Source: Street art in lower Manhattan. Wish I knew the creator so I could give proper credit.

Finding fit

Separating character from capability

Bill Young
Jul 10, 2017 · 12 min read

I have been lucky in my career to work with many great leaders, teammates, and colleagues. I have always been surrounded by intelligent, hardworking, and talented people, all of whom I respect for having many skills and areas of expertise beyond my own.

Yet I’ve found it hard to find companies and even co-workers that I naturally “gel” with. We get along fine and treat each other well in the workplace, but after a while it feels like something’s missing. Wondering if I was alone in this feeling (and thinking I was the culprit), I’ve had a number of conversations with friends in similar roles, only to hear them echo a similar mismatch: there’s no lack of smarts, but there is often a lack of fit.

Anyone I’ve talked to for career advice has emphasized the importance of finding fit, but none have given me a great answer to the natural follow-up question…

What is fit?

Prior to writing out my thoughts, I would have said that it’s a gut feeling that the person or the organization just seems “right.” But I know that’s a terribly vague, unsatisfactory answer, and over the years, I’ve found it helpful to think about fit along two dimensions: capability and character.

While delivering results will always be a top priority, fit isn’t simply being around successful people or companies. There are lots of ambitious, rich, and intelligent people I would never go into business with, because as I learned the hard way, it’s essential that we share the same values. How those results are achieved is just as important as the results themselves.

To better visualize the differences, I drew up a framework for understanding the people in my professional life. It’s a massive oversimplification, but even the rough contours are a useful guide.

Charting Character vs. Capability

I wish I could say I was always this methodical and did loads of research to draw precise conclusions, but the truth is that I learned it all through experience, working with hundreds of people often into the dark stretches of the night, sometimes hundreds or thousands of miles from home. It is in these difficult, dark hours when the stakes are high that people reveal who they really are.

As you read through each of the “types” above, it is important to remember that where someone falls within the chart varies by relationship. It’s possible to be a Role Model to some people and a Citizen to others. There are probably a few people at the firm that see the same person as a Brilliant Jerk, and maybe a handful with a dim view that the person’s just Deadweight. Our place in these boxes is not static and depends as much on our effort and actions as they do on the perception of others.

It’s also worth noting that none of these boxes imply seniority. I can think of plenty of junior colleagues that I consider Role Models, and more than once I’ve thought to myself, “I wish I was that good when I was at that stage of my career.”

To expand on the chart above, I’ll offer some high-level thoughts on each of the 4 boxes.

ARole Model is capable of driving great outcomes while being respectful to their colleagues. Even as they deliver impressive results, they solicit and incorporate feedback in the search to continue improving the end product and themselves, and they are generous with their time and energy to ensure the whole team wins. In short, Role Models embody your ideal values, and even in world-class organizations, they are tough gems to find.

Finding one requires a mix of hard work, shared values and goals, and luck (right place, right time). Because Role Models are highly sought after, they know they are valuable and want to ensure they share their hard-fought talents with those who will respect and appreciate what they can bring to the table.

In the same way you’re hoping the Role Model will share their experience with you, they’re doing the same as well, looking for the same characteristics that will make the relationship a great fit. This is true whether they’re more senior or junior. You have to embody their ideal values of a Role Model, too.

Scores high in terms of effort, but is not yet delivering sustainable value. Most people starting their careers fall into this box — inexperienced and in need of training and on-the-job learning opportunities. The Citizen’s key quality is their hunger and ability to learn quickly. Having a great attitude and being receptive to feedback can make up for a lot of missing experience. It’s much easier and more pleasant to work with people who don’t carry an ego and aren’t stuck in their ways.

However, Citizens must be held accountable to results, too. The trick is finding the right balance of providing guidance and structure so they hit important milestones while also giving them the freedom to manage their own time, priorities, and development. I find it helpful to communicate with Citizens frequently, without micromanaging them, to ensure alignment on expectations and to track progress together.

