How to Interview a Startup
Interviews can be daunting, and particularly interviews at startup are known for being long, unpredictable, and intense. As a startup project manager, you will be faced with interview questions ranging from the product management side of the spectrum, to leadership, to technical expertise. It’s truly a grab bag of topics and can be a beast to prepare for. But what about the other side of the coin - - the part where YOU conduct the interview?
We all know it’s important to do your homework prior to any interview and gather your own questions. The typical advice is to research the company by visiting their LinkedIn page and website, read recent press releases and blog posts, and of course ensure you understand the product or service that is being provided. But this is really just surface level stuff. How do you dig deeper into the organization to understand if it’s going to be a healthy choice? Well, you start by asking questions!
There are startups of all shapes and size, and while they all have their quirks and none are perfect, there are some which should be avoided at all costs. No matter how desperate you feel you are for the job, a toxic workplace is rarely the solution. Sometimes those red flags fly high on the first conversation, and other times, they can be a little more difficult to spot. The only way to know for sure if it’s the right startup for you is to ask telling questions, listen to your intuition, and then decide for yourself.
Here are some questions I like to ask when interviewing for startup project manager roles:
How many clients do you currently support? What is your churn rate? How do you measure client satisfaction and what are those scores? There’s a couple of important pieces of information here: first off, does the organization actually have paying clients? Second, how well do they know their own customer data? And, third, how much importance do they place on client support? An established organization with a weak client support function is on to be wary of.
How is work currently organized? This question is important as more often than not you will find that very new startups (and sometimes even well-established ones) do not have an organizational system in place. You will need to determine how much work lays before you, how much support you will receive from leadership for this effort, and how the team feels about changing their workflow to accommodate a new system. It’s ok if the team is up front and honest with you about their lack of project management in the past, but if there is literally no organization and they want you to pull it together by yourself in 30 days, along with a laundry list of other responsibilities, then it may be worth having a conversation to re-evaluate the job duties. No one wants to be set up for failure.
How do you describe the organizational culture and what does that mean to you? How do you measure whether someone will be a good fit culturally? It’s easy to talk about an ideal culture, but it’s much more difficult to pull it off. Does the wording around culture sound regurgitated, or are there actual data and anecdotes to back it up? Additionally, it’s helpful if you can meet with a few different team members throughout the interview process to get a feel for the energy you will be around daily.
How much employee turnover has the organization experienced? It’s important to always ask about the position you are applying for to understand if it’s a new position or, if not, why they are looking for a replacement. And in addition to that, it’s incredibly telling to understand how much turnover the company has had in general. Now, if there has been a lot of turnover then you likely won’t get a straight answer, so pay close attention to the response and read between the lines when it feels off.
How did you determine which positions to hire after this latest round of funding? This question applies if there has been a recent round of fundraising and subsequent hiring. Many times startups will hire based on the fact they have more money, instead of basing this important decision on strategy and data. Are they simply hiring to hire, or do they have a plan in place? This goes to leadership’s overall ability to manage resources.
How are financial figures, sales goals, and other important metrics communicated to the team? Many startups will use the word “transparent” in their initial pitch to recruits. Once again, this is an “actions speak louder than words” type of situation. Ask for specifics about these numbers and how/when they are communicated to the team. Whenever possible, talk with existing team members and get a feel for leadership’s involvement in the day to day.
Is the plan to sell the company, or grow it to cash flow under the same ownership? There is nothing inherently wrong with either answer, but honesty is key here. If there is no plan or there seems to be a hidden agenda, then tread carefully.
What is the CEO’s vision, and how engaged are the CEO and leadership team in the day to day management of the organization? This question is usually the most telling and is best asked to the CEO directly. A disengaged CEO or one with misguided motives and expectations is a BIG red flag. If you can’t speak with the CEO directly, look for videos and other information online. Does the CEO inspire you? Has the CEO openly engaged in sketchy behavior? Is the CEO checked out of the day to day operations of the company? You are looking for a strong leader, you will know when you see the opposite. Trust your gut.