Emergent Strategy and the Power of Small Improvements

It’s the feedback loop, dummy.

Photo by Matt Seymour on Unsplash

A Founder and a Consultant Walk Into a Bar…

A few years ago, I met a local startup founder at a hotel bar for a drink. After being introduced through a mutual friend, things had progressed. This was an interview. He was considering me for a job on his leadership team.

Before our meeting, I took a bit of a risk. That job description he sent me? I rewrote it and sent him my new version. A little presumptuous, sure. But I wanted to accomplish two things. Yes, I wanted to look smart. But I also wanted to figure out who he was really looking for and what he needed me to build. Reading between the lines, I sensed the founder was hungry for more repeatability in his business. More process. More structure. A bullet on my rewritten job description read: “This person should be a great process engineer.”

We sat down at the bar and I slid a copy of the document over to him. He read it quietly. I sipped my drink. After what felt like a long time, he pointed to the “great process engineer” bullet and asked a fair but terrifying question: What did that mean? Could I tell him what made someone a great process engineer?

I panicked for a second. Then I gave it my best shot which, looking back, was nothing more than an abstract regurgitation of some far-off consulting training lodged in the back of my brain somewhere. Something about observing best practices, writing them down, and then training and motivating the team to follow the new process. He listened politely, waiting for me to finish. I eventually trailed off, begging him with my eyes to jump in and rescue me. Finally, he did.

“I think that’s part of it,” he said, mercifully. “But to me, it’s more about the feedback loop. Are you actually paying attention to what’s happening and then fixing the little problems that arise as you go? That’s what good process engineers do.”

I sat there, nodding. Well shit, I thought. That’s a much better answer.

We finished our cocktails, parted ways, and I continued the interview process over the next few weeks. I met the team, got to know the company, and eventually landed an offer. Though I ultimately decided to take another role, I couldn’t stop thinking about what the founder had said about process and feedback.

Sure, good process involves writing things down. Standardizing them. But it’s what happens next that really matters. A well-documented process, with its individual steps clarified and exposed, lets you zoom in and make small changes without starting over. Write it down. Then make it better. I had completely whiffed on that second part. The more important part.

A Different Kind of Strategy

There’s a church of managerial thought that worships the feedback loop. It’s called “emergent strategy.” Introduced by management scholars Henry Mintzberg and James Waters in the 1980’s, emergent strategy is “the decision to follow a new path when opportunity knocks unexpectedly, or when an unexpected roadblock arises.” Franklin Delano Roosevelt defined it more succinctly when he said:

“It is common sense to take a method and try it. If it fails, admit it frankly and try another. But above all, try something.”

Take your best shot, pay close attention to what happens, and then adjust. That’s emergent strategy. Done well, it’s about asking 3 simple questions in a specific order:

1. What are we doing? (The process)
2. How is it going? (The feedback loop)
3. What should we do about it? (The tweak)

If this sounds basic, you’re not wrong. Emergent strategy is simple. But that doesn’t mean it’s easy. Most people lack the discipline it takes to follow these steps for more than one or two cycles. As a result, very few reap emergent strategy’s rewards — which can be huge.

Here’s an example from my world of B2B software sales. It’s hard to talk to a sales team without talking about “the funnel” — the process of qualifying, prioritizing, and sorting through a large number of potential customers until you find the handful that actually want to buy. Every B2B software company divides their funnel (and their sales process) into compartmentalized stages, designed to mimic the steps that buyers follow when making a purchasing decision — from recognizing their problem to evaluating solutions to picking and purchasing a product.

How do you analyze a sales funnel? You look at conversion rates. How many customers “make it” from your first sales stage to the second, and from the second to third, and so on. Improve the conversion rate from one stage to the next (e.g., by building a better demo, launching a new marketing program, or training your team on how to talk clearly about what you do and how you can help) and you pick up a few more customers. But improve multiple conversion rates at different points in your funnel, and the impact can be exponential — literally. Several small tweaks have the power to change the trajectory of an entire company.

Ok, fine — you’re convinced. Small improvements make a big difference. But where to start? How do you make these tweaks? How do you make use of your own feedback loop?

Here’s where to start.

