Why You Hate Sales and How to Love It Again


“Perhaps the next step for sales [I wish I could offer more wisdom on] is to change the perception of sales people back to a positive one.” – final words of The Sales Acceleration Formula by Mark Roberge SVP of Sales (grew sales from $0 to $100M at Hubspot) (paraphrased)



I recently had a conversation with one of my friends who runs the largest sales meetup group in the world. First of all, you need to be pretty passionate about sales to start something like that, especially since an organization like that is about knowledge over making money. He told me how he got into running the group, and mentioned that he took a completely different direction in his life after being a burnt-out account executive. He actually got two masters degrees in marketing and then realized, after years of education (to further himself from it), he wanted to get back into sales, and not only sales, but start a meetup for it. Perhaps his time away gave him appreciation for it.

I had a similar trajectory. I did sales for some amazing companies, got burnt out, did some other stuff to distance myself, only to return to it and appreciate it even more. Not only that, I’ve now read numerous books on it, I sell sales software to sales people and I’m enthusiastic about helping my customers and LinkedIn connections get better at it with my sappy essays like this…. how meta.

Yep, I’m a teacher’s pet of sales, and I’m even a vegan. So is Tony Robbins. Yikes. Pathetic. Anyways, the key takeaway here is how can you get jazzed about sales? Do you need time apart from it? After all, it’s a grind, isn’t it? After all, people reject you daily, don’t they? After all, your friends, family and the world looks at you as a greasy, chauvinistic, careless, cacophonous, cash-crazed chimpanzee, don’t they?

Well, sure – if that’s what you choose to believe.

But I don’t believe that anymore, and voila, it’s no longer a grind. I don’t get rejected (not harshly or ineffectively at least), I have friends who think I’m somewhat cool and I even appear to have an education! (did you see those mad alliteration skills above, yo?!)

So what’s the problem? Did I discover the key? Possibly. In my opinion, to love sales again, and for the long run, there’s some deep sh*t you need to take care of, and it’s going to take going against the grain. At first it might feel like taking the red pill. Trust me, do this – if you really want to crush it.

Let’s discuss some steps you can take to make you love sales again and get money. These have worked for my and many others. They’re a more predictable path than random career explorations and chance. Let’s do this.

Stop seeking money, start seeking knowledge

Taking the student mentality instead of a desperate ‘how can I hit this month’s quota’ mentality will instantly put you into a state of excitement and relaxation. You’ll look at sending cold emails as “how can I send an email that makes prospects love me”, rather than “how many emails can I send to get a buck or two”. You’ll look at goals as challenges and a code to be cracked, rather than an fear-based stressful act of valor. You might even find that you give yourself a proper education, in sales, and you can then tell others how to do it, aka be a boss! Sales, in fact is both an art and a science. Another aspect of this is what’s called the scarcity vs abundance (attraction) mentality. Which one do you think is better to subscribe to when it comes to happiness and success in sales and other areas of life?


Stop drinking Red Bull, start eating Kale

What you put in your body is directly correlated to how much you value your own quality of life, and even your long term sales productivity. Whoa Cole, not that, ‘ol hippy sh*t again! Ok, it’s not just kale. Yes, there is a perception that sales folks drink Red Bull, excessive alcohol, and stay out late. Maybe you do, and I realize it has a place and a time (I was in a frat). The problem is, as you get into the real world, what you put in your body is now matters and correlates to the vibe you put out there, how people (your boss, your customers and your friends) perceive you and decide to be influenced by you. The best sales folks I’ve seen, are pro’s at influencing people. They are role models from the inside out.

Those who go far think about hitting their quota holistically.

Get proper sleep, eat a balanced diet, exercise and make your body happy. It will lead to more energy and a better vibe for everyone around you. You’ll feel like the world is your oyster, instead of the world is against you.. Stop with the short term caffeine gain from a Red-Bull and opt for a workout, good sleep and a salad instead. Start the good feelings internally and you’ll be nice to deal with and you’ll sell more. It’s a long term game, but it’s worth it.


Stop putting yourself first, start putting others first

This is the most repeated concept in the most famous book on networking. Not only that, but in a recent sales mentor meeting I had, I was told…

“The only person who cares about you over themselves is your mother, maybe.”

“Sales people talk to customers as if their customers care more about the sales person than themselves.” (This couldn’t be more wrong!)

(He’s the top 5 Angel investor and advisor in Silicon valley, btw)

At LeadIQ, we do a quarterly webinar and event called RateMyPitch. We read hundreds of cold email pitches from sales folks around the world. The top issue with the wording is that it’s, well, a pitch. Most sales folks communicate in a way that says “ME ME ME” (self-serving, asking for something, pitching), when in fact, it should be “YOU YOU YOU” (serving the prospect, adding value).

The good part about thinking along the lines of adding value, is it forces you to think of ways to help someone, even for free, up front. One unforeseen benefit is that you’ll start to feel happier. Yes, at first you might feel like it’s a waste of time, but trust me, karma is real. It will begin to result in higher response rates, more conversations, more trust with prospects and more closed won deals.

Send a prospect a $20 gift that relates to their interests on LinkedIn. That $20 could turn into a $20K deal. Worth it? Hey, if $20 breaks the bank, how about an email that simply shares an article that might help them be better at their job without asking for a meeting.

Also, how about using this method internally? Next meeting you have with your boss, talk about how you helped someone else hit quota, or discovered a new email template format that could help the team increase their cold email outreach response rates. Chances are your boss will like you for more than just being a quota robot. Wouldn’t that be nice for a change?

Do this type of action with this mindset on 30 prospects. See what happens.

In order to be great at sales, you need to fall in love with it as a discipline and profession, just like learning a musical instrument. Treat it like a skill to master over the years, with every discovery call and demo as a rehearsal of you singing a cooler and cooler song that gets you more fans. Take care of your body and lifestyle on the inside, so you’re happy and please people on the outside because you’re glowing with good energy. Finally, focus on giving value upfront and treat people like your family. im to truly want to help them, evenif you don’t end up selling them something.

Yes, there are tactics and books you can read to better yourself in certain situations, just like there are tactics and books to pick up women and men. Working on deeper issues like those listed above are going to lead to not only better sales and dating, but a more fulfilled career and life.

This will set the groundwork to become passionate about sales unto itself, and you’ll notice you win more. While it may seem like it at first, it’s not really that hard, and it’s not going to take more time out of your day. It’s just a different mentality. I recognize this isn’t easy, or your boss might think it’s bullsh*t, and such change won’t happen overnight. I also recognize that these are pretty touchy-feely philosophies, but they’ve worked for me and many others. If enough of us subscribe to this, maybe people will consider sales to be a respected profession one day, even though it technically already is, because everyone is doing it, all the time, as much as we don’t want to admit it. If we all work on loving our sales career, other people will love it too. Let’s make sales great again.

I hope this was helpful. What helps you love sales more?