How to Stop Losing Deals You Should Have Won

Written by: James White
You’ve just come off the phone with a potential prospect and you’re buzzing with excitement!
The call went really well.
They asked you lots of questions and you felt there was a great connection between you.
They’ve requested you send them more information including your service offerings and prices.
You’re in!
It’s time to send a proposal.
Everything on your “to-do” gets pushed back and you make this proposal a priority.
You want to nail this. I mean who wouldn’t, right?!?
And so, you spend ages (I’m talking a good day or so), making sure it includes everything they need and it reads well.
You’ve even ask a colleague to sanity check it a few times in case you’ve missed anything.
After obsessing over every line you finally feel it’s good enough to send out.
And so you click the button and you hope and pray the prospect comes back to you with a big thumbs up.
A week or so passes and after a couple of friendly nudges you receive an email…
But it’s not what you were hoping for 🙁
“Thank you so much for your time, we really appreciate it. However, we’ve decided not to move forward on this occasion. Wishing you all the best. Kind Regards XYZ”
At first you’re stunned…Huh? What happened? They loved me!
And then you’re angry.
And then, more than likely you do one of two things:
Forget about it. Move on and carry on making the same mistakes, hoping one day you’ll get the thumbs up.
Use this experience to reflect, review and figure out how to do things differently next time.
If the latter is more your style but you’d really like some support navigating what happened and more importantly what to do next time, then here are 10 things I recommend thinking about:

#1 You didn’t do enough research and planning

Not doing enough research and planning at the beginning stages of the sales process is a surefire way of losing the deal. Whilst most salespeople will tell me they do research and plan, more often than not, it only goes as far as a quick look at social media profiles and a company website. 
I really recommend researching and planning out the following key things: 
Research the following: 
  • How does the company and their team present themselves on social media?
  • What does the company’s organisational structure look like? 
  • How would you describe their culture? 
  • How do they communicate to their audience? 
  • What can you find out about them? Any press releases? Any useful conversations on social media? Any news alerts? 
  • Who else works with them? 
  • Do they partner with other companies? 
Think about and plan out the following: 
  • What are the biggest challenges or potential issues in their world right now? How can you become someone they feel is an educator or value creator?
  • What could be their biggest problem/want right now? 
  • What could be blocking them from finding a solution or getting to where they want to be? 
  • What questions would they be thinking about asking you? 
  • What reasons would they potentially resist buying from you? What concerns may they have about you? 
  • How would you want to be convinced if you were them? 
  • What thought-provoking questions could you ask them that would make them feel you really know them? 
  • What options would they have potentially pursued before speaking with you?

#2 You didn’t convince the right people

Determining the decision making process is fundamental to winning a sale and yet more often than not, salespeople don’t spend enough time finding out who the key players in the process are and how decisions are made. 
Here are a few example questions you can ask your prospect to determine this: 
  • Who else is involved in making the decision alongside yourself? 
  • How do you go about making decisions as an organisation?
  • Who will be taking ultimate ownership of the project?
  • What is key for them when they work with new providers? 
  • Which other people or groups will use this solution? How do they feel about this? 
  • What other information and material would be useful for you to have for other stakeholders?
  • Is there anyone else we should involve in these conversations? 
Once this information is gathered, I recommend drawing up a customer map and plan of all the key players in the process and where they would sit within the following three levels:
  1. The ultimate decision maker(s)
  2. The influencer(s)
  3. The implementor(s) 
Once you have done this, start to consider who is involved in this project or who contributes to it and what is their role and impact within the process? How big of a factor are they? How much does their voice get heard when it comes to key decisions?
I once lost a deal because I engaged with the CEO of a business and just ‘assumed’ he was the ultimate decision maker until I found out he actually worked for the owner of the business who made big investment decisions. Needless to say, I lost that deal because I hadn’t asked the right questions. Don’t make that same mistake yourself.
Building a full plan of who the key players are within the organisation will not only put you on the right path for sales success, but will also help you build a stronger relationship with your  prospect. It shows them that you are really interested in understanding them and their company and want the project to reflect well on the buyer with other key stakeholders.

#3 You didn’t uncover the true pain

If you’ve participated in sales training or read a fair few sales books, you’ll know that people tend to buy/invest because they have a big problem which needs solving or they have a great desire they want to fulfil. 
It’s your job as a salesperson to determine exactly what this is and whilst that sounds easy, to get to the true pain or desire takes real skill and practice. 
  • It takes empathy. 
  • It involves digging beneath the surface of superficial answers; and 
  • It involves reading body language, tone and language to drive the conversation and get the prospect to trust and open up to you. 
Here are a few key questions you can ask to help start the conversation and dig into the real pain/desire: 
  • How has this issue impacted you and your business? 
  • What would be the implications of not getting this resolved? 
  • It sounds like you’ve tried something before and it didn’t work. Tell me more about what happened there? 
  • How confident on a scale of 1-10 (with 10 being totally confident) that what you have in place now is going to be enough if XYZ happens? 
  • If you could wave a magic wand right now, what would your world look like? 
  • How will you feel if this time next year you’re having the same conversation about the problem? 
When you REALLY get to understand the problems and desires that are causing the organisation to want to invest, then you can provide solutions and evidence that will make them intrigued and keen to talk with you.

