There’s a gap growing inside your agency, and most leaders can’t see it clearly because they’re standing too close to it. It’s affecting revenue, client retention, not to mention the leaderships skills of your middle management team. It’s called “commercial confidence” and this blog is going to break down exactly what it is, common scenarios it crops up in (with practical examples to help spot it) and how to tackle it.
What is the meaning of “commercial confidence”?
So – let’s dive in and talk more about this “commercial confidence” gap and exactly what it is…
First, where do we find it? This is the gap that widens between your senior leadership team and the next layer down, typically known as middle management.
Now I want to be totally clear here – this isn’t a technical knowledge issue, a client relationship capability problem, or about strategic thinking (although that is often another gap – so I’ll cover that in a later blog).
This is very specifically a skill gap that develops around commercial acumen, and your new-to-management team’s ability to understand it and discuss it confidently with senior stakeholders – and by that I mean, people who are more senior than them.
Let’s split the two words apart and put it in an agency context: having a “commercial” eye means someone is able to take the business outcomes into consideration in their day-to-day role.
They understand the broader aims of the company, what they’re working towards. They’re able to spot opportunities for growth easily when chatting with clients. They have value front of mind. We’re talking about money and opportunities.
But “confidence” means doing something without fear. Confidence comes from certainty – a sense of knowing.
Here’s a little exercise to prove it: think of any skill in any area of life that you are confident with… now answer me this: why do you feel confident with it?
Is it because you’ve been doing it for years? Because you’ve put the hours in? Because you’ve practiced it over and over and over? You feel confident because you KNOW with absolute certainty how to do “that thing” – and this ranges from knowing how to tie shoelaces to running a department.
Over time, you developed processes, methods, techniques, default responses – in other words, you made them a habit, something you do almost automatically.
So: commercial confidence is the ability to have value-led conversations about growth opportunities with a sense of conviction and certainty (whether that’s with senior decision-makers, with clients, or colleagues) – or simply put, talk about money and “upselling” without it causing fear.
That’s it. It’s not complicated in theory, but in practice and across a variety of scaling agencies right now, it’s becoming one of the most significant missing skills in growing teams.
Now – there are three very specific steps you need to take in order to develop this well within your organisation, but we’ll get to that!
First, let’s look at the four distinct reasons this gap develops, why this is such a valuable and urgent skill to instil, and some of the warning signs you’re dealing with it…
Reason one: people are promoted into roles they don’t know how to do
Let’s cover the biggest issue first, and this one is almost universal: leadership and management is often seen as a hierarchical system rather than a role… which it is
You’ll have seen this yourself: someone is brilliant at their craft – execution, delivery, doing a particular hard skill really well – and so they get promoted.
They become a manager – and on paper, they were absolutely the right choice, based on the evidence available, their “time in the saddle” and so on.
But being exceptional at execution and process management doesn’t mean someone will be exceptional at leadership and people management.
Being incredible at the roles and responsibilities required for delivery doesn’t mean you’re automatically equipped to lead commercial conversations with stakeholders who are more senior than you.
The leap often made from exec to lead requires two entirely different skill sets.
Nobody told them that.
Nobody trained them for it.
And now, they’re sitting across the table from a client’s MD, Commercial Director or CMO, being asked questions about results, strategy and commercial impact, and they have nothing to fall back on.
So the mind and body do the only thing it was designed to do when all else fails: it initiates a threat response.
So they fight, fly or freeze to deal with the situation.
What does that look like:
- They “fight” by acting defensive, sometimes aggressively, externalising – blaming other people for the results and coming up with excuses as to why things haven’t been done, or didn’t hit target and so on
- They “freeze” and internalise things instead – they go quiet when you try to talk to them about it, or go quiet on the call with the client, even worse they ignore the problem, don’t respond to the client email and wait for you to flag them on it, where they finally say: “yea… I just didn’t know how to deal with it”
- They go into “flight” mode and run from the problem – they shut down the conversation with the client as fast as possible and 9 times out of 10 will escalate it to you or someone else more senior
To be clear, this isn’t a character flaw – it’s biology!
At that moment, their brain and body can’t tell the difference between that client who’s trying to get more work out of the business for the same rate, and a tiger about to pounce, so it floods the system with a cocktail of hormones designed to deal with the threat.