Most Citizens, when properly challenged and managed, will earn their way into the top right box. There are unfortunate cases, however, when a Citizen is unable to make the cut. Despite their earnest efforts, a tiny minority may not produce outcomes at a level needed to support the business. I believe an effort should be made to help these Citizens find a good exit, which can include helping them find another career with hopefully better long-term fit, a positive reference, and severance. Reed Hastings, CEO of Netflix, noted the same in his fairly famous presentation on culture (see slide 22, shown below).

Excerpt from presentation on company culture by Reed Hastings (Source: Netflix)

While his position will strike most people as tough, I’ve seen that high-performing companies tend to be both careful and decisive when it comes to managing their talent bench (slide 38 emphasizes this point as well).

One of the more dangerous types to meet in the workplace. As the name suggests, Brilliant Jerks are sharp, smart, and often fast risers in their profession. They are respected for their track record. However, the Brilliant Jerk is ultimately not a great person to work for or manage, and will eventually present a problem if the company culture is not strong enough to re-shape or address their behavior.

It can be difficult at first to separate The Brilliant Jerk from The Role Model because they often look the same on the surface. It’s easy for a Brilliant Jerk to play the part of a genial team player when the stakes are low. Similarly, Role Models will be put in tough positions where they must take a stand, even if it rubs others in the wrong way. It takes time and usually a high-pressure event to weather away the veneer and reveal the true nature of the person within.

When a big outcome is on the line, stress levels are high, and there’s risk involved, who will really have your back? Who will stand up for you and put their credibility and capital on the line? Of course, you must earn that right by doing great work in the past and building up a reserve of goodwill, but once you have, will they reciprocate and do right by you as well?

Relationships are a two-way street, and while there will be times you feel you are contributing more than you are giving, the opposite should occur during crucial times in your career. When you work for a Brilliant Jerk, you end up feeling used.

This leads to erosion in the cohesive bonds that require a company to work effectively. The most talented employees always know they have options and will pursue them when they feel they’ve been treated unfairly, leaving a company with a shrinking number of high-performing workers. Hiring and retaining Brilliant Jerks may boost short-term results, but will hurt the culture and long-term stability of the firm.

While Netflix doesn’t go so far as to say, “Don’t be a jerk,” one of their core values is “Selflessness.” (Source: Netflix)

Like I said earlier, if you work at the right firms, the hallways and meeting rooms are teeming with smart, talented people. I’ve been fortunate in my career that I’ve rarely met Deadweight. They are incapable and, worse yet, show no interest in improving. If you ever hear someone say, “I don’t think I can learn how to do that,” when it’s a core function of their job, you have probably just met a card-carrying member of The Deadweight.

I always get worried whenever I meet too many people who are Deadweight in an organization. They are a drain on the company and major source of frustration for more capable, motivated employees. It’s even worse when they are promoted, which I’ve seen happen firsthand. It indicates that management lacks good judgment. Deadweight can only be allowed to continue or succeed because the leadership within the organization tolerates or promotes a set of values that deviates from merit. Tenure is an oft-cited reason for promotion, and while I appreciate people who have stuck with a company for a very long time, that needs to be paired with a known history of accomplishment.


Case in point

To bring these concepts to life, I’ll share two experiences I had while managing more junior colleagues. The first was a failure from earlier in my career, and the second a more recent success.

Early in my career I had the opportunity to manage a consulting team. The first step was to recruit talent to help me with a high priority project for a senior client. One consultant, Bob (not his real name), had come highly recommended by another manager. Bob was very knowledgeable about the subject matter, even though he was not used to working with senior executives or handling big picture strategy assignments.

Thinking I had a rock star on my hands, I sought ways to partner up with Bob beyond the immediate work, offering development opportunities such as greater exposure and interactions with senior clients and independently leading up his own piece of the project work. After a couple of weeks, I realized he was not performing at the level I expected, and learned that while he did a great job on prior assignments, those were typically more limited in scope and impact. There was also growing friction as Bob increasingly thought of himself as a manager, too, and did not feel the need to coordinate his work with the rest of the team.

