Learning how to Pivot

What are the skills you need to be successful in your career? It’s a common question I hear, whether it’s at recruiting events, working with clients, or simply talking with friends. While there are skills that most would agree are important such as hard work, subject matter knowledge, leadership and communication, one that is overlooked but important is a diverse set of skills and experiences attained throughout your professional career.

A few months ago, LinkedIn released research after analyzing it’s database of members on what where common characteristics of people who made it to the C-Suite. One of their conclusions was that the people who made it to the C-suite demonstrated a broad and diverse range of skills and experiences as opposed to a narrow and focused view:

“To get a job as a top executive, new evidence shows, it helps greatly to have experience in as many of a business’s functional areas as possible. A person who burrows down for years in, say, the finance department stands less of a chance of reaching a top executive job than a corporate finance specialist who has also spent time in, say, marketing. Or engineering. Or both of those, plus others.’

The pace of change and innovation is moving at a breakneck speed. To keep up or stay ahead, you need to identify opportunities, learn new skills, and take action before you get left behind. While it seems overwhelming, there’s a path forward, and by using a career pivot, you can do all these things.

This idea of the Pivot comes from Jenny Blake, author of the book Pivot: The Only Move that Matters is your next one. According to Jenny, a Pivot is “a methodical shift in a new, related direction based on a foundation of your strengths and what is already working.”

Here’s a quick rundown of the Pivot Framework:

Stage 1: Plant – Double-down on existing strengths, interests, and experiences What are you currently enjoying most? What is working best? What is success one year from now?

Stage 2: Scan – Find new opportunities and identify skills to develop without falling prey to analysis-paralysis and compare-and-despair  Who do you admire? Who can you talk to? What new skills interest you?

Stage 3: Pilot – Run small experiments to determine next steps – What experiments could you run in the next month? What about next 6 months?

Stage 4: Launch – Take smart risks to launch with confidence in a new direction

As business and society continues to evolve, one thing that is becoming clear is that the only constant will be change itself. Jenny’s Pivot strategy is a great asset for helping people get comfortable with the idea of constantly changing and evolving and provides a framework for how to think through a change and then get started.

While some of our pivots will mean moving from one job to another, or from one function to another, not all will. In my career I’ve already made a number of pivots and I’ve only worked for one company throughout my entire 20’s. Even if you are progressing at a healthy pace and content with your job the Pivot Framework is important as it can help you identify and vet potential opportunities that can lead to additional growth and development. As the pace of change in business and society evolves and accelerates, pivots will ensure you have the learning, skills and experiences to keep up or even be one step ahead.

For many of us, we don’t know what we’ll be doing in 5-10  years, and given how different the Future of Work could look it’s probably tough to predict what we will be doing. However, utilizing the Pivot Framework can help us make the decisions along the way to identify and move into new opportunities that use our strengths, help us develop new skills, and find meaning and opportunities in the work we do.

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.