Uploaded by Thao Vo

Insight Series

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Series #1
The What / Why / How
1) What is the problem the prospect is coming to them with? i.e struggling to close
leads
2) Why is that a problem? i.e Why is struggling to close leads a problem for this
prospect and their business? (an answer to this question almost always leads us to
discover the Business Problem i.e Declining Revenue)
3) How is the problem impacting the organization and prospect? (every deal needs
the emotional and rational component in order to complete the picture)

Emotional component = how the prospect feels about the problem

Rational component = how the problem impacts the business
You need both in order to perform at your best.
Finding the What / Why / How is an excellent first step and the quality of his calls
immediately improved.
He was “getting straight to it” much faster.
But then another problem came up (as it often does!)
He didn’t build on the answers to the “How” question.
He would ask once but didn’t press for details.
He merely dipped his toes in the pool of Chad, but didn’t jump in.
Define EVERYTHING
: You say revenue is declining due to a inability to close leads.. would you be
open enough to define what you mean using numbers?
Chad note: I use “Be open enough” to increase the odds of agreement by triggering
cognitive dissonance. Nobody likes to think of themselves as “not open”
People buy emotionally and justify intellectually. And in order to accomplish the
“justify intellectually” bit there must be an airtight business case (ROI) to working with
you.
The expected value of working with you must exceed the cost to work with you
by a large margin in order for it to make “business sense” to work with you.
Get to the numbers.
Only then if the numbers are compelling would I then dig in to the root causes of
their stated problem
If one of the root causes happens to be a problem my solution can solve then my
chances of winning the deal are higher because I’ll be able to make a sound
recommendation for how to solve the problem.
Know which problem the prospect really has
A client told me his problem wasn’t closing enough deals and his client retention
wasn’t great.
I was naturally skeptical because I knew the problem the prospect brings is never the
real problem to be solved.
I probed a bit and discovered a few interesting points:
1) His demo → close rate is ~20% (not bad.. but not great either)
2) His clients don’t actually need him for the long term and he never explicitly
qualifies them on this point. When I asked him why they don’t need him for the long
term he told me they have real limitations that prevent them from signing on for
longer engagements.
The answer to me was obvious.. he didn’t have a closing problem, he had
a targeting problem.
He was selling to the “wrong” buyers.
I advised him to change his ICP and his offer accordingly. I also advised him to
challenge the new ICP based on a few key criteria including the “ability and
willingness to partner for long term engagement”
This should fix his retention problem.
I also suggested he stick with the status quo regarding how he conducts his sales
calls with the new ICP. We can always revisit his closing rates if it remains a problem.
Changing too many things at once can cause more harm than good.
All of this was discovered because I didn’t let him self diagnose without challenging
and stress testing him and his assumptions.
I don’t know if he will follow my recommendations, but I did my job successfully.
The more granular, the better
A client requested my help for outreach. I asked him to create a PICS chart prior to
our meeting.
Upon quick glance I saw the “Problems” he put were simply too vague i.e "stay in
sync with business requirements”
A good litmus test for if your problems are too vague:
When the prospect is in the thick of it is this really what they are b*tching about?
Does a prospect really say “Oh man I wish we could stay in sync with our business
requirements!”
Or are they more likely to say:
“Why the F&*! do I always need to talk to someone in order to see what’s going on
with a project?”
Imagine 2 sales reps cold calling a VP.
Sales rep 1 asks if the VP is struggling to keep in sync with business requirements
and Sales rep 2 asks if the VP has ever wondered why they need to speak with
someone in order to see the current state of a project
Which one is more likely to get a positive response?
In sales, the gold is always in the details and “realness” of your message
Never be in a rush
A client has been working on a renewal deal with a current account. Unfortunately,
this customer outsources their IT decisions to a 3rd party. So my client has to sell to
a middle man who will then present recommendations to the current customer for a
final decision.
This was a complex deal.
Frame lost in 10 seconds
My client and the 3rd party had a call scheduled to go over the new packages and
pricing.
From my client’s (the seller) perspective, this call was important. This was the
“presentation” part of his sales process. He needed the 3rd party’s full and undivided
attention. Unfortunately, the 3rd party told my client in the first 10 seconds that he
had to cut the call short and that he was in a rush.
It sounded like this:
Prospect: We need to move through this as quick as possible because I’ve got
another call coming up. Are you okay with that?
Seller: Yeah I mean how much time do you have?
Prospect: as little time as possible to knock this out
Seller: It’s gonna take us about 45 min to get through everything
Prospect: I only have 30 minutes.. *and then begins recapping what has been
covered prior and what needs to be covered, basically setting the agenda, in an
attempt to save face*
Seller: *goes along with it*
*pause*
A lot to unpack in this short exchange. My notes below in bold:
Prospect: We need to move through this as quick as possible because I’ve got
another call coming up. Are you okay with that?
Seller: Yeah I mean how much time do you have?
Prospect: as little time as possible to knock this out
Analysis

