The cheat sheet on figuring out the right time to leave a job and whether a new job is the right one
No one else will ever be able to answer these questions for you, but today I'm sharing my extensive list of questions and considerations for these scenarios as thought starters
Welcome back! This week I’m writing about something that’s come up a lot in conversations with friends over the past half year or so. It seems that every few years, there’s a big wave of turnover in jobs and many conversations start to centre around knowing when to switch jobs.
It’s a loaded question, and often leads to countless other questions, including:
How much further can I get in my current role? Do I have a good setup to succeed and keep growing?
What is most important for me out of my job right now? (Am I getting that at my current role or do I see a path to that?)
How do I know if this new opportunity is any good? What are the right criteria to use when assessing a potential role? What are the critical questions to ask as I meet potential teammates and managers?
Am I in the best role possible for myself at the moment, or is there something better out there? If there is, what are the tradeoffs I’d face if I left my current role?
What’s my long term vision for my career?
Not only does this topic generally unravel into a lot of existential questioning, it is also a topic that can feel really divisive and revealing of differences in background, upbringing, value systems, and beliefs. As I think back on countless conversations I’ve had on this matter over the past few years, I know that my own views have changed drastically, in large part as I’ve seen my husband, E, go through lots of job changes. (Having only held two jobs myself, I feel a lot less “qualified” to speak from firsthand experience here.)
Everyone’s circumstances are different, and I can’t speak to levels of comfort with instability or uncertainty, and that’s a big part of any job transition. Instead, I want to share some of my own notes on a few of the questions I’ve raised above and hope that these can be useful as reference if any of you are ever considering a job change.
First, how to think about your current role.
How much further can I get in my current role? Do I have a good setup to succeed and keep growing?
Here are the characteristics I consider essential for setting someone up for success. These criteria apply to a current job or a potential job, but it’s easiest to start by taking a step back and critically looking at your current job when trying to figure out whether to stay or try something different.
Good mentorship. This includes someone (or multiple people) who has time and bandwidth to provide clarity on expectations, your pace, expected output, ways of working, along with regular feedback that’s actionable and understandable. Ideally, you also have a network of other champions who see the work you’re doing and can celebrate it.
Space to grow. This means you need to have a good spot in the org chart. Are you in a place where you have a next role or title that you’re aiming for? Are there going to be openings in those spaces when you get there? If there are people who are more senior who are struggling to get promoted, this could mean there will be a bottleneck that keeps you from a promotion in due time.
Alignment between the work that needs to be done and your skills. Are there well-suited projects that you are going to work on where you have appropriate ownership and opportunities to showcase your skills and/or develop your skills? If there isn’t enough work to go around or the work that’s most critical isn’t aligned with the areas where you excel or want to focus, then you may not be set up for success.
Team culture and alignment with personal values. This is perhaps the most nebulous of all, but are you enjoying everything outside of the work itself? This may involve how the work gets done, how you interact with your coworkers, how the company is making broader decisions, and the difference that the company is making in the world.
There are times when you may need all four of these criteria to be met. There are times when some will outweigh others and not all of the boxes need to be checked. There are also definitely factors beyond this list that can tip the scales, but these are the considerations that come to mind the most frequently in my conversations with friends.
Second, how to figure out what you’re looking for.
What is most important for me out of my job right now? (Am I getting that at my current role or do I see a path to that?)
I am going to draw on a combination of my own experience pondering this question and considerations that my friends have shared with me. When I was considering my role at TestBox, I put together an entire rubric to assess the role against my other options.
I thought through:
What is it that makes me excited to go to work every day right now? What is behind the moments where I get really drawn into the work and don’t notice the hours passing by?
What is it that makes me dread going to work? What do I complain about the most?
