5 Deal Disasters to Avoid in Future Sales


Some industries have had to do a lot of belt-tightening recently, and it shows.

Research from late 2020 shows that touches to close rose 65% from pre-COVID-19 pandemic levels. Companies have been cautious with their budgets, and as a result, deals have lengthened.

Deal disasters you’ll want your team to avoid

The silver lining is that hard times are great learning opportunities. When the selling is good, it’s all about scaling, but when there’s less margin for error, it’s easier to pinpoint where your organization isn’t up to snuff and make improvements.

That’s exactly what we’ve done. We’ve identified five common deal disasters that wreck potentially winnable deals – the low-hanging fruit when it comes to boosting win rate. Let’s have a look at what you can do to prepare and empower your team to avoid them so you can start beating that quota.

Related: Losing Big Deals? Fix These 5 Sales Process Fails

1. Not involving the decision-maker

Do your sales reps know who they’re supposed to be targeting?

Recent research indicates that at smaller sales organizations, the inability to identify decision-makers is still a major deal killer. As a sales leader, you may have the perfect view of what your ICP looks like, but you need to make sure that the same is true for your team.

Deals are 80% less likely to close when a decision-maker isn’t directly involved in the experience. So how can your team identify those decision-makers?

How to prep and empower your team

Essential collateral: buyer personas, deal milestone timelines

To ensure the right people are involved in the conversation at the correct times, you need to provide your employees with the right materials, training, and guidance.

Start by making sure that your team has access to robust buyer personas built out by sales enablement and marketing, using data from historical deals. Equally as important? Make sure that your reps are learning them. Once reps are familiar with who the ideal buyer is, they’ll have an easier time finding and engaging them.

Next, map out deal milestones for when specific DMs come into successful deals vs lost deals, or who is usually not included in lost deals. This will give sellers goals to shoot for, e.g. “Head of IT involved by deal stage 60%,” and also help them focus their energy on deals that are likely to win by recognizing deals on the wrong track.

Once reps have the materials they need, make the decision-makers a standard part of your coaching. Track which reps repeatedly have a problem getting DMs involved and coach them on it.

Ask these questions:

  • Who’s the DM in this deal and why do you think so?
  • What’s your plan to get them more involved?
  • This person didn’t turn out to be a DM, what lessons can you take out of this?

Involving decision-makers is a major part of successful sales. If you aren’t coaching reps on how to get it done, you could be losing a significant percentage of deals that would otherwise be won.

2. Overlooking the multi-threaded deal

Although your reps need to ensure they’re including the right decision-makers in their sales strategy, this doesn’t mean they should focus solely on leadership. Building rapport and doing discovery with C-levels and executives can be difficult, time-consuming, and expensive.

Taking a multi-threaded approach to deals by connecting with multiple stakeholders allows you to unlock more engagement and possibilities. The result is a better chance of winning. On average, won deals tend to have at least three people involved on the buyer’s side, including the decision-maker.

Deals with fewer than that are easily lost even if the contact is a champion for the product since they could move to another company unexpectedly, change roles, lose influence, or otherwise drop out of the buying process.

How to prep and empower your team

Essential collateral: plays or scripts with qualifying questions that round out the buying team

The average deal now has 5.8 decision-makers who need to be involved. It’s crucial to train reps to build out the buying team from the start of each deal to ensure that deals are multi-threaded.

Some reps can feel awkward trying to get other roles involved without stepping on toes. Others can act awkward and step on toes while trying to get them involved. Make sure you’re running training sessions with good tactics to bring new people into deals.

Train your reps to:

  • Start with lower roles and ask qualifying questions that help them uncover who needs to be involved in a deal from the start.
  • Get actual names for each role mentioned.
  • Move forward with engaging them in a timely manner.
  • Learn from lower roles first and then leverage that information with higher-level DMs.

Again, collaborate with sales ops and enablement to check historical deals and build a map of likely roles that need to be involved which reps can refer to.

3. Low email velocity

Chances are, you’re already running sales activity metrics for insight into things like stage conversion rate, deal velocity, and win rate. Don’t forget about engagement metrics. Email velocity (measuring the rate of messages sent between prospects and your sales reps) is an especially potent leading indicator.

Most winning deals include an exchange of around six to eight emails per week, while one-two emails a week is more likely for losing deals. The more engagement you have with your customer, the more likely they are to close a deal with you. The question for a lot of companies is how to help reps build up email velocity the right way.

Simply bombarding your leads with emails isn’t going to make a difference. Send too many of the wrong emails and you risk alienating your contact.

How to prep and empower your team

Essential collateral: email templates, marketing content, buyer personas, sales tech

Email velocity is a direct indicator of how interested the prospect (or account in general) is.

Unfortunately, that means there’s no two-step plan to boost email velocity – there are too many factors involved. So let’s focus on the controllables and assume that leads are being properly qualified, personas/pain points are well-developed, and you have a decent product/market fit to begin with.

In that case, the best you can do for email velocity is make sure that your reps are reaching out to the right roles with the right messaging and support their efforts with valuable content from marketing.

Make sure you’re reviewing email threads (and calls and meetings) with reps when marginal deals are lost.

