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You are losing deals you should be winning. Not because your product is weak. Not because your price is wrong.
But because you are spending time and energy on people who will never champion you, while ignoring the ones who actually matter.
The problem is that most leaders spend all their time thinking about who is on their side. Who is the champion? Who is going to push the deal forward? That is important. But it is only half the equation.
The other half, the half that costs you deals and wastes your time, is this: Who is actively working against you?
Was this newsletter forwarded to you?
Because they are there. Inside your customer’s organization, right now, building a case for your competitor. Slowing down your deal. Creating obstacles. Whispering doubts to the decision-maker. And you probably have no idea they exist.
You are in the room with them. You shake their hand. You present to them. You assume they are neutral or just not convinced yet. But they are not neutral. They have already decided. They just have not told you.
This is how deals die slowly. Not because you lose a battle. But because you are fighting the wrong war with the wrong people.
Let’s dance.
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The Cost of Missing the Blockers
When you do not understand who is actively working against you, three things happen.
First, you waste resources. You spend months nurturing a contact who will never move the needle. You create presentations for a committee that has already decided to go with your competitor. You make trips to customer sites to meet with people who have zero influence over the decision.
All that time and energy could have gone somewhere else. Somewhere, it actually matters.
Second, you miss the real battle. While you are presenting to neutral stakeholders, your competitor is building relationships with the people who actually matter. They are identifying the blockers and figuring out how to neutralize them. You are not even in the game they are playing.
Third, you lose deals you could have won if you had just understood the landscape. The deal does not fail because you are not good enough. It fails because you did not see the trap until it was too late.
The Five-Part Stakeholder Reality Check
Before you spend another month on a deal, you need to know exactly who you are dealing with.
I have written extensively on stakeholder engagement. Check out my past articles here:
5 Ways Your Customer Champions Will Help You Win
It’s Called a Go/No-Go Decision for a Reason – Master It to Win
How to Build Your Customer Stakeholder Map & Free eBook
Part 1: Map the Entire Stakeholder Universe
Stop thinking of your customer as “the account.” Start thinking of them as an organization with competing interests, agendas, and politics.
Who is involved in this buying decision? Not just the people you have met. Everyone.
The end user who will actually use your product. The procurement person who cares about cost. The IT person who cares about security and integration. The finance person who cares about budget justification. The executive sponsor who cares about outcomes. The peer department that might be competing for the same budget.
Write them all down. Map them out. Understand the entire ecosystem.
If you cannot name ten people involved in the decision, you do not understand the account well enough yet.
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Ten. Yes…10.
Part 2: Identify Your True Champion
Not everyone who is nice to you is a champion. A real champion is someone who will fight for you internally when you are not in the room.
Your champion has power. Your champion believes in your solution. Your champion has something to gain if you win.
If I had to ask you on the spot who your champion for a specific opportunity would be, who would you say?
But here is the critical part: Your champion has already made a decision. They have already decided you are the right choice. They are not still evaluating. They are already sold.
If you are not sure who your champion is, or if you think you have multiple champions with equal power, you do not have a champion. You have contacts.
Ask directly: If you had to bet your reputation on this deal right now, would you bet on us winning?
If the answer is not an immediate and enthusiastic yes, that person is not your champion. They are someone you are wasting time on.
Part 3: Identify the Blockers
This is the part most sales leaders skip, and it is the one that costs them the most.
Who in this organization does not want you to win?
There is almost always someone. The person whose budget gets cut if you win. The person who championed a competitor and now has an ego invested in that choice. The person who does not like change. The person who benefits from the status quo.
They are not going to tell you they are against you. They will be polite. They will take your meetings. They will ask questions. But they are already working against you.
You need to identify them. Not to like them. Not to change their mind. But to understand that they are a force you have to navigate.
Part 4: Understand Why They Are Blockers
This is where most people get it wrong. They assume blockers are just difficult people or threatened by change.
Sometimes. But usually, there is a specific reason.
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Ask your champion: Why is [Person X] hesitant? What is their concern? What do they benefit from if we do not win?
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Get specific. Do not accept vague answers like “he is just cautious” or “she prefers our competitor.”
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Dig deeper. Is he worried about his job? Is she protecting a relationship with your competitor? Does he want to avoid risk? Does she have a better offer on the table from someone else?
The reason matters because it tells you whether the blocker is actually blockable or if they are a lost cause.
