Square Pegs and Round Holes

You may have heard the expression of “square peg in a round hole.” It’s a metaphor I’ve thought a lot  for my own career and I think it’s an appropriate for how some people feel within the confines of a large organization when they don’t exactly fit the mold of everyone else.

Large organizations introduce structure, process, and controls to effectively and efficiently manage at scale. Without these things, there would be chaos. Bureaucracy tends to get a pejorative connotation, but in this case it can be helpful when you have to manage 100,000 employees across multiple continents. It becomes even more important when you introduce things like government regulations, shareholders, and laws.

This is important and necessary from an organizational perspective. If square pegs are in square holes and round pegs are in round holes, an organization can march forward and efficiently achieve goals. However, it doesn’t always bode well for an individual employee.


For the majority of employees, being put into a group, department, team, or function and given guidance on competencies, promotion paths, and career guidance  is all well and good, but for those people who feel like square pegs in round holes, who don’t fit the mold, or just enjoy going off the beaten path, it can be pretty frustrating and stifling.

You may not want that career path. You may not feel like the skills/competencies you’re being told you need to have match up with you. This can be frustrating  and hinder your engagement and ability to do your job. So if you are a square peg in a round hole, what can you do?

First, you can find a new job, whether that’s in your organization or at another organization. That’s an easy fix. As a self-proclaimed square peg in round hole, I’ve managed to stay and succeed in the same large organization for my entire career, and have learned a few things that I’ve found helpful to my progress:


Understand your strengths and weaknesses – To thrive in any organization, you need to add value and make an impact. In order for you to do that, you need to have a sense of self-awareness of why you are a valuable employee. Getting a hold of both your strengths and weaknesses is the first step, and is necessary to identifying a non-traditional path. Understanding your weaknesses will identify the spots you are not adding value in while identifying strengths will help you build your business case for why you are still valuable to the team despite your weaknesses. If you can confidently answer questions like “what are you strengths?” and “What unique value do you add to the team?” you are on the right track.


Identify what’s measured, and do just enough – Even though you feel different and probably are different, you are still going to be measured and evaluated like everyone else. As such, you need to understand what’s being evaluated, (ex: skills, competencies, metrics) and do just enough of it. It may not be fun, it may not be interesting, but if you want to eventually start doing things that you like to do, it’s the baseline you need to start from. The goal here is to when evaluated, show that you understand what’s expected of you, and that you are capable of doing it at a adequate level, but where you really shine, is in another area. You need the basics first.


Intimately know the business, and what you can contribute to it – To thrive in an organization regardless of your role, you need to use your strengths and skills to drive impact to the business. This is even more important if you plan on going off the beaten path, because what you are doing will inherently be different than what your peers are doing.

The best way to figure out how to drive impact is to understand how the business itself works and then to use the strengths to find ways to impact it using you skills. Essentially, you are saying, “yes, what I am doing is different, but I’m contributing positively at the same level as my peers if not at a greater level.” Your ability to demonstrate this and execute this is what is going to help you thrive, and it starts with truly understanding the business.

Stay one step ahead – In addition to using those strengths to impact the business, you will also need to continue to find ways to find new ways to impact the business. Since you’re going naturally going to stand out for doing something different, it can be easy for others to question why you are on a different path, or try to knock you off the path. But if you’re constantly adding value, and finding even more ways to add value, you are going to not only strengthen the business case for what you are doing, but also develop your reputation.

Align with Leaders who have influence – If you want to survive as  square peg in a round hole, you are going to need more than your own skills and reputation, you’re also going to need some support and help, especially from leaders who have influence. Unless you have a significant amount of power and influence, you are going to need the support of others, especially leaders, to thrive. Peter Drucker famously said that “what gets measured gets managed,” and that adage still holds true. Knowing this, its important to find leaders who control what gets measured, as they can help be the ones who can give you the aircover, support, and opportunities to leverage your skillsets in unique ways.

At a base level, this means identifying and building relationships with senior leaders. It’s more than just setting up a coffee chat, or an occasional email check in here and there, but instead, finding ways to build a meaningful relationship to the point where they want to use their position and influence to help you thrive in the organization.

Being a square peg in a round hole in a large organization is not meant for everyone. However, if you feel it is meant for you, it truly can be an exciting and fulfilling experience. As someone who has done this throughout their entire working career I have been able to work on projects that I never would have gotten had I gone on the traditional path. I’ve had the chance to help my company innovate and enter into new markets and businesses.  I’ve been able to work with some of the most senior leaders of our organization up to the CEO and Board, and to work with people who truly value my skillset and strength and go out of their way to put me in positions where I can unleash it. Above all,  I’ve gotten an incredible amount of fulfillment and engagement out of being able to make an impact at scale to my colleagues, my clients, and the organization.

On the downside, I’ve had to invest a significant amount of extra effort in building the right relationships to build credibility and influence in the organization. I’ve had to endure many conversations with leaders who have encouraged me to stick to the traditional path. Each year, I have to do a ton of extra work behind the scenes to make sure that the right people stick up for me in performance reviews so I get acknowledged for the work I do.  And internally, I have battled with my own insecurities about wondering if I’m “just as good” as my peers, and questioning if what I am doing is truly worth it. This causes extra stress and concern. There are times when I tell myself that I’d be less stressed and better off if I just stayed the course, and there are times when I wonder if I’ll have a future at the firm, which certainly weigh against the benefits.

I’m a true believer in that people who are successful are the ones who understand their strengths and find opportunities to put them to use. I’ve come to the conclusion that being a square peg in a round hole enables me to do this, and despite the challenges feel truly privileged and have gained so much from the opportunities I’ve been given, and if at some point I think otherwise, I know I can change direction.

If being a square peg in a round hole is the path that’s meant for you, these techniques can help you find ways to thrive in your organization. If you’re currently a square peg in a round hole at your organization I’d love to hear what you are doing in order to succeed.

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