Why are sales teams failing and what can sales leaders do to support them?

According to Salesforce 67% of all salespeople will fail to hit their quota and over half of all sales people close at less than 40%.  This is a very clear challenge for sales teams and often a constant cause of stress for sales leaders.

To discuss this challenge further, and the solutions out there, we sat down with Calum Kilgour and John Bissett from Slingshot Edge.

Calum and John have been selling complex IT and software solutions for more years than they care to remember (!) and have experienced first-hand the challenges faced by sellers every day. Having grown up in highly competitive sales environments (where they’ve had more than their fair share of dogfights) they’ve had to learn to sell the hard way.  As well as being sellers they’ve also managed sales teams. They’ve always been intrigued to understand what behaviours separate the great sales people from the rest of the pack,  and how buyers think and make decisions.

Calum started Slingshot Edge eight years ago to help organisations selling in the B2B space overcome some specific “deal-killing” problems.  Businesses that have worked with Slingshot are arming their marketeers and sellers with new skills,  conversational frameworks, and stories to help them win more business. The Slingshot approach is underpinned with powerful decision-making science.


So, you’ve both worked in Sales for quite a few years, what’s changed in recent years and what are the trends you’re coming across in sales teams today?

We need to take it back a step here and start with asking ourselves what’s changed from the buyers’ perspective?

1. Access to information

With the Internet and sheer volume of information available buyers are much more educated on the technology product or service that they are buying. They used to have to rely on the salesperson for this education but that’s often not the case now.   This means buyers have already formed strong opinions or even preferred solutions before they’ve spoken to any sales rep. If you’re not their preferred option, then you’ve got a lot of work on your hands to change their bias!

2. Attitude

We think sales is the best profession in the world – when done right! But often it’s not and it’s the buyers who tend to suffer in the process. For years, buyers have been mis-sold to, or promised things that were never delivered. Or they’ve been on the receiving end of shitty closing techniques that force them into a corner and make them feel uncomfortable. Or their inbox and voicemails have been relentlessly spammed by pushy sellers raving on about their products!  And most have had to sit through endless hours of coma-inducing sales presentations…. The list goes on and on, but the impact is that the poor sellers have ruined it for the good ones. Many buyers are cynical or turned off by the sales community as a whole. We should add that It’s not always the seller’s fault. Often these wrong behaviours are being encouraged by sales leaders.

3. Competition

Whatever the solution and no matter how ‘unique’ your offering is, there’s always increasing competition flooding into the market.  It can be hard for your buyer to see why they should choose you over other vendors. If they can’t see the difference, then you end up in a price war!

4. Number of stakeholders

What people are buying is becoming more complex. Whether it’s a new technology, product or service there’s an increasingly large number of stakeholders impacted. That means more people tend to be involved in the decision-making process than ever before.

This is especially true when you’re selling a big ticket product or service.  The more people involved in the process the longer the process, and the more likely that someone will say no and the deal will be killed.

5. Internal Structure of Sales Teams

Many vendors are introducing specialist functions that nurture the buyer through the sale from awareness up to the final purchase and beyond. This often includes Sales Development/Business Development Reps,  Account Execs, Customer Success Managers and Sales Engineers. This can work well when it is seamlessly executed. But it can also be a frustrating experience for buyers who are experiencing too many poorly executed hand-offs from one person to another throughout their journey.

6. Technology and Automation

The machines are here – or not quite J  Companies are looking to things like A.I.  to drive more efficiencies in their marketing and sales processes. This can be incredibly powerful – especially earlier in the process where you’re looking to identify and target prospects. However it could also be a threat if implemented poorly.  For instance, AI can help you reach your prospect accounts easier and faster. But if the message and approach is wrong then you risk doing more damage even quicker than before!

We’ve heard that sales people are increasingly failing to hit their targets, why do you think this is?

OK, so let’s assume that the targets are achievable first! We’ve all been in a scenario where the senior leadership team have set unrealistic and unattainable targets and then question why the teams aren’t hitting them.

Getting your buyer’s attention in the first place is tougher now than it’s ever been. Everyone seems to be leading busier lives. And because of the internet we’re all bombarded with so much noise every day – and your buyers are just the same. Cutting through it and grabbing their attention is hard. Sales Development reps and marketeers need to make sure they’re pushing the right emotional buttons in their prospect’s heads.

Once you get past this, the biggest threat to any sales funnel is the dreaded “no decision”. It’s a silent killer. Analysts like Sales Benchmark Index reckon about 60% of qualified leads end up this way. The number of decision makers in the buyer’s decision-making unit is getting larger. This is especially true where your selling a complex solution. It’s not just a new bit of software or service it’s a change. And most people don’t like change – it’s difficult and a risk. As a seller your selling change first and foremost. You have to show your customer that the risk of doing nothing or keeping the status quo is greater than the risk of change.  But most sellers are missing the tools and training to do this in the right way.

