Why Poor Discovery Is Killing Your Deals (and How to Fix It)

When I sit down with a founder (or salesperson) to review a deal that has lost momentum or completely died, I can almost always trace the root cause of failure back to not doing enough, and critically not doing deep enough, discovery in the early stages of a deal.

To win a deal of any meaningful size, you need to show every key stakeholder in the buying chain that your solution solves high-priority problems for them and delivers significant value to them that their existing solutions do not.

The starting point for doing this is great discovery:

• Discovery to understand the problems that your solution can uniquely address.
• Discovery to understand how they prioritise these problems relative to other issues they’re facing.
• Discovery to understand how much impact these problems are causing them and how much value you can create by taking these problems away.

If you aren’t doing deep enough discovery to uncover each of these, you will struggle to articulate real value to your key stakeholders and will be putting your deal at huge risk.

Discovering Pain, Priority and Value

Your end goal with discovery is to find somewhere between 1 and 3 high-priority problems that your solution can uniquely solve for your prospect, and the value that you can create by taking these problems away.

It’s important to keep in mind that you’re unlikely to get everything you need out of a single meeting. Discovery is an iterative process, not a single event, that deepens as you develop your relationship with a prospect, and as you engage with more stakeholders.

In your first meeting with a prospect, for example, understanding the main problems and gaining some idea of priorities are good goals. Though you may not even be able to get all of that and still need to do more discovery in the next meeting before you even start getting to an understanding of the value you can create. And as you meet with new stakeholders, each of them will have different challenges and different perspectives on problems and value as well.

For a more detailed explanation of how problems and value can vary by different stakeholders, please see our booklet Value Creation Explained

To get to a deep understanding of problems, priorities and value, I find it helpful to follow an hourglass methodology of discovery, as shown below:

This model has three main phases (and again, it’s worth repeating that these may happen over the course of several meetings, and you will likely iterate and refine what you learn in each phase as you get deeper into the account).

The Three Phases of Discovery

Phase 1 – Understand the Problem

Open your discovery by going wide, asking open-ended questions that relate to the area in which your solution works. You’re fishing for pain, trying to identify problems that need solving. You should start with questions that begin mainly with What and How.

It’s important to start your discovery with easy, non-threatening questions to get the conversation started, particularly when you first meet someone. A great place to start is to simply ask some version of:

‘Can you walk me through how you’re doing X today?’

Where X is the area your solution would help them with.

You could also bring in some elements of what you’ve uncovered in your previous contact with the prospect:

‘In our email exchange, you mentioned you were looking to make some changes to X – perhaps you could walk me through how X works today?’

‘You mentioned in our LinkedIn exchange you were interested in understanding more about how we do X – perhaps you could tell me a bit about how you’re doing X today?

As your prospect starts to talk, you can ask follow-up questions to understand exactly what they’re looking to change, what they want to achieve, how they want to achieve this and what sort of timeframe they have in mind to make this change.

Or if you have no real context for why the prospect has agreed to meet, you can even start with something as simple as ‘What prompted you to take my call today?’

My favourite question in the whole world is ‘Could you tell me a bit more about that?’ This is a great question to dig into the details of anything your prospect has said (or a great buffer question if you need time to think!)

Often the most useful questions are very specific to the solution you’re providing – hopefully the summary below of the above questions and a few other question types I like will give you some inspiration for questions that are specific to your situation:

‘Can you walk me through how X works today?’

‘Can you tell me a bit more about that?’

‘How is X impacting your / your team’s day to day work?’

‘What are some of the key bottlenecks with X?’

‘What areas of X are you looking to do differently?’

‘What would you like to change about X?’ (Asking about ‘change’ can be less contentious than asking what they’d like to ‘improve’)

‘What have you heard from your team about how X is impacting them?’

‘Have your management had any input into what should be changed with X?’ (You really want to know what their boss has to say, this is just a less direct way of asking that)

‘What workarounds have you tried so far?’ (If the problem is important enough, they should have tried something, if not, dig into whether it really is a priority)

‘How would that help you?’

‘Have you thought about what your ideal solution would look like?’

‘What sort of timeframe are you looking at to make this change?’

It’s often the follow-up questions that actually elicit the best answers. If you hear something interesting, dig in further with your ‘What’ and ‘How’ questions.