The prospect is using a Time Frame stacked with a Power Frame.

The prospect assumes the High Status position by commoditizing
the seller’s time and deal value. The subtext here is the seller is just
another task to deal with because the prospect has more important
things to do.

I understand that people are busy but a high stakes situation with 6
figures on the line is literally the last thing you want to be rushing
through
—
Seller: It’s gonna take us about 45 min to get through everything
Prospect: I only have 30 minutes.. *and then begins recapping what has been
covered prior and what needs to be covered, basically setting the agenda, in an
attempt to save face*
Seller: *goes along with it*
Analysis

A weak attempt by the seller to regain control of the Frame.

The prospect doubles down on the Time & Power Frame. Another
Time Frame used i.e “I only have 30 minutes” and the Power Frame
by steamrolling ahead with the agenda assuming it is okay to do so.

The prospect isn’t in the wrong here because the seller did “agree”
to it by asking how much time he has. This is what happens when
you are passive and don’t set boundaries.
I advised him next time a prospect does that to assertively set his boundaries.
Prospect: We need to move through this as quick as possible because I’ve got
another call coming up. Are you okay with that?
: Actually that’s not going to work as I need the full hour with you. I need your full
attention as the stuff we’re going to be covering is important so let’s reschedule
^ a Moral Authority Frame ending with a suggestion to move things forward.
Frame & Status intact.
Series #2
Insight #1: People buy from people *like* them
One of my clients has been struggling with cold email and wasn’t seeing much
success using my templates.
I reviewed the templates he used and did a Lay of the Land exercise with him to
learn more about his buyer and their world.
He sells to compliance (pray for him)
And the templates he used were short, vague, and informal emails.
Anyone who has gone through my course should be able to spot the problem..
His messaging resonated with High D personalities.. but he was selling to High
C’s and S’s
To succeed with cold email you need alignment on 3 things:
1. Your message (what you actually say + the medium you use)
2. Your buyer
3. Your offer (product / market fit needs to be strong)
The more in alignment these 3 things are, the more successful your cold email
campaigns will be.
In my clients case, #1 and #2 were not in alignment.
And since we can’t change who his buyer is we must change his messaging.
We changed his emails from:

Short

Informal

Vague

Intriguing

Formal
To:

