Why Failing To Understand Key Stakeholders Is Killing Your Deals (And How To Fix It)

As a founder, the majority of deals you lose will not be lost to competitors, but will be lost because your prospect was simply unable to make a buying decision.
The bigger the deal, the larger the prospect’s company, the more likely this becomes.

Key Deal Stakeholders
One of the most common reasons for not making a buying decision is because the right stakeholders were not engaged during the deal at the right time and in the right way.
You may think it’s your prospect’s job to do this, after all they’re the ones doing the buying, right?
WRONG!
Mapping out all the stakeholders required to get a buying decision signed off is YOUR RESPONSIBILITY, and there’s a simple reason why.
Most companies suck at buying technology!
There’s usually no clear process, no handbook telling them who needs to be involved and why, so working out who all the key stakeholders are and getting the right meetings booked at the right time falls to you.

How to categorise key stakeholders
To help make the task of finding and engaging key stakeholders easier, get into the habit of categorising them using something like the Miller Heiman model, which has four main personas:
- Economic Buyer
An Economic Buyer (aka ‘EB’) is the person who actually owns the budget to pay for your product and will normally have final sign off. Budgetary authority varies from level to level, and differs by company, so you may find Economic Buyers at different levels of management.
- Champion
Your Champion needs to be an enthusiastic advocate for your solution, but they also need to have sufficient authority or influence to help you navigate the internal buying process and engage the Economic Buyer.
- User Buyer
The User Buyer is the person or people who will evaluate your product usually based on features, functionality and user experience and will likely use it in their daily work.
Keep in mind that even if a User Buyer loves your product, that is not enough for them to qualify as your Champion. To be a true Champion they need sufficient authority or influence with the Economic Buyer and be able to help you navigate their company’s internal buying process.
- Technical Buyer
These are the people who can say ‘No’. They could be from IT, Infosec, Legal, Finance, Procurement, or a team specific to your solution. Their job is to evaluate whether it is feasible or safe to implement your product.
Any one of the Technical Buyers could veto a purchase, so understanding who they are and what their priorities are is vital.
Let’s imagine you’re selling an enterprise developer tool to an engineering organisation. This is how you might use the Miller Heiman model to map potential stakeholders in your prospect’s organisation:

Stakeholder meetings
For anything other than a low-cost credit card level of purchase, it’s likely you’ll need several meetings to get a buying decision.
In large enterprise deals, it’s not uncommon to have 20+ meetings in different tracks, commercial, technical, security etc.
First Meeting
In your first meeting, you’re usually trying to do discovery to understand what they need and get them hooked on the idea that your solution solves a high-priority problem (see my Discovery article for some pro tips).
It’s usually premature to start asking about key stakeholders in this first meeting, but you should save seven to eight minutes at the end to agree and book the next meeting (see my BAMFAM article for pro tips on this)
This last seven to eight minutes is the perfect opportunity to understand if anyone else should be invited to the next meeting, so a great question to ask is:
‘Who else does this impact?’ (and if you have time ‘How would it impact them?’)
You can also ask something along the lines of:
‘What sort of timeline are you looking at to evaluate your options?’
This is a great question to help understand whether the prospect is in a real buying cycle – if you get any kind of response on timeline you can follow-up with:
‘Who is driving that timeline?’
This should give you some insight into whether there’s a senior stakeholder already involved.
If the person you’re speaking to names their manager as someone driving the timeline, you should definitely suggest including them in the next meeting.
They may not agree to do this, but at least you’re starting to condition them that you will, at some point, need to speak to more senior people within the organisation.
If there doesn’t appear to be a timeline or no one driving the timeline, you’ll know you have more work to do in subsequent meetings to see if there is a real buying opportunity here at all.
In this first meeting, it’s also worth starting to think about what role the person you’re talking to might play in the buying process.
It’s very easy, particularly when you’re selling a technical solution, to mistake a technical individual contributor for a potential Champion.
For any meaningful Enterprise deal, it’s likely you’ll need someone more senior as a real Champion. Remember, a true Champion needs the Influence or Authority to get you in front of the right stakeholders and help you navigate their internal processes.
If you find yourself with an IC in this first meeting, there’s no immediate action, just know you will need to proactively navigate up the management chain as you progress the deal.
Second meeting
The second meeting is where you need to start digging into the buying process and the key stakeholders involved. You may still not get a full understanding here, but you want to walk away with at least some understanding of who the key stakeholders are likely to be.
Again, be deliberate about saving time at the end of this meeting (a minimum of fifteen minutes for a 60 minute meeting) to determine and book the next steps.
Here’s some example questions you can use in this last phase of the meeting, keeping in mind you may need to ask them over several meetings as there’s a lot to uncover:
‘What’s the typical process for buying software in your business?’
‘Who would typically be the most senior person to get involved?’
- ‘What do you think will be most important to them regarding this project?
‘Who would typically own the budget for this type of project?’
- ‘How would they usually get involved?’
- ‘What do you think will be important to them about this project?’
‘How would your manager usually get involved in this sort of decision?’
- ‘What do you think will be most important to them regarding this project?’
‘Who else would normally need to be involved?’
- ‘What will be their role in this project?’
Who else will be interested in this project?
- ‘What would you think their role would be in this project?’
- ‘What will they care about most?’
If you struggle to get answers, you can use some alternative framings:
‘With most customers I’ve worked with, the decision to move ahead normally sits with X or Y – would that be the same for you?’
‘I’ve often also found it very helpful to include Z in these discussions – would that make sense for you?’

Ask Early, Ask Often
The earlier you start asking these questions, the easier it is to condition your initial contact that you’ll need to involve other people in the conversation, and that you may need them to make an introduction for you.
Once you’ve identified a real Champion, it’s important for you to dig into the buying process in as much detail as you can.
For example, who is the real EB? What do they care about? Why is this a priority for them? What metrics are important to them relating to this project?
Ideally, as your deal progresses you should be aiming to meet your prospects in person as it’s easier ask about key stakeholders and much easier for you to suggest bringing other people to meetings, or perhaps meeting a key stakeholder for lunch or coffee, when you’re onsite.
For a deeper dive into how to understand the value different stakeholders care about please see our booklet Value Creation Explained.

This Process Never Stops
Once you’ve identified your champion, it’s important to keep checking in with them to make sure nothing has changed as the deal progresses. In particular, when pricing is agreed, confirm you still have the right EB with the right sign-off authority.
Even when you get to the point of contract signing, you still need to keep asking. Who in legal or procurement will you be dealing with? What are their priorities? How quickly do they typically turn things around? What’s the process for getting the final contract in front of the person who needs to sign it?
And don’t forget, one of the keys to success is making sure you save time at the end of every meeting to ask these questions and to confirm and book the next steps.
Any questions, just DM me or email me at ben@crane.vc.
Best of luck with mapping your stakeholders!