Finding the Right Room: Putting Yourself in an Environment to Learn Good Selling Habits

Many of us have heard variations of the quote:

“If you're the smartest person in the room, you are in the wrong room.”

It intuitively makes sense, yet it is potentially difficult to follow advice. Especially early on in your career, when you are just trying to get into the room to begin with.

Unless you are a 20-something year old with exceptional skills that the market will pay for, initially the goal is to get the best possible job that has a combination of interesting work, good pay, and a nice environment.

As you progress through your 20s and begin gaining technical and soft skills, you begin to realize that not everyone at your company (whether it's a startup or big company) works equally hard or efficiently.

You start to see the high performers separate from the low performers. And those who produce results from those who are all talk, with very little output.

Then, at some point in your mid to late 20s, you may decide to shift companies and pursue a new opportunity. What you will realize then is that the dynamic of high versus low performers persists at other companies, even if the company is just a startup.

The ratio of the people who bring value and contribute to the company’s goals may vary, let’s call it the ratio of high to low performers. And if you aspire to be a high performer, a high ratio of low performers at a company will frustrate you over time.

Because although they make you look really talented and good at your job (because they are not), they will also drag the company down with their inefficiency and inability to do their job as needed. They will create more work for you, because they will not provide you with the support you need to get yours done well.

It will also be a bit frustrating to see that they continue to collect a paycheck with little contribution relative to the value they are bringing.

If you think about it, a company that seeks to become a successful and profitable business (if not now then eventually), must be generating more business value per employee than the average salary per employee.

If this equation is off, and employees cost more than they generate revenue wise, then the company eventually will run out of money and die.

In this way, companies function off of labor cost arbitrage. Generating more value per employee than the salaries paid. So, employees that cost more than the market value they bring only weigh a company, especially a startup, down.

As a seller, you have a lot of control over your destiny at an individual level. How many prospects you reach out to, the quality of your sales conversations, the overall value you bring to potential customers.

However, there are still macro factors that will influence how successful you can be as a seller. You still are at the mercy of the quality of the product you are selling, the positioning of the product that your leadership has developed, abd the product’s ability to serve an existing market need.

This ultimately means that you must also pick an environment to sell in with a strong product, marketing, engineering and overall, leadership team. If you don’t, no matter how good of sales skills you have, or think you have, you will not be able to maximize your potential.

Brandon Fluharty is a previous strategic account executive at LivePerson, and pulled in $1M+ in sales commissions over multiple years in this role.

One of the first tips that he provides on aspiring for $1M / year in commissions is to put yourself in the right environment.

This advice is underrated when you are in your 20s. Sometimes it’s more straightforward and easier to chase flashier things - a high base salary or on-target-earnings (OTE), a sexy new company with cool offices, a hot product riding a technology trend (crypto, anyone?).

But, the reality is that the environment you put yourself in will dictate your success, but it will also build the foundation of the habits and skills that you develop.

In my first sales role, I picked the cool, new product to sell. It was a product in an emerging industry that was beginning to pick up steam. The CEO was inspiring and charismatic and had a small exit under his belt from a previous startup.

The marketing collateral the team was publicly producing looked interesting. The product seemed neat (hint: I didn’t say useful or necessary).

To be fair, I had never held a quota or been a salesperson before, so it’s not like I had a ton of options for sales roles to take. So I took this one.

And over the next 2 years, I learned the fundamentals of software sales, successfully selling over $500K+ of complex software. There are no regrets and it was a fantastic learning experience with the opportunity to work with cool people on fun problems.

Eventually, I ended up moving to a new sales role (my current one), also at a startup, but one that appeared to be intentional with product, marketing and engineering decisions. Ideally, a much better environment had been built as a foundation before I joined as a seller.

Looking back at my first sales role, and now at my 2nd sales role, I’ve realized a few things.

Not being the smartest or best seller in the room now is a very uncomfortable feeling. I have had to start really balancing the anxiety produced as a result by reminding myself to be patient with results, as I am still early on into my new role.

But what I love about the new role is that I am learning a lot and I feel like I am upleveling my sales skills quickly by observing and learning from the other sales reps and managers.

There are already things that I’ve picked up in my first quarter in the new role, where I find myself imagining applying to my last role. If I knew then what I know now, it's possible that different, more positive outcomes could’ve been produced as a result (i.e. selling more deals).

The thing I have to tell myself constantly is that I will be successful, and in the worst case scenario if this new gig doesn’t work out, I have new skill sets I am building that I can carry over to another role.

Looking at this diagram, I was in the comfort zone in my previous role. When I first started my current role I was in the fear zone for a couple of weeks. Now, in my 2nd month, I am in the learning zone. And hopefully within a few more weeks I can progress into the growth zone.

From personal experience, navigating these different zones is an unpleasant experience. Why would anyone leave the comfort zone for the fear zone? Well, if you want to achieve anything extraordinary in life professionally, you will also need to leave your comfort zone eventually.

Be self-aware of available capacity in your personal life, but if you have the space to devote a bit more time to growing professionally, I would highly recommend pushing yourself into the fear (and eventually) the learning zone.

This could be through changing jobs, but it could also be through making smaller changes like taking courses, joining a professional group or even traveling to a conference.

It is worth saying, don’t push yourself out of your comfort zone just for the sake of it. Evaluate if going out of the comfort zone aligns with your goals - personally and/or professionally.

I have made the jump out of my comfort zone too quickly before in starting a small business. And let me tell you, if you are outside of your comfort zone, you will always grow, but if you have not pushed yourself in the direction you want to grow, it will stress you out.

Really think about if the direction you are pushing yourself in will get you closer to your goals. I have jumped out of the comfort zone before, only to realize what I was working on was misaligned with the direction in which I wanted to go.

Even so, I learned a lot, and the only thing I lost was time. But I gained experience and now am self-aware enough to know that being an entrepreneur is really hard. So, if you are still unsure, make the leap. Most decisions in life, especially professional ones can be reversed, just set check-ins with yourself to make sure you are going in the direction you want to.

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