Career Advice

10 Questions to Ask Before You Take That New Job

If you’re considering a new job, or accepting an offer, I wanted to share some thoughts on how to make a better, rational and emotional decision.

As the saying goes, the grass is not always greener on the other side. Through these 10 questions, I hope you can get clarify and feel more confident about your career decisions.

Here goes:

  1. What are your dreams and goals? Think about your career, your family, your financial goals. Does this job help you get closer to reaching them? Every job I took helped me either learn something new, make more money, get more responsibility, make more important connections, and/or get more exposure in my field. I remember in one job, I actually took a drastic paycut because it helped me take a huge step toward my dreams and goals (getting to graduate school). Because of that particular decision and my overwhelming desire to take that step, I overlooked or minimized other questions in this list. It was well worth the decision and sacrifices I made in salary and other things (like liking your boss, who I tolerated mostly). By the way, I wrote more about this in my post titled More Money not Key to Happiness.
  2. Is this the job you really want to do? And are you clear on what’s expected and the wins for you? Do you know what you’ll be called to do each day and week? And if so, will you like doing the work? Is it in a field you enjoy? You need a passion for the work. It’ll drive you to improve and grow and thus be rewarded and recognized for it.
  3. Will you enjoy who you work for? Bosses havs a significant influencer over your happiness. You don’t have to be best friends, but will you enjoy (and thrive) working in line with this person? Are you values and work ethic aligned? Do you share the vision for your role with that person? Can you see yourself being rewarded for doing a great job? Will this person invest in your career and you? The best bosses I had were ones who cared about me, and also, provided I worked hard for them, wanted the best for me, even if that meant leaving for another job. I took the last job I had before starting iThemes because I believed in the leader of that organization. I also immensely liked him and his vision and style. I embraced it. And the more time I spent with him, the more committed I was to him and the work. It made my work feel effortless at times because I believed in where he was leading us.
  4. Are you going to enjoy working with this team? Being on a team that you fit in with as well as like the company of those you’re working with is a huge benefit for your personal and career happiness. We hire for fit, then talent and potential because this is absolutely vital. We want those on our team to enjoy each other. We don’t have to be best friends. But we want to at least enjoy each other’s company because we spend more time with each other than our own families. I’ve been places where people didn’t like each other much. It sucks. Who wants to go to a place every day where you want to avoid people?!
  5. Do you have opportunities to learn and grow? Not only will this position help you learn and grow, but does the company and your supervisor and team care about your learning and growth? One of my Strengths is Learner. And we have a lot of learners on our team because I believe that if you want learners, you must hire learners. One of the things we did to show we believe in learning is buying Amazon Kindles and starting a sharing library.
  6. Will you have the tools, coaching, help you need to do your work & be successful? I can’t imagine a car mechanic not having access to the right size sockets for the job OR a tool that would make their work faster and easier. You must have the right tools and resources to do your job. Some organizations are stingy and thus short-sighted, but the best seek to make the right resources available to help you do your best. For instance, we don’t buy the most elaborate or expensive items at iThemes, but when our people need the right tools for the job … and can offer a great Why and How [insert tool or resources] is going to help them, it’s an easy decision.
  7. Is this an organization that will reward and value what I can do and offer? Look at track record and see if they have promoted within and the stories of the people who are in the positions they now have. For exmaple, I’m very proud of the fact that people on our team like Matt Danner, our COO, started answering sales emails, and people like Kristen Wright, who started as our first office wrangler and is now our communications coordinator.
  8. Do you have an opportunity for advancement? Whether inside or outside of the new organization, does it open up more opportunities for you than your current job?
  9. Is the timing right? Sometimes the timing isn’t right. Sometimes you’re overdue for a switch. This is a tough one. One you might doubt yourself about. But you need to evaluate if the timing is right. And does it FEEL right? In one of my past jobs, I knew I was 6 months overdue for a job switch. I wasn’t learning. I wasn’t growing. And frankly, I was getting bitter. Thankfully a job popped up and I took it, or else I don’t know the long-term consequences of staying in that job or position to my outlook and career.
  10. How much is all of this worth to you? Add up all the tangible (insurance, retirement, vacation/PTO) and intangibles. If there is a gap in salary and/or benefits, find that exact number, subtract for taxes, then divide by 24 (the number of paychecks most of us have) and decide if that number is far outweighed by Do you feel confident about taking the new position? How does the overall score of these questions make you feel now about your job? If you’ve found gaps and possible concerns, consider asking for clarification before taking the job … and if there are red flags, hold until you feel right about it.



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