Personality Over Process

When people get in the way of how things work & what to do about it.

Here’s a truth it took me a while to accept: in any organization, the personalities of the people we work with—especially leaders—are one of the most critical determinants of how things get done. Try as we (I) might to use processes to create consistency and efficiency; most processes are no match for the strong personalities and preferences of leaders and cultural influencers who need to champion those processes for them to succeed.

The ongoing internet dialogue about “Founder Mode” has got me thinking a lot about this balance between process and personality. For a founder, their personality is often part of the very DNA of a company. Founder values are company values. Founder ways of working are the ways of working. Where they exist, processes are born of the founder’s personality. And while I’m not inclined to believe it’s good for founders just to keep acting like stereotypical founders at scale, I also think PG and co. might be misdiagnosing what causes failures to occur when leaders start delegating in “manager mode.” There is no shortage of founder-led businesses succeeding while relying on delegation-heavy models. However, where “manager mode” is unsuccessful, I’d like to suggest that it’s not because of some intrinsic flaw with delegation but rather because as companies scale, they often begin to introduce processes that are fundamentally at odds with the personalities at the top. Regardless of who is leading your business and their relationship to the company, my experience is that no process—founder-related or not—will succeed if its aim is changing, dampening, or drastically reorienting the personality-driven instincts of a leader.

When it comes to leaders, personality eats process for breakfast.

Aligning Your Business’s Personalities & Processes

So what’s to be done? As businesses grow and working methods change to support the new scale, many of us are quick to rush to throw what we know at the wall: goal-setting practices that worked at our last business, communication models that we heard about on podcasts, etc. 

But to avoid building conflict and circumvention into your company’s mutating DNA as you scale, it’s critical to be mindful of who is at the helm. To keep the processes and personalities aligned with scale, you’ll need to figure a few things out: 

1. What your leaders’ default behaviors and primary incentives are

2. The relational dynamics between high-influence members of the company

3. How much deviation from habit your company’s culture supports 

There’s no one way to wrap your arms around these things. But after years of trying to diagnose and adjust to these dynamics in my workplaces, here are some good places to start…

Step 1 | Understand Your Leaders’ Personalities & Preferences 

First and foremost, you will have to figure out what motivates the people who lead your organization and their habits. When I say habits, I don’t mean if they cold plunge every morning. I mean the work behaviors they fall back on most regularly, like jumping to “I’ll do it myself” mode when a delegated task doesn’t meet expectations. Many of us rely on caricatures to understand our leaders: we think of engineering leaders as detail-oriented fixers or CEOs as scrappy, intuition-led visionaries. And while these stereotypes may be right often, they’re a dim guide for understanding who a leader is and what they’re about. Instead of giving into the stereotypes, you can build an understanding of your leaders by being observant and listening carefully. Next time you have the opportunity to observe your leaders, ask yourself the following:

• What motivates them? Does your leader live for recognition and gratitude from the team? Are they trying to help others in the way no one ever helped them? Are they gunning for fame and interest from the press? Maybe they’re service-oriented and need to be able to see how they help others tangibly, or perhaps they’re obsessive about your competition and driven to win. Whatever their motives, you can begin seeing them in what excites leaders most. Pay attention to what lights them up and what doesn’t seem to motivate at all. If you can figure out the difference, you can build systems and processes that use incentive structures aligned with what your leaders actually care about.

• How do they understand and express ideas? I’ve worked with leaders who are highly visual communicators and others who are really verbal. Figuring out how your leaders best make sense of information and communicate their own thoughts can help you figure out what type of deliverables your business needs to be working in. And while I personally wish I could force everyone to write docs and outlaw slides entirely (rant for another time), if you’re working for people who understand visual stories better than written ones, you’ll be able to create better cross-level communication by staying true to your leaders’ expression styles.  Watch for how your leaders communicate. Are they sending out manifestos after long nights of thinking? Do they always seem to end up drawing on the whiteboard to communicate ideas? These clues can help you figure out the right format to use to transmit context and information throughout the business and avoid the terrible trouble of scale, where suddenly leaders feel like they “never know what’s going on anymore.”

• How do they feel about risk? Is your leader always pointing out how things could go wrong and wanting to hear Plan B? Or do they get annoyed when the team spends too much time thinking about obstacles? We all have different relationships to risk, and understanding how cautious your processes should be will depend on the risk tolerance of your leaders. Bringing many contingency plans to a high-risk tolerance leader will make you seem cautious and slow. But skipping risk-management steps with a conservative leader will make you seem reckless and send you taking backward steps to get approval for ideas. Pay attention to when and how often your leaders ask and speak about risk and how they react when others bring risks up. Build in safeguards and risk analyses accordingly. 