Cortisol, adrenaline, cognitive function is handed over to the primitive mind and they just… react, because their logical brain is coming up blank with how to deal with it.
This is the training gap that was created the moment they were promoted and handed a new set of responsibilities without any of the tools to navigate them.
Reason two: under pressure, senior leaders hoard the conversations that would develop their teams
This one might hurt a little bit (sorry), but I’ve got be honest with you – and as a side not, it’s not done maliciously, it’s just what happens when the pressure is on…
Due to many factors (like economic uncertainty, missed targets, department performance reviews, or just the fear of losing an account) it’s often the case that when learning opportunities to build commercial confidence comes up, more experienced leaders would rather do it themselves.
Why? “They won’t do as good a job as me, and we can’t afford to lose this.”
When you’re under immense pressure (like the kind only financials will bring) the natural instinct for seniors is to take back control, because everything else feels out of their control.
“We must put the most experienced person in the room for every important conversation at the moment – we CANNOT afford for this to go wrong.”
The problem is that every time a senior leader steps in to “handle it”, the gap widens, because the person below them loses another learning opportunity. The senior becomes even more practiced and comfortable (it’s just another day at the office for them) while the exec becomes even less so, and the distance between those two layers keeps growing.
What used to be a shadow opportunity – “just come in and watch how I handle this” – becomes yet another conversation they never got to see up close.
In a different environment, a junior might have overheard that phone call, or been pulled into that meeting last-minute to observe, but in a hybrid world, where people aren’t physically present in the same room, out of sight genuinely does mean out of mind (more on this in a second).
The result: a team of seniors who become increasingly overloaded and burnt out, while the confidence of the layer below erodes over time.
Reason three: learning by osmosis has almost disappeared
Speaking of being in the room, this is a major contributing factor to this gap wreaking havoc over the last few years…
There used to be a type of learning that happened without anyone designing it. Think about when you were in the office, developing your skillset over the pre-pandemic decades…
You overheard how your manager handled a call while they were sat near you. You got pulled into a meeting at short notice. You watched how your manager handled a difficult client in real time.
You absorbed it, even if you didn’t realise you were doing it, and that learning is largely gone now.
Hybrid working has largely stripped it out of most workplaces – and even on the days when teams are in the office, it’s often driven by a different metric of success.
Social over skillsets.
People come in on the days when their colleagues are so they have social interaction, so it’s driven by social preference, not by a skill-sharing opportunity. And because those moments of incidental learning require physical proximity, they’re not happening, and no one has replaced them with anything equivalent.
This means that an entire layer of informal commercial education (the kind that used to be baked into the texture of agency life) has quietly disappeared… and the skill gap has widened in its wake.
Reason four: commercial conversations require skills nobody is actually taught
Storytelling. Strategic thinking. The ability to hold a conversation about business performance and outcomes without defaulting to delivery-speak.
These are the skills at the heart of commercial confidence – and here’s the pattern I’ve witnessed again and again: the best leaders got to where they did partly because they were naturally good at this.
And you know who I mean – you’ll see the green shoots of this in people on your team right now. The ones who just seem to “get it”… so those are the ones you’d naturally put up for promotion or see as more valuable, right?
You give them recognition for it, you put them in front of clients, give opportunities because of it… and so they got better and better.
But – two key things to remember:
- just because you see something in one person doesn’t mean the rest of the team can’t do it – like any skill, commercial confidence can be taught, it just might not come naturally to everyone on the team
- just because someone has a natural aptitude for something doesn’t guarantee that they enjoy it or want to be recognised for it – which is where you end up creating roles for people that they stay in out of fear of being gotten rid of, rather than out of the fulfilment of the role
The thing is, this is no longer a skill you can even afford to “pick and choose” with now – you need everyone below that senior leadership layer to also be able to think strategically, spot opportunities, and have confident commercial conversations.
If nobody is sitting your account managers and client team down and teaching them how to construct a compelling business narrative for a client’s board, it’s an issue.
If nobody is walking PMs through how to connect what they deliver to commercial outcomes in a language that resonates with the client contact, it’s a problem.
