The 4 Step Loop That Can Transform Your Sales Org
The OODA loop: funny name, serious results. Just ask the Marines.
tl;dr - Sales operates in a chaotic, competitive environment that requires fast adaptation. The OODA loop framework, borrowed from military strategy, helps sales leaders continuously refine their execution and outmaneuver competitors.
Sales isn’t war but there are similarities - Militaries have spent centuries learning how to succeed despite incomplete information, bad luck and clever competitors. Sound familiar?
Intro to the OODA loop - How Colonel John Boyd showed that optimizing an observation-orientation-decision-action loop could lead to battlefield success.
OODA loops in practice - Identify the OODA loops in your org and optimize them to accelerate growth. Includes an example for pipeline creation.
Read on for the full story.
CROs are practical people. They have one job: make the number.1 As a consequence, most of the best CROs I’ve met don’t ruminate on grand theories. They set a strategic course and execute.
Sometimes though, it’s important to step back. Strategy and execution are themselves built on a foundation—a way of evolving and improving them to get the desired outcomes. That seems pretty meta (and it literally is) but the job of a leader is to build the foundation for growth.
This might sound like continuous improvement processes in a manufacturing context. Those ideas focus on how to more efficiently convert inputs into outputs. The problem is the real world lurking just outside the factory often gets ignored. Unreliable machines that break down are considered, but they don’t have much to say about a competitor sneaking in and setting the factory on fire (or, less dramatically, lowering prices by 50%). Unfortunately, sales can’t simplify all that away.
The real world is messiness and chaos. Competitors, economic conditions, technology shocks, politics, inertia, human nature—all these things intrude into a sales process. Even when you do everything right, there’s a combination of random bad luck (the CEO gets fired on the day she’s supposed to sign) and competitors trying to defeat you (they’ll do it for half price).
This is, perhaps, why sales leaders love military analogies. Militaries don’t operate in an idealized environment. Otherwise perfectly conceived and executed campaigns can fail due to bad luck or clever enemies. Yet they still need to deliver results under the highest possible pressure.
While sales teams aren’t literally rallying troops and taking territory and waging (real) campaigns, they do have to execute in a chaotic environment where the enemy gets a vote. Militaries know this and have developed frameworks that allow them to improve, adapt and win.
I want to introduce one such framework that’s both a) particularly applicable to building a winning sales org and b) very strangely named: the OODA loop.
But first, a little historical context.
Colonel John Boyd and rethinking warfare
John Boyd was an Air Force Colonel who has a claim to be the actual most interesting man in the world. Here are just a few highlights:
He was one of the greatest fighter pilots of all time—as close to a real life Maverick as you can get. After serving in Korea, he became a flight instructor. He had a standing $40 bet that any pilot could start on his tail and he’d take them out in 40 seconds. He never lost.
He designed the F-15 and F-16 despite not being an aircraft designer. Better yet, he did it by developing a new theory with stolen mainframe computer time. This nearly got him court-martialed.
He didn’t just stick to the Air Force. He ultimately influenced multiple branches of the world’s most powerful military—especially the Marines2. He came out of retirement to help plan the Gulf War and was instrumental in designing the “left hook” maneuver that caused the Iraqi army to collapse.
Colonel Boyd was clearly built different. He was an original thinker that wasn’t afraid to challenge orthodoxy from first principles. He also shared his ideas in a different way. While the military has a rich practice of giving briefings—essentially presentations—Colonel Boyd took it to another level. He never wrote a book about his ideas. Instead he eventually compiled everything into a single 327-slide, 15-hour briefing he called A Discourse on Winning and Losing.3
This briefing was a tour-de-force of the history of warfare along with a general theory about how to win in complex, adversarial environments. He gave this briefing over and over to thousands of people at the Pentagon, continually adjusting and improving.
Embedded in this mountain of information and ideas was a framework that ultimately changed US military doctrine. Colonel Boyd was much better at strategy than branding, so he called it The OODA loop.
What’s an OODA loop?
The OODA loop is a framework for how to win in a complex, competitive environment. Here’s how it works:
Observe - take in data from the world around you (e.g. your market, your team, your product, your internal metics, competitor behavior)
Orient - use your experience and your knowledge of the world to understand what you’ve observed and form hypotheses (note that this also provides Guidance for how to Act now and what to Observe in the future)
Decide - make a decision about what to do
Act - take an action which generates both external Response and internal Feedback to observe, starting the loop again
The Response and Feedback lines coming from the Act step in the graphic above deserve special emphasis. The external Response is where “the enemy gets a vote”. Your competitors and the market aren’t static—they’re part of the real world and they’ll have a response to your actions. By the same token, you’ll get internal Feedback from your fellow executives, stakeholders and your team on how your actions are impacting them and the business as a whole.
