Trying Easier Instead of Trying Harder



Some of you may already know that I am training for a marathon. I signed up for it in December. I have never run more than 10 miles before. Plus, I hate running.

I bring this up only because in a book on how to run a marathon, I read the following:

“Try easier. It means continuing to put a lot of effort into both the physical and mental training. It means going out to run on the days the schedule calls for even when you don’t feel like it. But trying easier also means adopting an approach to the training that includes keeping things in perspective. It is something you HAVE CHOSEN to do, something you WANT to do.”

The passage ends by stating that trying harder will kill the fun, and when the fun goes, so does the motivation.

We love the story of the hustler. Much like the ballpark hot dog vendor in my previous post, we admire the gumption and competitive spirit and sheer grittiness of the hard worker. In some ways, it is a core American value to glorify the “work hard” mentality. If we just try a little harder, work a little longer and grit our teeth and fight on, then we will win.

There was a time and a place when the try harder approach made sense. The door-to-door salesman. The intrepid entrepreneur in the dawn of the industrial age. The lowly mail clerk striving towards a seat in the boardroom. If you just out worked and out hustled everyone else, you would win. It may take decades, but the vindication and the prize is yours.

That era is dead. The sheer odds are stacked against you. America in the ‘60s is not America in 2016. There is a world of 7 billion people connected globally and they all want a share of that prize. There are systems, agreements and forces at play that have significant consequences in what you do and how you do things. And we are all working from the same 24 hours in the day.

To try harder is to try running faster in the hamster wheel. Many people will not tell you this, however, they think the same playbook that worked in 1983 will work today. This means sales managers tell reps to hit the 100 dials a day. That means using high-pressure, “closing techniques” to get deals signed by the end of a quarter. It means sending more spam emails to more people more regularly. Old-school sales leaders call for “more”, “more”, “more!”

Perhaps instead of more, we should be thinking of better. Rather than focusing on sheer numbers to drive results, we can focus on smarter strategies so we are more effective with the limited hours in our day. I dare to say this, but maybe trying harder simply does not work anymore.

Don’t get me wrong; grit and hustle are incredibly important life traits essential for any sales professional. Sales is a tough job and you need to be mentally strong to overcome the negativity and rejection. It is maddening, however, when I see capable and motivated individuals wasting their energy on activities that are low value, low impact, and light on results. We waste our two most precious assets when we emphasize low-yield activities; human potential and time.


You may get the impression that I think “cold calling” is ineffective or that automated emails are not useful. Those are just channels however and not sales strategies. And like any strategy, you want diversity of activity, data-driven decision making, a results oriented perspective and a culture that supports experimentation and testing assumptions. Cold calling is effective when you coordinate efforts across other channels like social, use highly targeted lists, and incorporate regularly scheduled call coaching sessions. It is not the channel that is broken, it is the approach.

Brute force is a bitch. It lulls us into thinking that things are working when we get a response. But when we get 99 “no” responses and a 1% “success” rate, it is not a wise use of resources. We are just doing what everyone else is doing. Instead of trying harder and doing a lot of things that are minimally effective, we should be “trying easier”.

So what would a “try easier” approach to sales look like? Here are a few thoughts:

  • MOTIVATION: We often neglect to explore the “why” behind what we do. Why are you in sales? What led you to sales? What do you enjoy about sales? How does being a sales professional lead you to your broader life goals? Everything starts with your personal why and at the core of middling results is always a misalignment of activity and goals; a disconnect between behaviors and motivation. So take time to access your personal why, right down the answers, and remind yourself of your why on a daily basis.
  • PERSPECTIVE: Just like the quote from my marathon book, you need to keep things in perspective and internalize the fact that you choose your path. You are the captain of your journey and you have control over your decisions. We often give up that control to our boss or to ‘the company” or to something that is “out there”. That is a false viewpoint and you do have power over what you choose to do, how you do it, and the results you want to achieve. When you own your decisions, your work does not feel like hard drudgery, and you begin to enjoy the freedom of control.
  • QUESTION: If you believe you control your destiny, then you can begin to probe why behind the processes of work. We often do things because that is the way we have always done things. Status quo is comfortable, but it is also poison for organizations. You need to have the boldness to ask the tough questions and have a critical eye to how you do things today. Use meetings to explore alternatives, create mini-experiments to push new approaches, foster a culture of risk-taking and embracing of failure as a means to learning and growth.
  • MEASURE: All superior performance comes from a love of data. Why? Because when we have the data, we can understand where we are, what progress we have made, and how close we are to our goals. But you have to choose the right metrics. Most sales organizations still operate in an activity orientation when you need to have a results orientation. Number of dials does not matter; it’s how many engaged conversations lead to booked appointments. Measure what moves the needle, not the needle itself.
  • GOALS: You cannot know where you are going if you have no destination in mind. Yet that is how sales often operates. You may protest, but revenue attainment is not the goal of sales, it is the result of value creation in the market. Revenue is obviously important, but it is a metric that guides you to your long-term goal. When you set the proper goals (not just quotas), you set the expectation that sales has a higher purpose, which drives strategies and tactics and ultimately lifts motivation.
  • RELAX: This may seem to counteract how sales operate, the mental mindset is important. I wonder if most sales teams would say they are truly having fun. Sure, the tough stretches and lean times are hard, but you need to have the proper mindset to sustain yourself. We neglect the emotional and mental side of sales too frequently. As Mike Sadeghpour says, salespeople are not machines. Do the work, but make sure you are not driving yourself to burnout and that your mindset is positive. Without the right attitude, none of the business acumen, sales mechanics, product knowledge, or hard work will matter.

I want to leave you with one last thought. It is easy to get stuck in a “sales rut”. You know what I mean, and I feel it right now in my marathon training. Like a 15-mile training run, some of our deals feel like a long march through the desert. Sometimes we are just not excited for the day and that is why it is important to step back sometimes, evaluate and shift gears.

At the Boston Enterprise Sales Meetup, we are going to tackle the mental and emotional side of sales in a talk called “Sales Mindset & the Psychology of Performance” on Monday, June 13. Our speaker was captain of a Division I college hockey championship team, a Division I coach, and a long-time sales executive. He understands the mental game better than anyone else. I invite you to join us and hope that this informative talk will get you re-energized, change your mindset and get you focused on “trying easier”.


Reprinted by permission.

Image credit: CC by Peppe702

About the author: Mark Birch

Mark is an early stage technology investor and entrepreneur based in NYC. Through Birch Ventures, he works with a portfolio of early stage B2B SaaS technology startups providing both capital and guidance in the areas of marketing, sales, strategic planning and funding.

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