If the blocker is worried about implementation risk, that is something you can address. If the blocker is protecting a relationship with a competitor who is paying them a consulting fee, that is a different problem. You are not going to overcome that.
Part 5: Calculate Your Real Runway and Win Probability
Here is the question nobody wants to ask: Can you actually win this deal?
Not “do we have a shot?” Not “is it possible?” But can you actually win given the blockers, the politics, and the timeline?
Ask your champion this directly: Given where we are right now, how much time do we have to move this forward? What is the decision timeline?
Then ask: Can we realistically overcome the objections from [Blocker X] in that timeframe? Or are we fighting a battle we cannot win?
Be honest. If you need six months to build consensus and your customer has a two-month decision timeline, you are not going to win. You are just going to waste time and resources.
If the blocker has already committed to a competitor and you have no relationship with the decision-maker, you are not going to win. You need to walk away and allocate those resources somewhere else.
This is the hardest question to answer because it requires accepting that some deals are unwinnable. But that acceptance is what separates good sales leaders from great ones.
How to Navigate
Once you understand who the blockers are and why they are blocking, you have three options.
Option 1: Neutralize Them
Can you address the specific concern that is driving the blocker? If the blocker is worried about cost, can you restructure your pricing? If they are worried about implementation, can you bring in a trusted partner or offer additional support?
Sometimes, addressing the underlying concern changes the blocker into a neutral party or even a supporter.
But be realistic. Not every blocker can be neutralized. Some people have already decided. Your job is to figure out which ones are worth the effort.
Option 2: Build Around Them
If you cannot neutralize the blocker, can you build enough support with other stakeholders that the blocker does not matter?
If your champion is powerful enough, if you have built relationships with other key decision-makers, if the business case is strong enough, sometimes a blocker becomes irrelevant.
But this requires having real champions and real relationships with multiple stakeholders. If you only have one champion, this strategy fails.
Option 3: Walk Away
Sometimes the right move is to accept that you cannot win and allocate your time elsewhere.
This is the hardest decision, but it is the most important one.
If the blockers are too powerful, if the timeline is too short, if you do not have real champions, if the customer is too committed to a competitor, then you are not going to win. And continuing to invest time in a losing deal is how you lose deals you could have won.
The Reality Check You Need to Do Right Now
Before you spend another month on your top deals, do this exercise.
For your three biggest opportunities right now, map out:
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All the stakeholders involved
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Your one true champion (and confirm they are actually championing you)
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The blockers and why they are blocking
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Your realistic runway and win probability
If you cannot answer all of these, you do not understand the deal well enough.
If your win probability is low, if the blockers are too powerful, if you do not have a real champion, then ask yourself: Is this worth my time right now? Or should I be focusing on deals where I actually have a chance to win?
This is not pessimism. This is a strategy.
What the Internet Taught Me This Week
From new tools, recent trends, and market updates, here is what has been on my mind.
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Green card holders barred from US small business loans. Check it out here
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AWS says Europe’s power grid delays could reach seven years. Check it out here
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Cheap hydrogen could change where data centers are built. Check it out here
The deals you lose are not usually lost to better competitors or better solutions. They are lost because you did not understand the internal landscape. You did not identify the blockers. You did not build enough support with the right people.
Smart sales leaders understand stakeholder maps. They know who wants them to win and who wants them to lose. They know which battles are winnable and which ones are traps.
They focus their energy accordingly.
Stop wasting time on people who will never champion you. Stop fighting blockers you cannot overcome. Focus on the deals where you have real champions, where you can actually neutralize the obstacles, or where the blocker is irrelevant.
That is how you stop losing deals. That is how you start winning them.
See you next week.
Whenever You’re Ready, Here are 4 Ways I Can Help You:
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Unlocking Hidden Potential – Reconnecting with Past Clients for Explosive Growth – Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.
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AI for Business Development – Download our free eBook on how you can effectively leverage AI prompts to your advantage. From properly setting up your preferred AI tool, to how to shape your prompts, save time, and get the outputs you are looking for.
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Sales Resources at Your Fingertips – From tools, tips, demos, and how-tos, check out our Pages and content that can provide you with additional support, whether it be social selling, account management, or something else.
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Cribworks Advisor Program – Want more than just resources? Reach out to me and see if our Advisor Program can help you scale your business.