When I made an earnest effort to deliver feedback, Bob pushed back and resisted any subsequent attempts to coach his performance. I made the mistake of trying to mentor someone who didn’t see me as one. We didn’t share the same values, he wasn’t interested in learning (at least not from me), and my attempts to have a meaningful dialogue felt more like debates. Despite good intentions, it only led to tension and heartache for both of us.

Things came to a head when Bob tried to work with the senior client directly, cutting out the rest of the team. This led to an uncomfortable series of meetings, first with the client’s senior executives questioning if we had our team under control, and then with the project team explaining to internal management that it’d be best if we finished our work without Bob.

Even though the project was a success, I paid a terrible price. I had to work harder to cover the gap in our team, a number of colleagues thought I had treated Bob unfairly (a Role Model in their eyes), and it added tension to a new client relationship that required a lot of effort to recover.

A few years later while working on one of the biggest cases of my career, I met another colleague, Mike, quite randomly. He was already on the case before I joined and had a minor role as a subject matter expert, but was not intended to be a day-to-day member of the team. Unlike Bob, no one I knew vouched for Mike because no one seemed to know him, and he wasn’t part of our consulting staff. Experts like Mike were considered a shared resource meant to support multiple cases remotely. Their involvement was often limited to the occasional phone call and light follow-up work. Mike had never been a consultant before, lacked the traditional consulting skill set, and did not have a background typical of most colleagues (e.g., no Ivy League pedigree).

However, Mike punched well above his weight. In the first week after only a couple phone calls, he proved he could work hard, produce great work, had a keen intuition for a client’s needs, and was open to feedback. The regular consulting team I had with me was running hot (working 100+ hour weeks), and we could’ve used another pair of safe hands to alleviate the workload. I made the call to pull him on as more than just a remote guru and flew him in to work side-by-side with us as part of the full team. In short, he was incredible.

When I step back to think about what made the partnership work between Mike and the rest of the team, it wasn’t just his knowledge or ability to execute. (In fact, there were a lot of areas where he could improve the end product.) What made Mike stand out was his lack of ego. He seemed happy just having the opportunity to do interesting, tough work. He never complained and always sought ways to add value to the team. Even when I advocated a position he disagreed with, he was respectful about his alternate viewpoint, articulated dispassionately his reasons for pursuing a different path, and kept an open mind. In a stressful, fast-paced environment, that kind of easygoing attitude made life easier for everyone.

In return, I’ve tried to be thoughtful about ways I can help further his career, and I’ve gone to bat for him in the past and will continue to do so. I’ve found his perspective and knowledge to be a meaningful contribution to my own. I’m happy we had the opportunity to work with one another because it helped me uncover a Role Model.

There are many days I remind myself to emulate the same attitude and behaviors Mike did when asked to leave his home, fly into a 100 hour a week shitshow, and hit the ground running. Even if Mike technically reported into me, that right there is a Role Model worth looking up to.


A moment for introspection

Hopefully, the framework and examples I provided offer a useful way to think about how to manage personalities and capabilities across both dimensions, both to maximize the performance of the teams you work with and to be cognizant of your own preferences and habits.

I don’t religiously follow this framework because each individual and situation has its own nuances. It took me a long time to realize that I am or have been in all of the boxes at different points in my career and to different people. Chances are you have been, too. Different people will frame your performance and behaviors differently, and it’s always subject to change depending on new circumstances as you grow your career. It’s dynamic, not static.

Likewise, the same person will often behave differently given the other personalities in the room, the specific situation or task at hand, and the amount of stress or pressure they are feeling from competing professional and personal demands. It is hard to be on your A-game all the time, and character is a skill that requires development. The same way students improve their math skills by crunching numbers, I try to reflect on lessons learned or how a certain situation could have been handled better and further my maturity in and out of the office.

I’m still learning every day, and the more often I can find myself in the top right corner — as a role model to more people in more situations — the happier I’ll be with my career.


A special thanks to the excellent Ada Chen Rekhi for providing helpful reactions and insights — you can read her great work at adachen.com — and to Mike Heywood for his review and blessing to be a part of the story.

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