Combine all these components together and you’ve got a clear, continuous framework for making decisions, taking action and adapting to whatever the world throws at you.
There’s one more thing: speed matters.
The faster you execute the loop, the better you’ll perform against competitors. Those of you old enough to remember the Gulf War may recall some military folks on CNN talking about getting “inside the enemy’s loop”—meaning to disrupt their OODA loop while operating yours effectively. Here’s a good example from the time:
In maneuver warfare terms the air campaign not only put the allies “inside” the Iraqi observation-orientation-decision-action (OODA) loop but actually destroyed Iraq’s ability to employ an OODA cycle and carry out coordinated action.
Speed matters. It's true for the military and it's true for your sales team.
The OODA loop in sales
If you step back, you can see that hitting the number for a quarter is one big OODA loop. You observe the state of your pipeline, orient yourself, make decisions about what to do and act—then you do it all again and again throughout the quarter. The speed of this loop varies but usually has some kind of weekly cadence centered on deal reviews and forecast calls.
Hitting the number for the year looks similar. It usually tends to have fixed periods of orienting and deciding (e.g. annual planning) followed by actions throughout the year and smaller updates as you go. It typically operates on a much slower cycle than your quarterly cadence.
It doesn’t stop there. Sales orgs have many OODA loops operating simultaneously at all scales—from the org level (e.g. hitting the number) all the way down to the rep level (working a specific deal).
Let’s consider how the framework gives a first principles way to help you identify problems. We’ll use pipeline generation as an example.
Pipeline generation OODA loops
You can think of the pipeline generation OODA loop as one big process similar to hitting the revenue number: observe progress to goal along with what’s working, orient yourself, make decisions and then act. To really diagnose issues, it’s helpful to break it down into even more specific OODA loops. For example:
Activity Loop - we’re continually adjusting the types of outreach, our channels and activity levels based on feedback
Messaging Loop - whether it’s call scripts, email templates or new product messaging we’re constantly tweaking what we say based on feedback
Contact Loop - we’re always getting new folks to call and frequently tweaking the personas that we’re looking for based on what seems to be working
Account Loop - we change up accounts once a year with a few tweaks mid-year based on feedback
I know we’re talking about loops, but I also find this pyramid helpful to visualize how they all build on each other:
One of those things is not like the other! We operate tight loops for activity, messaging and contacts but only act on feedback from our account strategy once or twice a year.
This is especially problematic because account strategy represents the foundation on which the other loops are built.
Breaking down the problem like this provides a way to find opportunities to see where slow decision making may be hurting you. Remember, speed matters!
In this case, your account strategy sits at the base of your GTM motion, slowing everything down. If you think territory and account allocations are just an annual planning thing, you’re signing up to slow down all the other OODA loops that depend on it.
A faster, more dynamic, OODA loop for account coverage could help you build pipeline faster and “get inside” your competitor’s loop. By covering the right ground faster, you’ll be there when a buyer is considering a solution—while your competitor is still waiting for a “signal”.
If this particular example piques your interest, I gave a whole talk about this at the at the Pavilion CRO Summit. Sadly they didn’t film the slides but you can download them here.
Wrapping up
Sales leaders love military metaphors for a good reason. Sales isn’t life or death, but sales—more than any other part of the business—operates daily in an adversarial environment. You win, you lose and the competition most certainly gets a vote.
The OODA loop is the perfect military import for sales leaders. It gives you a framework to help evaluate (and re-evaluate) your strategy and execution from first principles.
After reading this, you’ll probably start seeing OODA loops everywhere. Once you see them, you can direct your team to find ways to speed them up. It’s incredibly high leverage because this kind of improvement doesn’t just impact one deal, it impacts the system that produces all your deals. Focus on that and you’ll accelerate your own growth while keeping your competitors on their heels.
Which requires answering two questions.
Boyd was instrumental in getting the Marines to adopt “Maneuver Warfare” as official doctrine. It’s all about rapid, unexpected movement to confuse and break down the enemy.
This was before PowerPoint. My guy had to carry around 327 transparencies.