From Good to Great: How to Lead Your CSMs to Success

It was a little bit over five years ago that I was asked to manage my first team of Strategic CSMs at Gainsight. Since then, I’ve hired and coached many managers and directors of CSMs, at Gainsight and other companies. Over these years, I’ve seen some common threads and concepts that could help first-time (and even more experienced) CS leaders navigate the wonderfully challenging job of leading CSMs.

I wanted to share five of these with you today.

Confidence vs. Competence

As a first time manager of CSMs, it’s easy to mistake these two “C”s as being one and the same when looking at your CSMs and thinking through their performance and growth. It’s easy to automatically assume that a CSM who speaks with confidence is competent, and that your recent soft-spoken CSM hire who lacks confidence is incompetent.

While this could sometimes be true, it’s definitely not always true. Learning to map your team on the “Confidence vs. Competence” two-by-two can help you tailor your management style and adjust your approach accordingly, and thus be a better coach for your team:

Managing someone in the top-left quadrant is very different from managing someone in the bottom-right quadrant. With the former (“humble down”), work on self-awareness, identification of skill gaps, and building competency. With the latter (“Build confidence”), work on realizing their worth, find ways for them to shine and help them build on their strengths to become more confident.

Keep that in mind as you work with each of the CSMs in your team, hopefully moving them into the upper-right quadrant over time.

Employee Success

At Gainsight, we often spoke about the basic Customer Success Equation:

Customer Success = Customer Outcomes + Customer Experience

To make a customer truly successful, not only must you deliver a seamless, optimal customer experience (and make them “happy”) - you must also help them achieve the outcomes they’re looking for from your product or solution.

I like building on this equation and translating it into the Employee Success realm as well, which is relevant to any manager of people, and specifically manager of CSMs:

Employee Success = Employee Outcomes + Employee Experience

To make any of your CSMs successful, you must understand their desired career outcomes from the job, and ensure they have a great experience working in your team and company. Just like a Customer Success Manager has to understand their customers’ desired business outcomes, and help guide them towards achieving these outcomes, even if that means challenging them to change course and being prescriptive - a manager needs to do the same with their employees. It’s not about making the customer/employee “happy” - it’s about ensuring they are realizing their full potential.

To make your CSMs successful, you need to deliver these desired outcomes while also ensuring your CSMs are having a great experience through key “Moments of Truth” with your company. Any manager that is able to deliver outcomes and experiences to their employees - will be able to unlock the full power of their employees and this will in turn propel the company’s (and investors’) success by delivering on business goals.

To demonstrate, yet another 2x2:

Those employees who are realizing their desired outcomes and getting a great experience (upper-right) are likely to stay longer in your team, be engaged, dedicate more of their energy to their jobs, and advocate for your company helping you attract and retain other employees.

Focusing on delivering just one of these (outcomes or experience) might seem to be working for some time, but does not fully capitalize on the power of your employees. Delivering experiences without outcomes (e.g. great onboarding experience, friendly relationship with you as their boss and culture, but limited career growth, or pay that’s not competitive) might result in employees who are advocates who love your company, but when a better offer comes along they might leave as they’re not truly realizing their desired outcomes from their jobs.

The flip side (bottom-right) can be thought of as “trapped employees” - they might not leave your company as they are getting their desired outcomes, but because they’re not having a great experience, they are not truly advocates of your company, and they are less likely to bring their whole selves to work or be fully engaged in their work.

Managing Up, Down, Across, and Within

First-time managers of CS often think of their job as managing their teams. And while this is an important part of the job, I recommend first-time managers of CSMs think about their job more broadly, as 360-degree management. Specifically:

1. Managing Up - managing your managers
2. Managing Across - managing your peer and cross-functional relationships
3. Managing Down - managing your team
4. Managing Within - managing yourself - your well-being, your career

Leaders differ immensely in terms of how they allocate their time, effort, and energy across these different vectors of management. Focusing on each of these angles on its own will only get you to a certain point, but it’s when you holistically and strategically allocate your efforts across these directions, and continuously reallocate your energy as the needs and the environment changes, that you can be the best version of yourself.

I used to think that being a manager meant spending 95% of your effort on “3” - being there for your team, and making your teammates successful and I now believe different times, settings, and company cultures might require you to prioritize these differently.

