Should you work harder or smarter in sales?

High sales performance requires a dynamic combination of hard and smart work… Duh. Everyone knows that. Most, however don’t know what that proportion between the two should be. Why do you perform the way you do? Could you improve? If yes, then how? These questions keep popping up whenever I hear this subject discussed. Luckily, I have an answer for this – I know whether you should be working harder, smarter, or both.

Where do you start

There are 4 sales pipeline levers that add up to achieving better sales results. The principles behind those levers are simple, and they lead to a conclusion that is relevant for all salespeople. The more deals you’re able to drive through your pipeline (#), the bigger they are ($), the better the percentage of them you are able to close (%), and the less time it takes to get a customer (T)… the bigger your revenue and your profit.

The “secret” to how you should work lies with four pipeline levers set on a hard vs smart work matrix below. These pipeline levers can all be located in different places on the matrix. Some require more hard work, while others more smart.

The question here is which area should you focus on the most – where do you start?

Hard Work Smart Work Chart

Start from hard work, then benchmark

  • The easiest step to sales success is hard work. So if you’re new to sales, always start by working harder – experience is the only way to get smart in sales.
  • If you already have experience and smarts then you probably have a decent conversion rate. Now, you need to figure out whether you need to go for bigger deals, or get through your deals faster (losing fast is key). If you don’t know which of the two to go for, start by benchmarking against your industry, peers or goals. If in doubt about your conversion, benchmark that as well.

When you go through each of the levers, take a look at whether you’re positioned in a similar spot to your benchmark. Your comparison points should be your team members, your industry and your goals – get their statistics and compare those to yours.

I will now go through all the areas one by one, and jump straight into what’s relevant for you.

More deals = hard work

The first lever you can pull is how many deals you put into the pipeline. A real estate sales manager once asked me for advice on what to do with the weakest salesperson in his team. This was my advice – get him to work harder. The simple truth was that if he was currently adding 2 new deals to his property deals pipeline every day, and the team average was 3 then already after 22 days the salesman was going to have 22 fewer deals than average. All else equal, and you already know who’s going to have a bonus check that’s 50% larger than the weak salesman – all thanks to 1 more deal prospected every single day.

Welder pipeline

There is, of course a drop of smart work involved, especially when it comes to list-making and how to get creative in coming up with prospect ideas. We’ve covered a couple of ways in our blog, and so has the best-selling author Geoffrey James who’s drawn up a few techniques in his article for Inc. Magazine.

Now, the really hard part about increasing the number of new deals is not the increase itself – it’s keeping up the standard. Once you’ve made the jump, you need to persevere and keep to the new number, no matter what. There are no hacks or secret tricks here, since this one’s mostly all about putting in hard work.

Measure the size of your deals – getting bigger deals is hard work mentally

Imagine a scenario where you’re told to go and ask your employer for a salary that is 10 times bigger than currently. So if you’re making 60,000 a year, imagine you have to go and ask for a salary of 600,000 a year. It seems and sounds crazy, but that’s exactly the feeling you get when you’re told to sell twice or three times as much to a customer as you’re currently doing.

We Sell Boxes Billboard

Going after bigger deals requires a shift in your mindset – reaching the understanding that achieving double or triple the sales is even possible is hard work. And it requires, as Hercule Poirot would put it, “exercising your grey cells”. Once you start believing that larger deals are reachable, you can start putting in the smart work – answering the how. Whether it’s upselling, cross-selling, approaching bigger clients or just asking for more money for your product – it only becomes achievable after the shift in your mindset/you’ve realized you can.

Improve the way in which you present the value of your solution, so that your prospects understand what they gain by buying from you. After that, you’ll be able to increase the size of your deals, and close bigger deals.

Neil Patel – the co-founder of Crazy Egg and KissMetrics (i.e. a man who knows a fair bit about closing big deals) wrote a guide containing 5 helpful tips focusing on how part of closing big deals, which is definitely worth a read.

Get your deals flowing faster – hard work with a touch of smart

Getting a deal through your sales pipeline quicker is quite a challenge. It’s even more complicated when you have a lot of deals in your pipeline and they are really big.

It would make a hell of a difference when you close $10,000 worth of deals in 20 days, rather than in 30 days. You’d be able to put through 50% more deals in the same time as the guy with a sales cycle of 30 days.

The objection you often hear is that you shouldn’t rush clients, because you’ll seem aggressive. While I agree that you shouldn’t be aggressive, I do think you should be to-the-point and apply gentle and helpful pressure. It’s important to have the mindset that it’s OK to speed things up. People hate to be sold, but love to buy – Help them pleasantly understand whether they gain value from your solution or not.

Knowing the buying process of your customers will help apply the gentle pressure, as well as get you concrete answers quicker. You either need to keep the deals moving forward or declare them lost, otherwise the opportunity cost – the time you’re not focusing on deals you could actually win – can get very large.

Bullet Train


  • Have you discovered the prospect’s needs?
  • If yes, have you proposed a solution?
  • If yes, stop waiting and get a response (but be nice).


Higher conversion = smart work

Conversion is what exhibits how smart you do your sales work. This applies both to the overall close rate and stage-to-stage conversion rate.

Imagine a situation where you and Ted both close the same number of deals per month, say 6. Now if Ted’s close rate is 12% and and yours is 8%, it means that you have to approach 75 prospects instead of Ted’s 50. This means that you’re doing a lot more work than Ted – simple. To understand if you work hard or smart is to understand at which stage you lose your prospects.

