Square Pegs and Round Holes

During my career, I’ve been fortunate to work at two world-class organizations with thousands of smart, hard-working and driven colleagues. While this has been inspiring and instrumental to my growth, working in a high-performing organization where everyone is accomplish can also feel overwhelming. If you’re anything like me, you may look around at your co-workers and their strengths and accomplishments and feel in awe. You may even feel like you’re a little different, that you don’t quite measure up, or perhaps like a 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 bad rap, and while to an extreme it can be a hindrance it can be helpful when you have to manage hundreds or thousands of 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 who feels like they are out of sync.

For many employees, being put into a group, department, team, or function and given guidance on competencies, promotion paths, and career marching orders 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 frustrating and stifling.

Feeling like this can often breed a sense of imposter syndrome, or just a sense of not feeling like you fit in or belong. Or, it can sometimes pressure you into pursuing a path that you may not want, but you choose to pursue because you feel like you need to “fit in.” You may question why you are here, or if you’re really worth of the title you have, responsibilities your assigned, or achievements/success you’ve gained. This burden can be taxing mentally and emotionally, as you constantly are questioning every step you make, or constantly comparing yourself to others.

So if you feel like you’re a square peg and everyone else is a round peg, what can you do? 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?

As a self-proclaimed square peg in round hole, I’ve felt my fare share of imposter syndrome, and had plenty of doubts about whether or not I was on the right track. Despite this, I’ve been fortunate to have a fulfilling career while being able to pursue opportunities that I not only wanted but were at times off the beaten path and different from what everyone else was doing. During this time, I’ve learned a few things during my journey that have enabled me to chart my own unique journey:

Understand your strengths and weaknesses — First and foremost, it’s acknowledging that all people have strengths and weaknesses. Your goal is to figure out what they are, and how you can use them to drive impact.

Your strengths are a great place to start. By identifying your strengths, and figuring out how to use them at work, you’ll have a better time identifying where you can apply them to drive impact. Understanding your weaknesses will identify the spots that you can work quickly to improve upon and get “good enough” at. Furthermore, if you plan on taking another path that’s different than what everyone else is doing, being able to articulate how you are using your strengths to contribute will help you make your case for things like projects, promotions and assignments.

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, so naturally, people may assume that you’re not following the rules. If you can make a case for how what you really want to do positively impacts the business, you’re going to be more likely to get support to pursue that opportunity.

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.” If you can prove that what you are doing moves the needle for the business, it will greatly strengthen your case to pursue the path you are on.

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 who is similar to you in title, level, at least initially. 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 an adequate level, but where you really shine, is in another area. You need the basics first.

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. It also means making sure that the right people are aware of what you are doing and how it’s contributing to the organization. Whether that means taking the time to identify the decision makers and keeping them in the loop on your work, or working through those leaders you’ve aligned yourself to make sure others know what you are doing, getting the word out there to the key stakeholders will ensure you are properly supported by your organization.

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.

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. Whether it was working with senior leaders on strategic projects, working on innovative/stealth ideas/projects, or simply working on things I was excited about as opposed to what I was “supposed to do” taking ownership of being a square peg in a round hole gave me an incredible amount of fulfillment and engagement in pursuing goals and opportunities that were meant for me.

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’ve had to make put in a lot of extra work during the performance management process 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 big believer that people who are successful are the ones who understand their strengths and find opportunities to put them to use. For me, that’s meant being a square peg in a round hole, and despite the challenges along the way, the feeling of following your own unique path is worth the challenges and struggles.

Leave a Reply

Your email address will not be published. Required fields are marked *