Sales Meeting Prep

Deals are won in the work you do preparing for your client meetings.

We’ve all been on a sales call as a prospective buyer when the salesperson shows up to the call, unprepared, asks a million questions (you aren’t sure where they are headed with any of it), and then proceeds to deliver an epic monologue pitch that doesn’t really hit the spot. Then, they try to lock down your calendar for next week to continue the conversation and either you give them a baloney response of “let me circle back internally” (which you have no intent to do so) or you obligingly agree, but then cancel the meeting last minute and indefinitely ghost that person moving forward despite how many emails, calls, and texts they follow up with. 

As a career salesperson, one day, when I was sick of getting ghosted, sick of chasing deals (that in retrospect weren’t deals at all), I had the opportunity to learn from two sales guys who were the sales engine behind a business that grew during under their direction from modest tech startup to publicly-traded decacorn. These guys can probably teach me a thing or two about sales… I figured. 

What I learned from them is this: 

• Good salespeople love the pitch, they get high off the feeling of a great meeting where decision makers have come together to solve a problem, and that problem can be solved with the product the salesperson is selling. 

• Great salespeople, on the other hand, also love the pitch, and the feeling that follows, AND perhaps most important, they know how to get this outcome consistently – and know that more often than not, this outcome is generated by how prepared they are – researched the account, prepared for the meeting (and potential objections), execute and improvise flawlessly, and follow up based on an mutual plan which is established in collaboration with the client stakeholders. 

And it’s what I learned from them that took me from solid salesperson to sales person with the sauce. In this three part series, I am going to dive into the three lessons I learned and how to apply them in your own business and selling context. 

Lesson 1 - Meeting Prep → This blog’s focus

Sales meetings are won by great dynamic, charismatic salespeople 

Sales are often won and lost in how a salesperson prepares for their meetings 

Lesson 2 - Meeting 

Great sales meetings have an agenda and demo 

Great sales meetings have an upfront contract and an outside-in perspective of how a solution can help 

Lesson 3 - Mutual Plan Follow Through 

Great sales meetings end in Next Steps & Follow Up 

Great sales meetings end in a mutual plan established in collaboration with the client. 

Lesson 1 - Meeting Prep

In today’s competitive selling environment, one of the worst things that can happen to a salesperson is to make a poor first impression on a key stakeholder at an ideal prospect account, and you only get one shot at a first impression.

It’s because of this, the art of the meeting prep is so critical to success. 

So what does meeting prep entail? A number of things that we’re going to dive into. 

That said it all starts with this: the outcome you are hoping to drive by meeting with the prospect. In general, that outcome is this: 

• You’ve helped the prospect objectively debate the potential for change in their organization, as well as the costs of doing something, or doing nothing. 

• And after this conversation with you, they believe that the cost of doing nothing > the cost of doing something (with your solution), and therefore, they should at a minimum investigate it further with others in their organization who would be similarly impacted in a positive way.  

• If you are able to do this, your role as a salesperson simply becomes as a guide in helping them through a process that nets out to them realizing the change you promised. 

So how do you use your first meeting to get them there?

Know their Strategic Priorities 

First, you need to understand your prospects' goals for the coming year. What are they hoping to accomplish as a business and how do they plan on accomplishing those things?

While you can use discovery time on the call to learn about this directly from them, I’ve found that a quick google or Gemini search will typically turn up some information that allows you to get a handle on things before you get on the call with the prospect. As an example I might ask: “Gemini - what are the top three strategic initiatives for [account name] in [year] according to their executive leadership team?”

Note: For publicly traded companies, you can always find their Annual Reports on the Investors section of their website. These reports hold golden information for people in sales as it lays out the company’s strategy, priorities, and in many cases notes who is at the helm of driving those initiatives forward within the organization. 

For non-publicly traded companies, you can search for mentions from senior executives in the news, and/or see what they are posting about on LinkedIn/Instagram. From these resources, you can triangulate some of their areas of focus – grow core business, expand distribution, innovate, etc. 

Here’ what this typically looks like for me in practice:

Map out their Organizational Structure 

Next, spend a few minutes making your best effort to map out their organizational structure. When I am doing this, I typically start with their executive leadership team (typically you can find their exec leadership team on their website in the About section for both public and private companies) and then build the org chart down to the person you are going to be meeting with, making assumptions about where they most likely fit into that org chart (and therefore who’s strategic priorities they are acting in service of). 

Here’s what this typically looks like for me in practice:

Develop an outside in perspective

Now that you know what their objectives are, and where the person you are going to be speaking with likely fits in with respect to driving the corresponding initiatives forward, hypothesize what your angle with them could be: From the outside looking in, knowing what you do about their strategic priorities, and who you are talking to, how do you believe your product or service can help them? And what would be the impact of that help? New revenue unlocked? Cost savings? Reducing the need to hire? Etc. This is your initial angle for your meeting with the prospect, and what you use to prep your talk track, slides, any potential demo materials etc., ensuring they are infused with only the most relevant capabilities you have for helping them solve their problems.

