Discovery: The Critical First Step in Enterprise Sales

Enterprise sales are long-term campaigns. They can take 4 to 6 months (or more) to close. That’s a long time for something to go wrong, even if you are prepared. And you must be prepared, because every meeting poses unique and unexpected challenges. At AlphaSense, we have a weekly, “deal workshop” open to anyone in the company to join us for a few hours in a conference room to discuss mid-stage opportunities expected to close this quarter. We bring together account executives, account managers, SDRs, product managers, executive management and others. The owner of the opportunity briefly presents details, and the room asks questions, tests assumptions and offers suggestions on next steps. I typically find the information necessary to move these opportunities into late stage is missing – and its absence is exposed during the workshop. The most critical bits of information have yet to come from the customer – underscoring the need for discovery.

Recently, I wrote a post on the benefits of choreographing your enterprise sales process, outlining that every time you interact with a prospect or client, you have the potential to impact the outcome of the deal. And by breaking the sales cycle into phases to create a strategy for each, you can pivot when the need arises and leave nothing to chance.

Contrary to sacrificing authenticity, this kind of planning and rehearsal frees you to adapt and improvise – seizing opportunities others might have missed.

But before the first meeting, you must understand the concerns and challenges that motivate a prospect. Once you understand these, you can work with them to implement a solution. Your solution.

Therefore, the first step in enterprise sales is discovery. It is, by far, the most important part of the sales cycle, because it has the potential to add the most value to a deal.


Discovery sets you up for success

Every meeting should have a clear purpose. Some may be for building rapport or creating influence or advocacy. Others are for negotiation or closing. And others are pure information gathering to help you build a color-coded org. chart or account development plan.

Regardless of the purpose for your meeting, all of these meetings should include some level of discovery. And during this portion of the meeting, you’ll ask questions, listen to your prospect, assess needs and identify areas where you can help. You will be probing for answers and insights that will pay dividends down the road. And you guessed it, discovery starts by doing your homework.


The lay of the land: pre-discovery research

Before you first meet with a prospect, you should have a high-level understanding of the following:

  • Industry. What trends are driving change in their industry? Are there any disruptive new entrants or technologies? What about major mergers and acquisitions? Don’t forget about upcoming legal changes in the U.S. or Europe affecting the space.
  • Company. What is the current state of their business? Review their website and annual reports. Learn about their high-level strategies. What are their recent initiatives? Most profitable products? Are they acquisitive? Do they want to expand their product offerings or enter new markets? Who are their competitors?
  • Function. Familiarize yourself with the various departments and roles within their business – especially for the people you’ll be meeting. Check job boards for lists of responsibilities and scour LinkedIn profiles for insights. Understand how this function measures success.
  • People. You’ll notice we’re getting increasingly specific. Now it’s time to learn about prospects as individuals. How long have they been in a role? Did they come from a different company in the same industry or from outside? Is there anything you can glean from LinkedIn, Twitter, Facebook or via a simple Google search of their name?

This information allows you to speak intelligently and confidently and shows a prospect that you understand their situation.

You should also consider where a prospect is in the solution-seeking process. They may have spoken with other solution providers or worked on the problem internally. Find out as much as you can ahead of time. And definitely ask or confirm what you’ve heard in the meeting. Then, it’s time to dig deeper.


Create connections: Discover with intention

When I think about enterprise sales discovery, I always come back to archaeology.

Archaeologists spend the majority of their time surveying land, looking at maps, analyzing climate changes and conducting extensive in-office research. They spend only a fraction of their time digging in the field and an even smaller remainder of their time actually finding anything.

Perhaps I like the analogy, because I used to be an archaeologist. When visiting our grandparent’s house, my brother and I would dig in their yard for buried treasures. Sometimes we’d uncover an old axe head or a small crystal from a chandelier or maybe a chipped piece of pottery.

As we found items (or didn’t), we pondered why they were (or weren’t) there to begin with. Our grandparents encouraged us to make connections between the items and think about the people who once owned them. They even took us to a museum to get our finds appraised.