The competitive landscape is also getting increasingly crowded for many sellers. They’re often in a dogfight trying to win a deal. Maybe they had some solution “uniques” a couple of years ago, but the competition has caught up.  That’s making it harder for sellers to show their buyer why they should choose them over the other vendors. If your buyer can’t see the difference, then price is often the only differentiating factor

Now more than ever, buyers are navigating unchartered waters. They’re buying things today they’ve never bought before. That means there’s not always some nice clear, linear buying process that maps to your sales process. Despite this, sales leaders are still asking their teams the same questions about their deals they were asking 5 years ago. And they’re getting frustrated when the buyer isn’t moving forward in line with THEIR sales process!


What measures can you implement in your sales teams to improve their performance?

Look at what your top reps are doing differently.  How can you help the rest of your team to act in the same way? If you think about the distribution of your sales talent, the biggest impact you can make is taking the middle 30-40% and helping them improve a few points. Top sales reps have great emotional intelligence and they’re good at pulling the right levers in your buyer’s mind. They do a lot of the right things naturally but it’s also possible to arm your average sellers with skills, content and tools to help them replicate some of this.

Recognise that buyers are buying differently today than they were before. That means your sales process has to be less rigid and more agile to align with your buyer’s journey. It also means you need to be influencing your buyer effectively well before any of your sellers has spoken to them. To do that you need to be driving strong alignment between your marketing team and sales teams. According to research from Salesforce, teams that align sales and marketing add 25% to quota achievement and increases the win rate by 15%.  Overall revenue achievement can be up to 25% greater at companies where sales and marketing are perceived to work well together.

Start enabling your sellers differently. Too much focus is still on training sellers about product features, functions and benefits rather than solving their buyers’ problems.

Stay curious and keep learning! That’s what the best salespeople and sales leaders do.  Read! Some of our top picks are (not necessarily book on sales but more about the psychology of decision making):

      • Daniel Kahneman – Thinking, Fast and Slow
      • Malcom Gladwell – Outliers: The Story of Success
      • Robert Cialdini – Influence: The Psychology of Persuasion
      • Prof. Steve Peters – The Chimp Paradox
      • Never Split the Difference – Chris Voss

There’s loads of free info online too. And if you’re not a reader there’s plenty of great podcasts or resources on YouTube or social platforms like LinkedIn.

Finally, invest in sales enablement and invest in yourself. And don’t wait for your company to do it for you either


What traits should you look for or develop in successful sales people and teams?

From our experience,  we’ve found that the most successful sales people will always share these personality traits:

      • High emotional intelligence
      • Problem Solvers
      • Consistent and driven work ethic
      • Insatiable curiosity
      • Tenacity
      • The appetite for continuous development and learning
      • Great team players
      • Mental strength underlines all of the above, sales people must be resilient to being knocked back and be able to take rejection repeatedly.


How can you test for these behaviours in the recruitment process?

It’s a hard thing to do, recruitment is a big challenge for every sales leader, so start with the basics. Look for any red flags on their CV like jumping from company to company every 12 months or so.

Of course it’s easy to make a CV look good. Try and build some role play into your interview process to test the candidate’s approach to selling.  For example, you could give them some information and a scenario based on a discovery call and ask them to present back to you. You’re not necessarily expecting them to know much about your solutions at this stage but you can get a feel for their potential and approach:

      • Did they do any research based on the info you provided or resources you pointed them to?
      • Did they take a customer and problem centric approach to their presentation?
      • Were they curios/asking the right questions?
      • How did they handle any objections?
      • Did you warm to them?
      • Did they agree next steps?

Not everyone who has the potential to be a great sales person has sold before.  Scenario based role plays can be a good way to spot someone with some of the key ingredients who might not have the experience on their CV yet.

You will also be able to tell quite a lot simply from meeting the candidate.  You can test their emotional intelligence simply by asking yourself how you felt in the interview with them.  They are selling themselves to you, so however they have made you feel is likely to be how the buyer will feel.

Some questions we like to ask:

      • Talk us through a deal that you won. What did you do? What did you learn? How have you changed since that experience?
      • Same question but a deal that they lost.
      • What do you do in your free time to further your career or development? Sales people should be treating their career as their own business and investing in themselves. In this answer you want to hear about a few occasions where they have invested in their own training, using their own time or money (or both).


We’d like to thank Calum and John for sharing their insights with us.  For more from Slingshot Edge make sure to visit their website or watch their videos on YouTube.  If you think your sales team could benefit from their support make sure to email info@slingshotedge.com.