• How are they with details? While we often think of leaders as people who are out of the details, many people instinctually crave infinite detail to help them understand things. I find that this is the place where systems like “manager mode” are most likely to go wrong. Calibrating to what level of detail your leaders are responsive to is one of the hardest things to figure out. If your leader is naturally detail-oriented, trying to give them the TL;DR for their sake will always leave you going back and forth about why your proposals and plans aren’t more specific. And if your leader can’t be bothered with details, trying to engage them in granularity will likely result in glazed eyes and wasted time. Pay close attention to the altitude of questions your leaders ask. While it may be frustrating to deal with leaders who feel like they’re at the “wrong” altitude, remember that someone’s desire for detail is often an immutable trait. Meet them where they’re at. Teach others in your business to do the same. 

These are just a few traits and qualities that can be useful to identify in leaders before deciding how to build processes on their teams. But nailing even those few can be the first step to creating ways of working that your leaders will actually champion and support. 

Step 2 | Understanding Relational Dynamics in Your Business  

Once you’ve got a grasp on the personalities of the people who lead you, you’ll need to also grapple with the fact that they never exist in a vacuum. To build great processes that your teams and leaders can use, you’ll also have to figure out the dynamics between people—who tend to dominate conversations and decisions, who hangs back, who is cashing in favors, and how these interactions shape the company. It’s easy to assume that loud, strong personalities and people with the most significant positional authority always steer the ship. In practice, that isn’t always the case though, and actual flows of influence can take more intention and time to see.. Learning to read dynamics to understand whose personalities dictate how things work, where those influences appear, and how they can be harnessed for good is your next crucial step in building better deliberative and decision-making processes. 

How do you map out influence in your business? To be honest—it’s not a simple task. However, a few of the things that I first look for in a company are patterns and give-aways in how information and language flow between people. This part may also start to sound a little Machiavellian. But bear with me. 

One of the easiest ways to understand who is influencing whom is by watching the proliferation of idiosyncratic language, whose verbal habits, catch-phrases, and ways of describing things catch traction and seem to spread. A silly example, perhaps, but at a previous job, I had a boss who always greeted people by saying “howdy.” The first time I noticed it, I didn’t think much of it until suddenly, I heard everyone else saying it. Everywhere I went, people in the company were greeting each other like we were at the rodeo, and it was immediately apparent whose influence drove it. Our CEO’s yee-haw greeting spread like wildfire because, just like how founders’ personalities do, his personality was interlaced with the firm’s entire culture. 

Observing information flows can also help you understand how and where influence travels. Every business has informal communication networks, and figuring out who runs them can help reveal alliance structures, where social process is filling in for official process, and where clashes between personalities may be creating dangerous information chasms. Which leaders and parts of the organization never seem to be in the know? Whose side of the story wins out as the social truth most often? While I don’t mean to suggest you get out the red string and push pins any time soon, paying even 10% more attention to these things can help you understand who influences behavior (via influencing “truth”) at a company and where information siloes may also create risks. You may not need to know these things to do your job, but if you’re responsible for creating and socializing ways of working or changing existing processes, doing it without a grasp on where and how influence travels will leave you facing invisible obstacles the whole way through. 

Step 3 | Understand Your  Leaders’ Openness to Change

My final suggestion for building better processes that harness your leaders’ personalities instead of fighting them is to start assessing their openness to change—essentially, how far the personalities at play can bend until they snap back into place. 

I regret to inform you that this diagnosis is best made through brute force repetitive testing (i.e., lots of trying and failing). But I promise it’s worth your while. Not all leaders’ personal preferences are carved into stone at the same depths, and knowing how deep the habits and behaviors run can help you invest your energy more efficiently by keeping you focused on what you can change. 

If you’re in the business of designing processes, start by figuring out how agreeable your leaders are to ways of working that they disagree with. Often, this trait is a function of a leader’s predisposition toward discipline and willingness to fight their instincts to support new behaviors. However, it is also often a byproduct of how involved they were in building their ways of working, where their ego lies, and how closely tied their practices are to core beliefs. 

As a rule of thumb, you will not get someone to adopt a behavior that conflicts with a pillar of their identity, like a core belief of value. To figure out what these are so you can avoid trying to change them, talk to your leaders about what they care about and listen to how they describe themselves. Watch what they reward if you don’t have an avenue into a conversation. People usually acknowledge and celebrate the traits in others that they hold dear in themselves. 

Through a process of low-stakes attempts, try to see how the people around you react to different types of change suggestions. How do they take prompting to slow down? What about communicating differently? If you’re really unsure about how these types of suggestions will land, try them out on lower-stakes parts of your work, and don’t get frustrated when the people around you don’t act the way you want. Remember, you’re looking for information, not a perfect record of success. And every time you learn what types of things you can’t get people to do, catalog the information, save it, and let it make the next thing you do better. 

Best of luck & thanks for reading.

Talk soon.