Work Smarter Not Harder

To do this, you need to measure your stage-to-stage conversions. Discovering the differences between you and Ted will uncover areas of improvement. A smart thing to take into account is that you will always lose some deals. In the case above of closing 8%, you anyways lose 92%. It’s better to make sure you lose them early.

So here are the two things you can do to improve your conversion:

  1. Measure your stage-to-stage conversions and compare with colleagues. Learn how those with better metrics achieve their results. In most cases, the successful salespeople lose early and fast – they don’t spend time generating proposals and holding negotiations with deals which eventually end up as “lost” or that have rather small value. Qualification is key.

  2. Read about the ways to convert better – sales literature is extensive and there’s always something good out there to be read.

Improving your conversions and making sure you lose unqualified deals at the right time (read: early on) will make you far more efficient than now, and save you a lot of energy.

Work hard, work smart, profit

Get your four levers in shape and you’ll see an increase in your revenue and profit. It’s as simple (or tough) as that. But the important thing is that it’s achievable for any salesperson willing to put in the work.

As always, leave the comments below or get in touch via twitter.

Image courtesy: Pipedrive and Flickr Creative Commons

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Timo Rein

CEO and Co-Founder of Pipedrive

  • Kamel Touzaline

    Excellent article Timo!
    Can we say that social selling could be used as a leverage to accelerate stage-to-stage-conversions?

  • Thanks, Kamel! 🙂
    I think you can if you can find a way how that context helps you to the next step. Your homework usually gives you much better points to explain why it makes sense for the prospect to explore the opportunity further with you. The other big area is choosing which prospects to start working with, by figuring out who’s your ideal customer, and staying away from approaching everybody. It’s more valuable to find the right prospects than to influence the wrong ones to move forward.

  • Really great blog post. You gave me a lot to think about working in Sales. Thx.

  • Michelle

    Thank you

  • Mark

    Just how many more ways can the same crap be re-written? Folks really must be dolts to think this is some new novel idea. In truth, one can get lucky and inherit a great territory, or have the good luck of going to work for a company that happens to be the latest hot jndustry. Or you have connection through family, or friends, that keep you going. For the rest, it is mostly a turn and burn situation, then look for the next job that gives you a paycheck. It’s who you know, a lot more than what you know. Always has been, always will be.

    • Tim

      I could not disagree with you more. I have previously been through Sandler and Brooks Group sales training (2 of the Top 5 sales training companies in the US) during my 10 year career. They like others before them used old concepts I’m quite sure as a premise for their new version (Carnegie, etc).

      I believe what Timo attempted to do in this post was crystallize these ideas into very simple, detailed points. He was successful.

      While some do gain great territories or have contacts or get lucky…over the long haul that is simply not a formula that puts a person in the top 20% of his profession.

      Is your glass half full or half empty? I hope half full. All the best to you, Mark.

    • Cody

      I have seen the same thing Mark. I know what you are talking about. Sometimes it feels hard to fight for more when others seem to be handed so much, whether its luck or lineage. I believe its really important to work your tail off to break those stereotypes though. You can accept it or you can fix it. Regardless, it will only affect you. Whether the glass is half full or not is only important to the person who has to (or rather- gets to) drink it. I think I am going to try applying these principles, even though I have heard them a thousand times. I think I am going to try and make myself into one of the top 10%. I am starting with no “blessed territory” and the only connections I know are the ones I make. Wish me luck!….. better yet…. Join me! Lets rock it! Lets sell the pants off of every silver spoon out there! 😉

    • Mark, thank you for sharing your point of view! And, you know what – you could be right. If that principle has worked best for you, and helped you improve over time, then who am I to argue with this, right? I can only share observations based on my experience, and that has shown me that who you know is not the only thing that matters. So, I respectfully disagree with you on this :).

      Further on my view – I love to take the approach that you can start anywhere and achieve great results, that you don’t need to have a ‘great territory’, or ‘latest hot company’, or know many important people to begin with. I think that doing the hard and smart work, and learning from it should be given a chance. I’ve seen way too many examples when people without the above mentioned advantages have outsold the ones with them. So, I know, it’s a matter of belief, but I’ve seen this belief materialize in results for so many others. (As for me – if I didn’t have that belief, I would have never been able to co-create Pipedrive :))

      • Rahuel Stone

        Great reply Timo.. Loved the way you asserted your point with total respect.. Yet another trait of a Smart Sales guy !! Cheers …

  • Timo, i see that you sold books with Southwestern. I did 3 years in Education Divison from 82-85. Love Pipedrive. Accept my LinkedIn invitation!

  • Dennise Lannister

    This is great example of hard, but smart work. Because this article is very helpful for the sales professional. I will use this four levers as a pattern on achieving my goals and daily tasks. You don’t just have to work harder, but we also have to work smarter. I will practice this pattern on my daily selling as a sales professional. I have to be more productive. With hard work and being smart, I know I can do that.

    I just joined helps me to know more about sales. Invisume gives detail of what’s best for me, and I have no fear of losing my current job for it gives 100 percent privacy on everything I do. I’m not saying I hate my current job, I love my job but I want to be more connected to leading companies that I never taught was waiting for me, I want to experience more about sales because we all know that experience will help us to be better sales professional. Thanks for this post, this great insight inspires me.

  • alessandra pignotti

    Interesting read. I do believe that a salesperson should both work hard and smart in order to succeed.

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