Sales Checklist: 10 Ways to Keep Yourself in Check Each Quarter



Have you ever photocopied a piece of paper so many times that the copies faded and became hard to read? This is called a transcription error, and it happens when little mistakes add up over time to make a big difference. This also happens in sales when you repeat your pitch over and over again until small details get lost, the delivery gets muddied, and your pitch loses its edge and effectiveness.

Once a quarter, it’s important to reset your habits to make sure that you’re not falling victim to this process. Essentially, you need to get back to the basics and start fresh.

A big part of this refresh involves motivating yourself. Do you remember the bright and shiny optimism that you felt when you first started your job? How absolutely certain you were about your product? How you looked up to the more tenured salespeople and picked their brains to find out what they were doing differently? To dial in on this energy, you need to do assess yourself to determine what you’re doing well and poorly.

So use this checklist to see how you stack up. If you start to feel a little inadequate, that’s great! You’ve identified the key areas that you need to work on, and there’s reassurance in knowing exactly what you need to do. And if you’re not selling more than you want to be (who is, really?), then this gives you a clear path forward to start the quarter with a crisp, clean page.


1. Are my goals written down and up-to-date? 
Goals change over time, so it’s a good idea to revisit them. Keeping them consistent is good so you can track your progress, but it’s okay to tweak them occasionally. People learn as they go, and you shouldn’t stick to anything that doesn’t still make sense. Write your goals down, keep them visible, and share them with peers to hold yourself accountable.

Don’t have any goals written down from last quarter? There’s never a better time to start than now.

Sample goals:

  • Achieve a 35% closed-won opportunity conversion by April 1
  • Hit 110% of year-to-date plan by April 1
  • Generate 3 new outbound sales opportunities each month, 9 per quarter this year

2. Am I on-track with my goals? Did I reach them? If not, where can I improve?
Keep yourself honest. Many people set goals, but very few people keep them (just look at gym attendance in January versus February). Make sure your goals are SMART (simple, measurable, attainable, realistic, and time-bound). This is a great article if you’re interested in the specifics on goal setting.


3. Am I following a template for discovery calls, or have I gotten lazy and just started winging it? What about my emails?
This is where those nasty transcription errors start slipping in. I’ve found that over time, I may forget to do basic things like set agendas for my discovery calls, and then run into issues where we don’t cover the right topics in order (or at all). If your company doesn’t have a defined template, try your hand at making one. Consolidating your tried-and-true best practices into a template can be a great team exercise.

4. Did I refresh my prospecting emails and content links?
The content that you share with your prospects can become stale, and links can get broken or outdated. Make sure that you’re not sending around any whitepapers from 2011 or videos that don’t work. This is a great time to check-in with the marketing team to see what new and exciting content you can share.

5. Am I still looking for leads in the same places?
It might just be part of the nature of being a salesperson, but there’s a certain sense of fear that comes over you when you feel like you’ve run out of leads. Either you’re account-based and telling your boss “I need the Glengarry leads!” or you’re territory-based and you’re convinced that you’ve already sold to every single company in the state of New Jersey. Whether you’re a small start-up or large enterprise, you’re probably wrong. The total addressable market of territories—even mid-sized companies—is tens of thousands of leads. What’s really happened is that you’ve “photocopied” the same prospecting idea so many times that it’s become a blank piece of paper. So get a new piece of paper!

Refresh your approach by having someone else take a look at what you’ve done and poke holes in it. Have you tried looking at the competitors of companies you’ve sold to? Have you tried looking at companies that your current customers have previously worked for? I promise you, the issue is not in the number of leads available, but your mindset. If you are able to shift it, you’ll magically start seeing new lists and thinking up new sources.

Here’s a good exercise to help you find your focus:
List off all of the deals that you won in the last quarter. Did the majority of your deals come from one vertical, region, or account? If there’s a noticeable trend, prioritize your efforts in the new quarter on that. And don’t forget to ask your now happy customers for referrals!

6. Am I utilizing all of my tools?
Are you utilizing all of your sales channels or have you defaulted to just sending emails when you could be calling? If it’s the latter, create a goal for yourself to rectify that. A successful rep uses every available channel, so optimize your outbound prospecting strategy.

Don’t forget about the tools that your company provides that you may not be taking advantage of. Some examples include data sources, partner co-selling, and email marketing tools. If none of these exist, be an innovator and start doing your own. Find a list of partners and start building a relationship with them to see if you can pass each other leads or help each other close deals.

And there are personal skills and tools—what about your company’s learning-reimbursement program? Most companies will pay you to take classes in related areas that can either deepen your current skills or prepare you for your next role.

Sales Skills

7. Am I selling to the best of my ability?
Your selling skill is another place where transcription errors come into play, so have your colleagues listen to one of your cold calls and provide honest feedback. As salespeople, we may stop doing things by the book over time, including important parts of a call like up-front contracts, agendas, and staying on client’s calendars. Identify which fundamentals you need to touch up on, and nothing helps you do this faster than an impartial outside perspective.

If you’re truly interested in improving, show your colleagues your worst calls. Don’t be shy, your colleagues feedback can only help you and will encourage a supportive relationship. Only sharing the best ones is like inviting guests in through the back door because the front of the house is on fire.

8. What are the top skills that I need to work on?
As a salesperson, you’re probably well aware of your strengths and use these to your advantage whenever you can. But it’s just as important to identify your weaknesses and improve on them so that you can truly become invincible.

To identify the skills you need to work on, draw a table with two columns like I’ve done for myself below. In the left column, list off all of your lost opportunities, and then in the right column, list all of the reasons why they didn’t close. Which ones occurred the most?

Figure A

Other examples:

  • Not qualified properly
  • Didn’t build a relationship
  • Competitor told a better story
  • Pricing

Next to each reason, list the frequency, and then come up with ways to improve.

Figure B

Team Building

9. Did I make time for my team outside of work?
Team building is crucial to building and developing relationships with your peers, but when things get busy, group activities are typically the first thing on the chopping block. Change this by getting lunch with your team and making time outside of work to catch up with them. Strong team ties can help you close deals.

10. Did I get to know people outside of my department?
It’s extremely important for your success in sales to be aligned with departments beyond your own; you never know when you’re going to have to approach engineering or support with a question. By building these relationships early, you can avoid bothering them at the eleventh hour of your deal cycle when you’re completely frantic and begging for help.

Tackle all of these one-by-one to set yourself up for a fantastic quarter. Remember, no matter how good of a salesperson you are, all skills are perishable and fade over time. If you’ve just been photocopying the same pitch over and over for too many months now, it’s guaranteed to missing some key details. Do yourself a favor and turn over a new page. ­

What other things should be on this checklist? Let me know in the comments below!