Why New CS Leaders Struggle Asking for Help

Why New CS Leaders Struggle Asking for Help

As new leaders, we often find ourselves in a position of having to prove ourselves. Early last year, I joined LinearB to build and lead our Customer Success team. Being my first leadership opportunity, I felt I had a lot to prove.

Looking back at what I’ve been able to accomplish, however, it’s clear I couldn’t have done so without help. Here’s why it’s important to ask for help as a new leader and how to make it work for you.

We think we can be experts at everything

Sometimes, our ego and fear of being seen as incompetent get in the way of asking for help. We often face a disconnect between how we view ourselves and how others view us. At this juncture, it’s important to understand that we each have our strengths and weaknesses; we can’t be experts at everything.. The more we hesitate to seek help in genuine cases, the more this may also cause unnecessary delays in delivering value. Additionally, as a new leader, it’s not just about you – your team matters, too! It’s about getting help not just because you need it, but for the betterment of your team.

Different perspectives challenge our thinking

You know that feeling when you’re stumped by a complex problem, but someone else’s answer to it seems so simple? Prior to asking for help on a problem, we’re likely looking at it with tunnel vision. Asking for help, particularly from those who’ve ‘been there, done that’, will bring diverse and reliable perspectives.

In fact, "researchers found that when diverse teams made a business decision, they outperformed individual decision-makers up to 87 percent of the time".

While it may seem uncomfortable to ask for help, we grow from these experiences – think of it as a way of doing your due diligence as a new leader.

We fear we'll lose ownership of our work

You may fear asking for help thinking you’ll lose ownership of your work. But remember – you’re still driving the initiative. Be determined to seek help and remind yourself that the problems your team face are your responsibility. Seek additional perspectives but don't look to pass problems onto anyone else.

Here’s how I used these principles as a new leader at LinearB.

As I ramped up in my new role and met more customers at LinearB, I was faced with the challenge of investigating our growing churn rate and lack of engagement. In a small company like ours, even a little churn is highly visible and occupies a large percentage of our customer base.

We had several customers tell us that they just didn’t have time to make use of our product, but I felt there was more to it. As I dug more I discovered that engineering leaders in our customer organizations didn’t feel like we truly “got” them.

To make matters more difficult, I hadn’t been an engineering leader in my career so my ability to speak their language was limited. Nevertheless, my goal was to reduce churn as soon as possible and keep it that way.

So, I put my Customer Success toolkit to work at LinearB right away to ensure that our customer onboarding was smooth, questions and concerns were promptly answered, and engagement was strong.

Even with these efforts, retention didn’t improve.

In part, I fell short as a trusted consultant given my lack of experience in this area. I had a lot to learn and this learning couldn’t happen overnight despite my best efforts.

To resolve the issue, I asked our COO for help as I knew he had been an engineering leader in his previous role (in fact, this was what drove him to start LinearB). He was already deeply involved in our day-to-day Customer Success operations and was eager to help.

I broke my plan down into short-term and long-term game plans.

Short-term game plan: Reduce churn as soon as possible

As an immediate step, I worked with our COO to build a knowledge base on various pain points engineering leaders were experiencing, with easy yet effective breakdowns on how our product could provide value. Then, I went back to existing at-risk customers and put our Customer Success anti-churn play into action.

This re-engagement session was meant to help customers realize value from our product based on tips from our knowledge base. (Of course, if they don’t feel they’ve realized this value, they are free to leave in due course.)

Long-term game plan: Keep it that way

To avoid the risk of churn in the first place, my team and I also had several brainstorming sessions around what we felt was and was not working well in our onboarding process.

This led to meaningful input that I used to overhaul our customer onboarding process and ensure our time-to-value for customers was dramatically reduced. (Bonus takeaway: Strike while the customer is still hot!).

I’m also working towards having our knowledge base material built directly into our product as we scale so that it’s even easier for our customers to realize value.

Thanks to these steps, we’re seeing customers on the brink of churn return to engage with renewed interest, a better ability to maintain healthy customers, and having new customers flow through our onboarding process without dropping off along the way.


As new leaders, we’ve got to start somewhere – a structured way of asking for help in genuine cases is a great way to expand our perspectives and grow without losing ownership of our work.

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