How do I navigate complex projects?

The greater impact we want to make, the more people it will affect. For sales, this creates a significant challenge.

Sales is all about efficiency. How can we create and realize as much value in a set amount of time as possible? Often, this means creating some combination of small deals that are relatively low-effort and large deals that feel like moving the heavens themselves.

The ability to start reliably closing large deals is genuinely life-changing for sellers, but it can feel like an uncrossable chasm. It’s important to note: all of this is true for your buyer as well. Their internal impact will be a mix of small steps with leaps and bounds.

So, how do we win these projects like the best of the best?

1. Know the stakeholders

All of the stakeholders. The takeaway from Home Alone should be that if you accidentally leave Kevin at home, Christmas in Paris is ruined for everyone. In a small deal, you can circumvent some stakeholders because you’re low impact, and they have bigger fish to fry. When you’re the biggest fish at the fry, you need approval from everyone. Your deal has almost no chance of closing if you’re trying to sneak past stakeholders or strong-arm them into agreement.

The challenge here is that your buyer has a full-time job that isn’t buying your product and also isn’t impact analysis. In other words, they probably don’t know who all the stakeholders are, and they may not be able to uncover all the answers on their own.

You need to be a trusted advisor and lean on the experience of how other projects that look like this one have closed. That could be a sale by your company to a similar buyer-type. It could be talking to a seller at a different company who sold to your current buyer (highly recommend building these relationships). It could even be learning from a seller that you know is outstanding how they have approached similar deals in the past.

Next, you need to be paranoid that there’s always one more stakeholder. When you’re in the early days of your project, there’s no sense in rushing. You’re building a root system, so you want to ask every new stakeholder who else they think would be affected by such a thing. When you’ve built your roots, you can get to work.

2. Know what level of “buy-in” is required from each stakeholder

Not everyone has to love you (it’s ok. I can’t internalize that either). Think back to those wonderful summer days when your family was on the way home for dinner and you wanted to get ice cream. There’s a simple progression: 1. Can we get ice cream?! (high excitement) 2. Does anyone mind if we stop for ice cream? (uncovering objections) 3. What do you think? (parent to parent final approval).

In step two, we don’t need everyone to be as excited as our instigator is in step one. We just need them to not having pressing matters that require their presence at home. Only a select few of your stakeholders need to be to the level of “hell yes.” These are the ones you need to galvanize to get everyone else to “not mind.” They’re also the ones who are going to care the most about competitive differentiation.

If you pass the requirements of a level 2 stakeholder, they are going to have very little opinion on which competitor ultimately wins. They will want to understand the “why anything,” and they will want to make sure it isn’t going to cause them problems.

Level 3? We obsess with level 3 because they are the final decision makers, but they rarely force top-down decisions. If there’s a good reason for a “no” that they know that no one else does, it isn’t happening. You have to have executive alignment because level 3 decision makers have the final say, but they best way to win with those leaders is to give them a clear win that’s going to make levels 1 and 2 happy.

3. Know what software they have at home

The larger your deal gets, the more likely you are to compete with existing spend, not one-to-one competitors. After all, it’s just as difficult for your competitors to take the deal from start to finish as it is for you.

Existing spend means that you’re about to find out that you have a free competitor buried somewhere in the dredges of a Microsoft (Oracle, SAP, Salesforce, etc.) licensing bundle. You have a big disadvantage here because you’re almost guaranteed to have someone at the company push back and say “we might as well try what we already have first.” This process is a double-edged sword because project success means they’re fine without you, and project failure usually points back to “was this a good idea in the first place?”

This is when we point back to the amazing work we did in step two. Every uncovered objection is now usable as the internal rubric for judging you against your new in-house competitor. Specific requirements give you the foundation to call out exactly where the project is and isn’t viable.

Competing with “we have that at home” is about allergies and non-viability, not flavors and distaste.

4. People buy confidence*value

I write this every time value or ROI comes up. Your best chance to win to to make it clear that you are the path that’s going to succeed. You need the dollars and cents of your ROI to work, but that ROI is always heavily caveated with “if” this works.

Your “how” is the sales cycle within the sales cycle.

Every follow-up you send on-time gains confidence. Every clear agenda gains confidence. Every box that’s properly addressed and checked builds confidence. Your execution is the silent variable that wins or loses your biggest deal ever. In the final decision, your buyer has to believe you can execute, and that is the sum of how you have sold from day one.

5. Build a real relationship

Finally… have fun and be easy to work with. Your buyer is going to have to burn a few matches from their box to make the project successful. Don’t burn all of those in the first month. Your relationship is going to be critical to success, and you want to built it on honesty, empathy, and genuinely giving a shit.

Enterprise sales is real life. These can be years-long engagements where you’re going to go through all the things you do in the rest of your relationships. You’re going to argue. You’re going to apologize. Don’t be afraid of anyone of that. The best thing about sales is that it’s written in your first language: being human.

Be authentically you. Work like crazy. Close the biggest deal of your life.