Get your mind right for your sales call 

As discussed in another post, a common misconception in sales is that sales is about selling. Ultimately, as a salesperson you are measured on the revenue you generate for your company. However, sales is actually less about selling, and more about working with your prospects to determine if and how your solution can help them achieve their big goals. Remember, your customer is the main character in their own story, and they only care about what you can do to help them, so take the pressure of yourself and “having to sell” and instead change your mindset to “I am eager to determine if and how I can help them.” Instead of bringing energy that says “I can’t wait to close this deal, and what can I say to prove to them they need my product?” plan to bring energy that says “I am eager to determine if and how I might be able to help you. I have helped others like you in the past, which leads me to believe there could be a fit for you too. We will determine that together. And because I care, it is okay and honest to push back at times.” 

Remember, your role in sales is to help get them out of the mindset of “we’ve always done it this way” to objectively debating (in their own heads) if the cost of doing things the way they’ve always done it is greater than the cost of making some changes with the thing you are proposing. When you get them out of the subjective, defensive mindset of well this is just how we do it, you open them up to considering how change might actually help them achieve their goals with less effort and more ease, and how your solution could be just what they need for that. 

Confirm the meeting a day in advance 

For 1-1 meetings: Confirming the meeting a day in advance does two things: First, it tells the prospect “Hey, I am thinking about you because you are a priority for me and I am looking forward to the time we are going to spend together.” Second, it gives the prospect a (in most cases) much needed reminder that they are going to be spending some time with you the following day, so they can spend just a few moments remembering why they set the meeting up in the first place and establish for themselves what they hope to get out of the call. 

Pro-tip: A lot of times, you may set a meeting up with someone individually, but then others are subsequently added to the invite. Instead of sending one big group email here’s what I recommend instead. 

For small group meetings (esp those with execs): Reach out 1-2 days in advance and say something to this effect “Hi there, we haven’t met yet, but by way of introduction I am [your name] and I work for [company name], we [succinctly describe your impact] for companies/teams like yours. I am looking forward to tomorrow’s conversation, [if you’ve genuinely enjoyed working with someone on their team or one of their direct reports, mention it here with something like ‘Jen has been great to work with so far, and from our conversations I get the sense there could be some really good stuff should we decide to partner together’]. In advance, I wanted to reach out to simply put a face to my name/company’s name, and share my contact information should you have any questions you wanted to send my way in advance or after our conversation tomorrow.”

^ What I love about this move is two things: First, similar to what I said above, it demonstrates your care for this account and creating space to understand their business and help them evaluate if your company is in a position to help them with their goals. Second, is it allows you to get multi-threaded and build rapport with stakeholders individually ahead of your group call. This allows you and them to show up already a little warmed up to each other, and in my experience this can really help with getting people to open up more when you do Discovery. 

Build your “six-box” bingo card and ideal mutual plan 

I promise this is the last thing I will add to your pre-meeting to do list! 

Pretend for a second that your meeting goes incredibly well and you get the sense that the prospect wants to move extremely fast. 

• Who will need to be involved on their end? 

• What’s the fastest timeline your company is in a position to execute against? 

• What are the major milestones you will have to check off the to do list together in order to formalize a partnership? 

While this part is certainly an optional step, in my experience this has always been true. If I have already visualized and mapped out the “happy path” for getting this deal over the line, I feel like I am in a position to lead the client, should it be relevant, down this path. I can say things like:

“In my experience, we typically would need to have someone like this person involved. I did a little internet stalking in advance, and would guess perhaps that would be [Executive] or maybe one of their direct reports – do you think it's worth getting them involved?”

And

“In my experience, it typically takes six weeks from contract signatures to getting you stood up on our platform, given what you shared about your need for this by [date], I’m thinking we’ll need to move fast – here’s the typical next steps we’d go through. Would you agree it makes sense to get started on these?” 

So what is the six-box bingo card? And what is the ideal mutual plan? 

The six box maps out who the key decision makers and sponsors are on your deal. In enterprise software sales a lot of times there are multiple cooks in the kitchen, the six box helps you map out who they are and what their sentiment is towards your solution. 

The reverse timeline helps you map out the time between today and getting the deal done, so you know the key milestones you need to cross with the client between now and then should everything go according to plan and schedule. (Note: it won’t, but if you haven’t at least though it through, then you won’t be as prepared to ask and establish the mutual plan and reverse timeline with them). 

Summary of Lesson 1

As salespeople it is easy to simply show up on a sales call and be our-charismatic-selves, but in my experience that drives less consistent results. Since implementing my pre-work checklist, I have delivered more revenue, more easily, with less effort, and less surprises than before I implemented this system.

Albeit, I may not be this prepared for every single meeting, I do try to create time in my calendar to actively prepare in advance of meetings to ensure the best experience (and therefore outcome) for both my client, and myself.

Lesson 2 >>> coming soon.