Leaders Sell

Drew Dillon
ProductMan
Published in
6 min readSep 10, 2015

5 Lessons In Leadership From Enterprise Sales

I posted this to Facebook a while back:

Predictably, all my friends with Sales experience liked it. My friends who hadn’t worked in Sales gave me the side-eye. Non-salespeople have this image of used car sales or Alec Baldwin from Glengarry Glen Ross.

But here’s the bottom line:

understanding Sales makes you a more effective leader

When I say leader, I don’t mean manager. I mean there are some people who collect their paycheck and go home. Jack Welch called them b-players. They’re fine with the status quo and don’t rock the boat.

b-players don’t change the world

Then there are people who drive your organization forward. They find inefficiency and seem to have this magical ability to rally diverse groups to fix it.

No one wants to see themselves as a b-player, but many of us get stuck. You see the inefficiencies, but can’t seem to do anything about them.

Enterprise Sales has a lot to teach us about this aspect of leadership.

1. Navigating Strategic Decision Making

Enterprise Sales is a tough racket. You think you’ve been working with the person who can sign the PO and then they say they need to go talk to their manager.

The most successful reps I worked with, developed a three-pronged approach to closing:

If SaaS Products Sell Themselves, Why Do We Need Sales?
  1. “How will this decision be made?” Ask very early on, “Who is involved in purchasing something like this?” “How do they communicate?” “What does their approval process look like?” Your goal is to strategically insinuate yourself into this flow.
  2. Follow the contract. Never let your contract be handed off to a VP, Legal, Procurement, anywhere without getting that person’s contact info (preferably their phone number).
  3. Work up and down the chain. The rep’s job is to get as high as possible within the organization to make sure the deal goes smoothly. The sales engineer’s job is to navigate to the people who will deploy the solution and make sure they’re happy to do it.

2. Understanding Motivations

Let’s say you want a raise, but your company wants to save money. You’ll probably approach your boss with a proposal and negotiate until you and the company are equally unhappy with the outcome.

If this sounds like a good idea, you might suck at negotiating.

This binary salary negotiation means that not only are you and the company negotiating for the same thing, you assume you have the same level of interest in that thing.

The key to negotiation is understanding motivations. Any intro to negotiating will tell you that people negotiate based on a number of factors and place different relative values on each.

Through repetition, Sales drills into you what motivates your prospects. When I sold security, my customers wanted to:

  • check a compliance checkbox
  • achieve a little real security out of it
  • look good to their companies and bosses
  • not have to do a lot of legwork
  • not to break the bank

Each cared about these things in different proportions, but they were always there. These myriad motivations form the negotiating table. Your job as a salesperson is to figure out the weighting and adjust accordingly.

3. The Art Of The Soft No

In many Sales situations, your prospect will ask you for something your product doesn’t do. They do this for a lot of reasons:

  • idle curiosity
  • the competition has it
  • it’s something their boss asked about
  • it’s on the list of things they believe they need to achieve their goals

You talk to hundreds of people just like this one every week. The worst thing you can do on the call is drop a “No.” The prospect shuts down, the rest of the call is a wash.

Tap dance, “You know, I’m not sure. Let me look into that for you.” “I know the team working on that feature, let me double check the dates and get back to you.”

Then dig for context, “What’re you looking to do with that feature?” “Do you need that at launch or could you kickoff without it and bring it in later?”

The prospect wanted a binary outcome: yes or no.

Maybe they really do need that thing and you don’t have it, but honestly that’s rare. More often than not, you continue a productive discussion, learn a lot more about their motivations (see above), and probably come up with a way to address their needs.

4. Positioning Is Never Done

The market isn’t stagnant. The competitive advantage you had last week won’t necessarily work this week. Competitors are learning and adding new features. And, as the market moves, the fit between your product and the market grows looser.

Sales is the last department consulted on how to adjust and typically the first bear the brunt. Prospects are more than happy to parrot the competition’s reps if they like their solution or think it’ll get them a better deal.

This is a nerve wracking moment in Sales. Most of your pitch is automatic, you’ve heard all the questions before, then comes this dagger for your heart.

But it isn’t ever done and you know that. So you pick a new position and fight (and please make sure that information gets back to your PMs).

5. Never Bring A Director To A VP Fight

On the very first call, your prospect identifies their VP as the person who will make the ultimate decision. You have to talk to this person, but the VP has given your current point of contact this job and they don’t want to appear ineffective by just handing off every vendor.

You have two options:

  1. Reach out to the VP directly. Very risky, if you piss off your contact, they may crush your deal out of spite. Even more likely, the VP will be annoyed that a rep tried to pitch them directly.
  2. Level-match. Find a reason to bring a VP from your company into the conversation and intimate that they’ll be expecting a VP from the prospect’s company.

The benefit of the level-match is that the conversation between two VPs is very different. It’s not about the product or the money, but about a strategic partnership.

Lets Put It All Together

You spot an inefficiency in the organization. It’s something you believe you can fix with proper help and company buy-in.

  1. Understand the strategic decision-making landscape
    - How will this decision get made? Model off of similar past projects.
    - Where will the various decision points be?
    - Who will be involved, top-to-bottom? Don’t just manage up.
  2. This is a negotiation, what motivates these groups? What do you have to offer? What’s the benefit you’ll be providing in exchange for their efforts?
  3. Don’t let questions/concerns be obstacles, use them to foster dialog about goals and learn more about your colleagues’ motivations.
  4. Be adaptable. Things change week-to-week, make sure you can articulate the business value of your proposal in light of new conditions.
  5. Level-match your discussion to the role of the person you’re talking to. VPs want to talk strategy, Directors want to talk process optimization, and individual contributors want to talk execution.

If you are able to regularly drive positive cross-functional change within your organization, you too will become one of those magical get-shit-done people. Your impact will be recognized and greater opportunities will follow.

And you can thank Sales.

I write, when I can, here.
I tweet things like this more regularly here.

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