New information and deeper connections helped us anticipate where future discoveries might be. The more we thought about what we were looking for and where to dig for them, the more treasures we found per dig.

It wasn’t until years later that I learned my grandparents hid the items for us to find. (How cool is that?) And even later, I also realized this “game” had remarkable benefits when applied to enterprise sales.

The more planning you do and the more information you discover will lead to better answers and deeper connections, which yield the most valuable results.


Be an archaeologist: Optimize your discovery process

I coach my enterprise sales team on four key tenets of discovery. Incidentally, these also match what famous archaeologist, David Hurst Thomas, said about his work:

“Archaeology is not about what you find, it’s what you find out.”

The art of enterprise sales, as with archaeology, lies in uncovering the best way to arrive at the most valuable solution (or major find). To do this, you should:

  1. Start early. Begin discovery during introductions. Greet your prospects and ask about their roles at the company, their goals and how they fit into the organizational structure. Get them talking.
  2. Establish connections. Are people in the room saying similar things, or do they have different concerns? What business problems do they share? Look for places to build agreement between prospects about your value.
  3. Come prepared. Decide what information is critical to get at each meeting. Bring questions to get those answers. Then, as conversations unfold, take notes – you may discover unexpected opportunities or identify topics to address at a later meeting.
  4. Keep digging. Make conversations open-ended. Get the prospects talking. It’s okay if your answers don’t come up right away. You just need to find your spot. Keep asking questions. Probe for the information you need.

What I liked most about playing the archaeologist as a child, and what I like most about enterprise sales discovery today, is the sense of adventure. Discovery is exciting – there is almost always a game-changing piece of information waiting for you, if you are patient and thorough.

In my 20 years of experience, I’ve found that enterprise sellers who are genuinely curious with their questions and passionate about solving problems – not just closing deals – are the ones with the highest conversion rates.


Don’t jump the gun: Sell late for bigger sales

One last anecdote about archaeology, and then I promise I’m done.

Never sell an incomplete skeleton to a museum. By digging a little deeper, you might discover a new cache of bones and realize too late that the velociraptor you thought you found was really a tyrannosaurus rex.

This would be embarrassing for any archaeologist, but when the idea is applied to enterprise sales, it could mean the loss of significant profits. How?

Many enterprise salespeople falsely believe that their initial research and conversations tell them everything about a prospect’s needs. This is rarely the case. The true value is often buried deep and tends to surface later in the discovery phase.

Finding the piece of information that can transform the scope of a deal takes time and careful digging. And the only place to get this information is through face-to-face research. Ask questions. Probe and listen. Let the prospect tell you what they really need.


Have a plan: Use a discovery checklist

By creating a plan, digging deep and selling late, you give yourself more tools and information to use in a creative, adaptive way. Keep these key discovery questions in mind as you go:

  • What is their current workflow?
  • Can you identify their biggest challenges?
  • What is the quantifiable impact these challenges are having on their business?
  • Who’s affected by the challenge?
  • Who’s involved in finding a solution?
  • Have they considered tools (internal or external) to solve this challenge?
  • Do they have a timeline for solving the challenge?
  • Have they allocated budget for solving this challenge?

Remember, missing or incomplete information poses one of the biggest risks in the mid-to-late phase of a deal. You must be able to help prospects understand why the value vs. cost of your solution is worth paying for to prevent long-term sales from petering out.

Now you’re ready to approach the most important part of the enterprise sales process, discovery, with a strategic plan to uncover critical information from your prospects. This process can also lay the groundwork for expanded sales opportunities beyond the initial deal.

Kiva Kolstein
Kiva Kolstein
President and Chief Revenue Officer

Kiva is President and Chief Revenue Officer at AlphaSense. Beyond his current role, he has spent the last 25+ years building high-growth companies and teams at Handshake (sold to Shopify), Percolate (sold to Seismic), Gerson Lehrman Group (“GLG”), Kastle Systems, Global Crossing, and WinStar. He is also an advisor and/or Board member to several high growth start-ups, member of YPO, and Dean of the CRO School for Pavilion.

Read all posts written by Kiva Kolstein