This mattered a lot to me because I didn’t want to simply take the role because it sounded good. I wanted to make sure that it was objectively aligned with what I wanted out of my job, and not just something I was doing because the opportunity had presented itself. I’m a big proponent of making deliberate life choices rather than just jumping at opportunities that have a low barrier to entry. Making this rubric was a big part of me taking a step back to more objectively reflect on what I would look for, independently of having been offered this opportunity.
As I came up with my list, I started to stack rank the criteria. I looked at each pair of criteria and thought to myself, which one would I rather have if I could only pick one. I also assigned numerical values to each criteria to reflect how much it mattered. In the end, here’s the list I came up with:
Good people, fun work environment
Working with an ex-consulting manager/colleagues
Good pay and trajectory/exit opportunities
Sustainable hours
Purview of role/freedom (interesting work) and learnings
Prestige/clout
Consistent with my values
Working in a consumer facing space
When I was considering my role at TestBox, I actually took these criteria, turned it into a rubric and ranked the role at TestBox against my Bain consulting role, as well as two other hypothetical exit opportunities in which I was interested. (Funnily enough, TestBox didn’t end up being the highest ranked on a numerical basis but I found myself rationalizing why the numbers weren’t lining up and trying to edit the rubric to tell a different story. Lesson learned here is that making and using the rubric led me through a healthy process of introspection and reflection, but ultimately probably functioned like a coin flip to tell me what I truly wanted.)
Finally, how to assess different opportunities.
How do I know if this new opportunity is any good? What are the right criteria to use when assessing a potential role? What are the critical questions to ask as I meet potential teammates and managers?
At the time I was considering the TestBox role, I asked a lot of questions about the business itself. I didn’t necessarily know what else to ask, but as we’ve built out our team at TestBox and hired many many people, I’ve started to keep a list of questions that I would ask if on the other side of the table:
What are the plans for this team? Are you hiring more people soon?
Is this role a backfill for someone? If so, can you share more on why the previous employee has moved on?
What does a high-level 30/60/90 day plan look like? Or, in certain circumstances, you can put together your own and bring this to a potential manager and ask if it aligns with their vision
How would you describe the culture of this team? Can you share an example of a new process or change that was implemented recently?
What do you anticipate will be the biggest challenge for someone who starts in this new role?
What are you most excited to not have to worry about, once this new hire starts?
Are you excited to find someone who complements the rest of the team or works in a similar way to the rest of the team?
How does the team provide feedback for one another? Does this go in all directions?
Is there anything else I should know about the team or the company that you haven’t already shared?
I spend a lot of time telling my friends to ask more of these questions.
Often, they’re hesitant and wonder about how they’ll be perceived if they ask questions that venture out of “safe” territory. Having been on the flip side for the past while, I find that being asked these questions shows me that the candidate is being thoughtful about where they’re headed next. They’re not just taking a job on the presumption that it’s exactly as it looks at face value. They’re being a critical thinker and also using the interview process to see if it’s a good fit for them.
I’m open when asked these questions. When there are challenges that the team is facing, I share them because someone who doesn’t shy away from those challenges and is still excited about the role is going to be a much more resilient member of the team. By the same token, if I am open and honest, and someone doesn’t feel that my answers resonate with what they’re looking for, it’s much better for both parties to know that sooner rather than later.
All in all, none of this is a science.
It’s way more of an art, as evidenced by my own experience making a quantitative rubric, only to pick an option that didn’t rank the highest numerically. Making decisions around leaving a job and picking a new job is overwhelming, and I’m hopeful that some of these questions here are good food for thought. At the end of the day, from the countless discussions I’ve had with friends on this topic, I know that no one else can give you the right answer. It takes a lot of self-exploration, reflection and introspection, and talking to others helps the most with sorting out thoughts but not necessarily getting to answers.
Tl;dr
I’ve shared a lot of questions to think through if considering a job change:
Start by thinking about your current role and if it’s still serving your goals and needs.
Figure out what matters the most to you in a job and what you’re looking for.
Finally, ask the right questions when assessing potential opportunities.
Read the full post above for the detailed list of considerations.