#4 You were up against it from the start

Sometimes the odds are simply stacked against you from the start. Your prospect might be 99% certain they are moving forward with someone else or via a different route but wanted to explore every option for peace of mind. 
The sooner you find this out the better and there are some tactical questions you can use to get a sense of whether or not you were in with a chance in the first place: 
Find out who else has been asked to quote for the project: 
  • Who else has been asked to quote? 
  • How are you currently solving this challenge at the moment? 
Get clarity on why the customer has asked you to be involved:
  • What made you decide to approach us for this project? 
  • How do we compare with the others you’re considering?
Don’t be the person to just make up the numbers. It will drain your time, energy and emotion to keep doing this. Get clarity from the other side on why you have been asked to quote or be involved and ask them what you need to show in order to be successful. 
Be curious without being interrogative! If they can’t or won’t share this information with you then it’s a warning sign that you need to think again about whether it’s worth spending huge amounts of time on this opportunity.

#5 It wasn’t a good match

It’s so important to ensure the prospect you’re engaging with is a good match and although this sounds obvious and simple enough, I see so many salespeople waste time trying to fit a square “prospect” peg into a round “prospect” hole.  
It’s got to be a good fit for you and your business. You may deep down want the business but if what you offer isn’t suitable for that company or you can’t provide evidence of someone similar that you have worked with before, then reconsider whether to provide a proposal.
Before you even begin to engage with a prospect, I really recommend doing the following: 
  • Create a list of the 6-8 criteria of your ideal customer. We have a customer qualification sheet we can share with you if you would like? Email us at xx
  • Ask yourself: Does the prospect score well in this list?
  • If not, consider whether it’s worth pursuing. 
  • Clarify with the prospect what the perfect solution looks like: “What would the perfect solution look like for you and what would make you feel like it’s been a nightmare?”
  • Ask yourself: Can you match this? Can you REALLY solve the problem for the prospect?
Doing this will save you so much time and energy engaging with the wrong type of prospects for your business. 
Know your position within the marketplace and match yourself to potential buyers who are an ideal fit for what you do.

#6 You didn’t address the money issue well enough

It’s amazing how many salespeople shy away from discussing price and then when they’ve got no choice, they talk through the prices really quickly, projecting an energy of awkwardness and uncomfortability. 
It’s so important you get comfortable and feel confident talking about money. 
Remember, this is an investment someone is willing to make to ensure a pain is being taken away from them or a great desire is being fulfilled. It’s not a cost.
What would be the impact if they don’t fix the problem or don’t get what their heart truly desires? What is the impact on them personally for not getting this resolved? How would it make them feel? When we tap into the ‘emotions’ of the buyer, we can find out how much this is really costing them and the value they place on solving it.
If it’s a priority, if the timing is great and if they genuinely see the value in your service offering, they won’t let money stop them from moving things forward.
  • Get comfortable talking about your price. Practice saying it aloud so you don’t stumble the words and you sound confident in real life. 
  • Replace the word cost with “investment” 
  • Use a price range and then watch for reactions: “Typically our services range between £1000-£1500. How does that fit within your financial plans?”
  • If you get price objections, you’ve probably not shown them the value.
  • Use some of the tips in this resource to help you move price objections forward in your sales conversations: click here
The most important thing to remember is if you sound uncomfortable talking about your price, prospects will start questioning your credibility and value.

#7 You couldn’t outline your true value

Think back to the last deal you lost. 
Do you feel they really understood the tremendous value you provide in your service offerings? 
What evidence did you share to prove your value is credible? 
We all put a “value” on what we offer as companies and the key to sales is being able to match the price of what we charge versus the value that the other side puts on the service. If the other side doesn’t understand the true value of something or doesn’t value the parts which you think have value, they won’t buy!
Your job in sales is to communicate your value and convince the other side that you are worth this.
This involves maybe educating them on an issue that is key to them but which they didn’t know. Or sharing some research or insights that allows them to get ahead of their market. Or providing some ideas that could allow them to take a stronger position in their marketplace. 
Or it could be that your service combined with what they have now creates a powerful engine for growth in their business. 
  • Did you share resources and content they could use without expecting anything in return? 
  • Did you tell stories of how other clients have found your service valuable? 
  • Did you offer to introduce your clients to your prospect?
  • Did you offer to make a connection through your network that could help them solve a separate challenge or issue? 
  • Did you present yourself as an expert/thought-leader or educator in this space and does this shine through your marketing platforms? 
Creating value means providing something that someone else feels is useful and in sales we want the buyer to come off the phone or zoom call thinking ‘Wow they were really helpful and useful’

