How Does a Customer Success Leader Manage Up?

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This post is mostly a reminder to myself and an example of the importance of sharpening the saw of my management skills ala Stephen Covey. It could also be useful in coaching your direct reports on working with their favorite manager.

Pro Tips to Manage Up Effectively

How did you learn to manage your boss’ expectations and help her help you deliver on your commitments? If you’re in a big company, you may have access to training. Or you invest in your professional self and you read a lot and work with an executive coach on specific skills. Since I usually work in smaller companies, I’ve taken the latter path. But what about your team?

There are many great tips for managing your relationship with your boss effectively. Here are a few I try to use that probably apply to many industries/relationships. I’ll conclude with specific tips for the next generation of customer success leaders.

Agree on a status report or scorecard format

Do you know how your boss thinks you’re doing? Avoid surprises. Agree on a report card format, even if informally, that contains the KPIs and outcomes you own. Provide periodic updates verbally and in writing. Even if your boss prefers to walk and talk, make sure you stay aligned on important areas by summarizing in writing your progress.

Pro Tips:

  • If you don’t use a goals or other management system, use a document shared with your boss and add updates and accomplishments to this doc.
  • Each meeting can be captured by a date formatted as a Heading 1. Include a Table of Contents at the top of the doc.
  • In meeting summaries succinctly capture, decisions, action items, victories, and any red flags. See Customer Report below for key things to share.
  • Give your boss a chance to provide clear feedback by sending an email summary and asking for improvements/corrections if necessary.

Meet/communicate regularly

You haven’t spoken to your boss in over 2 weeks? That’s great. No news is good news, right? Early on, I assumed since I knew how to run my area and deliver on my commitments, it was OK that I didn’t speak to my boss regularly. But inevitably Something Horrific and Incredibly Terrible happens. Either it’s an attrition, or company priorities change. The best way to stay aligned is to talk/meet regularly.

Pro Tips:

  • Be sure to either do your 1-on-1 regularly, or schedule time to have coffee or lunch and chat.
  • Prepare an agenda in writing by adding the date to the doc mentioned above and send an email to you boss asking for his thoughts on the agenda.

Get feedback

You must do this periodically in advance of a formal performance review. On a monthly or quarterly check-in, add a “Feedback” topic and frame the request: “I think things are going well. We’re hitting our numbers and delivering on our commitments. Is there anything else you think we should be focusing on?”

Pro Tips:

  • Be sure to use an open-ended question that invites your boss to share any concerns he may be having.

Never forget your boss is only human

In a business environment where people are paid to deliver results, it can be tempting to justify dog-eat-dog behaviors as a way of helping the company succeed, “I’m not paid to make friends…” Remember that such behaviors destroy mutual respect and culture, a culture you still have to live in.

Pro Tips:

  • Don’t flip the bozo bit. While it can be satisfying to dismiss others as being incompetent or unskilled when they make an important mistake, don’t. Flipping the bozo bit on your boss and assuming he’s not capable will only ensure your relationship will suffer, and that your career will suffer.
  • Golden rule applies. Especially with your boss and your direct reports, treat them as you’d want to be treated. Duh.

Managing up as a Customer Success Leader

I’m biased. I think Customer Success leaders are predisposed towards being good managers and leaders as success CS leaders usually have high EQ and are operationally capable. So what’s key for Customer Success leaders and practitioners to understand about managing up?

Publish a Customer Report regularly

Make sure your boss and peers know what your group is working on and delivering by creating a report that summarizes and communicates the most important KPIs/outcomes you own. Have categories like:

  • Revenue: Growth and Renewal
  • Customer Health
  • Product usage
  • NPS/Customer satisfaction
  • Victories
  • Blockers
  • Red Alerts

This is basically a report that summarizes other reports. Publish this report monthly or quarterly in a prominent location on the company intranet or wiki.

Pro Tips:

  • Schedule and allocate time to update the report consistently. The report will work against you if you don’t publish it reliably.
  • Have individuals on your team own and prepare their section; it helps them understand what’s important and will help them feel invested. Acknowledge the contributions visibly and vocally.
  • Send an email to your boss with the more important highlights in the body of the email. Include a link to the full report.
  • Share the report with your boss and colleagues.
  • Review the report with your boss in your 1-on-1s.
  • Use a system like Strikedeck to make the tracking and reporting of KPIs/outcomes much easier (or even possible!).
  • Review relevant sections with your peers in person. E.g. cover the prodcut feedback section with Product in your weekly/bi-weekly status meetings.

Introduce customers and tell their stories

The Product team may create “personas” to represent customer types to help them understand users, but you actually know your customers. You know their names. They tell you their stories. Who do you tell?

Even if it’s for internal use only, capture the personal stories of users. Understand them, and tell the ones that your boss needs to hear today. Sales teams love and leverage these very specific tales, even if they can only share them anonymously.

Pro Tips:

  • Include stories in your customer report in a victories or customer stories section.
  • Create and maintain a program to develop these stories as part of your ongoing customer engagement. This can be the groundwork for your external marketing efforts.
  • Add story collection as a metric by which you assess your customer facing teams.
  • Use your CRM or other system to track the collection of these stories so you can report on them.

Resources and recommended reading

Managing Up on
Become the Leader of Your Boss