Most importantly - don’t forget “4” - similar to the “put on your own oxygen mask” metaphor - you should never neglect to dedicate time to yourself, your own well-being, and your career progression - being a big advocate for your team is great, but if you don’t take care of yourself, you won’t last for too long and everyone will lose. Burnout is a common pitfall for first-time managers of CS - and thinking about this proactively could help set the right boundaries and priorities.

Coaching vs. Solving

This is something I see first-time managers of CS struggle with all the time. It usually works like this - you were one of the best CSMs on your team. You knew how to make your customers successful. You get the product, use case, and domain. So you get promoted to managers, and now you think you need to “teach” the rest of the team how to be so great. Well, you have all the answers, right?

More often than not, you don’t. Or at least over time, you won’t. As a first-time manager of CSMs, resist the urge to “teach” your team how to do their job, or “solve” all the problems they come to you with. Focus on being a coach by taking a step back and asking insightful questions to help your team find their own answers. Over time, this is a much more scalable leadership style and one that your team will appreciate more - empowering them and eventually leading to better answers over time.

This is true across fast-growing companies today, but it’s especially key in customer success. With many teams growing fast and employees being promoted to managers early without having many years of experience, or even more experience than the people they’re managing - managers often don’t have all the answers and solutions, and instead can empower their employees and draw on their experience while supporting their development by using coaching methods to collaboratively problem solve

Doing vs. Talking

This is something I’ve grappled with personally and I’ve seen many leaders struggling with it over the years. Whether it is due to cultural differences, alternate upbringing styles, or just personality - people’s level of comfort with talking about their work, successes, and ideas - differs widely.

Over time, I’ve noticed that some people tend to see the world as if there are two groups of leaders out there:

• The Talkers - think that guy in the corporate offsite who just won’t shut up. We all know these types. They have to ask “thoughtful” questions in a big group setting, opine loudly and often, and can’t stop telling everyone about the great success they’ve had in fill-in-the-blank. Gotta love them.
• The Doers - those leaders who just do good work. They have a lot to bring to the table. They come across as shyer and don’t like self-boasting or tooting their own horn. They focus on doing - executing, getting results - and not promoting their work or themselves.

The Doers usually see the Talkers as empty air balloons and look down upon them. The Talkers think the Doers are too quiet, maybe mistaking them for being underconfident or incompetent. These two groups have significantly different standards for what makes for a worthy comment in a meeting or what type of success is worthy of a company-wide email or a Reply All.

I personally think that CS leaders who want to succeed simply can’t think of this as an “or” statement (Am I a Talker or am I a Doer) but an “and” statement - to be successful in the CS world, a leader has to find a way to be a Talker and a Doer. And there are many different ways of doing the “Talking” - it doesn’t have to manifest itself in the empty, negative way they so despise.

If you are just focused on talking and not doing - you might seemingly climb up the ladder and succeed (in some environments) but it’s only a matter of time until the absence of real essence and substance will catch up to you - your team won’t appreciate you, and at some point, that reputation of just being a Talker will get out.

On the flip side - one might hope or believe that “actions speak louder than words” and that a good, dedicated leader might find success just by “Doing” and the word will spread - good work and good results will lead you to success. Still, waters run deep, they’ll tell you. The reality is, however, that these types of leaders will probably hit a ceiling, or a wall, sooner or later.

Becoming comfortable with confidently showcasing your work and getting the credit you deserve is paramount to actually realizing your career success. You are always out there, competing for a Share of Voice with other leaders around you - and any time you don’t seize an opportunity to increase your share of voice, you’re essentially losing your share of voice.

Another way to think of it is something I like to call the Substance-to-Voice ratio - how much of the substance you have to bring to the table are you actually voicing and sharing with others? You might be the most thoughtful ideator or thinker, but if you don’t find the way to voice these with whoever needs to hear them (be it your team, your exec team, or your clients) - all that substance isn’t coming into light.

We all should strive to be a “1” on that substance/voice ratio - 100% of our substance comes into light and is being voiced. When that ratio is much lower (say 0.5) - only half of what you have to bring to the table is being realized. And when it’s higher (say 1.5) - you use too much of your voice, or may I say, noise, that it’s out of sync with your actual substance and you might risk losing your credibility. You might want to take a deep look and reconnect with some substance and dial down the talking.

I’ve gotten the feedback before (and recently) that maybe not as much of my substance is being brought out as it should - and this was partly a motivator for writing this post. So here’s my attempt at increasing my own Substance-to-Voice ratio.

Cheers!