#1: Document how things work

As I’ve written about before, good leaders tend to be good reminders. They’re constantly scanning, looking for things to improve and opportunities to coach, recognize, and repeat. This is where we’re going, they say. This is why, and this is what it’s going to take. They’re not afraid of being repetitive. In fact, they accept and embrace that it’s part of the job. They’ve learned that when they’re sick of saying it, the team is only starting to hear them. There’s a simple tactic that makes all this reminding easier: Writing things down. When you write something down — a process, a how-to, a value, or anything really — you not only make it easier to share, you also send a powerful signal. This matters, you’re saying. This is how we do things here. Writing things down also contributes to a powerful form of managerial encirclement — when you hear something, see it written down, and see others doing it, it’s a lot harder to resist. When you write things down, people tend to get with the program. So don’t overthink what’s worth documenting. As CEO coach Matt Mochary puts it, “When you say it twice, write it down.”

#2: Make it safe to share improvements

Building a better company starts by building an environment where it’s safe to talk about what needs fixing. An environment where people are worried about missing potential blind spots — not about bringing them up. There’s a term for this, coined by Harvard professor Amy Edmondson: Psychological Safety. Professor Edmondson has made a career out of studying the differences between great teams and average ones. Psychological Safety is her #1 differentiator. Safe team environments don’t just happen. They are built, interaction by interaction, through specific leadership behaviors. Here are three that Professor Edmondson emphasizes:

• “Frame the work as a learning opportunity” — Uncertainty is real. Acknowledge it. Admitting the uncertainty inherent in your work tells your team that they don’t have to be perfect —they just have to learn as they go. This provides a powerful nudge to bring things up and contribute to the feedback loop. Paraphrasing Sebastian Junger, “We can’t win the war until we admit where we’re losing it.” Framing the work appropriately makes it easier to admit when people are behind or confused —the most important signs that your process might need some adjusting.
• “Acknowledge your own fallibility” — We’re tribal animals. We’re constantly on the lookout for markers of hierarchy, and (consciously or subconsciously) we all think twice before challenging someone with more authority or status than we have. It’s important to recognize this and reinforce that we as leaders don’t know everything. Sprinkle in reassurances like, “I’m probably missing something here…” or “Please help me out as I go through this.” Acknowledging that your understanding is incomplete invites others to help you see the whole picture, and assures them they don’t need to weigh the rewards of doing so against the potential repercussions.
• “Model curiosity by asking questions” — Asking questions creates what Professor Edmondson calls “a necessity for voice.” When you ask questions, you’re not just encouraging others to chime in — you are requiring it, negating the need for the team to pick their spots or wonder when they should raise an issue.

#3: Encourage self-assessment

When possible, encourage your team to regularly assess themselves — ideally against the standards you’ve already written down and reinforced. An example from our portfolio: The sales training we use emphasizes three skills — uncovering customer pain, handling resistance / objections, and focusing on next steps. Each week, we ask our sales reps to rate themselves on a simple scale across those three skills:

• 0 = “I didn’t do it.”
• 1 = “I did it.”
• 2 = “I did it well.”

We don’t crunch the numbers. We don’t run regressions. We just ask that people think about their week — where they succeeded, and what they can work on. As author Ryan Holiday puts it, “Self-awareness is poison. Reflection and review is the antidote.” Make it easy for people to think about how they can improve, and they usually will.

#4: Build measurement into your weekly meetings

Even in a trusting environment, it can be scary to broach certain topics. Not hitting your plan? Worried about an operational risk? Behind on a project? “Going there” is a two-step journey. First you need to bring it up. Then you have to talk about it. My advice is this: Short-circuit the first step. By agreeing ahead of time on how you’ll know if you’re on-track or off-track (using metrics, dates, or just some simple milestones) and then reviewing your “scoreboard” each week, you not only improve accountability within your team — you also reduce the need for individual courage. There’s no need to worry about bringing up “how it’s going.” You’ve already agreed on how you’ll measure your progress, and you do it every week. All your team has to do is show up.

Final Thoughts

Here’s my favorite passage out of Work Rules! by Lazslo Bock:

“Anders Ericsson, a professor of psychology at Florida State University, has studied the acquisition of expert-level skill for decades. The conventional wisdom is that it takes ten thousand hours of effort to become an expert. Ericsson instead found that it’s not about how much time you spend learning, but rather how you spend that time. He finds evidence that people who attain mastery of a field, whether they are violinists, surgeons, athletes, or even spelling bee champions, approach learning in a different way from the rest of us. They shard their activities into tiny actions, like hitting the same golf shot in the rain for hours, and repeat them relentlessly. Each time, they observe what happens, make minor — almost imperceptible — adjustments, and improve. Ericsson refers to this as deliberate practice: intentional repetitions of similar, small tasks with immediate feedback, correction, and experimentation.”

Whether you’re trying to master a skill or working on improving your business, the right approach is always the same:

1. Try something.
2. See what happens.
3. Adjust from there.