#8 You took the wrong actions at the wrong time

Sales is like a game of chess. If you take the wrong action at the wrong time, and if you do so repeatedly, you will end up losing the game. You can’t take the wrong action back and so it’s really important you think about your strategy and be two steps ahead of your prospect’s thoughts. 
Here are some examples where I’ve seen the wrong action being taken at the wrong time: 
  • Selling too early into the sales process or conversation 
  • Introducing the company before getting to know the prospect 
  • Persuading instead of asking thought provoking questions 
  • Overcoming objections at the end of the conversation instead of openly discussing them early on 
  • Reeling off benefits instead of focusing on outcomes first. 
  • Sending out terms of business or contracts before getting a definite yes 
  • Realising you’re not sure what the aim of the conversation is until half way through the conversation. 
  • Taking too long to follow up after meetings or reply to emails
  • Chasing for the next conversation instead of clarifying the next steps and booking in a time/date to catch up at the end of the call. 
It’s so important to think about the actions you’re about to take and whether it’s the right thing to do at the right time. Not doing so, will definitely lead to a few missed opportunities and lost deals. 

#9 You didn’t use your emotional intelligence

Emotional Intelligence or EQ is a phrase which gets thrown around a lot and whilst most people have a broad understanding of what it means and represents, very few people work on it as a skill to be able to really understand what prospects are thinking and nurture relationships. 
So, what are the key traits of a person with a high level of ESI (Emotional Sales Intelligence)? 
  • They are MOTIVATED and are driven by a bigger vision. They understand their purpose in life (here’s a small tip – its not linked to money!) and are passionate about bringing that vision to life within the work they do.
  • They are able to socialise and build relationships. They understand that SOCIALISATION is key to sales success and that means having the ability to meet new people and cultivate friendships. You can’t win in sales if people don’t like you and want to be around you!
  • They are SELF AWARE. They know when they are talking too much or when the other person they are talking to has switched off. They adjust their behaviour in subtle ways to get conversations back on track. They can be self reflective without being overly self critical
  • They exercise SELF CONTROL. They know when to shut up and when to talk. They know when to respond and when to hang back. They accept they don’t have to win the ‘short battle of words’ if it means they win the deal in the end. The very best salespeople can rein themselves in and resist the desire to say or do something now. They control themselves rather than letting the situation control them.
  • They demonstrate EMPATHY. They really put themselves in the shoes of the other person and see life through someone else’s lens. They try to think about what issues and challenges the other side is going through and then react based on this. They do this in a way that makes the other person feel valued and important. They get people on their side through their ability to be in the other person’s shoes. 
So based around this, the next time you have a conversation with a prospect, ask yourself: 
  • Did I get a good sense and understanding of what the prospect was thinking and feeling? 
  • Did I ask thought-provoking questions? 
  • Did I demonstrate empathy? And did the prospect feel I really understood them?
  • Did I react or did I respond with pause and thought? How in control am I of my own emotions? 
  • Did I resist the urge to continue talking when I felt I had something important to say?
  • Did I really put myself in the other person’s shoes and think for a moment what it would have been like for them?
Mastering these skills is what the VERY BEST salespeople do. And as a result of them doing it, they win more deals than they lose. 

#10 You didn’t make a big enough impact

When you leave a sales conversation, it’s really important you ask yourself: “Did the prospect walk away feeling like they know me, they like me and trust me?” 
If the answer to any of the above is a no or a question mark, you probably didn’t make a big enough impact. 
Remember, no matter how great your service offering is, you are the face of the business and people still buy from people. 
You want your prospect to leave the conversation feeling excited and/or relieved- feeling like they’ve finally spoken to someone who just gets them and who can potentially support them with their big problem. 
You don’t want to be that salesperson who will be forgotten in a few hours. 
So what are some practical ways you can make an impact? 
  • Remember the small things. Show your prospect you listened and were really interested in the things they last shared with you. That might be somewhere they were heading for dinner or that their son or daughter were doing something nice at school. Note those things down and use them in follow up conversations. You will be amazed at how people react to this
  • Take notes during your conversations and repeat/summarise. It shows you’re not just listening to them, but you’ve truly heard them. 
  • Follow up with valuable resources and information based on the conversation you’ve had. Show you’re really trying to support them to overcome their problem or reach their goal. 
  • Explore all their options and the pros/cons with them like a coach. Don’t just go for the bulls eye and persuade them to use your solution. 
  • Share your insights and previous experiences with them. 
  • Ask them thought provoking questions that will make them think about things differently. 
  • Remember to give them the option to say no or to allow them a ‘get out’. This is one of the most powerful skills you can build as a sales person and when you master using this at the right time, incredible things happen. If you want to know more about using the word ‘No’ in a sales situation, let us know and we will send our guide to you.
Don’t be that salesperson everyone forgets. Be the salesperson your prospect is excited to work with! Putting these tips into practice will result in you leaving a great impression and making a big impact on your prospect 🙂 
So there you have it. Why you lost the deal and 10 ways to avoid losing it next time. 
Do these resonate with you? Do you feel there are other reasons you lost the deal? I’d love to know! You can email me: or catch me on the social media platforms below. 
In the meantime,
Serve authentically, Sell brilliantly! 
Warm wishes 
Publish date: 7 April 2022

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