As a native New Yorker, we’re very “no bullsh*t” folks.
I have a particularly low BS tolerance for the facade hiring managers put on during the interview process, especially when everything is presented as rainbows and butterflies: happy clients, 5-star ratings, “rocketship growth,” etc.
I’m here to talk about what no one ever talks about: how to “sniff” out weak leadership.
Compensation, job scope, brand equity, product fit are important factors to consider when evaluating if a job is right for you.
However, the critical difference between a great job and a terrible one comes down to leadership.
I’ve been fortunate during my career to have great managers. I’ve also been unfortunate enough to have terrible managers who should have no business leading others.
And with over a decade of career and interviewing experience, I’m happy to share the wisdom I’ve gained along the way.
This guide will equip you with the right questions to ask to get to the real “nitty gritty” so that you can find a leader and an organization where you can truly thrive in your customer success career.
So let’s get into it!
When I started my career, I let the interviewer lead the conversation and made the mistake of falling for shiny terms, like career growth, unlimited PTO and a “family-like” culture because I wasn’t asking the hard questions.
The traditional interview approach can be risky for a few reasons:
Over the years, I’ve learned how to quickly and effectively vet potential managers using reverse interviewing. It’s where the interviewee “flips the script” and asks the hiring manager questions about their leadership style, values and expectations for the role, rather than the traditional approach, where the interviewer asks all the questions. This allows the interviewee to gain a deeper understanding of their prospective leader, the team and company culture and to properly evaluate if their values and goals align with those of the company and manager.
Reverse interviewing is a lot like courtship before marriage. Deciding who to tie the knot with as your life partner is the most important life decision you will ever make and choosing your leader determines your career path for years to come. So choose wisely.
Treat the interview the same way you would during the courtship process before marriage by going beyond the job description, asking the hard questions and getting to the real “nitty gritty” by uncovering what can’t be easily found online or through surface-level conversation.
Remember, a big part of being a customer success manager is navigating through difficult conversations with customers and internal stakeholders. So showcase those skills on the interview and show that hiring manager you’re a natural! 💪
Now let’s get into the topics I like to cover, red and green flags to look for and good diagnostic questions to ask your potential hiring manager.
If there's anything you're going to take away from this article, let it be this: your success as a customer success manager depends on your manager's leadership abilities working with the executive stakeholders, both in the c-suite and with other senior executives.
There is so much more to leadership in customer success than just hitting numbers, meeting growth quotas and operational efficiency. It’s understanding when it’s time to improve internal processes, let go of a bad-fit customer, upgrade internal software, re-evaluate workload and team responsibilities, initiate discussions on comp structure, etc.
Strong leadership in customer success is having the skills, tact and most importantly, the confidence to be a strong advocate for you.
I worked for a hyper growth pre-IPO startup, backed by some of the most successful VC firms in tech where I had what most would consider a "cool" manager. She was personable, valued work-life balance, was ready to help whenever needed and happily coached you through difficult client situations. She was hilarious after a few glasses of wine and was genuinely fun to be around. She sold me on her quirky personality, transparency about her prior toxic leadership and her desire to cultivate a strong culture for her team. In a lot of ways, I felt connected with her and I think a lot of my teammates shared the same sentiment. But we quickly realized our “cool” manager wasn’t fit to lead us and once we got through onboarding, it was the blind leading the blind.
She lacked the skills needed to solve critical problems, effectively work with the c-suite and senior executives to tackle those problems and be an advocate for us. She was a people-pleaser and overly cautious not to step on any toes. To be fair, the CEO was an absolute tyrant who seemed to get joy out of publicly belittling people, so I don’t blame her for walking on eggshells, but customer success leadership isn’t for the faint of heart. It was by far the most toxic, strangest culture I've ever worked in. The problems for us as customer success managers started when there were huge bottlenecks in the customer journey, major miscommunication between teams and an urgent need for defined processes and documentation to support scale that she should have been at the forefront of.
