Interviewing for a Customer Success Role at a Startup? Look Out for These Red Flags.

Interviewing for a Customer Success Role at a Startup? Look Out for These Red Flags.

I started a dream job with a wonderful company about 4 months ago.

The interview process was a dream. Every touchpoint was brilliant. Every email *chefs kiss*. Day 1 was incredible. And I can say that, 4 months in, I’m thrilled with this opportunity. Everything that was shared during the interview process is in fact as they stated.

But I don’t want to talk about that. I want to talk about the OTHER experiences. You see, life is a journey, and sometimes the road is pretty bumpy. Sometimes there isn’t even a road to travel on. Sometimes it’s all built on lies and puffery.

So what should you look for when interviewing at early/mid-stage startups? What questions should you ask to help identify the REAL gold from the fool's gold? I’ve biffed on this in the past. I’ve also spent a whole lot of time working with other CSMs on interview prep and debriefings, and I’ve worked for some shitty founders who taught me lots of hard lessons.

These are the red flags 🚩🚩🚩I dig into when I’m interviewing for a new role.

PUFFERY: “Exaggerated or false praise” Are they pumping up their team members or sales numbers or accomplishments? Does it feel “too good to be true?” It probably is. Boom. 🚩🚩🚩

FAUX CULTURE: If YOU ask about CULTURE and THEY talk about PERKS?? Boom. 🚩🚩🚩

EGO: If they believe they can “do no wrong” they are probably “doing copious amounts of wrong” i.e. 🚩🚩🚩

METRICS: The best interview is an honest interview. Are they hiring to backfill a position? Do they have a specific problem that they need to solve? What are the supporting numbers behind this need? If they don’t have those metrics Or can’t explain their need then we have ourselves a 🚩🚩🚩

FreakinREVENUE: Follow the money. If it’s not there and they don’t have a plan to get there. And then they tell you it is there?? (see where I’m going with this) 🚩🚩🚩

Ok, so we have our red flags. Now, we want to work on uncovering those in the interview process. It may not seem like an easy task but, there are some very simple things you can do to identify a potentially bad fit role before you accept those shiny RSUs (Restricted Stock Units).

But first, a story: “a short while ago” I was in a role that I was happy with. Had a book of business that was growing. Made decent money. Had a strong relationship with executive leadership. Hitting my numbers.

And *BAM* out of nowhere, I got the “EMAIL” on LinkedIn.

You know the one. The “are you interested in a new opportunity”? It was a recent major acquisition. Lots of good marketing. Lots of promises of growth and great customers. And to be honest I love a good acquisition. And I’ve always wanted to be a part of a great integration. It was a space I understood, I saw value in the product and the seniority of the outreach was excellent. All things pointed to a “reason to get on the phone”.

Shortly after starting, I learned that this email was actually from a junior team member using an executive's LinkedIn. It was far from the “personalized" and "tailored for me, picked you out of the weeds” story I was told while interviewing.

A LOT of red flags followed. Interviewers didn’t show up for scheduled Interviews. I’d got a text asking for a phone call when a zoom link had already been sent. There was no follow up, no follow-through, and no attention to the actual conversation to begin with. It was “red flag” central.

Those red flags carried over into acceptance, onboarding, training, onramp, and functional. Little to no follow-through and no focus on the things I value. Had I asked the right questions and paid attention to the red flags I would have seen it coming before I submitted my resignation. Frick.

So, what do we do to avoid this?

1. Write down what you want out of your next role

List out the why and the drivers behind your choices. Keep that list on your desk as you are interviewing. This is your main filter.

Do you want to further your career so you can buy a home? Save for kids college? Put yourself through college? Put it on the list. If you can remind yourself of the WHY, it’ll be easier to keep focus if someone drops a huge number in front of you. These are often used to hide the truth of the situation.

A few example questions you can ask your interviewer:

Q: Can you share a recent story about how you helped promote a successful team member within your team?"

  • i.e. If you keep crushing it, will they look out for your long-term career WITH you? Or will you need to fight for it?

Q: Can you share your view on comp adjustments for team members who increase their ownership within your team?

  • i.e. If they give you more work, will they give you more money freely? Or will you have to fight for it?

If you are seeking career growth make sure there’s someone on your immediate team who will be able to help you grow and find opportunities that you can't on your own.

If every conversation around growth, comp, or extended projects is a battle, with little to no support from your direct leadership?#thankyounext

2. Identify “non-starters”

What are the things that you simply will not do? List them out and make them simple. During your interviews spend most of your time around these. Ask probing questions to uncover their view on this list. Probing questions are not answered by Yes/No, they require explanation.

An example question you can ask your interviewer:

Q: Can you give me a specific example of how you’ve handled conflict with a direct report in the past 6 months?

If they cannot give you one, ask for a cross-functional example. If they still can't give you one, ask for ideological differences. The key is to keep digging. If they don’t have a direct example on the first try, start probing again (respectfully, of course).

But what if it’s all sunshine and roses and there has never been any conflict? Just forced grins and promises that “everyone gets along”? #thankyounext

Remember, not all conflict is bad. But how folks deal with conflict (like NOT dealing with it at all??) could be a red flag.

3. Ask them to show you the money

Take detailed notes at every step of the interview and verify with other folks on the team. If your interviewer shared specific data, like churn was 40%, or NRR was 120%, write it down and verify during the next interview.

If you find inconsistencies, ask:

Q: What are the main drivers for churn within this segment?

  • Product issues?
  • Bad fit?
  • Low usage?
  • Low adoption?

From there keep probing with questions like:

  • How aligned is the product team on these issues?
  • What's the handoff process between sales/cs?
  • What does onboarding look like?
  • How much influence will this role have over the training process?

Churn issues aren't necessarily a red flag. The power you will have to influence those reasons are. If you have none? #thankyounext

At the top, I mentioned I’d found my “dream job”. So, why? It’s actually quite simple. I feel respected. I feel heard. And I have a seat at the table. I am managed by a skilled and respectful leader who supports me in my goals and directs me toward resources and processes that will also help me meet my goals.

I’ look forward to hearing about your dream role next. With as few 🚩🚩🚩 as possible.

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