The #1 productivity hack every Customer Success Manager should follow

Sunday funday! I definitely love my Sundays but I also get some anxiety knowing how much I need to get done in the upcoming week. The best advice I received from one of my mentors, Paul Teshima, on how to be more productive and reduce my anxiety was to perform what he called “Sunday Night Prep”. There are various approaches to this. I’ll outline what I’ve done as a Customer Success Manager and I hope you add to the conversation as well. This one hack will prepare you to do battle with your customers and make the best use of your time.

The three components of Sunday Night Prep: Reflect, Prep and Monitor (RPM)

There are lots of ways to be more productive at work but nothing and I mean nothing will assist you more than the conducting a Sunday Night Prep to ensure you are spending your time in the most optimal way. There are three parts to this: Reflect, Prep and Monitor (RPM). I will break these down in greater detail. I usually take an hour of my Sunday afternoon or evening and follow these steps as part of my Sunday Night Prep:

I. REFLECT on what you accomplished versus what you expected to accomplish

Review your task/project management tool and ask yourself these questions:

  • Which planned tasks/projects didn’t get done this past week? Why didn’t they get done? Are you taking in too much? What are the hold ups? what needs to happen to get them unstuck? Do you need to meet with anyone to get these tasks done? Do they still need to be done? Consider using Stephen Covey’s Urgent Important Matrix.
  • If you have a defined goal plan (such as OKRs), review and track your progress. Determine what you want to accomplish in the next few weeks.
  • From the book “The One Thing”, I recommend determining what is the one thing that you need to accomplish. This is defined as “the one thing you can do such that by doing it everything else would be easier or unnecessary”. In the world of Customer Success, you can change this slightly to include, which task/project should I work on that will have the biggest impact to our business or such that by not doing it may lead to significant churn. This may not be easy to answer so consider reviewing it with your manager during your 1:1.

Once you’ve determined which outstanding tasks/projects/goals that need to be worked on, schedule time in your calendar to get theses tasks done, choose the stakeholders you need to meet with, and update your task/project tool with the revised due date(s).This will assist you as you move to the prep section and review your scheduled meetings.

II. PREP for your upcoming meetings for the next two weeks

Review your calendar and ask yourself these questions:

  • Are all of these scheduled meetings necessary? Are there some that you don’t need to attend or can cancel? Is anyone that is key to the meeting away? Can you reduce the time of the meeting?
  • Is the meeting frequency correct? If you have a weekly or bi-weekly customer meeting, would it make sense to change that? For example, it may make more sense to meet with your clients monthly once they have been onboarded.
  • Do you have agendas for all of the meetings? You can always update the meeting invite with a tentative agenda and confirm it with the attendees closer to the meeting. Bonus: You may also realize that the meeting isn’t needed.
  • What is needed to make these meetings successful? Do the other people need to prep for the meeting? What information do you need? What information do they need to make it a successful meeting?
  • Which meetings are missing from your calendar? Is there a client you should be meeting with or someone internally you need to meet with based on what you gathered from your reflection time? Do you have time blocked or meetings setup that will help you tackle your “one thing”?
  • For Customer Success leaders: what’s your upcoming mix of meetings: internal vs external, within your team vs cross-functional, regular vs strategic (based on your goals). As an added tip, I like to colour code my meeting types so at a glance I can determine where I will be spending the majority of my time that week.

Once you’ve completed this review, update your calendar appropriately, schedule the meetings that you need to and complete the necessary meeting preparation.

III. MONITOR reports and tools that will provide you with key insights.

Here are some sample of questions that you may need to answer based on the definition of your Customer Success role. You may need to review data and insights from your CRM, Support, Project Management, BI, Marketing Automation, Learning Management and/or Customer Success Tools:

  • Which customers are coming up for renewal? What is being done to secure the renewal?
  • Which customers have an upsell/expansion opportunity? What is being done to move this forward?
  • Which customers will go live this week? Which are stuck in Onboarding and why? What needs to be done?
  • Which customers have you not engaged with recently? Who will you reach out to this week?
  • Based on your established customer lifecycle, which client milestones are coming up? For example, who do you need to schedule a Quarterly Business Review with?
  • Which customers are in poor health? What is the root cause and is there a plan to get them back on track? What help do you need?
  • Is the manual health score up to date and reflective of the current situation? Are the comments about this customer in the CRM up to date?
  • Customer Success Leaders may have more high level reports to review and monitor. For example, how are we trending in terms of days it takes to launch clients? What is the breakdown of churn reasons from the last three months by tiers? Part of your tasks may also include preparing a summary of data for an executive meeting, board review or company communication.

After completing your review of the data and systems you have, you may need to go back to the prep stage and schedule some new meetings. The key takeaway here is that you or your upper management should rarely be surprised regarding a client situation. Monitor the data that you have and plan accordingly. Communicate any issues you uncover and get the help you need.

5 planning tips that you don’t want to forget

Here are a few additional tips that I recommend:

  1. Setup a recurring time in your calendar on Sunday nights/afternoons to do this exercise.
  2. Don’t do this exercise Monday morning. Planning for what you want to accomplish on the morning of won’t get you the results that you want. You need to plan ahead.
  3. If you need to collect information for a meeting, don’t send that email out on the Sunday night and mess up other people’s nights. There are many free tools like Boomerang that will delay the email from going until Monday (unless it’s critical). Don’t be THAT person.
  4. If you’re not prepared for an upcoming meeting, see if you can push it back. Don’t waste people’s time.
  5. Reflection shouldn’t just be a weekly event. It’s something I recommend you do on a daily basis. In addition, your reflection can go well beyond your tasks. You should also reflect on some of your personal development goals. For example, ask yourself what you could have done better the previous week or how you will incorporate a skill that you previously learned into your day to day.

So there you have the key tool that I employ to optimize my time: Reflect, Prep and Monitor (RPM) which is part of my Sunday Night Prep routine. While I prefer to take an hour and do this Sunday night, you can also do this exercise on Friday afternoon. For me, I like to go to sleep on Sunday knowing exactly what I need to get done in the upcoming week. While this exercise appears to be daunting and it may cut into a regular Sunday night Netflix binge spree, it’s easier than you think once you get the hang of it. It’s similar to the prep that people do to ensure that they eat right for the upcoming week. It will pay off in the long run.

As I mentioned earlier, your manager probably doesn’t like surprises. Do the necessary Sunday Night Prep and you will be set for the week and better position yourself to progress in your career.

Let me know if you have any similar approaches to maximizing your time.



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