Think about the more detailed questions you would like to ask that are relevant to your specific solution. What are the important elements of your prospect’s current situation that you need to understand to get a better idea of the problems they may be facing?

Two things to bear in mind during your discovery:

• Don’t turn discovery into an interrogation. Keep your questions, and your tone, as conversational and natural as you can. Sometimes you have to circle a question to come back to later (possibly in a later meeting) to avoid going into interrogation mode.

• Don’t start selling while you’re doing discovery. It can be very tempting, particularly if you hear a problem you know you can fix, to go into solution mode and start talking about how you can solve that problem. If you do, it ruins the trust you’re building with your discovery and often prevents you from uncovering the deeper insights that you need.

Phase 2 – Narrow down to High-Priority

Here you want to take whatever you’ve heard and narrow down to the real high-priority pains you can address. And by high-priority, I mean high-priority for your prospect right now, not what you think should be high-priority for them.

A good way to move into this phase is to recap what you’ve heard so far.

‘If I can just play back to you what I’ve heard so far…’

And then summarise the key pain points or key objectives you’ve heard from your prospect. This is also a great way to check that you did actually understand everything correctly, and also helps reinforce with your prospect that you really are paying attention.

To understand their relative priorities, you can then ask questions such as:

‘If you had to rank these, which ones would be the most important?’

‘Which of these has the biggest impact on you right now?’

‘Which of these are most important for you to address?’

‘What are you hearing from senior management about the relative importance of addressing these?’ (Again, by ‘from senior management’, you really mean ‘from your boss’)

I can’t emphasize enough how important it is to focus on high-priority pains. For you to sell a deal of any meaningful size, you will have to engage with a number of different stakeholders. If you’re solving a problem that is low priority for anyone in your buying chain, the chance of you getting your deal done is drastically reduced.

Phase 3 – Deepen your understanding of Value Impact

Once you’ve understood the problems your prospect is looking to solve, and their relative priorities, now you want to understand the value impacts of the high-priority pains. Again, you’re unlikely to have time to get into this in a first meeting; it’s much more likely that you’ll start being able to dig into the value impact in subsequent meetings.

The reason you need to understand the value impact is because every stakeholder needs you to answer the question ‘What’s in it for me?’, so you need to understand the value you can create for each of your key buying stakeholders. At some point you will also need to work with your Champion to put together a value proposition for the Economic Buyer that articulates how much value you can create for the broader business. Without a concrete value proposition, it is very easy for someone in the buying chain to say ‘no’, or not say ‘yes’, and for your deal momentum to slow and eventually die.

While I’d never recommend phrasing an actual question in this way, what you want to do here is essentially ask a series of ‘So what?’ questions. You’re trying to uncover the true impact of the problem and the real value that you can create for each key stakeholder in your deal. It’s important to keep digging until you have a deep understanding of this.

Your User Buyers, the people who will use your solution day to day, usually care most about how your solution makes their lives easier and generally don’t care about higher-level benefits to the business. Your questions for User Buyers need to focus on the impact of the way they’re doing things today to understand how your solution can deliver value to them personally.

Your Champions, who are often first or second line managers who run the team(s) where your solution will be implemented (though they can be even more senior in large complex deals) will usually have team targets, KPIs or OKRs and will usually care most about how you help them hit these. Your questions for your Champions, therefore, need to focus on trying to understand how their current situation impacts these targets negatively, and the value you can create for them by improving their ability to hit or even exceed these goals.

Your Economic Buyers, usually the most senior person involved in signing off a deal, will likely care more about strategic priorities for the company, as well as the cold hard cash of the three main economic drivers of Increasing Revenue, Reducing Costs and Mitigating Risk. While you should always try and build a relationship directly with the EB in a deal, you will often find it helpful to work with your Champion to understand the EB’s needs and then work together to build a value proposition showing the value you can deliver. Once this is created, you, or possibly your Champion, can then take this to your EB to confirm it meets their needs.

You can find a more detailed breakdown of the different stakeholders you will encounter in your deals, how they typically think of value, and the strategies you can use to articulate that value, in our booklet Value Creation Explained.

Any questions, just DM me or email me at ben@crane.vc.

Best of luck with your discovery!