10 Mid-Year Tips for CSMs to Stay on Track

Mid-year is a great time to take a step back and take stock of your world. Don't wait for the next review with your company or the next QBR. Invest some time now before you get caught up in the end of the year pressures.

Here are ten practical steps you can take with minimal time and maximum benefit.

1. Update contact details in CRM

Let’s face it. Every CRM gets messy and out of date quickly and to a CSM, customer contact info is like oxygen. If you don't have a way to reach your customers, you won't be effective in your job. Period.

Ask Yourself:

• Do I have relationships with at least three contacts at three different levels for each of my customers?
• Can I honestly identify them as either champions (influencers with authority), coaches (influencers without authority), decision-makers, or detractors?
• Do I have accurate contact details to reach any of them at any time (email, cell phone, texting)?

✅ Take Action: If the answer is no to any of these questions, prioritize your customers and then get to work.

2. Brush up on current customer case studies

As a CSM, your role is to consult your customers; therefore, storytelling is critical to influencing the outcomes you manage. You need to be able to set up a natural segue into a relevant success story, share it authentically to drive the outcomes you hope for and guide the customer to the next desired action.

Ask Yourself:

• Am I aware of the latest success stories and use cases that my company has published? Can I talk about them in an authentic and convincing way with a customer?
• Can I articulate the main value propositions of all new features released in the first half of the year?

✅ Take Action: Form a study group with your teammates and do some live practicing. Yes, I know most people avoid role playing, but the ones who practice are the best in live situations. Push yourself.

3. Make sure your Success Plans are current

Let’s face it. Every CRM gets messy and out of date quickly, and to a CSM, customer contact info is like oxygen. If you don't have a way to reach your customers, you won't be effective in your job. Period

Ask Yourself:

• How long has it been since you updated the plan?
• Are you working with the right person?
• Have you lost track of measurable goals?
• Has anything changed within your customer's business that warrants an out-of-rhythm update?

✅ Take Action: Prioritize a list of success plans that need attention and challenge yourself and your customer to update them by a specific date. If you get pushback from the customer, use this as an opportunity to figure out why they are resistant and uncover risk.

4. Audit your career progression

Don’t wait for your next performance review. Capture your accomplishments, learnings, and progress from 1H while they are still fresh in your head. Give yourself an honest assessment about how you are moving towards your goals and whether you need to make any adjustments in the back half of the year.

Ask Yourself:

• Are you satisfied with how you are advancing in your career this year?
• Are you involved in projects or company initiatives that will expose you to new challenges?
• Who are your biggest advocates in leadership positions? Would they vouch for you if you were to apply to be promoted?

✅ Take Action: Write down details about your performance in the first half of the year and save them for reference in your next performance review. Invest in building and nurturing relationships with your internal advocates. Volunteer for a project that will stretch you and expose you to new opportunities.

5. Ask: How are YOU doing?

Burnout is a massive problem in Customer Success, and if you don’t actively manage and prevent it, you are at risk. Please don’t wait until you reach burn-out level; it is too late by then. Instead, proactively be honest about where you might need to adjust.

Ask Yourself:

• How is your work-life rhythm?
• Have you repeatedly compromised on personal boundaries lately? Do they need to be reinforced or modified?
• Are you feeling resentful about work?

✅ Take Action: Personal boundaries are a personal decision and, therefore, a personal responsibility. No one is going to do this for you. You’ve got to be honest with yourself, but sometimes, in order to do that, you need some external perspective. Ask trusted ones around you if they have noticed changes in your work-life rhythm and if they are concerned. If you have a trusted relationship with your direct manager or work mentor, ask them to help you make sure you don’t cross that red line.

6. Audit your recurring meetings

Despite the many statistics that show how unproductive meetings can be, we are still drowning in them. The main culprits on your calendar are likely recurring meetings… Once they get booked, they rarely come off and often lose their value over time.

Time is your most important resource as a CSM - are you using it effectively?

Ask Yourself:

• Which meetings have lost their original value?
• Which meetings did you get attached to that you don't need to attend?
• Which meetings do I find myself multi-tasking in?
• Which meetings need to get rebooted, overhauled or eliminated?

✅ Take Action: Start with meetings that you own and scrutinize each of them. Update agendas, ensure the attendee list is current, be clear on responsibilities, and adjust the time needed. Then, move on to meetings you’ve been invited to and list the ones you feel you should be excused from and why. If needed, get permission from your manager and then excuse yourself professionally.

7. Pretend that it is December

Q4 is defined by the activities that you do in Q3. While everyone else is vacationing or slowing down, you can prepare. As crazy as it sounds, the holidays will be here before you know it.

Ask Yourself:

• What customers are due for renewal in December, and how can I secure their commitment by the end of October?
• What projects need to be completed by the end of the year that depend on other parties who may not be available in December?
• What can I do now that will help make my end-of-year go smoothly?
• Am I taking any time off at the end of the year that I should proactively plan for and get ahead of?
• Do I know if any of my customers have unusual needs or restrictions during the end of the year?

✅ Take Action: Block out time each week starting now to focus on activities that will directly impact the end of your year.

8. Get ready for budget season

For companies whose fiscal year ends in December, budget season usually begins around September. This means that your primary contacts will be pulling together their prioritized requests for the next fiscal year. Don't wait to be asked... this is a good time to check with your customers to ensure that you are aligned and are empowering them with the information they need to ensure your product gets the budget it needs.

Ask Yourself:

• Do I know the fiscal year of each of my customers?
• Do I know when their budget season begins and ends?
• Do they have everything they need from me to ensure no issues with the renewal or expansion?

✅ Take Action: Ensure you are at the top of your game on budgetary objection handling and ask your customers what information they need to properly budget for their renewal in 2025.

9. Make space for learning

Personal development is often the first thing to be eliminated when you get stressed and busy. And just like the gym, it is hard to get back to it if you stop. Don’t neglect your own skills and knowledge, or you risk falling behind in your career journey and goals.

Ask Yourself:

• What will I commit to learning before the end of the year?
• What is one business area that I can expand my knowledge of?
• Have I given up pursuing an area of study because I have been too busy and have not prioritized it?

✅ Take Action: Set a realistic goal for yourself that prioritizes an area of learning. This could be anything from as small as reading for 15 minutes a day to taking an MBA course. If your budget has been a barrier, reach out to your HR team to see if any company benefits might help you cover the cost of a class.

10. Socialize

Employee satisfaction drops when you don’t have personal friendships at work. Especially in today’s hybrid and remote work environments, you have to be deliberate about setting up time to connect with others in your work, or you lose connection.

Ask Yourself:

• Who do I want to build a better relationship with at work?
• Do I have enough fun while at work?
• How often do I get to have non-work-related interactions with friendly colleagues?

✅ Take Action: Deliberately schedule time with select colleagues that isn’t tied to the daily grind of work. Virtual activities like virtual coffees, online games, and podcast clubs can be a much-needed way to insert some fun into your busy weeks and increase your enjoyment.