When to Hire Sales Enablement
August 27, 2026How to fix the system, and not the salesperson
September 27, 2026It asks people to do things they’ve never done before.
If your growth ambitions require people – especially salespeople – to do things they have never done before, one of three things usually happens:
- They never do it, because they don’t know how – they have never done it before!
- They try to do it, but get knocked back quickly and give up.
- They gather evidence that says, this is not possible. We’ve all practised that one!
Growth strategies often become transformation and change programmes, accompanied by the inevitable town halls, meetings and discussions about why “change takes time.”
This is particularly relevant to sales because, of all the functions expected to change, sales is usually expected to change – and deliver – the fastest. And strangely, Sales is often at the bottom of the list for getting funded while other departments are ramping up resources to implement a new growth phase.
One of the biggest challenges any salesperson can face is being asked to do something they have never done before.
For example:
- Sell in a new way that requires a different commercial language: “We’re introducing a more consultative approach.”
- Sell to new personas who may know more than they do – and may dismiss them mentally within two minutes.
- Replace relationship-based order-taking and account management with proactive business development. Very few people volunteer for that one.
- Sell something new to existing customers who know and value the company for what it has always sold – and are surprisingly negative about the new offering or approach. Customers hate change too!
- Enter a new territory or country without the familiarity, reputation or relationship safety net they previously relied upon.
- Selling into a category with big, well-funded players, category leaders and brands. You can go from great to amateur in a morning.
- Selling into a commodity or mature category, at a noticeable price premium. That’s a particularly unattractive prospect for a salesperson.
This does not mean people lack the ability to succeed. It means they have never done what the growth goals now require them to do, before.
That creates a gap in execution capability. It is not a gap that can be filled through discussions about mindset, emotional intelligence or the psychology of change. These are only comfortable and interesting distractions.
If people are being asked to do something they have never done before, they must acquire the capability to do it. It’s very fashionable today to talk about the “why” but if you lack the “how”, it’s very hard to change.
And this exposes the big gap at the company – not seller – level.
You cannot ask salespeople to tell a new value story if the company has not given you the language. The company may have a deck, but the capability lies in the language, not the headline. Marketing may have come up with great “messaging”, but sales needs language. Without the language, the seller has no choice but to invent their own version of the message.
You cannot expect a salesperson to create preference for a premium proposition if nobody has established how. If there are ten different and conflicting and unclear answers to the question, “why are you more expensive”, the seller is not going to be able to acquire the necessary capability. At best, they’ll invent explanation number 11.
You cannot measure execution when no standard exists. A company is essentially a set of answers – when seen through sales eyes – and only the company can supply the answers playbook, e.g. what changes after a customer uses us?
Yet the usual development model is to send people out to attempt the new work and learn through experience. Experience is a slow teacher. People get the test first and the lesson afterwards. Knowing you don’t know can be the biggest de-motivator.
The answer is to define what people must now do that they will have never done before and then equip them with the required expertise and language, build fluency through practice, and transfer that capability into live execution.
So when a new strategy is launched, the most useful question may not be:
How will we persuade people to embrace change?
It is:
What must our sales people be able to do to execute this strategy that they have never had to do before?
That is where transformation becomes a practical capability-building challenge. It’s now about providing the “how.
The company’s responsibility is to match its growth strategy with an inventory of the capabilities required to execute it and provide a fast, practical way to acquire them.
This is not really about changing people or fixing their mindset. It is about giving them an opportunity to engage with capability-building assets.
Some will prefer to keep doing what they already do well. That may be the right outcome for them. You just need enough people to start acquiring the required capabilities to support the strategy – and some of those people may not yet even be hired. And when you do hire them, you will be looking for what they still need to learn.
At the very least, a defined capability-building programme reveals who is prepared to make that journey.
Compression of Learning is the Challenge
When a growth clock is ticking, learning cannot be left to experience alone. It must be compressed: practise before execution, learn from real attempts, correct quickly and feed those lessons back into the next practice.
The company cannot remove the risk of doing something new. But it can provide the boot camp and identify who is willing to step into it.
The big boost for SMBs
For the 95% of SMBs that don’t have a sales support function such as enablement, the tools are increasingly becoming available that means they can quickly distribute and compress the acquisition of the company’s unique expertise, language and the accompanying execution skills.
If you’ve spent for example, 20 years building the business, and the next growth phase is the critical one, you need the tooling to compress the learning.
An Example of what salespeople will not know or have never done before:
Suppose you give me a new product or solution to sell. I’ll probably get the product and solution training. But what I really need, just as a starting point, before I do anything is the company approved answer – not any answer – to questions like these. If I have never had to answer these questions before, it’s better you give me an answer that is to a company standard, or I’ll invent my own. And so will everyone else.
- What exactly is it?
- Who is it for?
- What’s better or different compared to current alternatives?
- Why does our difference matter?
- What’s the blind spot we help customers identify?
- What business outcomes do we ultimately help customers achieve?
- What changes for customers after working with us?
- What existing product, solution, approach, operating model or way of working are we replacing or improving?
- What changes would a customer or user have to make to realise the value we have identified?
- What jobs do we help customers get done, and what new possibilities do we create?
- What conventional industry belief or assumption does our point of view challenge?
- What measurable indicators demonstrate that our approach is working?
- What might we be asking a customer to do that they have probably not had to do before?
- What alternatives, including named competitors, are available?
- What required change is the buyer least likely to make or resist?
By just providing a set of company-approved answers, you are giving me a starting point. I now have distilled knowledge and even expertise. Next, I need to do some practice or at least test myself. If I don’t want to even learn the stuff, now you know where I stand and you know your execution gap.


