The Dreamer and the Diplomat: Who Buys Software for Your Business?

A lot of times when people talk about software, they’re talking about the software industry: Microsoft, IBM, SAP, Salesforce–companies that sell software as their primary business. But someone has to buy all that software. And by “buy” I don’t mean “install Microsoft Office,” I mean “spend millions of dollars on large, customized, business-critical platforms.” 

Let’s start with the obvious: The great majority of businesses are not in the business of software. Software is a means to an end. It sits alongside operational centers like human resources and finance. It’s a gear in the machine. But the history of software in business is more complex than that. Over the last 40 or so years, the relationship between business and software has bred different species of stakeholders that view software in distinctly different ways. In our work with clients, I’ve noticed that there are two kinds of stakeholders: The Détente Stakeholder, and the Dreamer.

The Détente Stakeholder

Through a particular lens, the US-Soviet Union Cold War was a success. We didn’t obliterate each other. That’s good! We kept the peace (however tense and divisive). 

For the détente stakeholder, software is neither enemy nor ally. Keeping the peace is success. Diplomacy is always better than military maneuvering. Doing less means less of a chance of sunk costs and misinformed adventures that lead to apps nobody uses.

A handful of motivators drive détente stakeholders:

• Mitigating risk. There are certain nightmare scenarios that haunt business leaders. Your technology infrastructure melting down is one of them. Whether through egregious error or malicious attack, CTOs around the world spend a lot of time investing in stabilizing and protecting their platforms. It’s boring and uninspiring but very necessary.
• Ensuring stability. Inventory management. HR systems. CRMs. They just need to work reliably. The latest Salesforce features are nice and all, but the most critical feature is stability. This isn’t limited to software running reliably. Too much change can create instability in terms of processes and friction around re-educating users. Change is scary. 
• Competitive pressure. Competition is little more than a nuisance for the détente stakeholder. Things are rolling just fine and before you know it, the bank across the street releases an app that lets you deposit checks by taking pictures on your phone. Détente stakeholders don’t care for change. But business is business, and when the CEO calls you in asking what you’re doing about depositing checks on mobile phones, you need to be ready with a plan. 

The détente stakeholder is your classic buyer. For many key decision-makers in business, software is a superpower across the ocean. Keeping the peace with software is good enough. Yes, you need that system, but let’s invest just enough to keep the machine running. 

The Dreamer Stakeholder

The dreamer stakeholder views software very differently. With an eye towards competitive advantage and driven by innovation, dreamers see latent opportunity in software. Rather than viewing it as an opposing superpower, software is part of your own arsenal for succeeding.

The dreamer often has to make a business case to justify the investment and risk in trying something new. After all, you don’t need this new thing. Non-technical stakeholders (CEOs, CFOs, and the like) have to be sold not only on why they should invest but also why they should tolerate the risk associated with such new initiatives. This is partly why the dreamer is the rarer breed of stakeholder. 

I’ve made it sound like there’s a clear dichotomy between détente and dreamer. In reality, most stakeholders are a mix of the two, with a clear disadvantage to dreaming. Everyone dreams but everyone also has careers and professional reputations to protect and nurture. The really big dreamer is the entrepreneur, living outside the uncompromising gravitational pull of Big Corp. 

What’s a dreamer to do? It turns out there’s a lot they can do:

• Be a source of stability. Build a reputation as superintendent of the software ecosystem (or some part of it). Share guidance and ideas that bring stability and calm. Find opportunities to improve efficiency and reliability. In other words: do the boring stuff really really well and cultivate a reputation of ownership driven by pragmatism with an eye towards quality. 
• Little dreams. Find opportunities to get little wins. The more visible the wins the better. Performance improvements, cool little tweaks that delight users, and anything else that can lead to whispers in the hallways. The aim is to shift the perception of software away from necessary evil. The executives probably won’t see these changes directly, but they will hear about them through others.  
• Create fear and anxiety. Loudly warn the business leaders of the dangers of falling behind–whether that’s lagging competitively or resetting because consumer or user behavior is changing in meaningful ways. The biggest software decisions within companies are driven by business needs. Few executives want to commit to software initiatives because they think something is cool. Embark on a campaign that frames the initiative as absolutely necessary, bordering on existential.
• Build the sandbox. The innovation sandbox is a dangerous double-edged sword. You’ll often see new software initiatives walled off in “innovation” groups. The sandbox is set up away from the core business. This way the kids can’t get behind the wheel and drive the business into a wall. The downside of such an approach is that innovation teams often aren’t real. The investment (both financial and political) are often half-hearted. It is a line-item in finance that shows the board that “we’re innovating.” Still, it can be a powerful springboard for change. The key is to truly empower the groups within and to give them the mandate to release real software into the world (not just prototypes and alphas). Innovation teams have to be able to fail. 
• When you’re ready, go big. After months of evangelism, goodwill-building, whispers of fear and uncertainty, the non-technologists are convinced. Something big needs to happen. The software case is powered by a compelling business case. It is a glorious moment. Don’t squander it. Ask for enough investment and political cover to truly execute and then some. Well-executed software can transform a business. When you lay out that plan, don’t be coy about the time and resources it’s going to take. If the executives get wobbly, it may not be the right time.

Software gets meaningful investment via two distinct drivers: vision or pressure. The visionary stakeholder—the dreamer—is not driven by pressure because they are inherently less reactive. Instead, they are thinking much further ahead, powered by the possibility of delivering a great platform. 

Figure out where you sit on the detente/dreamer range, and accept it. Almost no one is truly both. (If they are, they’re running a chunk of Apple or Facebook.) That’s why partnership is key. 

If you’re a diplomat, find a dreamer to keep you thinking about the impact of the platform. If you’re a dreamer, find an operator, or you’ll be yet another tech leader who couldn’t bring the change they promised. Promote each other, advocate for each other, and keep each other accountable. Build something good, ambitious, and realistic at once. 

Software has impact–but only when it ships. And impact is how careers are built.

Rich Ziade (@richziade) is co-founder and President of Postlight. Drop him a note: rich.ziade@postlight.com.