Targeting prospects who are “trying but struggling”


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An uninformed and superficial review of the principles of “challenger®️ selling” might lead some people to conclude that it depends on introducing a problem or opportunity that our potential prospect has never previously given any active consideration to.

But even assuming that these projects don’t fall at the first hurdle and that we can turn them into an active opportunity, these “previously unconsidered initiative” projects – particularly if they are dependent on new budget being found – can often result in complex, lengthy and often ultimately unsuccessful sales cycles.

I’m not suggesting that such projects are always likely to end in failure – but they are far from the only way in which we can successfully challenge our customer’s current thinking. There are many other ways in which we can bring fresh perspectives to our prospects in a way that has a good chance of being rapidly accepted and implemented…

Some of the most obvious opportunities lie with prospects that are “trying but struggling”. They have already recognised that they need to deal with an identified issue or initiative. They have already allocated budget and resources to the programme. They have identified and are implementing a “solution”. It’s just that it isn’t yet delivering anything like the desired results, and they may be starting to wonder if a different approach might be necessary.

This is a perfect opportunity to constructively challenge the thinking that led them to try and solve the problem with the approach that they are currently struggling with. Clearly, we need to be cognizant of the egos and politics that led to the existing “solution” being chosen and adopted. But assuming we can find ways of navigating around them, we have a perfect opportunity to introduce our prospect to a fresh perspective.


We can open our prospective customer’s minds to the implications and consequences of their existing situation that they may not have been aware of or taken into account when they made their initial choice. We can introduce new considerations that reflect the accumulated experiences of other organisations who are trying to deal with similar circumstances.

We can characterise the implications of our prospective customer’s current situation in a way that leads naturally towards the uniquely relevant capabilities of our solution without coming across as insensitive or overtly “salesy”. And we can progressively open their eyes to the limitations of the approach they are currently struggling to implement.


Change is hard – and your customers understand this, often through bitter experience. They know that not all change initiatives succeed the first time around. But as long as their goals are important enough, they will usually be open to rethinking their position if (with our help) they recognise that their current approach is pointing in the wrong direction or not moving in the right direction anything like quickly enough.

We can help them to rationalise the need for a fresh approach. We can share our experiences of helping similar organisations to master the transition they they are currently struggling with. We can build their confidence that we are are the right partner with whom to achieve their goals. We can make it easy to segue from their current path to ours. And we can help them to position the need to change their approach in a constructive manner that is most likely to secure internal understanding and approval.


Perhaps best of all, the budget already exists. It’s a matter of switching these existing funds from the current approach that they now acknowledge is failing them to our solution, in the confidence that this time they are more likely to achieve the desired results.

These sort of pivots can’t be finessed through anything that comes across as a naïve, confrontational, “you’re idiots for making a bad decision” sales approach. They require skilled and emotionally intelligent salespersonship that puts us in our customer’s shoes.

I’ve pointed out that change is hard – I’m sure you recognise this for yourselves. You might be surprised to realise how many “trying but struggling” projects there are out there. If you look carefully in the right places, you can probably identify the signs. When you do, I advise you to approach the subject in a respectful and constructive manner, and to challenge without confronting.


Some of these opportunities are probably right under your nose. It’s always worth revisiting previous opportunities that either ended in a competitive win, or a decision to solve the problem in a completely different way.

A decision to develop a system using in-house IT resources is a classic opportunity for this sort of turn-around, as long as you can work out how to manage the complexities of the internal politics. These in-house IT developments almost inevitably end up taking longer, costing more and achieving less than the way there were originally specified, to the great and growing disadvantage of the user departments involved.

But you also need to be aware that your recent sales can get displaced, as well: if you’ve sold something that isn’t yet delivering on your promises, you too could be vulnerable to being displaced by an unhappy client. And if you sold them the wrong thing in the first place, no amount of customer success heroics are likely to rescue that baby, and your company is likely to end up losing far more than the notional profit on the deal.

Trying but struggling… take a look around your prospect base. Look for organisations that are pursuing important initiatives but are not making the progress they had hoped for. Work out a suitable angle. And then constructively challenge your prospective customer’s current thinking in a way that progressively leads them towards your approach.

Republished with author's permission from original post.

Bob Apollo
Bob Apollo is the CEO of UK-based Inflexion-Point Strategy Partners, the B2B sales performance improvement specialists. Following a varied corporate career, Bob now works with a rapidly expanding client base of B2B-focused growth-phase technology companies, helping them to implement systematic sales processes that drive predictable revenue growth.


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