders to serve on a Trustee board; working with other trustees is an excellent way to develop more diverse thinking. Check out Reach Volunteering or LinkedIn for trustee roles in your area.
• Consciously network more widely than your own current sector or social circle. Think about attending a conference looking at future trends and wider issues beyond your business, such as environmental impact.
• Look at joining a Peer Network where you can draw on external viewpoints and ideas to solve specific challenges.
• Use specialists to facilitate development sessions, since they can create a space for more creative thinking.
• Hire an external coach to work with the senior team.
• Consider volunteering as a mentor to entrepreneurs or individuals (there are many non-profit organisations looking for mentors).

This is not an exhaustive list and some of these ideas require no investment other than time.

All these ideas are either about bringing in different viewpoints from the outside or seeking to develop your own thinking through exposure to new environments.

Having to provide governance, advice and support to people and organisations that are different to your own and, importantly, where you no longer have established authority, can be a great learning experience.

The programmes are offered on a fully-funded basis, available to eligible charities, social enterprises, CICs and SMEs based in rural locations to support their leadership and organisational development.

Through diverse cohort groups, business leaders and managers collaboratively work through common business issues. This interactive action learning approach enables you to discuss your own challenges, gain and reflect on valuable feedback and implement practical solutions to overcome them.

Each Peer Networks includes

• 6 virtual learning sessions – delivered in a practical, engaging, action learning style around topics that focus on the current opportunities and challenges faced by the participants. This could include: Mitigating covid impact : Income Generation: Virtual Leadership and team management : Best application of digital technologies : Leader as Coach :  etc. etc.

•  Tailored one-to-one support – provided by a coach or specialist to work with you on a topic of your choice.

This will be a powerful, friendly, positive development opportunity – no assignments or assessments! – just ‘action’ and improvement.

David Regler from Maine Associates will be supporting SkillsReach to deliver this exciting programme of learning and business development.

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.

Gaining an independent and objective perspective when making key decisions can be extremely valuable.

We’ve written a brief guide on what to consider when looking for and selecting a business mentor.

So, let’s start with our definition of business mentoring.

What is a business mentor?

Before we get into the question of what to consider when looking for a business mentor, let’s first establish what a business mentor is.

In the context here, a business mentor is someone who works with business owners and leaders on a range of business issues.

That’s intentionally a very broad definition.

The distinction we would make about a business mentor is that mentoring is focused on both the person and the business.

Again, that’s just our definition.

What to consider when looking for a business mentor

We believe that there are 4 key areas to consider when looking to work with a business mentor.

This holds true regardless of whether it’s an informal relationship, a mentor who’s assigned to you, or someone you’ve hired yourself to work with.

These 4 areas are:

1. Experience
2. Mentoring style
3. Chemistry
4. Scope of engagement

Let’s look at them in more detail

1)     Experience

This may seem the most obvious thing to consider, but it can often be overlooked due the broad definition of a business mentor.

To determine what experience you are looking for in a business mentor, it’s important to define the challenges and business issues that you are dealing with.

Are you an early-stage founder looking to raise investment? Are you an established business owner with an eye on succession-planning and exit?

What’s missing in your own personal competences and experiences where a business mentor may add the most value?

For example, if you are a founder without a formal sales or business development background (such as a technology or domain knowledge experts, such as a consultant) then a mentor with strong commercial acumen would be a good fit.

Or if you are looking for a business mentor who can support you with preparing your business for sale. In this case you’d want to find someone who’s been through that process (ideally more than once).

Sector experience is another interesting consideration, we often people over-estimate it’s importance.

In our experience, the majority of business issues cut across all sectors (e.g. strategy development, hiring talent, etc).

Indeed, a business mentor who was worked across a diverse range of sectors can provide a fresh perspective on the challenges you are facing.

However, in some circumstances, having a business mentor from your specific sector may be the right choice; particularly in very specialised industries.

In short, always think about the relevance of the mentor’s experience to the challenges you are facing.

2)     Mentoring style

Quite often people throw around terms such as “coaching” and “mentoring” as if they are the same.

