Editor’s Note: This post was originally published on Seattle 2.0, and imported to GeekWire as part of our acquisition of Seattle 2.0 and its archival content. For more background, see this post.

By David Aronchick

Lou Gerstner had it wrong – the question is not whether or Elephants can dance. They can dance very well. The problem is that they’re usually listening to entirely different music than you are, and, if you’re not careful you’re going to get stomped.

Elephants – the large, slow moving organizations in your industry who only engage in the largest deals – can make your quota for the year, which is pretty convenient, since it usually takes about that long to close them. The problem is that as a startup, spending that much time closing a single deal is a recipe for a very slow year, if you don’t go bankrupt in the meantime. So how do you dance with the big game without getting killed in the process? As someone who works in a company that works with many of these types of companies, I have two pieces of advice to make sure you’re lined up for success.

First, there are no stupid questions, just stupid people who forget to ask the right questions. Here are some that you need to be asking as you take on the challenge:

  • How big is the needle you have to move? – Deals have to be significant enough to make something happen– it’s just not worth the effort for a small deal, no matter how cool or significant it is for you.
  • Who’s your champion? – Are you being backed by a decision maker or a line-level employee? Both have their risks – from not getting enough attention to not having enough power to push the deal through without consensus. This will also certainly help you schedule when you expect to see results (if any).
  • When are you going to hear from them next? And what do they need to hear from you? – It may be completely normal for your entire account team to disappear for a week, or send 20 mails in 40 minutes. Understanding their schedules (sales cycles, quarter ends, company meetings) and when the natural milestones are is critical.
  • When it rains, how much is it going to pour? – How much work is going to be required when you hit your deal and project milestones? You could go months requiring no more than 20 minutes of your time a week, and, in the blink of an eye, you now have forty documents to finish in 24 hours.
  • Realistically, how many can you pursue at once? – Understand that the payoff for these deals can be abysmal – I’ve seen sales and BD pipelines that are 20 deep where just one of the deals actually turned into something, and it was still worth it. Every additional attempt takes resources, but do not, for the love of God, put all your eggs in one basket.

Once you know how things are going to lay out, my second piece of advice is something that many people are pushing now-a-days – go lean. That is short hand for saying, be ready to respond to change, listen to your customers and do not weigh yourself down with endless process or planning. Some tactical suggestions:

  • First, make sure your overall backlog of work is extremely fluid. You have no idea when a request will come in that will take your entire team sideways for a week. Making sure you have tasks/projects that are small enough to finish every couple of days means you’re not leaving large chunks of work unfinished.
  • Second, around the rough milestone when you expect to see some work start coming in, only book 80% of your time. It’s not like you’re going to send everyone home at 4 PM, but by keeping slack in the system, you can pick up and respond more readily. And there will always be little things that can be addressed to fill the hours until the request comes in.
  • Third, be crystal clear what’s important to them, and make it important to you. The KPI for elephants can vary wildly – page views, impressions, click-throughs, sales, video views, contest entries, and on and on. You need to put aside your own dashboard – you have a new one for the beginning, middle and end of this project.
  • Fourth, do not get married – to anything. One thing you will be amazed about is how quickly large portions of your work will be thrown out, without even an indication as to the reason why. No amount of begging, pleading, or documents signed in blood will help you avoid this. Just review your work early and often.
  • Fifth, when in doubt, over-communicate. These guys are enormous – they have more meetings and partnerships than they know what to do with, and you will fall through the cracks if you do not make sure you’re heard. As my friend likes to say, be lightly, but persistently, annoying.

One other thing to keep in mind – these companies LOVE to consider themselves “startup-like”, very nimble organizations with the decision making pushed down to the individuals. Don’t believe it for a second. The reason they are worth so much to land is because they are enormous – and you cannot get to that size without having far more friction than a true startup.

As a company that deals in the entertainment industry almost exclusively, we see elephants every way we look. They are absolutely worth going after, but you need to set your internal expectations correctly. You will be frustrated by speed of execution, amount of work, sales cycle – virtually every step of your engagement. But when you finish it, your company will be that much more successful for having navigated the Serengeti, and having come out alive.

Like what you're reading? Subscribe to GeekWire's free newsletters to catch every headline

Job Listings on GeekWork

Find more jobs on GeekWork. Employers, post a job here.