“A recruiter for a small start-up reached out to me about a new position. It would be a significant pay increase, and it's fully remote. The job description sounds good and the start-up seems to have serious investors behind it.

I've only ever worked at really large corporations. I’m the type of person who likes to have some stability and know what I’m doing in my job. I’m definitely worried about what would happen to my job if the broader economic situation impacts this newer company. Besides the standard questions about the role, what sort of things should I be asking the recruiter? What questions should I be asking myself as I (potentially) make the decision about whether to make a change?”

• Maybe moving

 

Hello Maybe. Kudos on doing the first step (and something I always recommend). 

Always take the call from the recruiter

It is important to know what opportunities are available in the marketplace. Talking to recruiters also gives you information about how you are being perceived by potential employers. 

Recruiters are calling you for a reason. If the roles and pay match your interests - great! That means your public information is sending the right signals.

If you are looking for product roles and you only get calls about operations….something needs to get updated. Your branding is not working for you.

Side note - I also recommend staying connected with recruiters because they tend to move companies frequently. If their current offer isn’t the right one, you can always follow up later to see if they have something better aligned.

Okay, back to how you make a decision about the opportunity in front of you. The first thing to do for anyone evaluating a potential new job.

Know what matters to you

Recruiters and the people working there will share their own version of what is important. Chances are that info won’t precisely align with what matters most to you. Know what is important to you so you can ask the right questions.

In practice, this means making a list of your team, role, and company needs. Make a full list of what is important to you right now. It can be about manager relationships, team size/structure, pay, stability, or a chance to learn something specific. Anything that feels meaningful during this chapter.

Once you have the master list, pick your top 2-4 things. This is the list you are going to solve for, I refer to this as your ‘hierarchy of needs’.

If you are struggling to prioritize, think about tradeoffs

Examples: Work-life balance is more important than having a manager you can be friends with. Flexibility to care for a child after school matters more than needing to answer emails on the weekends sometimes.

Make a note of any non-negotiables. For example, if you MUST work remotely 3 days a week, decide that you won’t consider anything that doesn’t have that option. Be clear with yourself and the recruiter about hard boundaries. You will be miserable if you don’t honor your own needs.

Side note: startups tend to change policies more frequently than established companies. Even if something is true today that doesn’t mean it will last forever. Recommend getting any non-negotiables in writing to protect yourself.

As you go through the process, use this list as your guide as you gather relevant information on your top priorities. Also, use the list to review your current role. How many of your needs are met today?

Know what type of role you want

Now think about what you want to be doing in 2 or 3 jobs from now. What type of work, what type of industry? What gaps do you need to close in order to get from here to there?

It is flattering when a recruiter calls and tells you that you’re a great fit for XX or YY role. We all like that.

However, if the role doesn’t get you closer to the next and next-next thing, that means it isn’t a good fit for you.

If the new job checks some boxes and helps move you toward the destination of your choosing - great! Continue down the path and go deeper into the process. If it doesn’t, this might be your exit point from the recruiting process.

Continuing down the path doesn’t mean you are committing to work for this company. You are simply gathering more information at each stage of the interview process. Just like they are doing with you.

Dig into the culture 

The next step is to look at the culture. You can directly ask about some elements of culture. Others you will need to suss out based on your interactions.

The people. You want to work with good people. Based on your hierarchy of needs, you know which people are most important to your happiness (i.e. managers, peers, team-mates). Ask to talk to those people.

Take note of your interactions with all the people at the company. HR folks, leaders you interview with, the recruiter, and the admins who are helping with logistics. See if people are generally kind and helpful.

The corporate values. You also want to get a sense of the real values of the company. The things that they reward people for. Ask some questions about what types of people are recognized as high performers. This will tell you about the ethos.

Is it a results-at-all-costs type of place? Is it a ‘take care of the humans (employees or customers) first and the rest will sort itself out’ place? You want to know if the culture runs counter to any of your deeply-held beliefs.

The vision. Because it’s a start-up, you definitely want to know where the company is going. Does leadership know? Do the associates know? Ask people what they think the destination is and how the team is moving towards it.

If you get the sense that there are a lot of skeptics - that might be a red flag. On the other hand, if it seems like an uphill battle with a lot of smart and enthusiastic people going after it, that could be a fun challenge.

You know what’s important to you, see if those same things are important to the company and the humans who work there.

Start-ups vs  big companies

If you like the culture, next up is looking at the organization itself.

You have been working at a big company. Start-ups operate differently. Sometimes in good ways, sometimes there are tradeoffs. Go back to your hierarchy of needs and bump that up against the typical small vs. large company factors.

Start-ups & small companies:

• Sometimes faster-growing organizations have more growth opportunities and people are asked to do things outside of their core roles. Is that exciting or daunting?

• There is a possibility to be impacted by external factors like a recession. How much risk tolerance do you have for a potential change in employment?  

• You can move fast - there are fewer controls and processes because you are building and shipping things quickly. Is that exciting or anxiety-inducing?

Big companies:

• Sometimes more established companies have more protection and employees are less likely to get lost in the shuffle. How valuable is that kind of backstop?

• More processes can also mean it takes longer to do things or change the inherent culture at a big company. Is that comforting or frustrating?

• Big companies may have more established benefits packages. Make sure to do some research on 401k match, healthcare, and tuition support (whichever current benefits matter most to you).

A few bonus questions for the start-up

• Can you get additional types of compensation to offset some of the risks? (ie options, ownership, etc). Is any of your comp tied to growth targets or company performance? 

• How much has the company grown, and how much does it expect to grow in the next year, 5 years (rapid growth can be exciting, and also chaotic)?

• How do they help people grow and develop (resources, investment, mentorship, etc)?

 

Once you do all this homework, evaluate how well this opportunity matches your personal needs, your career goals, and your values.

You will know if the move is attractive for you. I don't recommend change for the sake of change. But if it aligns with what you want out of your career and meets your needs - go for it!

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