5 Questions to Uncover Red Flags in CS Leadership Interviews

By Rachel Provan
red flags

Are you looking for a new job in CS?

A shocking number of CS leaders are.

In early-stage startups, the average CS leader lasts 1-2 years.

They either burn out, get replaced, or find another opportunity – hoping for a better experience somewhere else.

On second thought, maybe it’s not so shocking.

Most CS leaders I’ve spoken with have experienced working at a company where CS was set up to fail, due to a lack of understanding about what CS actually is, and the timelines and expenses involved. There were red flags everywhere – they just didn’t see them.

Once is frustrating. Twice is demoralizing. Three times… maybe waiting tables wasn’t so bad…

Good news

If this was the case everywhere, CS wouldn’t exist. There are a lot of companies where you can get it right!

But how do you know the difference?

You ask specific questions that unearth whether the company has a true understanding of what Customer Success is… and whether they’re willing to learn.

You don’t need to ask these all at once! Sprinkle them in as you progress through the interview process.

So as you’re out there looking, here are 5 red flags CS leaders should look for when considering a new company.


1 – Who does CS roll up to?

🚩 – Sales, Support, Marketing


While CS can definitely benefit those three departments and work closely with them, having CS sit under one of them shows they don’t understand that CS is its own function and its own department. If it rolls up to anyone else, its priorities get misaligned and things get messy quickly.

You can follow up with:

“I know it’s done differently at different companies – why did they decide to structure it that way here?”

This way you can see if there are possible reorgs on the horizon, or if they are married to the setup as it is.

⚠️ Chief Revenue Officer

This one is iffy. It’s more of an orange flag than yellow. There’s definitely some red in there.


Because while CS absolutely impacts revenue retention, the indicators are lagging. Someone focused solely on revenue sometimes won’t trust the benefits of a longer-term strategy that requires upfront investment of time and energy. They will see a small to moderate improvement in churn in the first six months, and decide CS is costing more than it is bringing in. So they will do one of two things:

Push upsells and cross-sells – before the customer has achieved their desired outcome.

Cut budget for the CS department in terms of tools and headcount – which makes an effective CS department even less likely.

WHEN IT CAN WORK – If the CS department has reached the maturity stage of being predictive, and there are data-backed plays for retention and expansion, yes. By that point, you are seeing the true ROI of CS – which DOES involve increased net revenue retention. But expecting that in the first 1 year (at least) is a recipe for failure.



CS is (yet again!) its own department. It has its own KPIs, structure, processes, software and budget. You wouldn’t put Marketing under Support. It just wouldn’t make sense! They have different objectives. The same applies here.

Bear in mind – this structure is unfortunately still rare at startups. You can’t say no to everything, so look for companies that seem to understand CS and its processes and benefits, and you think you can fight that battle down the line.

2. What do you hope Customer Success can do for your organization?

(Ask this of the CEO or highest level person you speak to, and be prepared to give your answer to it too!)

🚩 “Make the customer happy” (Too vague. How do you know when you’ve succeeded? A customer can love their CSM but hate the product…)

🚩 “Upsell and cross-sell”. That comes as a RESULT of customer success, but if you put it ahead of the customer’s goals, you are fighting a losing battle.

🚩 “Help the customer with their problems” – Ehhh, sometimes, but it’s not the point. CS is meant to be proactive. The point is to get them to their desired outcome smoothly. Not fight fires.

⚠️ It’s ok if they talk about reducing churn, providing product feedback, etc. But they should be mentioning things that benefit the CUSTOMER as well, not just their company.

✅ To make sure our clients achieve their goals with our products (or some variation of this)

3. Does the CS department have a seat at the table at executive team meetings? Does CS present to the board?

🚩 No, but….

No. If you don’t have some sort of representation at the top or your initiatives and budget will permanently be on the back burner.

⚠️ This is the first CS hire

I’d argue the point with them here that if they want the function, it needs to have influence. You need the CUSTOMER represented at the executive level.

✅ Yes.


4. Who is your “ideal customer”

🚩 Everyone!

Nope. Unless you are working for Google, this is probably not true.

⚠️ An industry (e.g. HR departments)

Getting closer, but which ones can you help? Enterprise? SMB? Why is your solution right for them vs something else? What are the use cases?

✅ A defined ICP

A well-defined product/market fit with an ideal customer, or a couple of different profiles. (Not necessarily a persona, think “HR departments working with over 1000 employees, vs Rita Recruiter)

5. How do you measure customer outcomes?

🚩 Blank stare

🚩 They are logging into the product

⚠️ We ask them (Ok, but this isn’t scalable. At least they’re asking though!)

⚠️ You tell us

Fair, but may be an uphill battle. They may expect this to be fast and easy. It’s not. Mention that you’d be thrilled to help with that, but they should be aware it takes time and effort to get there.

✅ We determined this with our ideal customer profile and have data points that correlate with success. (How they are measuring it can still be under construction, but they haven’t just decided it in their own head.)

6. How do you see this department evolving over the next year?

This is a gut check rather than right/wrong. See if they have realistic expectations or expect you to double their revenue single-handedly in six months. They should have SOME idea of where this department is going.


Look – most companies will get at least one of these wrong. And they won’t say the right answers word for word. That doesn’t mean it will be a nightmare. Get a sense if they are open to other ideas. Some of the best places I’ve worked have said to most of these – “I have no idea. We need you to tell us!”

Final tips:

Don’t ask all these questions at once.

Sprinkle them throughout your interviews with the company, and ask the relevant people. For example, the HR screener might not be the place to ask about how you measure client outcomes, but they should be able to answer who the CS team rolls up under and what they’re hoping CS can do for the organization. (Although that one you might want to ask of multiple stakeholders…)

Be curious, not critical

No one wants to work with someone negative, and they won’t want to talk to you if you make them feel like they have no idea of what they’re doing. Your tone should be friendly. They’re not trying to do this wrong, they might just not know.

I’m always here to help

Always feel free to shoot me an email for help if you have any one-off questions.

If you’d like more help than that with your job search, check out my CS Leadership Interview Prep

flashcards, or my 3-session Dream Job program.

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