The CS team ended up working 12+ hour days to fill in the gaps left by her ineffective leadership. It became abundantly clear she was just telling us what we needed to hear to satisfy our concerns and kept us hooked on the fantasy that brighter days were ahead and things would improve for us. Spoiler: they did not.
And although things were going great business-wise, the cracks in the foundation were never filled and basic core functions were not functioning. We weren’t just putting out fires, we were on fire, all aboard a sinking ship with no safe harbor in sight. It was abundantly clear the odds were stacked against us and I made the decision to resign. Shortly after I left, she was fired. And frankly, we were all surprised it took as long as it did, seeing as she really didn’t bring anything to the table essential to basic customer success functions.
I allowed myself to get hoodwinked and bamboozled because I didn’t ask the difficult, important questions during the interview process and got roped into a dumpster fire of chaos and incompetence. Every mistake is a learning opportunity for progress, but don’t let my experience become your reality.
What to consider while interviewing:
Questions you should ask:
Signs they are a strong leader:
Ultimately, your success as a customer success manager relies on your managers' ability to not only identify issues but devise action plans, create solutions and be a strong advocate for you.
So do your due diligence to ensure your manager has the skills to productively and effectively manage up and support your career success
In my experience, smaller companies and startups do not typically offer leadership training. But in this rapidly evolving career path and industry, it’s essential to have leadership who not only values the importance of upskilling and continuous training, but actively seeks it.
Remember, leadership isn’t just getting “sh*t done” and retaining customer contracts. Successful leadership is consistently doing the work to be the best leader they can be and more importantly, aren't stuck in their ways and consequently, hindering your growth.
Adapting in this ever-evolving industry takes not only a very strategic and confident leader, but a humble one. Customer success cannot successfully scale using old-school management methodologies, especially in a growing organization. Remember that even the best, most successful leaders are still works in progress.
What to consider:
Questions you should ask:
Signs they are a life-long learner:
As customer success managers, we either “evolve or die.”
Customer success is constantly evolving, so traditional “old school” leadership methodologies will not work. Make sure your manager employs a “constant evolution” mentality and does not believe they already possess the skills and expertise to be a leader in customer success.Your growth depends on it.
A few years ago, I was offered an incredible opportunity, my “best” job offer to date from a Silicon Valley tech company many customer success managers can only dream of. One of Silicon Valley’s ‘Best Places to Work’ for years and one of the most successful private companies within B2B technology. So successful that many customer success organizations even model their strategies after this company’s.
Everything sounded great; I connected well with the team, the product had a ton of equity in the industry, my salary would have increased considerably and it would have opened many doors for me. But I decided to turn it down.
So, why did I decide to turn down the best job offer I’ve ever gotten?
Even though this company was famously known as “one of the best places to work,” everyone I had met looked completely burnt out. I could literally feel their exhaustion and defeat. Everyone looked disheveled, like they hadn’t gotten a good night’s rest in a long time. This was during the summer too, notoriously one of the slowest times of year in B2B technology.
I knew what I would be in for if I accepted the opportunity: high stress and little or no work-life balance. Life is too short to sacrifice my mental and physical well-being in favor of the novelty of having big tech on my resume and LinkedIn.
What I’ve come to learn over the years is that a good work-life balance supported by leadership is the key to being a successful customer success manager.
Having been in this industry for almost a decade, between all of the meetings, demands of clients and long days, it is very easy to get burnt out. The last thing you want is a leader married to their job who expects you to do the same. Work should never come before family and personal health, so make sure your manager employs the same mentality and promotes R&R and work-life balance.
What to consider:
Questions you should ask:
If the interview is a more formal one and the above questions would be strange to ask, here is a good one you can ask:
Signs they value and promote work-life balance:
Great leaders are hard to come by. So do your due diligence during the interview to ensure your leader has what you need to grow and thrive in your career.
I hope this article helps any experienced or aspiring customer success managers find great leaders!
To write this article as authentically and raw as possible (and to not violate any NDA’s), CS Insider and I decided to keep it anonymous.
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