Why you Need to Learn how to Learn

About this time last year, I wrote about how companies like AT&T  are emphasizing the importance of learning on, during and outside the job for their employees as a means to compete in the digital age. They have recognized that the skills needed by the company and its employees to thrive in the future are not there yet today, and in order to compete they must adapt.

In a recent talk to college students at the University of Missouri St. Louis, AT&T CEO Randall Stephenson yet again touted the importance of learning, even urging students to retool and pivot after joining the workforce. He said, “I believe your skill set is two years in duration, max. Mine is two years in duration, max. I’m constantly retooling myself.”


Learning is a topic that is on the rise in the corporate world. According to research published by leading HR Analyst Josh Bersin, learning and development is one of the most important trends facing HR Executives this year. And while many companies are rolling out initiatives, whether it’s through courses like Udemy or in AT&T’s case, partnering with a college, I’m convinced the best results will come when each individual professional takes it upon themselves to identify and develop a learning plan to make sure they maintain and even stay ahead of the curve.

As a consultant, learning is a key driver to my success on the job. We are constantly being placed in new situations, new industries, new functions and new types of business problems that the only way we can adequately advise our clients is by forcing ourselves to learn and evolve our skillset.

Furthermore, as a result of the impact of technology and innovation, our clients are coming to us with problems that are more and more complex, interdisciplinary, and frankly, new and we have to learn in order to stay ahead of the curve to guide them through the process.

As someone who has made a conscious effort to continually learn throughout their career, I want to offer some actionable tips for how you can “learn how to learn” and develop in your career:

Become an Expert – In today’s knowledge economy, knowledge is power. The more knowledge and insight you can provide, the more valuable you can be to your team and organization.

One way to accumulate knowledge in a focused manner is to become an expert. That way, you can be the go-to person on a particular skill, issue, or idea on your team. First, you might already be on the path to becoming an expert based on your existing work experiences, so think about if there is anything you already are an expert in.

Next, a simple “Major/Minor” Framework can help you find other areas to be an expert in. For example, let’s say you work in Marketing, and specifically, within SEO and Blogging. In this example, your Major would be Marketing, and your Minor would be things like SEO, Social Media, blogging, and Google Analytics. From there, you can start building your knowledge in both your major and minor to eventually be seen as the Marketing/SEO/Social Media guru.

Look for the intersection points – Knowing your function or industry is important, but what’s also important is how your function or industry intersects with the broader organization and world. I call this, “playing at the edge.” If you can play at the edge, it forces you to not only understand your specific area of expertise at a deep level, but a few other adjacent areas. By applying your knowledge to other adjacent areas, you can expand your knowledge base but also, understand the bigger picture of how your area of expertise can either be applied to other areas, or how it impacts other areas.

For example, let’s say you work again in Marketing, but begin to study how what you do impacts the Sales team.  If you can understand how your SEO and content empower and drive sales, you can A) play a bigger role in working with the Sales team and B) produce better content for the sales team that helps win customers. This increases your own knowledge of marketing, helps you understand the broader impact of your work, and gives you more opportunities to engage with other areas of the organization, all of which are positive steps for your own career development.

Use Technology – The great thing about the internet is that everything, literally everything is on there. It’s literally never been easier to learn about something by using different digital tools and technologies that are made available. Platforms like Lynda.com, Udemy and Coursera are great resources. As are things like Twitter, blogs, websites and forums like Quora.  If you want to know how about the tools and apps I use to learn on a daily basis check out my post on how I learn to keep up with my job.

Read – The best writers and thinkers are often the best readers. It’s where they generate their ideas and insights. This tactic can work for you, in your quest to learn and develop subject matter knowledge. One way to do this is to configure your information diet. This consists of books, and/or articles on relevant topics and information, and should be consumed on a regular basis.

Talk to Others – Reading and learning on your own is great, but sharing ideas and putting your mind together with other intelligent but diverse groups of people is what will spur ideas and innovation in your head. Take the time to identify other people in your network who share your love of learning and find ways to talk and communicate with them. In some cases, you’ll want to talk about topics that are of importance to you, but in other cases, you may have to talk about topics that are not relevant to you. That’s okay! In fact, that sometimes can be really helpful as it can help you make connections that you would have never come up with if you spoke with someone who was as familiar with the topic as you. The key here is finding people who are as eager to learn and engage as you are.

Earlier this year, LinkedIn studied the career paths of executives in an attempt to identify common characteristics of those 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, or, said another way, those who focused on continuous learning, growth and development were the ones who made it to the top.

It’s been well documented that learning is good for your health. It also might be the thing that saves your career.

Further Reading

Objection Handling your way to success

If you work in sales, you’re probably familiar with the concept of objection handling. Objection handling is a way to prepare and anticipate the concerns or objections of a potential customer, and then to come up with solutions and responses that would address those anticipated concerns.

Its an excellent exercise that salespeople go through to ensure that even if they run into roadblocks with a potential customer (very common) they have the right messaging to help the customer overcome the concerns and buy the product.

In addition to helping salespeople sell, the concept of objection handling can be very useful to all of us non-salespeople in various aspects of our life. If we can anticipate potential concerns of say, our partner or spouse, perhaps we can pick a restaurant to go to that will meet both of our food tastes. Or, if we think about how our boss might be concerned about our decision to shift our priorities to some other projects before we meet with her, we can strengthen our business case to pursue those projects and win her support.


Here are a few use cases where doing an objection handling exercise can help you:

Presenting or Persuading your colleagues – Objection handling is perfect if you  have to make a presentation, sell an idea, or get buy in on a specific approach to a project. By identifying the other key players, thinking about their potential concerns to what you are proposing, and practicing how you’d respond to them you can increase your chances of getting support.

Convincing a recruiter to hire you – Anytime you are applying for a job, you are essentially marketing and selling yourself to a company, so similar to how a sales rep would want to have a customer overcome their concerns about your product, you want the recruiter to overcome their concerns about your product (yourself.) By identifying weakspots on your resume or work experience and highlighting how you would overcome those, you can be sure that you’re prepared for whatever they want to ask you in the interview.

Here’s my approach to practicing objection handling:

Find the holes – Every argument, no matter how strong it is, has some potential holes or concerns. Be objective, and identify what the holes or weak spots in your argument are, and write them down.

Come up with responses and alternatives – Take the list of weaknesses or holes, and develop responses or solutions to how you would either address those holes, or how the weaknesses are actually not as big of a deal as they are made out to be.

Practice – Take the time to say your responses out loud and practice how you would respond if someone were to drill you on those specific questions. If you do this enough, when it comes time to present, you’ll free comfortable with how to respond most of their questions or concerns.

Objection handling is a great way to prepare for potential challenges and pushback in various aspects of our life. You won’t win every time, but using this tactic can help you ensure you make a compelling case for whatever you’re supporting.

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.