This is not necessarily something that “they’ll pick it up” – for many, they won’t, and it’s your bottomline and talent retention figures that suffers.
Why is commercial confidence more urgent than it’s ever been?
If your management team are able to hold their own in those conversations, to walk away having represented your value clearly, rather than having conceded ground you didn’t want to give up, you end up with better performance all round.
Account growth and clients who feel supported, with less reports of stress and overwhelm from the team.
This, coupled with those four things alone would make this an obvious skillset to develop – but there’s a fifth factor that’s turning it from a growing issue into a critical one: AI is accelerating its takeover of execution.
The output work (the doing, the producing, the delivering) is increasingly being automated, streamlined, tightened, and generally being made more efficient with tech.
That means that the true value of working with a human agency partner is in a) the connection and relationship you’ve developed, and b) your ability to think creatively as well as reactively.
Five-figure retainers can no longer be justified through “hours spent doing the stuff” – the customer expects WAY more from you. They expect you to use AI to streamline things… so if you’re still going to charge the higher-ticket rates, you need to have a reason.
And expertise demonstrated through commercial acumen is one hell of a good reason to have you on their side.
Rather than just using a platform or a tool, the value of agencies is shifting rapidly towards the “human stuff”, like problem-solving, storytelling and generating impact while hitting business outcomes.
That’s exactly the territory that commercial confidence lives in.
If your team can’t hold a strategic, commercially-oriented conversation with a senior stakeholder, what’s the human value they’re bringing to the relationship between your company and the client?
This is also why the sector is increasingly treating commercial confidence as something that should show up in performance reviews, which creates its own problem… because it’s a “soft” skill.
I hate that term – I want to replace it with “human” skills, because that’s basically what the distinction will become.
The ability to tell a story, to think on your feet, creativity, strategy, being able to hold your own in a high-pressure conversation – these are things that often feel very intangible, and develop with practice and mentorship.
You can’t track them like you’d track a technical deliverable; you can’t put a number on “how well did they hold the room?”… but they’re being assessed in that way anyway.
In practice, that means people are being judged on a skill they’ve never been trained in, in situations they were never properly prepared for, often in an environment that systematically kept them away from the experiences that would have helped them develop it.
It makes your head spin, no wonder the gap keeps widening.
How to build commercial confidence in your middle management
I’ll be blunt – you need three things: certainty, context and courage….
1. Certainty
The starting point is to get specific about what commercial confidence means to your company, what does it look like in your business? Not in the abstract – in the room!
In your client conversations, in your review meetings and upsell discussions. What does “strategic” mean here? What does “value-led” look like in how your team talks to clients?
What are the specific situations where you need your seniors to be able to hold their own without you, and what does holding their own actually require in those moments?
You cannot train people in something you can’t define. Confidence comes from two things, and one is certainty. How do we get that? With clarity.
2. Context
Once we have the answers to those questions, contextual training is the answer.
With your company spec clearly articulated, you can build frameworks that are specific to your organisation and the conversations that cause threat responses in your team.
You can create protocols that fit with your wider processes for the high-pressure moments, so that when the brain wants to panic, there’s a plan to default to instead.
Context is everything, otherwise you end up sending them on a generic two-day training course, but still nothing changes, because there was never any talk of implementation.
3. Courage
I mentioned above that there were two things needed for confidence.
One is certainty, the other is courage, and this is where everyone slips up.
You can have the perfect training, with everything mapped out from that clarity workshop, but if you don’t help your team to still “show up” even when it’s really uncomfortable, you’ll never get that lasting change you really want.
This is where mindset is critical; if you want confidence, you must be courageous again and again and again, showing up to the action that scares you… until it becomes just another day at the office and any other skill in their tool belt.
The very next step…
These three things are where the magic happens – and it’s worth doing now, before the gap gets any wider, or before AI makes the lack of human strategic value even more expensive to ignore.
But that doesn’t mean they’re easy; if you’re sat there thinking “but I’m not sure how to unpick this” or “but I’m not sure of the questions to ask to give us that kind of clarity” – I get it.
If you’re ready to find out where the real gaps are in your team’s commercial confidence, and how to start closing them, drop me a message and I’ll help you look under the hood of what’s actually going on.