Detailed & Descriptive

Focused on the technical problems we’ve solved for other compliance
teams
You need to know who you are selling to on a personal level.. what kind of person
are they and what would they respond to?
Go beyond the obvious (job title / functions, etc)
Insight #2: No consequences, No sales
This client sells a specialized service for early stage startups and the buyer they
engage with is usually the founder of the company.
My client performs “well”.. I say “well” because while his numbers are on an upward
trajectory he still makes a lot of amateur mistakes.
So I challenge him because his current ceiling could very well be his current floor
(and he agrees)
Here’s an example of one of those amateur mistakes:
Going into sales mode when the buyer says “I don’t know what I’m doing”
Their conversations typically go like this:
: So why did you reach out to us?
Prospect: Because I need help with xyz.. I have no idea what I’m doing
: That’s okay John.. a lot of people we speak to aren’t familiar with how to do
xyz.. *begins explaining the service*
And then the rest of the conversation are softball questions from the seller side and
then a 35 minute demo.
They never move the conversation forward in order get to the Human Element of the
sale.
So I advised my client to add tough and uncomfortable questions designed to go
deeper.
Example
The conversation would then go like this:
: So why did you reach out to us?
Prospect: Because I need help with xyz.. I have no idea what I’m doing
: Makes sense. I’m assuming this is your first time doing xyz?
If yes, proceed to question 2A
If no, proceed to question 2B
2A: Okay. And a bit of a tough question but let’s pretend we’re 3 months into the
future. What will need to have happened in order for it to be clear working with us
was the right move?
2B: No? What happened last time?
Continuing Question chain 2B:
Prospect: I tried doing it myself with a different project and was unable to [get desired
outcome].. I ended up wasting a ton of money and time
: That’s super frustrating.. Unfortunately that’s not an uncommon experience. But
surely you must’ve learned from those mistakes.. why not try it again yourself?
Get them to fight for it.
Insight #3: Challenge their ability / willingness to
Change
This client sells enterprise software that can replace multiple separate tools
commonly used by his buyers. The value is there in terms of consolidating tech
stacks and cost savings.
However, every time he engages a new prospect they think his software is just
another add-on or an upgraded version of one their current add-ons.
So his challenge was also one of battling perceptions. This is common when selling
an innovative / disruptive solution.
My client has a solid technical background so is competent at diagnosing the
technical problems with the buyers current environment.
But he wasn’t yet familiar with the ways of the
So his conversations consisted of lots of technical questions and probing about their
current environment.
Nothing wrong with this.. The problem was the order in which he was handling
things.
His first priority should have been challenging their ability / willingness to change. He
needed to get comfortable asking questions like:
: Have you closed your mind to the possibility that your workflow can be made
easier and more efficient?
: When you say “you’re all set” do you mean you’re comfortable using 5 separate
tools and that it’s not worth the hassle of changing?
For his Discovery calls I had him using Pre-emptive Strikes as well.
Insight #4: The problem they complain about
isn’t the real problem to be solved
People buy emotionally and justify it intellectually.
What compels them to agree to a meeting with a salesperson?
They have a problem they want solved. That “problem” is a symptom causing them
Discomfort:
Symptom = missing project deadlines
This is where 99% of salespeople begin selling.
But what is causing them to miss those project deadlines?
It could be a number of different reasons!
So presenting solutions at this point is way too early.
You are skipping the prospects “alternatives analysis” they naturally do before
deciding to work with you (or anyone for that matter)
And instead of going through the alternatives with them on the call you let them do it
without you after the call.
NGMI.
You need to focus on the root causes that your solution can directly solve while
disqualifying the other reasons.
Sales is about getting the buyer to realize they need you or don’t need you through
the questions you ask.
Insight #5: Accumulate easy status points
: So where are you based?
Prospect: London how about you?
: Oh I love London! Definitely more fun than being in *redacted*
Prospect: Ha..
Why salespeople so willingly drop their pants is beyond me.
Stop self deprecating and giving them free Status points!
: So where are you based?
Prospect: London how about you?
: I’m in *redacted*.. London is cool but definitely more of a beach guy myself
though
Series #3
Insight #1: Choose your words carefully
I advise nearly all of my clients to start their calls by asking:
: What are you hoping to see or hear on this call today?
This question is designed to begin qualifying the prospect on their Buying Criteria.
One of my clients told me he’s been following the new frameworks I gave him but is
still struggling.
So I told him let’s review the call.
*start of the call*
: So what are you hoping to get out of today’s meeting?
I paused the call.
“You didn’t ask the question I told you to”
“But I did”
“No you didn’t. Listen again”
I replayed the recording.
: So what are you hoping to get out of today’s meeting?
I paused the call again.
“And now what’s the question that’s written in your script?”
: What are you hoping to see or hear on this call today?
Do you see the difference?
Do you see why there’s a difference?
He did.
Do you?
Part 2
Buyer says:
“We want to figure out how you guys can help”
vs
“We want to figure out if you guys can help”
Can you spot why there is a difference between the two?
There’s 2 levels for the buyers decision making.
Level 1: If = yes/no if you can help. This answer is absolute.
Level 2: How = process / degree to which you can help
So if I hear a buyer say:
“We want to figure out how you guys can help”
I know this buyer is likely to have already decided my category of solution or even
product/service is the right one for them and now it’s just a matter of aligning process.
If I hear a buyer say:
“We want to figure out if you guys can help”
I know this buyer still needs to be convinced.
Note: This convincing will be done through the questions I ask, not the
answers I give, so they can convince themselves.
Insight #2: Timelines vs Priorities
Salespeople love to ask their buyers about timelines when instead they should be
asking about priorities.
They do this because of assumptions and lack of experience.
They assume it’s a priority for the buyer because they are only asking about
timelines and not priorities.
And then they actually believe the prospects answer lol!
Write this on a post-it note and put in front of you when talking to buyers:
Priorities dictate Timelines.
Not the other way around.
This is especially and painfully true in Enterprise Sales.
Priorities / Company initiatives take priority over everything else.
See what I did there?
Insight #3: Whose ticking the boxes?
I know how bad you want to impress the buyer with your vast and hard earned
knowledge.
This is why you monologue to your buyers.
This is also why I get pissed when we pull up your call and I see:
Talk time
Seller: 77%
Buyer: 23%
But what really happens is the more you talk the more they are scrutinizing you and
“ticking the boxes” on their mental checklist.
The more you talk the more likely you are to say something wrong that (silently) kills
your deal.
The more the buyer talks the more you get to dust off that old and barely used
checklist so you can evaluate if you want them as your next customer!
You know what you do works. You have a successful business based on that fact!
You don’t have to prove that fact to the buyer.
Your solution is the independent variable.
The buyer is the dependent variable. Their situation, problems, and goals need to
align with what you can offer. If it doesn’t they aren’t suitable to be your next
customer. How can you discover this if you are too busy talking?
It all comes back to assumptions. You are assuming they are a good fit but they
haven’t made that decision yet! They decide by talking themselves into it, not by you
doing it for them.
Insight #4: Provide validation through the
questions you ask
The majority of buyers believe salespeople don’t really listen to them in their
conversations.
I agree with this. They don’t listen. They hear what they want to hear.
Giving validation is the easiest way to force yourself to listen and show the buyer they
are in fact being heard.
Unfortunately, salespeople providing validation is often either an
afterthought or overdone (sucking up to the buyer)
I don’t see many salespeople who are able to validate the buyer from a high
status position (that’s the kind of validation everyone craves)
I reviewed a Discovery call recently and had an epiphany:
The less effort it requires on your end to show the buyer validation,
the more likely the buyer is to perceive it as sucking up to them.
It’s just too easy and unbelievable to solely validate the prospect by saying / asking
things like:
“Sorry to hear”
“Did I get that right?”
We need to be even more subtle and sophisticated in our approach without
compromising on the power of validation.
One example would be to wrap the validation in the form of a socratic question:
Prospect: *asks question*
: Out of curiosity, are you asking me this because of what you said earlier about
[previous context]?
or
: You’re probably asking because of [previous context] right?
If yes, this stroke of validation + question combo will show them you’ve been
listening and keep them talking (a good thing for you!)
If no, they’ll still feel validated (that you’re listening) and either correct you so you can
answer the right question.
Win win.
Insight #5: Lead them to the conclusions you
want them to make
My client sells a niche service and noticed a gap in his market.
His objective was to get the buyer to discover for themselves that using his service
will give them a few key competitive advantages.
One of those advantages would be driving new business from referrals.
Here’s a line of statements/questions I created for him:
: I noticed referrals are a pretty significant source of new businesses in your
space..
Prospect: Yeah bla bla
: So how does it work? You guys do a good job with someone, they tell their
friends, and then those friends come to you?
Prospect: Yeah pretty much
Note: it can seem redundant to ask what their referral process looks like but it’s
important for the buyer to establish context in order for us to proceed creating what I
call “Logic Chains”
: And what about the clients you have to turn away and send to [more expensive
alternative]? What do you think they tell their friends then?
Prospect: Obviously they’d be disappointed
: Let me ask you a question.. how many opportunities do you think you’ve lost
directly or indirectly because you’ve had to send potential clients and their referrals
to [more expensive alternative] because you don’t have [solution]?
Prospect: A lot
: Now what do you think they’re going to tell their friends if you didn’t have to
send them to [expensive alternative] and that you could give them service and save
them money?
Prospect: That they obviously had a good experience
: And what are their friends are likely to do then?
Prospect: Work with us
: Great so what do you wanna do now?
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