New Customer Success Leaders: Be Prepared for These Six Things

New Customer Success Leaders: Be Prepared for These Six Things

I've learned quite a few unexpected things as a first-time leader in Customer Success.

If you’re stepping into a leadership position for the first time, it’s important to be prepared for the transition.

But - how do you prepare, and what should you expect?

Here are six things that I experienced as a new leader and how I handled them.

1. Being put on the spot to make quick decisions

In meetings with my team members, I was often asked how to approach problems.

My team looked to me for guidance, and I felt compelled to provide an answer on the spot - I didn't want to be perceived as an inept leader.

Sometimes the answer was clear, but other times, I wasn't sure and would say something I wasn’t completely set on. I’d later think to myself:

  • Oh, no. Did I really say that?
  • Did I have to continue to stick by what I just said?

If you’re anxious about not knowing all the answers, relax!

Leaders don't have everything figured out.

This is especially true for small organizations still figuring out how to do things. No matter what level you're at in a company, there are times when coming to the proper conclusion takes time and thought.

When you find yourself in this situation, here are two things to do:

  • Give yourself some space and time if the answer isn't apparent. Let your team know you don't have a firm answer and that you'll get back to them. Then, put in the time to work through possible solutions.
  • Loop in anyone who can help solve the problem if it’s too complicated. More on this here.

You don't have to figure out all the answers alone - another great option is to engage a subset of your team in dialogue. It's easier to innovate as a group than as an individual and doing so promotes strong teamwork.

A solid framework for getting things done as a team is the "Get Stuff Done" ("GSD") wheel, as outlined by the founder of the Radical Candor leadership philosophy, Kim Scott.

The GSD wheel outlines these initial steps:

  1. Listen to your team's ideas.
  2. Clarify and sharpen these ideas.
  3. Debate the pros and cons of each one.
  4. Finally, move on to the decision-making process.
Feedback loop taken from
Feedback loop taken from

2. Taking a step back to understand the big picture

It's easy to become hands-on with everything your team needs from you, thinking you're enabling them.

But often, you’re just getting in the way of them doing their work.

Be there for your team when they have questions, but also keep the bigger picture in mind when providing a path forward.

When in doubt, ask these questions:

  • Why do we need this?
  • What are we trying to accomplish?
  • Is this a repeating concern?
  • Is there a more significant problem here?
  • Is there a higher-level process inefficiency we could address to avoid going down this road repeatedly?

Asking these questions helps you identify team inefficiencies and ensure you're not straying from the larger path toward your goals.

For instance, at my company, we were struggling with driving the adoption of a particular feature of our platform. This feature, unfortunately, required work from the client to implement.  

To combat these falling numbers we tried to brute force our way to solving the problem by manually reaching out to struggling clients and educating them on how to make the change.

Sadly, it proved to be tedious, unscalable, and worst of all didn’t offer any guarantee of success.

I decided that despite some short-term pain, to work with our Product team to build an automated process that automatically made the change for our clients.

Boom - with some backend magic, we saw a massive boost in value creation.

3. Seeking buy-in from your team

In any company, there are many moving parts. The role of the team leader is to stay informed about developments (think new product features, changes in cross-functional interlock, growth strategy pivots, etc.) - for yourself and your team.

How can you ensure your team is kept in the loop?

Furthermore, how can you ensure they understand the ‘why’ behind new changes?

Here are some suggestions:

  1. Schedule some time for yourself on a quieter day of the week (perhaps Friday afternoon?) to catch up on recent developments. Use this time to read over notes you might have taken at meetings and other materials to help you catch up.
  2. Devise a game plan if there's anything required of you and your team.
  3. Finally, set aside a portion of your subsequent weekly team syncs to go over what's relevant for your team and answer their questions.

Once you meet with your team to go over recent developments, gauge their pulse and determine how to move forward. You should have a pulse on the following:

  • Overall, how do they feel about these developments?
  • Do they have any concerns or suggestions?
  • Should your team do anything differently moving forward? If so, what?

Pro tip: Find ways to coordinate knowledge sharing and training across departments to boost innovation and team effectiveness. This is particularly important to do with Product, especially if your software has regular updates and feature changes.

4. Building strong bonds with other team leaders

Do you know what makes cross-functional knowledge sharing easier?

Strong relationships with other department leaders.

How can you build these relationships?

One way is through regular check-ins.

Ideally, these meetings aren't just about business - they would be a way to get to know the other person.

Check-ins like these help to develop a closer relationship between your teams and grow your interdependence.

Here is one way you can structure your check-ins, particularly if you’re not sure where to start:

  1. Open the call with some friendly chatter. Do you notice anything about them, or in their background, that’s worthy of conversation? And if not, a good old “How’s your day going so far?” ought to do the trick!
  2. Give before getting: Ask the other department leader what you or your team can do to help their team. There’s always at least one cross-functional project that could use some attention, and involving yourself is a great way to position your team as a crucial backbone of the org.
  3. Finally, is there something this department leader or their team can do to help your team? Since you’ve offered help, it’s very likely they’ll be just as eager to help in return. Position the ask in a way that shows how it’ll benefit both sides (and usually, the overall org).

5. Knowing where to take charge and where to stay flexible

As new leaders, it’s natural to want to take charge and give orders. However, this often backfires.

Whenever I tried to set up a rigid process for reaching a goal, I was rebuffed by my senior team members.

One time I insisted that my team follow a strict outreach process to boost registrations for a company event. A senior member chimed in, offering a different way to drive registrations.

He was hesitant to follow my method, and I was left feeling inadequate.

I quickly realized, however, that I couldn't lead every member of my team in the same way. They all have different backgrounds, expectations, and styles of working.

As a leader, how do you take these differences into account?

By tuning your way of leading.

By knowing your team, you can adapt your leadership style to one that empowers them to give their best.

Use questionnaires to learn how your reports like to be treated - this helps create a strong working relationship.

For example, I found that junior members typically benefit from following a more rigid process. They value more direction.

Senior members, on the other hand, value flexibility. They want to own the process towards achieving their goals. It’s crucial to respect that and defer to them while providing general direction.

So - going back to my example above, I realized that my suggested method was unnecessarily tedious; we ended up meeting the goal with the senior team member’s approach.

In future instances, I was able to work more collaboratively with this senior team member - they were free to decide on their approach as long as our high-level goals were being met.

6. Developing your 'voice' as a leader - being persuasive and data-informed

This is much harder than it sounds!

Experience plays a big part in being persuasive. There are things you can do to hasten the process, such as letting data tell the story and planning your talking points ahead of time.

As a Customer Success leader, I found that I could always build a case for something using data.

For example, when we saw a sudden increase in churn, I felt much more confident speaking about it once I had the data to back it up.

Moreover, when I needed to have a challenging conversation with my team or even my own manager, I found that it helped to organize and write out my talking points first, and then rehearse before having the conversation.


Becoming a strong leader doesn't happen overnight, so it's normal not to ace it immediately. But with practice and patience, your leadership skills will grow.

Now get out there and lead!

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