6½ Expert Tips: How To Not Lose Your Sales Deal

Allie Reck
AppExchange and the Salesforce Ecosystem
4 min readJun 29, 2021

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Photo on Unsplash

The sales process is often unpredictable and different for every deal. In B2B sales especially, there are many moving parts and people involved that can easily throw things off course.

Because of this, it’s easy to get stuck in a ‘reactive’ mode rather than a ‘proactive’ mode. Let’s explore how to avoid that falling into that trap, and focus on 6 (and a half) tips for how not to lose your sales deals.

Learning And Introspection Are Key To Success In Sales

Underperforming salespeople fail in part because they aren’t taking the time to be introspective and reflect back on their own performance. You have to be willing to learn from your mistakes, otherwise, they just become failures and you’ll never improve.

As the provider of a sales performance management solution, the Ascent Cloud team has seen our fair share of missteps and learning opportunities from many different sales teams. We’ve talked to some of the experts on our own sales team, and they’ve shared some of the lessons they’ve learned (or have seen others learn) along the way.

1. Deals Can Go Sideways at any Point

This goes back to the familiar saying, ‘don’t count your chickens before they hatch.’ Never assume you have a sale in the bag until that contract is signed, sealed and delivered. Don’t let your guard down or stop being proactive, and always look out for any potential issues. It’s best to have a discussion early on with your prospect to understand exactly what their approval process involves.

You’ll want to know about any hoops you’ll have to jump through and be able to anticipate next steps.

2. Avoid the Game of Telephone

Remember that childhood game called Telephone? Kids would pass on the same message to the person next to them, until the last child relayed what they heard. It was always a completely different message by the end of the ‘telephone line’ — and that’s exactly what you don’t want to happen in your sales deal.

It’s crucial that you get everyone involved early in the sales process for this very reason. You’ll have more success if you understand the pain points and what the buyer is looking for in their own words. Problems can arise when you don’t deal directly with all parties involved in the final decision.

3. Err on the Side of Over-Communication

The best way to avoid losing a sale is to communicate thoroughly — both with the buyer and within your own organization. Ask prospects the right questions in order to get more information for context behind their pain points. Internally, keep relevant leaders in the loop on the opportunity’s progress, and secure anything you’ll need from them.

This is especially important during the legal process, which can be long and tedious. Embrace the opportunity to keep that open communication. It isn’t about saying yes or no, but figuring out why someone is objecting to a particular clause in the legal doc. Once you understand the context, you can work toward an agreement that satisfies both parties. Rather than seeing these outside players as hurdles, take a moment to see things from their perspective.

4. Use the Resources Available to You Internally

As you collaborate with others on your team, you’ll learn the resources at your company. Recognize the strengths of people on your team and lean on them for help.

Perhaps your CFO’s office has a legal expert, and can support you with a customer’s extensive Terms & Conditions. Or, perhaps an experienced sales leader can advise on a tough deal.

Recognizing any lack of experience isn’t a sign of weakness or failure. If you know how to ask the right questions of the right people, you’ll put yourself in a better position to succeed.

5. Always Be Learning

Your lost deals aren’t failures, they’re opportunities to learn from your mistakes. Understand what went wrong, and take the opportunity to see where your deals fell apart. Then, identify any patterns. The importance of self reflection can’t be overstated. If you feel like you’re at the top of the game, then you aren’t open to learning. Don’t let an ego get in the way of improvement. The moment you stop learning is the moment you could become obsolete.

6. Know When Not To Push

Every salesperson worth their salt knows how to push — it’s practically a requirement for the job. But the truly skilled salesperson also knows when not to push.

There’s a fine line between persistence and pushing too far… If you annoy your prospect, you’ve lost the sale. But, if you don’t follow up and stay top of mind, the deal could stall — maybe indefinitely. Find the balance between that fine line, and learn through trial and error.

6½ . Worst Case Scenario: What to do When You’ve Pushed too Hard

If you push a prospect a little too hard, or there’s a miscommunication resulting in a frustrated prospect, be open and transparent. Readjust by explaining the challenge, apologize, and move on. If you resolve to change the behavior that sparked the frustration in the first place, you still have a chance at a closed-won opportunity with the prospect.

If this doesn’t repair the relationship, don’t take it personally. Take advantage of this chance to be proactive. You’ll be a better salesperson if you do.

Check out apps that can help you optimize your sales process on AppExchange.

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