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Creating a frictionless sales win habit

If you’re in business, you have to sell your product or service. There’s no two ways about it. It’s pretty much have a sales win or die. And yes, a whole heap of people will have you thinking that it’s all about having a pretty instagram feed, sexy TicTok videos or yelling into the ether-sphere on twitter (Mastodon, Threadz or whatever platform is currently trending). However, I’ve got some bad news for you, if your clients are likely to be other businesses, it’s not. It’s really not.

Don’t get me wrong, I like Insta, LinkedIn, FaceBook etc as much as the next person (although my jury is currently out on Threadz as a Twitter replacement). It’s just that for your average B2B business owner, especially those in professional services or enterprise sales, they don’t deliver too much by way of new business. Which means, you actually need to go hunt your own wins. Sorry. Yep, I’ll be your dream crusher.

Filling your sales pipeline = another sales win

Sales is a numbers thing. More activity, more names in your pipe, more wins. The only way for you to really maintain a level of control over your revenue stream is to fill, and keep filling, your sales pipeline so your prospects routinely become your clients. But as you probably already know, selling is hard (big sigh).

Most of us business owners go into business because we like doing our do, not selling it. Hence it’s easy to get and stay ‘too busy’ to think about filling the pipe. And that’s a recipe for disaster (my own story of what happens when you ‘forget’ to do the work). Sales win or die, remember?

In order for your sales pipeline to work its magic, it needs to be regularly refuelled. Which means, yes, you guessed it, you need to find new people to reach out to and do it regularly enough to feed the pipe.

However, unless you love prospecting and hunting new business, in which case you’re a very rare beast — congratulations, you’ll need to learn the art of setting yourself up for success. Now you might be thinking, “Dang, I thought you were going to tell me about some new whiz bang AI that did it all for me.”? You were? Yeah, sorry about that. B2B businesses are still built by converting one prospect at a time, person to person and AI just can’t do that job well enough at the moment, so it’s going to be up to you for the foreseeable. I did tell you I was a dream crusher.

3 key steps to transform the sales pipeline process for another sales win

Okay, now that we’ve established winning more business is up to you, let’s get into how you move from never doing sales outreach to winning more business and transforming your win rate.

1.Make the activity a game/challenge

Gamify your new business development activities, rather than making it a task to be done or worse, a problem to be fixed. Games are fun and challenges have an energy about them; they propel you forward. Whereas tasks are hard, you already have too many of them and problems are, well, if you’re anything like me, they’re weighty, scary things to be avoided (which I was really good at — avoiding that is — don’t do that either – it ends badly).

2.Build a sales pipeline development habit

Turn your new business efforts into a routine part of your day (rather than when you ‘remember’ — which for me was, well, um, like never — please, I beg you, don’t do that).

Start small. So small it feels easy or silly or like it won’t make much of a difference.

What does small look like? Reaching out to one new person a day. Just one. But if you do it every business day for a month, that will be 20 or so new contacts you’ve added to your pipeline. If you do it for a year, you’ll have around 240 contacts (allowing for weekends, holidays and sick days). If you want smaller, reach out every second day.  But make sure you do something. Something is always better than nothing.

What you’ll find is that over time, you’ll build momentum. The more people you talk to, the more you’ll likely refine your conversations and possibly your product/service. Which of course means your conversion rates will improve. I went from nothing in my pipeline to more than 300 qualified prospects in the pipe in six months. And a full client roster to boot.

Sometimes, it can take a year or more for client to convert and that’s why having a full pipeline is critical in allowing things to take the time they take. It also means that no one potential client is the ‘all important one’ that you’re relying on to make payroll each month. I’ve done that in the past, and trust me, potential clients can smell desperation. The more you put into the pipe (and then stay in touch with — for as long as it takes), the greater the chance of a sales win. You just have to keep going.

3.Reduce the friction in your sales development habit

Sales outreach is hard enough without any added obstacles getting in your way (aka friction). In order to build a habit you can sustain long term, you need to look for ways to reduce the amount of effort required on your part. If you don’t do this step, it all becomes too difficult and it means you’re less likely to do it — ever (yep, been there, done that).

Beware distractions that ‘feel’ like doing the work. Unless you have a very sophisticated sales setup with autodiallers or a suite of admins/VAs doing your research for you, you’ll need to figure out who to reach out to on your own. And if you have to find and then call people, guess what? You’ll likely find five, ten, then 50, 100, then 1000 people who could be good to do business with, do lots of research, read lots of blogs, etc and end up calling/reaching out to no-one. You’ll get lost in the basics. Please don’t do that.

Even if you do actually start calling the first five or ten of a list of 1000, by the time you get even 20% through, much less to the end of the list, the information might be terribly out of date, as happens in uncertain times, and you’ll likely have to start researching again. Cue: the rabbit hole of ‘research’.

Keep things as simple as possible. Create a sales routine and separate your time into activity blocks.

  • Research — I found researching the afternoon prior (3pm), creating a small target list of no more than 10 people kept me focused on the task at hand. It generally takes no more than 30 mins to an hour. Plus, if you’re like me, 3pm can feel a bit sludgy after lunch and you don’t want to be doing ‘critical’ work (like client calls) at that point if you have a choice.
  • Schedule your calls for the morning when you’re fresh — I schedule time for calls with the latest list for the next morning. I do it at 11am — when apparently, according to research, everyone is on their game. No further research happens until I’ve reached out to those on the current list. Likewise, I don’t do follow ups in that time block either.
  • Monotask — When it’s time to do my outreach, I do nothing else in that time block. If I’m struggling that day to smile and dial, I sit and contemplate the calls, not allowing myself to do anything else. Eventually, I would get bored (or annoyed at myself) enough, to get on with it and do what needed to be done. You might try using something like Freedom app to block you from distractions that might get in the way if you’re tempted by fun screen time. As Nike so succinctly put it — Just Do It!

How to make the activity into a game/challenge

There are several ways you can do this.

  • If you like to compete against yourself, and improve on your own personal bests, you can track your progress — doing the previous effort + 1, every so often.
  • If you like to compete with others, find yourself an accountability partner in a different industry, track your outputs and outcomes and challenge each other. You can also pace yourself against a colleague.
  • Or you can make a game out of it like I did. Write yourself a list of sales pipeline building activities, pick one at random at the same time each day, use a random 1–10 number generator to see how many times you need to do the activity and set a timer for one hour and smash out the work.
  • Or you can just buy an existing game and get started.

Now it’s your turn

The trick with any of these is to have everything planned in advance, so you can just do your habit routine when your allotted time block begins. What you want is to be doing activities and recording activity outcomes, not thinking about what you should do and how you should do it. All planning and no action makes for no business wins.

Remember, though, to be kind to yourself as you begin a new routine. If you miss a day or two, don’t beat yourself up. In the grand scheme of things, it’s no great loss. Just get back to doing it as soon as you can. It’s a process that lasts as long as you wish to be in business, so there’s no prizes for getting anywhere first or quickest. Sustainability over the longer term is key.

If you build your pipeline day after day, more new business wins will come.

I wish you well building your business.


Kristin Austin is the creator of 1st in Business Revenue Building Game. And is currently writing an e-book version because it’s much, much easier to ship internationally. You can read more of her journey on

Thanks for reading. 

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