To some they are inter-changeable labels; to others its heretical to even mention them in the same sentence.

We think it’s more useful to ignore the labels and think about the style of mentoring.

Here’s a useful diagram below to describe this.

Some business mentors adopt a more “questioning” approach, while others are more “advising”.

Similarly, an approach can be more “process-driven” or it can be more “unstructured”, allowing the flow of conversation to be driven by the mentee.

Using this model, a “coaching” style of mentoring would be in the top left of the diagram, whereas a less formal mentoring relationship (perhaps peer-mentoring with someone who’s had no specific mentoring training) would be in the bottom right quadrant.

Neither is right or wrong necessarily.

For example, let’s say that you want a business mentor who can help you understand a specific challenge (such as handling a disciplinary matter or choosing an e-commerce platform for your startup).

You may just want to “pick their brains” and quickly get to an understanding.

Working with a mentor who is more advisory and unstructured in style may be perfect for this specific issue.

Alternatively, if you want to develop yourself and are also dealing with more complex and less clear-cut business issues, then working with someone who is on the left-hand side of the diagram would be a better choice.

As a rule of thumb, the left-side suits a longer-term business mentoring relationship, covering a broader range of business issues, whereas the right-side works better on more precise and shorter-term challenges.

3)     Chemistry

This is the most subjective consideration when looking for a business mentor, and one that only you will really know whether it’s right, or not.

However, unlike when you are looking to buy a house and you get that “I just know” feeling whether it’s right or not, this is different.

You might actually want a business mentor who makes you a little bit uncomfortable.

Perhaps you need someone who will challenge your thinking?

We’ve had feedback from clients who prefer a mentor who will “hold their feet to the fire” and keep them accountable.

Equally, sometimes a client needs a mentor who is very easy to speak with and open, which can help them deal with more personal challenges.

The point is that it’s subjective and the only way to know is to meet with a potential business mentor, and ideally have one or two discovery sessions first before you commit to working together.

Any professional business mentor would be happy to do this.

4)     Scope of engagement

This final consideration is about the type of relationship that you have with your business mentor.

There needs to be a clear alignment between the business mentor and mentee.

Things to consider are the frequency of sessions and how these sessions are delivered.

Will they always be face-to-face or via video call? Or a mix of both?

How often will you work together? Will it always be within business hours, or more flexible (for an international mentoring assignment this is even more relevant to agree).

It’s important to establish this up-front as, for both parties, having a session either very early or late in the day can be sub-optimal in terms of energy levels, concentration, etc.

Will your business mentor be available “on demand” if an important issue comes up? Or is the relationship confined to agreed sessions.

These are all parameters that you should explore with your business mentor.

We have a rule to only work with clients during business hours and not at weekends.

We do this because we think that every business owner needs to make time to work on their business.

You wouldn’t expect a board meeting to take place on a weekend, would you? Isn’t a mentoring session just important for the success of your business.

Another important part of agreeing the scope of a business mentoring engagement is how long you will be working together?

When you are dealing with ongoing business issues and challenges, this can be quite open-ended.

However, it’s critical to have a period in which you jointly review the relationship and then decide on whether it’s still adding value to you and your business.

Mentor dependency is something that any professional business mentor will be aware of and, ethically, needs to be avoided.

That’s not to say that a mentoring relationship cannot be enduring over many years, but it should be consciously reviewed periodically.

We never take on a business mentoring client for anything longer than 12 months without a clear point to mutually review and honestly evaluate the relationship.

Anyone arguing against this point probably doesn’t have your best interests at heart.

Summary

So, to summarise, if you are considering working with a business mentor, whether that’s a professional or informal relationship, considering these 4 things will help you think through what’s best for you:

1. Experience – is it relevant to what you need at this time?
2. Mentoring style – do you want to solve a clear, single issue or need wider support?
3. Chemistry – do you want someone who’s a challenger or an open sounding-board?
4. Scope of engagement – how will you both work together and for how long?

And always start with one or two discovery sessions to determine whether there’s a real fit before making a longer-term commitment.

That’s important for both you and your mentor, as getting the relationship right goes both ways.