  • Did they find and address a relevant pain point?
  • Did they miss important cues from a prospect?
  • Was the language and tone on point?
  • Could they have brought more value to the conversation?

“Multi-threadedness” comes up here again. The more people involved in a deal, the better odds of finding a champion (or a few) for your offering which will naturally boost email velocity.

Sales tech can also help, of course, by helping your sales team determine what has worked best in the past, and helping to continuously test new messaging and content.

4. Not addressing pricing properly

Pricing is always an important consideration for any buyer, no matter which industry you’re selling in. Prospects want to know that they can get the results they want for a good price. The focus on pricing is even more significant in the post-COVID-19 pandemic world because people are increasingly aware of how limited their budgets are.

It’s vital to make sure that you’re training your reps to approach pricing correctly. This starts with encouraging them to stop thinking about pricing as something to shy away from. The pricing you’ve developed exists for a reason and should be looked at as a symbol of the value you offer.

How to prep and empower your team

Essential collateral: buyer personas and UVP

Training and coaching are the key to making pricing a less stressful conversation for reps.

There are two elements here. The first is getting a deep understanding of prospects’ pain points and how they can be solved with the offering. When reps see the deep value of what they’re selling, the pricing conversation stops being so scary.

The second is just repetitive practice to get familiar with doing something that people find naturally uncomfortable. This is a problem to tackle head-on:

  • Set up mock calls to practice discussing pricing.
  • Share successful calls with the whole team so reps have good examples.
  • Discuss what went wrong in failed calls in one-to-ones.
  • Join reps on a call or have them listen in as you make a call.

But importantly, dig into the ‘why’ with reps that are having trouble. It’s completely valid to feel awkward discussing pricing. After all, most of us are on guard about extra expenses in our own lives and because of that, it’s hard to ask others for significant sums of money. It’s important to reframe the thought process around the value that the product will bring.

Speak about it on a personal level with reps: when you want to buy something with little functional value in your life, you might debate it, look for discounts, or feel buyer’s remorse afterwards. On the other hand, when you have a toothache, you’re happy to get your wallet out and pay to stop the pain, and the money you spend is of no concern afterwards.

The same is true for your prospects – when you can prove that you’ll solve their pain, pricing will be an afterthought. This means, once again, that your reps need to have their personas down pat.

All of that being said, it’s important to recognize when to be flexible about pricing. Teach reps to look out for when prospects legitimately need a price break and when they don’t think that the product is worth the cost. Prospects that object to pricing because they don’t see the value of your product are the hardest deals to close and least valuable clients.

5. Competitor discussions

What happens when your reps are in the middle of a call and the prospect brings up a competitor? Panic? Stalling? Disparaging comments?

Competitors are a delicate topic in most deals, and it’s important to ensure you approach this part of the conversation carefully. Buyers bringing up a competitor isn’t always a bad sign, but reps need to come prepared.

How to prep and empower your team

Essential collateral: battle cards, case studies.

Your reps need to be quick on the draw with competitive differentiation and they also need to pick up on which points matter the most for each particular prospect. No one cares about all the technical details of where your offering is superior. But if a competitor doesn’t meet an important requirement that you do, that’s a home run.

Make sure reps are supplied with battle cards of important differentiators and have studied them. Remind them to dig in and find one differentiator that’s key for each account—and then stick with it. Different stakeholders may return to competitors at various times throughout the deal, but having that response ready will repeatedly take the wind out of their sails.

If you have the resources, ask Sales Ops to research when in the deal cycle is most effective to bring up the competition. Since this can be industry and market specific, there’s no one-size-fits-all answer. Do you win more when you discuss it up front and get it out of the way, or is it something that you need to nail down in a technical comparison?

The competitor conversation isn’t only about technical capabilities: many times they won’t matter at all and it will come down to selling your offering better than your competitor. Powerful, specific case studies will help your reps prove that your offering has solved the prospect’s problems before.

Make sure that marketing and sales enablement have supplied case studies for multiple use cases and that reps know where to find them and how to speak about them.

Stop losing winnable deals

Some of these points might seem like basics, but in the end, avoiding the most common deal disasters (and taking your sales team or organization to the next level) is about nailing the basics – all of them –consistently.

One thing you might have noticed: almost all of these points call for help from outside of the actual sales team. If your team isn’t getting the collateral and training they need from marketing, sales enablement, sales ops, and revenue ops, speak up! You might have to do some lobbying to get your voice heard, but make the case for better sales with better equipped reps.

To wrap things up, here’s a list of questions to ask yourself as you get to work:

  • Are reps equipped with and familiar with up-to-date, revenue-proven buyer personas?
  • Can reps quickly name multiple pain points that the offering can address for a few different roles?
  • Are reps pushing for multi-threadedness every time?
  • Is the language that reps use in calls and emails getting reviewed on a regular basis? Do reps have assistance sharpening these skills?
  • Are deals stalling on pricing discussions or competitor conversations? Are reps getting coaching about these points after lost deals?

If you have any nos or 50 percentages, your work is cut out for you. Make the needed changes, and stop losing winnable deals.

Trending Now

You may also like...